KF #32. Balances Stakeholders Archives - How to be Awesome at Your Job

Pete Mockaitis
Melody, welcome back.

Melody Wilding
Thanks for having me again. So great to be here.

Pete Mockaitis
Oh, it is great to be chatting with you from the fine state of New Jersey, which we discussed is lovely.

Melody Wilding
That’s right. Beautiful state, very misunderstood, but we love our Jersey.

Pete Mockaitis
Lovely. Well, let’s talk about managing up. We haven’t discussed this issue in quite some time and I think it is so vitally important. Can you share with us maybe an extra surprising or counterintuitive discovery you’ve made as you researched this managing up stuff?

Melody Wilding
Well, I think, just like New Jersey, managing up is very misunderstood, and even when I began writing the book, I was resistant to the idea of calling it managing up and even zeroing in on that concept. I wanted to talk more about influence and persuasion, how do you build respect and recognition. And my publisher had to keep nudging me that, “Yeah, what you’re talking about is the skill set of managing up.”

And I think my resistance came, and what I’ve heard from many other people, is from these misconceptions we have. These old images of managing up from the ‘80s, the ‘90s, the person being the suck-up and running around with their boss’s coffee order. And who wants to do that? No one wants to compromise who they are or feel like they’re ingratiating themselves to the people around them. So, it’s no wonder why we resist this concept.

But what I know now, having done this work and researched this subject is that managing up is not something you do for your boss’s benefit at all. It’s really something you do for yourself to make your own work life, your own career, much easier, less stressful and on your own terms.

Pete Mockaitis
Yes, I dig that a lot. And while we’re talking about misconceptions, let’s clear them up, I recall, I think I was reading a piece by, Paul Graham, the Y Combinator guy, made a statement along the lines of “Professional managers are amongst the finest liars there are.” And folks are like, “Whoa, that’s some strong language. What do you mean?”

He’s like, “Ah, perhaps I should say, they are adept at managing up,” which sort of imply, well, more than imply, that managing up involves telling the folks above you a little bit of what they want to hear, and massaging their perceptions and expectations, and it really made it sound quite like it’s the art of deception in the professional, acceptable way that we can courteously do so in proper modern times,” Melody. So, have you picked up on those perceptions and how do you address that?

Melody Wilding
I think, again, that’s the older school way of thinking about it. And what I would argue is it’s less about massaging and contorting yourself to someone else’s perceptions and more about tweaking, or in the book I call it flexing, your approach so that your message is actually getting through to the people who need to hear it the most.

That may mean you do need to tweak how you present something, or the type of language you use so that it’s more resonant with the other person, but I don’t think, wholesale, it means that you have to change who you are or what you’re trying to say, because this book is really all about, “How do you have the tough conversations with your manager? How do you push back on extra work or give them tough feedback up the chain of command?”

That’s what managing up really is. It’s having those difficult conversations, sometimes having the courage to say what needs to be said, but doing so in a tactful diplomatic manner that actually earns you trust instead of just turning into a professional people-pleaser.

Pete Mockaitis
Okay. Well, could you share with us a nice story that inspires or brings this together in terms of what’s really at stake if we master this skillset?

Melody Wilding
Yes, I think the book actually starts with one of my personal stories which was a time I failed to manage up, and I think it’s a lesson in multiple ways. So, before I went full-time into my current business, I was working at a health care company, and I loved that job. I loved my boss. What I didn’t realize at the time that I saw in hindsight was that I had been hired to work on really a pet project of my managers that was kind of outside of the rest of the company’s scope, and my manager had been given a bit of budget and, unbeknownst to me, some timeline to see if this was viable or not.

And so, that was my first fail, was really not getting on the same page with my manager about “What was the context that this project came up in? What are the expectations? Who else needs to be bought in and on board with this?” And long story short, let’s flash forward, I ended up being laid off. My role was eliminated, and it felt like a shock to me, and it shouldn’t have.

And that is what’s at stake. That’s a very extreme example of what happens when you don’t manage up well, but I was really sideswiped because I hadn’t aligned with my manager. I didn’t have other advocates in the organization who were willing to fight for me and keep me because managing up has to go beyond your boss.

Do not make your manager your single point of failure. You might not get along with them very well despite all of your efforts. Who is leading you may change on a moment’s notice, so you need to make sure you have those other allies as well. And all of that was a very cautionary tale, but I think that’s what’s at stake, whether, again, in my case, it was extreme. I lost my role.

But every day, people feel like they’re overlooked for promotions and opportunities, it may go to someone else who seems less experienced, or we get into these minor frustrations that we end up taking personally, “You know, why does my boss cut me off? They never even allow me to hear my idea out,” or, “Why are they micromanaging me and on top of me about everything?” And so much of this can be solved by learning some key skills.

Pete Mockaitis
Certainly. Well, tell us, you lay out 10 key conversations for managing up well, which I love. And so, we’ve got alignment, styles, ownership, boundaries, feedback, networking, visibility, advancement, money, and quitting. So, I really dig this because I just love a framework and a set of distinctions and a delineation of categories that just helps make sense of the whole universe of managing up conversations. It feels like, “Yeah, that’s a pretty fine job of summing them up.”

So, I suppose I’m curious, do you have a gauge for what percent of folks ever actually proactively say, “Hey, I’d like to have a conversation about some of the fundamental ways we work and communicate with each other, and what would be best for both of us”? In a way, that almost seems like among the most foundational things one might do in the world of managing up. Is that fair? And how often is that happening?

Melody Wilding
It’s definitely fair. It’s very true, that it is so fundamental that, I think, we sometimes assume it. We assume that this has happened and we overlook it because of that. So, to your point, I would say maybe 10% of people are having those types of explicit conversations about how they work together with their manager, and that is a huge, huge opportunity.

Because if you are in that small minority of people who are doing this, you’re not only going to stand out as someone who is thoughtful, conscientious, you’re driven, you’re taking initiative, but you’re going to have intel and build rapport and trust much more quickly than anyone else.

Pete Mockaitis
Absolutely. I agree, and I’ve experienced it on both sides of the table. Because it’s rare, it feels very special, like, “Oh, wow, this person, I like them. They’re on top of things.” And I think it’s hard for that to go poorly. Maybe if you ask at just like the worst possible time, like, “Hey, that’s like the definition of a non-urgent situation and we’re in the midst of something on fire right now.” So, maybe that that’s one way it could go poorly. But tell us your take on that in terms of to what extent do managers welcome these discussions because I think there’s a bit of reluctance on the part of some folks to initiate?

Melody Wilding
There definitely is, yeah. And when I have this conversation with people, in the book, we’re talking about really the styles conversation, and that’s when we talk about how, “How do we work together? How do we communicate? What are your preferences? What are mine?” And going back to what I said a moment ago, when you understand the context of who your boss is, and also what your defaults are, you stop taking things so personally because you understand, “Oh, this is their style. This is their way of approaching and processing information.”

“And so, if they send a period instead of an exclamation point, I don’t need to make that mean that I’m getting fired, or they hate me, or they’re against me and they favorite somebody else.” We can be much more diplomatic and make those tweaks to how we communicate.

And in my experience, people are reluctant, yes, to bring this up, but when they do, their manager is overjoyed. And, of course, you need to bring this up in a tactful way. So, what I suggest is that you present it to your boss and say something along the lines where you show why this is in their benefit, to say, “I’m really committed to us being able to reach our goals together this year.”

Or, “I want to make sure that you can get the best performance out of me possible, that our work flows more smoothly, whatever it is. And to get there, what I would love to do is understand a bit more about how you work and how I can communicate with you better to get you the information you need. Does that sound good?”

And you can start by asking certain questions of your manager, whether it’s, “If I have to get certain updates to you, what format is best? Do you want those in Teams, in email? Should I present a slide deck? Do you prefer bullet points or should I do narratives?”

Understanding some of those preferences, when you are asking your manager questions, gives you opportunities to then say, “Great. Thank you so much for sharing that. From my standpoint, here’s what would be helpful. If you have feedback for me, take me aside after a meeting, or if you notice that I’m not being as concise as I could be in a presentation, shoot me a quick message on Teams so I can adjust on the fly.”

All of us have different preferences around that, but it turns it into more of a two-way street where, yes, you’re understanding what your manager wants, but you’re also finding opportunities to assert, or at least put on the table, “Here’s what I would like. Is that something that we can find a middle ground on together?”

Pete Mockaitis
That sounds great, yes. And as you say it, and I’m imagining the scene, that seems pleasant and welcome to hear such things. And I want to dive deep on a couple of these. I don’t think we could do all 10 in our time together, but one with regard to boundaries. I remember when I was reading through this, I recall a conversation I had with my friend, Kelsey. We were catching up at a wedding. It had been a long time.

And she was telling me all of, like, the cool things she was doing with, like, go to an Ironman Triathlon, and this and that. I was like, “Wait a minute. I’m sorry. Don’t you work in consulting?” And she’s like, “Yeah.” I was like, “How on earth are you finding the time to have all of these adventures and do all of these things when I recall my days of consulting were so brutal with regard to the hours of the travel and the unexpectedness of things?”

And she was like, “Oh, well, you know, I just kind of talked to my boss and said, ‘Well, hey, here’s what’s going on, here’s the nights I’m not available, and here’s the thing…” She just sort of laid it out in terms of what’s up, in terms of, “I’m going to over-deliver on these key metrics and expectations, and these are the nights I will not be available to be doing things.”

And I was like, “And they went for that?” My mouth dropped, I was like, “You can do that? That’s possible? Even in client services? Wow.” And so, I was struck at just what a managing-up boundary conversation can do for transforming a life into being sustainable and enjoyable in what can be demanding fields.

So, lay it on us, Melody, if we want to establish boundaries but we’re a little scared and we think that we might misstep, or seem like we’re not a team player, or we’re lazy, or we’re not really committed, or any of these other negative associations we fear, how do we play the boundary-setting conversation game?

Melody Wilding
Well, that’s the tension with it, right? We need to protect our well-being, but we also don’t want to look like a slacker, so we have to find that balance there. And the thing with the boundaries-conversation is that “no” may be a complete sentence in many areas of life, but at work it doesn’t go over so well if you just say, “No, I’m not going to do that,” or “I don’t want to do that,” right? It’s going to hurt your reputation for you to say that so you need to be more thoughtful about how you approach it.

And what I think is so telling about what your friend did is it sounds like she was assessing, what I call in the book, your pushback power. And your pushback power is the invisible leverage you do or don’t have to push back, to say no. And we all fall somewhere on the spectrum, higher to lower. Your pushback power is higher if you have more positional authority.

If you’re more seasoned, tenured in your career, you have more credibility behind you, you are a high performer, or you offer a very specialized skillset that people may be more willing to make accommodations for because it could be hard to replace you. And even things like the strength of your relationship with your boss, how you build trust and rapport, your boss’s values, the state of the organization.

If the team is in free fall, in crisis, it’s going to be harder to say, “I can’t pitch in this weekend,” or, “I can’t take on more of this project for a colleague who just left,” versus if you’re in a time of stability, it might be a little more receptive to that. So, taking into account that pushback power allows you to gauge “How directly or assertively can I say no? And how frequently can I say no?”

And it sounds like your friend did that with her manager. Because she was higher in pushback power, she was able to say, “I have these commitments, and so can we find a solution to work my workload around these commitments that I have?”

Now, for those of us that may be medium to lower in pushback power, there’s a number of different things you can do. One of my favorite approaches that I talk about is called the trade-off approach, and this is great because it allows you to set up binary options. So, you may say, “Okay, thank you for sharing that, you know, Y has come down as an important priority from the leadership team. A few weeks ago, we had talked about that you wanted me to focus on X.”

“And so, if X is truly still a priority, how would you like me to reprioritize to make room for Y? Or what would you like me to slow down on? What would you like us to delegate or temporarily deprioritize in order to make that possible?” And the beauty of this is that you are setting the parameters. You are setting the decision options, subtly saying, “Both of these cannot happen at the same time. Which one would you like to choose?”

But ultimately, you’re approaching it more as a problem-solving conversation instead of just dumping a problem back in your boss’s lap to say, “I don’t know. I can’t do it, so figure out someone else to get it done.” You’re approaching it more as a collaboration, which that person will appreciate, and the ultimate authority is back in their hands.

Pete Mockaitis
And I think that’s really handy because I think without the conversation, we can just assume, “Oh, I have to continue doing all the things we’ve ever discussed, as well as this new thing, and that’s just that,” and that is a dangerous, untenable place to live. So that’s handy with regard to the conversation. I’m curious, when it comes to increasing our pushback power over time, let’s discuss.

So, one of the levers is just the strength and quality of our relationship. Another is how special and wonderful and high-performing we are. Any others and what are the quickest, easiest ways to boost these so that we are growing in pushback power over time?

Melody Wilding
Well, let’s talk about the performance piece and building rapport and trust with your manager. There’s a conversation that comes before boundaries, and that’s called the ownership conversation. And that’s important here because the ownership conversation is all about looking for where can you take initiative of projects or problems you want to solve and run with, but by doing that really add value or solve an issue that’s a pain point for your manager, your team, the organization.

And when you do that, you build, you add to the pushback power you have because you’ve enhanced your value, you’ve shown you’re a problem solver, and that’s really valuable. So, the ownership conversation is all about “How do I not only spot those opportunities, but capitalize on them in a way that’s not going to step on the toes of other people around us?” Because that would backfire, of course.

And a lot of it comes down to choosing the right problem to start. And so, I talk about how there’s five worthwhile areas to look at. And a few of those may be bottlenecks. So, are there inefficiencies or broken processes, for example, that are slowing everyone down, including you, that if solved would make everybody’s lives much less stressful and easier?

Neglected needs is also a great place to look. What are the topics or agenda items that keep going to the bottom of the pile or keep rolling over month to month, quarter to quarter, that no one seems to have the time to get around to, but says, “Wouldn’t it be great? Wouldn’t it be great if we could do that? Or we really need to get to that”? Could you be the one to carry that torch forward?

And another one that I think can be easier to spot is feedback patterns. What are you hearing again and again from fellow team members, clients, your vendors, that if you took action on to make better, would add value to everyone else?

Pete Mockaitis
That’s cool. All right. Well, could you give us a story of this ownership in action? Because I think you’re really keying in on something in terms of differentiating and growing a career, because it’s quite possible to go years at a time in reactive mode of doing whatever somebody asks for, or seems to be perilously on fire.

It’s hard to be distinctive in such a place, as opposed to, with ownership, it’s like, “Oh, you know, that’s a fantastic result. Yeah, that was, really, I’m the person behind that.” That’s hugely awesome. So, could you give us a story about ownership in action?

Melody Wilding
Sure, I have two that come to mind, if that’s okay. So, the first one is, I had a client about a year ago, who, his organization was acquiring a new one and he worked on the legal side of this. And so, because of that, when they acquired this new organization, all of his colleagues were running in the direction of all of the new opportunities that were created by this acquisition and trying to capitalize on that, chasing shiny objects, everyone was trying to meet with the three key leaders.

And what he saw was that that change actually created this vacuum where he could step in, and that no one was tackling, there was a neglected need, in other words, with due diligence matters of closing everything that had to do with that transaction, you know, wrapping up all of the contracts, dotting the I’s and crossing the T’s to make sure the merger was complete.

And so, he said, “You know what? I’m actually going to zig while everybody else is zagging.” And he carved out that niche for himself as being the person who was buttoning up the deal, so to speak, which gave him a lot of exposure to not only he became a close confidant to his manager, but also his skip level, his boss’s boss, and some other key C-suite leaders in the organization who really cared about this going correctly, and who knew, “We have to get these compliance matters correct.”

And for him, that allowed him to build those relationships. He was seen as more of a partner to those people. And flash forward about a year later, he was actually promoted to partner because of that work that played a huge instrumental role. So, that’s one example that comes to mind of looking for opportunities that other people may be missing.

And then the other quick story I’ll share has to do with another client who, after the pandemic, was really interested in getting mental health days going for the organization, making sure that the team had time for development and rest, and weren’t just go, go, go, go, go all the time. And why this was ownership is because she had to create buy-in for this idea. This wasn’t something that others had thought of. This was something she was innovating from the ground up and had to push through.

And so, a couple things that she did really excellently was she came with proposals in hand, and so when she would have meetings with some of the key stakeholders and decision makers, she would come with a one-pager with talking points that they could use, just ready-made. She made their job easy, took the cognitive load off of them, and she proposed small steps.

So, in the book, I talk about this as the foot-in-the-door technique in psychology, where you propose, whether it’s a pilot project or a test or rolling something out to just a small sample. The people around you want to mitigate risk and potential exposure or failure. So, if you could say, “Let’s start with a mental health day and then we can actually roll that out to have these once a quarter and have more events around this.”

She just started with, “Let’s have this one day,” and that was easier for people to get on board with. And, eventually, she was successful in making it something bigger but I thought that was a great example of planting seeds, taking it step by step, and getting small agreements that lead to bigger ones.

Pete Mockaitis
That’s a really cool thing to take ownership of because, well, one, that’s just great for everybody, and two, boy, I sure would like that person in my organization, it’s like, “Oh, this is the person who got us all the mental health days. I want to do them favors whenever possible.”

Melody Wilding
Yes, great point. And that speaks to this idea of looking for triple wins. Is something going to be a win for you in terms of you’ll enjoy the work, it will add to your own credibility? Is it a win for your manager? Will it make them look good or advance their priorities? And, third, is it a win for the team or your organization as a whole?

Like you said, your colleagues are certainly going to love you, but, you know, at the end of the day, for everyone’s productivity, sustainability in their roles and long term the results of the organization, it was huge from that respect, too.

Pete Mockaitis
Okay. Well, tell us, within these 10 key conversations, could we pick perhaps one or two that seem to be super transformative and yet pretty easy to do? Any of your favorite tips here?

Melody Wilding
Let’s talk about visibility, if that’s good with you. Yeah, I think this is one that people know they need to do, but don’t quite know how to approach because it feels daunting. It feels daunting to feel like, “Ugh, I spend so much time working. Now you’re telling me I have to advertise that work as well and I have to bring more attention to it?”

And in some ways, yes, because we can expect our work to speak for itself. It’s not going to do that. We need to be the advocate for it. But there are some pretty simple, easy ways to build visibility into just the day-to-day of how you work instead of making it extra effort, and I think that’s the win-win. One way you can do this is by restructuring your one-on-ones.

So, I highly recommend that you start all of your one-on-ones with your manager with wins. And you can call it wins, you can call it progress or milestones or achievements, whatever language feels best to you, but the point of that is to not just dive into status updates of, “Oh, here’s where this project is. Here’s where this is. This is what’s coming up.”

But to more so utilize that time to show your manager, “Yes, here’s what we’ve done, but here’s what it means. Here’s the outcome, the results. Here’s also visibility into how I thought about solving a problem, the considerations that I made, or the people I talked to.” And all of that shows them, yes, you are actually getting things done. It gives them more insight into you operating at a more strategic, perhaps even higher level. And it also gives them information that they need to run up their own chain of command.

And so, it’s not really self-promotion to just puff yourself up. We really need to think about it more as, “I’m giving my boss the data they need to advocate for me, to advocate for the rest of the team, to have resources, opportunities, decision-making power at higher levels.”

Pete Mockaitis
Yeah, I think that’s excellent. And often, when we take ourselves out of the equation, there’s less self-consciousness, and it’s like, “Oh, this is this is handy. Like, if I were leading this organization, I would probably want to know about the skills, this asset, this resource, this person has in the mix to be deployed when useful and necessary. Otherwise, everyone just misses out.” And how about advancement?

Melody Wilding
Advancement, yes. And thank you for that great segue because visibility and advancement go hand in hand, right? And you can start to see how these conversations build on each other, intersect, because once people know more about what you’re achieving and know more about you, well, then you’re in a position to do bigger things.

And why I say that term “do bigger things” is because advancement doesn’t always have to be a promotion. It can be that you want to grow your scope, or the budget that you oversee, you want to go from two to four people on your team, or you want to work on a stretch project, or something that’s completely different from your current skillset.

For example, right now I have a lot of clients who are asking for stretch projects in AI, because that’s really important to them to learn and they know it will be a value-add to the organization. So, think more broadly about what advancement could mean, but also think about starting much earlier than you think you might need to.

Because I see way too many people get caught in the performance review paradox where they keep their head down, they think they’re sending signals to their manager about what they want and where they want to go, only for their performance review to arrive and no promotion, no salary increases, no being named to that committee. It seems to pass them by.

And that’s often because we either haven’t been explicit enough about what we want or we’ve waited too long to bring that conversation up, and your manager has already had to allocate headcount or resources or make those decisions. They were made months ago. So, this may mean starting three to six months in advance to plant those seeds.

Let’s say you did hit a big milestone. You may say, “This was such a valuable experience. I really loved getting to interact with these clients or that stakeholder or use this skill. I would love to do more of that. Do you think there’s an opportunity in the coming months?”

And so, you start to get that out there. You may even have more of a formal conversation with your manager to say, “In the next year, I would love to double the size of my team,” or, “I would love to move from manager to director level. What would you need to see to be comfortable with that change?”

And that allows you to surface objections because your manager may say, “Well, you’re not ready for that,” or, “We need to have these other people on this committee bought into this, so I need to rope other people in.” And it allows you to contract so that you can understand, “All right, by June, you need to see this. By December, you need to see that.”

And you can work against that and have follow-ups to say, “All right, I did what we discussed. Are we still on track here? Has anything else come up? Would anything else prevent us from making that decision at that point?” And so, it has advancement top of mind for you and your manager, and it prevents some of moving that goalpost that can happen.

Pete Mockaitis
Okay, beautiful. Well, Melody, tell me, any other final tips, tricks, do’s, don’ts before we hear about some of your favorite things?

Melody Wilding
Let’s talk about, briefly, the money conversation because if you have advanced and you’re taking on more, you probably want the salary that comes along with that. Money can also be very loaded and very sensitive, something many of us are not taught how to discuss in our personal lives, let alone in the workplace.

And one of the big mistakes or missteps I see people make here is that they focus way too much on what they’ve done already and not enough on what they can do in the future if they were given more money to do it, and that’s very important. You need to think about, “What’s the potential ROI if the organization gives me five, ten, fifty thousand more dollars, what else would I be able to do? Does it serve bigger clients, manage a bigger team?”

You need to paint that future so that your manager, again, see a theme here, can make a case to their own leadership about, “Why should we give this person more money?” It’s not enough that you want it or you feel you deserve it. That may be true and there needs to be a business case there. So that, combined with, instead of just saying, “I deserve this. I work really hard,” approach it from the standpoint of fairness.

We humans, we are wired for reciprocity. We want to make sure that people feel like they are being treated fairly or correctly. And so, if you can use language around that to say, “I want to make sure that my compensation matches the level that I’m performing at or is commensurate with the amount of value I’m bringing to the organization.” If you can use that sort of language, it makes it feel less like this request that you’re demanding, and again more like a trade.

Pete Mockaitis
Certainly. Well, thank you. Well, now, could you share with us a favorite study or experiment or bit of research?

Melody Wilding
In the book, I actually cite some of this research around micro-yeses. And so, if you can get a micro-yes, let’s say you have to give someone feedback, and instead of just diving into, “So, in that last meeting, I felt like you talked over me,” ask for permission first. Get a micro-yes, “Will now be a good time to talk?” “Yes, sure.” “Okay, I’d love to chat about that client meeting. Is that good with you?” “Yes, sure.” Get those micro yeses along the way so someone is a bit more bought in and not as surprised by what’s coming next.

Pete Mockaitis
All right. And a favorite book?

Melody Wilding
Difficult Conversations by Douglas Stone and Sheila Heen. Fantastic book, as well as their other book, Thanks for the Feedback. Both amazing books that really break down the nuances, the anatomy of how to have these difficult conversations.

Pete Mockaitis
All right. And a favorite tool?

Melody Wilding
I am a huge Oura user, so I have my Oura ring on here.

Pete Mockaitis
Oh, yeah. Mine is on my charger.

Melody Wilding
Yes, I probably have to charge mine today, too. But I’ve had it for years, and I just, especially since they have added the heart rate monitoring throughout the day, it is so helpful for me to see what spikes my stress when I go into restorative time. It’s just helped me manage my own schedule and my own energy much better.

Pete Mockaitis
And a favorite habit?

Melody Wilding
I am a go-to-the-gym-first-thing-in-the-morning person.

Pete Mockaitis
Okay. And is there a key nugget you share that really seems to connect and resonate with folks, you hear them quote it back to you often?

Melody Wilding
“You teach people how to treat you.”

Pete Mockaitis
All right. And if folks want to learn more or get in touch, where would you point them?

Melody Wilding
ManagingUp.com is where you can find all the information about the book. You can connect with me as well there, too.

Pete Mockaitis
All right. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Melody Wilding
Start today with having the alignment conversation, and that is a really simple entry point to begin managing up, to ask your boss, “What would success look like for you in the next three months? What does great performance look like in this role? Or, what metrics does your boss discuss with you?” Start there, and I think that’s going to establish a basis of trust and give you a lot of insight that will be really valuable.

Pete Mockaitis
All right. Melody, beautiful. Thank you.

Melody Wilding
Thank you.

Pete Mockaitis
Melody, welcome back.

Melody Wilding
Thanks for having me again. So great to be here.

Pete Mockaitis
Oh, it is great to be chatting with you from the fine state of New Jersey, which we discussed is lovely.

Melody Wilding
That’s right. Beautiful state, very misunderstood, but we love our Jersey.

Pete Mockaitis
Lovely. Well, let’s talk about managing up. We haven’t discussed this issue in quite some time and I think it is so vitally important. Can you share with us maybe an extra surprising or counterintuitive discovery you’ve made as you researched this managing up stuff?

Melody Wilding
Well, I think, just like New Jersey, managing up is very misunderstood, and even when I began writing the book, I was resistant to the idea of calling it managing up and even zeroing in on that concept. I wanted to talk more about influence and persuasion, how do you build respect and recognition. And my publisher had to keep nudging me that, “Yeah, what you’re talking about is the skill set of managing up.”

And I think my resistance came, and what I’ve heard from many other people, is from these misconceptions we have. These old images of managing up from the ‘80s, the ‘90s, the person being the suck-up and running around with their boss’s coffee order. And who wants to do that? No one wants to compromise who they are or feel like they’re ingratiating themselves to the people around them. So, it’s no wonder why we resist this concept.

But what I know now, having done this work and researched this subject is that managing up is not something you do for your boss’s benefit at all. It’s really something you do for yourself to make your own work life, your own career, much easier, less stressful and on your own terms.

Pete Mockaitis
Yes, I dig that a lot. And while we’re talking about misconceptions, let’s clear them up, I recall, I think I was reading a piece by, Paul Graham, the Y Combinator guy, made a statement along the lines of “Professional managers are amongst the finest liars there are.” And folks are like, “Whoa, that’s some strong language. What do you mean?”

He’s like, “Ah, perhaps I should say, they are adept at managing up,” which sort of imply, well, more than imply, that managing up involves telling the folks above you a little bit of what they want to hear, and massaging their perceptions and expectations, and it really made it sound quite like it’s the art of deception in the professional, acceptable way that we can courteously do so in proper modern times,” Melody. So, have you picked up on those perceptions and how do you address that?

Melody Wilding
I think, again, that’s the older school way of thinking about it. And what I would argue is it’s less about massaging and contorting yourself to someone else’s perceptions and more about tweaking, or in the book I call it flexing, your approach so that your message is actually getting through to the people who need to hear it the most.

That may mean you do need to tweak how you present something, or the type of language you use so that it’s more resonant with the other person, but I don’t think, wholesale, it means that you have to change who you are or what you’re trying to say, because this book is really all about, “How do you have the tough conversations with your manager? How do you push back on extra work or give them tough feedback up the chain of command?”

That’s what managing up really is. It’s having those difficult conversations, sometimes having the courage to say what needs to be said, but doing so in a tactful diplomatic manner that actually earns you trust instead of just turning into a professional people-pleaser.

Pete Mockaitis
Okay. Well, could you share with us a nice story that inspires or brings this together in terms of what’s really at stake if we master this skillset?

Melody Wilding
Yes, I think the book actually starts with one of my personal stories which was a time I failed to manage up, and I think it’s a lesson in multiple ways. So, before I went full-time into my current business, I was working at a health care company, and I loved that job. I loved my boss. What I didn’t realize at the time that I saw in hindsight was that I had been hired to work on really a pet project of my managers that was kind of outside of the rest of the company’s scope, and my manager had been given a bit of budget and, unbeknownst to me, some timeline to see if this was viable or not.

And so, that was my first fail, was really not getting on the same page with my manager about “What was the context that this project came up in? What are the expectations? Who else needs to be bought in and on board with this?” And long story short, let’s flash forward, I ended up being laid off. My role was eliminated, and it felt like a shock to me, and it shouldn’t have.

And that is what’s at stake. That’s a very extreme example of what happens when you don’t manage up well, but I was really sideswiped because I hadn’t aligned with my manager. I didn’t have other advocates in the organization who were willing to fight for me and keep me because managing up has to go beyond your boss.

Do not make your manager your single point of failure. You might not get along with them very well despite all of your efforts. Who is leading you may change on a moment’s notice, so you need to make sure you have those other allies as well. And all of that was a very cautionary tale, but I think that’s what’s at stake, whether, again, in my case, it was extreme. I lost my role.

But every day, people feel like they’re overlooked for promotions and opportunities, it may go to someone else who seems less experienced, or we get into these minor frustrations that we end up taking personally, “You know, why does my boss cut me off? They never even allow me to hear my idea out,” or, “Why are they micromanaging me and on top of me about everything?” And so much of this can be solved by learning some key skills.

Pete Mockaitis
Certainly. Well, tell us, you lay out 10 key conversations for managing up well, which I love. And so, we’ve got alignment, styles, ownership, boundaries, feedback, networking, visibility, advancement, money, and quitting. So, I really dig this because I just love a framework and a set of distinctions and a delineation of categories that just helps make sense of the whole universe of managing up conversations. It feels like, “Yeah, that’s a pretty fine job of summing them up.”

So, I suppose I’m curious, do you have a gauge for what percent of folks ever actually proactively say, “Hey, I’d like to have a conversation about some of the fundamental ways we work and communicate with each other, and what would be best for both of us”? In a way, that almost seems like among the most foundational things one might do in the world of managing up. Is that fair? And how often is that happening?

Melody Wilding
It’s definitely fair. It’s very true, that it is so fundamental that, I think, we sometimes assume it. We assume that this has happened and we overlook it because of that. So, to your point, I would say maybe 10% of people are having those types of explicit conversations about how they work together with their manager, and that is a huge, huge opportunity.

Because if you are in that small minority of people who are doing this, you’re not only going to stand out as someone who is thoughtful, conscientious, you’re driven, you’re taking initiative, but you’re going to have intel and build rapport and trust much more quickly than anyone else.

Pete Mockaitis
Absolutely. I agree, and I’ve experienced it on both sides of the table. Because it’s rare, it feels very special, like, “Oh, wow, this person, I like them. They’re on top of things.” And I think it’s hard for that to go poorly. Maybe if you ask at just like the worst possible time, like, “Hey, that’s like the definition of a non-urgent situation and we’re in the midst of something on fire right now.” So, maybe that that’s one way it could go poorly. But tell us your take on that in terms of to what extent do managers welcome these discussions because I think there’s a bit of reluctance on the part of some folks to initiate?

Melody Wilding
There definitely is, yeah. And when I have this conversation with people, in the book, we’re talking about really the styles conversation, and that’s when we talk about how, “How do we work together? How do we communicate? What are your preferences? What are mine?” And going back to what I said a moment ago, when you understand the context of who your boss is, and also what your defaults are, you stop taking things so personally because you understand, “Oh, this is their style. This is their way of approaching and processing information.”

“And so, if they send a period instead of an exclamation point, I don’t need to make that mean that I’m getting fired, or they hate me, or they’re against me and they favorite somebody else.” We can be much more diplomatic and make those tweaks to how we communicate.

And in my experience, people are reluctant, yes, to bring this up, but when they do, their manager is overjoyed. And, of course, you need to bring this up in a tactful way. So, what I suggest is that you present it to your boss and say something along the lines where you show why this is in their benefit, to say, “I’m really committed to us being able to reach our goals together this year.”

Or, “I want to make sure that you can get the best performance out of me possible, that our work flows more smoothly, whatever it is. And to get there, what I would love to do is understand a bit more about how you work and how I can communicate with you better to get you the information you need. Does that sound good?”

And you can start by asking certain questions of your manager, whether it’s, “If I have to get certain updates to you, what format is best? Do you want those in Teams, in email? Should I present a slide deck? Do you prefer bullet points or should I do narratives?”

Understanding some of those preferences, when you are asking your manager questions, gives you opportunities to then say, “Great. Thank you so much for sharing that. From my standpoint, here’s what would be helpful. If you have feedback for me, take me aside after a meeting, or if you notice that I’m not being as concise as I could be in a presentation, shoot me a quick message on Teams so I can adjust on the fly.”

All of us have different preferences around that, but it turns it into more of a two-way street where, yes, you’re understanding what your manager wants, but you’re also finding opportunities to assert, or at least put on the table, “Here’s what I would like. Is that something that we can find a middle ground on together?”

Pete Mockaitis
That sounds great, yes. And as you say it, and I’m imagining the scene, that seems pleasant and welcome to hear such things. And I want to dive deep on a couple of these. I don’t think we could do all 10 in our time together, but one with regard to boundaries. I remember when I was reading through this, I recall a conversation I had with my friend, Kelsey. We were catching up at a wedding. It had been a long time.

And she was telling me all of, like, the cool things she was doing with, like, go to an Ironman Triathlon, and this and that. I was like, “Wait a minute. I’m sorry. Don’t you work in consulting?” And she’s like, “Yeah.” I was like, “How on earth are you finding the time to have all of these adventures and do all of these things when I recall my days of consulting were so brutal with regard to the hours of the travel and the unexpectedness of things?”

And she was like, “Oh, well, you know, I just kind of talked to my boss and said, ‘Well, hey, here’s what’s going on, here’s the nights I’m not available, and here’s the thing…” She just sort of laid it out in terms of what’s up, in terms of, “I’m going to over-deliver on these key metrics and expectations, and these are the nights I will not be available to be doing things.”

And I was like, “And they went for that?” My mouth dropped, I was like, “You can do that? That’s possible? Even in client services? Wow.” And so, I was struck at just what a managing-up boundary conversation can do for transforming a life into being sustainable and enjoyable in what can be demanding fields.

So, lay it on us, Melody, if we want to establish boundaries but we’re a little scared and we think that we might misstep, or seem like we’re not a team player, or we’re lazy, or we’re not really committed, or any of these other negative associations we fear, how do we play the boundary-setting conversation game?

Melody Wilding
Well, that’s the tension with it, right? We need to protect our well-being, but we also don’t want to look like a slacker, so we have to find that balance there. And the thing with the boundaries-conversation is that “no” may be a complete sentence in many areas of life, but at work it doesn’t go over so well if you just say, “No, I’m not going to do that,” or “I don’t want to do that,” right? It’s going to hurt your reputation for you to say that so you need to be more thoughtful about how you approach it.

And what I think is so telling about what your friend did is it sounds like she was assessing, what I call in the book, your pushback power. And your pushback power is the invisible leverage you do or don’t have to push back, to say no. And we all fall somewhere on the spectrum, higher to lower. Your pushback power is higher if you have more positional authority.

If you’re more seasoned, tenured in your career, you have more credibility behind you, you are a high performer, or you offer a very specialized skillset that people may be more willing to make accommodations for because it could be hard to replace you. And even things like the strength of your relationship with your boss, how you build trust and rapport, your boss’s values, the state of the organization.

If the team is in free fall, in crisis, it’s going to be harder to say, “I can’t pitch in this weekend,” or, “I can’t take on more of this project for a colleague who just left,” versus if you’re in a time of stability, it might be a little more receptive to that. So, taking into account that pushback power allows you to gauge “How directly or assertively can I say no? And how frequently can I say no?”

And it sounds like your friend did that with her manager. Because she was higher in pushback power, she was able to say, “I have these commitments, and so can we find a solution to work my workload around these commitments that I have?”

Now, for those of us that may be medium to lower in pushback power, there’s a number of different things you can do. One of my favorite approaches that I talk about is called the trade-off approach, and this is great because it allows you to set up binary options. So, you may say, “Okay, thank you for sharing that, you know, Y has come down as an important priority from the leadership team. A few weeks ago, we had talked about that you wanted me to focus on X.”

“And so, if X is truly still a priority, how would you like me to reprioritize to make room for Y? Or what would you like me to slow down on? What would you like us to delegate or temporarily deprioritize in order to make that possible?” And the beauty of this is that you are setting the parameters. You are setting the decision options, subtly saying, “Both of these cannot happen at the same time. Which one would you like to choose?”

But ultimately, you’re approaching it more as a problem-solving conversation instead of just dumping a problem back in your boss’s lap to say, “I don’t know. I can’t do it, so figure out someone else to get it done.” You’re approaching it more as a collaboration, which that person will appreciate, and the ultimate authority is back in their hands.

Pete Mockaitis
And I think that’s really handy because I think without the conversation, we can just assume, “Oh, I have to continue doing all the things we’ve ever discussed, as well as this new thing, and that’s just that,” and that is a dangerous, untenable place to live. So that’s handy with regard to the conversation. I’m curious, when it comes to increasing our pushback power over time, let’s discuss.

So, one of the levers is just the strength and quality of our relationship. Another is how special and wonderful and high-performing we are. Any others and what are the quickest, easiest ways to boost these so that we are growing in pushback power over time?

Melody Wilding
Well, let’s talk about the performance piece and building rapport and trust with your manager. There’s a conversation that comes before boundaries, and that’s called the ownership conversation. And that’s important here because the ownership conversation is all about looking for where can you take initiative of projects or problems you want to solve and run with, but by doing that really add value or solve an issue that’s a pain point for your manager, your team, the organization.

And when you do that, you build, you add to the pushback power you have because you’ve enhanced your value, you’ve shown you’re a problem solver, and that’s really valuable. So, the ownership conversation is all about “How do I not only spot those opportunities, but capitalize on them in a way that’s not going to step on the toes of other people around us?” Because that would backfire, of course.

And a lot of it comes down to choosing the right problem to start. And so, I talk about how there’s five worthwhile areas to look at. And a few of those may be bottlenecks. So, are there inefficiencies or broken processes, for example, that are slowing everyone down, including you, that if solved would make everybody’s lives much less stressful and easier?

Neglected needs is also a great place to look. What are the topics or agenda items that keep going to the bottom of the pile or keep rolling over month to month, quarter to quarter, that no one seems to have the time to get around to, but says, “Wouldn’t it be great? Wouldn’t it be great if we could do that? Or we really need to get to that”? Could you be the one to carry that torch forward?

And another one that I think can be easier to spot is feedback patterns. What are you hearing again and again from fellow team members, clients, your vendors, that if you took action on to make better, would add value to everyone else?

Pete Mockaitis
That’s cool. All right. Well, could you give us a story of this ownership in action? Because I think you’re really keying in on something in terms of differentiating and growing a career, because it’s quite possible to go years at a time in reactive mode of doing whatever somebody asks for, or seems to be perilously on fire.

It’s hard to be distinctive in such a place, as opposed to, with ownership, it’s like, “Oh, you know, that’s a fantastic result. Yeah, that was, really, I’m the person behind that.” That’s hugely awesome. So, could you give us a story about ownership in action?

Melody Wilding
Sure, I have two that come to mind, if that’s okay. So, the first one is, I had a client about a year ago, who, his organization was acquiring a new one and he worked on the legal side of this. And so, because of that, when they acquired this new organization, all of his colleagues were running in the direction of all of the new opportunities that were created by this acquisition and trying to capitalize on that, chasing shiny objects, everyone was trying to meet with the three key leaders.

And what he saw was that that change actually created this vacuum where he could step in, and that no one was tackling, there was a neglected need, in other words, with due diligence matters of closing everything that had to do with that transaction, you know, wrapping up all of the contracts, dotting the I’s and crossing the T’s to make sure the merger was complete.

And so, he said, “You know what? I’m actually going to zig while everybody else is zagging.” And he carved out that niche for himself as being the person who was buttoning up the deal, so to speak, which gave him a lot of exposure to not only he became a close confidant to his manager, but also his skip level, his boss’s boss, and some other key C-suite leaders in the organization who really cared about this going correctly, and who knew, “We have to get these compliance matters correct.”

And for him, that allowed him to build those relationships. He was seen as more of a partner to those people. And flash forward about a year later, he was actually promoted to partner because of that work that played a huge instrumental role. So, that’s one example that comes to mind of looking for opportunities that other people may be missing.

And then the other quick story I’ll share has to do with another client who, after the pandemic, was really interested in getting mental health days going for the organization, making sure that the team had time for development and rest, and weren’t just go, go, go, go, go all the time. And why this was ownership is because she had to create buy-in for this idea. This wasn’t something that others had thought of. This was something she was innovating from the ground up and had to push through.

And so, a couple things that she did really excellently was she came with proposals in hand, and so when she would have meetings with some of the key stakeholders and decision makers, she would come with a one-pager with talking points that they could use, just ready-made. She made their job easy, took the cognitive load off of them, and she proposed small steps.

So, in the book, I talk about this as the foot-in-the-door technique in psychology, where you propose, whether it’s a pilot project or a test or rolling something out to just a small sample. The people around you want to mitigate risk and potential exposure or failure. So, if you could say, “Let’s start with a mental health day and then we can actually roll that out to have these once a quarter and have more events around this.”

She just started with, “Let’s have this one day,” and that was easier for people to get on board with. And, eventually, she was successful in making it something bigger but I thought that was a great example of planting seeds, taking it step by step, and getting small agreements that lead to bigger ones.

Pete Mockaitis
That’s a really cool thing to take ownership of because, well, one, that’s just great for everybody, and two, boy, I sure would like that person in my organization, it’s like, “Oh, this is the person who got us all the mental health days. I want to do them favors whenever possible.”

Melody Wilding
Yes, great point. And that speaks to this idea of looking for triple wins. Is something going to be a win for you in terms of you’ll enjoy the work, it will add to your own credibility? Is it a win for your manager? Will it make them look good or advance their priorities? And, third, is it a win for the team or your organization as a whole?

Like you said, your colleagues are certainly going to love you, but, you know, at the end of the day, for everyone’s productivity, sustainability in their roles and long term the results of the organization, it was huge from that respect, too.

Pete Mockaitis
Okay. Well, tell us, within these 10 key conversations, could we pick perhaps one or two that seem to be super transformative and yet pretty easy to do? Any of your favorite tips here?

Melody Wilding
Let’s talk about visibility, if that’s good with you. Yeah, I think this is one that people know they need to do, but don’t quite know how to approach because it feels daunting. It feels daunting to feel like, “Ugh, I spend so much time working. Now you’re telling me I have to advertise that work as well and I have to bring more attention to it?”

And in some ways, yes, because we can expect our work to speak for itself. It’s not going to do that. We need to be the advocate for it. But there are some pretty simple, easy ways to build visibility into just the day-to-day of how you work instead of making it extra effort, and I think that’s the win-win. One way you can do this is by restructuring your one-on-ones.

So, I highly recommend that you start all of your one-on-ones with your manager with wins. And you can call it wins, you can call it progress or milestones or achievements, whatever language feels best to you, but the point of that is to not just dive into status updates of, “Oh, here’s where this project is. Here’s where this is. This is what’s coming up.”

But to more so utilize that time to show your manager, “Yes, here’s what we’ve done, but here’s what it means. Here’s the outcome, the results. Here’s also visibility into how I thought about solving a problem, the considerations that I made, or the people I talked to.” And all of that shows them, yes, you are actually getting things done. It gives them more insight into you operating at a more strategic, perhaps even higher level. And it also gives them information that they need to run up their own chain of command.

And so, it’s not really self-promotion to just puff yourself up. We really need to think about it more as, “I’m giving my boss the data they need to advocate for me, to advocate for the rest of the team, to have resources, opportunities, decision-making power at higher levels.”

Pete Mockaitis
Yeah, I think that’s excellent. And often, when we take ourselves out of the equation, there’s less self-consciousness, and it’s like, “Oh, this is this is handy. Like, if I were leading this organization, I would probably want to know about the skills, this asset, this resource, this person has in the mix to be deployed when useful and necessary. Otherwise, everyone just misses out.” And how about advancement?

Melody Wilding
Advancement, yes. And thank you for that great segue because visibility and advancement go hand in hand, right? And you can start to see how these conversations build on each other, intersect, because once people know more about what you’re achieving and know more about you, well, then you’re in a position to do bigger things.

And why I say that term “do bigger things” is because advancement doesn’t always have to be a promotion. It can be that you want to grow your scope, or the budget that you oversee, you want to go from two to four people on your team, or you want to work on a stretch project, or something that’s completely different from your current skillset.

For example, right now I have a lot of clients who are asking for stretch projects in AI, because that’s really important to them to learn and they know it will be a value-add to the organization. So, think more broadly about what advancement could mean, but also think about starting much earlier than you think you might need to.

Because I see way too many people get caught in the performance review paradox where they keep their head down, they think they’re sending signals to their manager about what they want and where they want to go, only for their performance review to arrive and no promotion, no salary increases, no being named to that committee. It seems to pass them by.

And that’s often because we either haven’t been explicit enough about what we want or we’ve waited too long to bring that conversation up, and your manager has already had to allocate headcount or resources or make those decisions. They were made months ago. So, this may mean starting three to six months in advance to plant those seeds.

Let’s say you did hit a big milestone. You may say, “This was such a valuable experience. I really loved getting to interact with these clients or that stakeholder or use this skill. I would love to do more of that. Do you think there’s an opportunity in the coming months?”

And so, you start to get that out there. You may even have more of a formal conversation with your manager to say, “In the next year, I would love to double the size of my team,” or, “I would love to move from manager to director level. What would you need to see to be comfortable with that change?”

And that allows you to surface objections because your manager may say, “Well, you’re not ready for that,” or, “We need to have these other people on this committee bought into this, so I need to rope other people in.” And it allows you to contract so that you can understand, “All right, by June, you need to see this. By December, you need to see that.”

And you can work against that and have follow-ups to say, “All right, I did what we discussed. Are we still on track here? Has anything else come up? Would anything else prevent us from making that decision at that point?” And so, it has advancement top of mind for you and your manager, and it prevents some of moving that goalpost that can happen.

Pete Mockaitis
Okay, beautiful. Well, Melody, tell me, any other final tips, tricks, do’s, don’ts before we hear about some of your favorite things?

Melody Wilding
Let’s talk about, briefly, the money conversation because if you have advanced and you’re taking on more, you probably want the salary that comes along with that. Money can also be very loaded and very sensitive, something many of us are not taught how to discuss in our personal lives, let alone in the workplace.

And one of the big mistakes or missteps I see people make here is that they focus way too much on what they’ve done already and not enough on what they can do in the future if they were given more money to do it, and that’s very important. You need to think about, “What’s the potential ROI if the organization gives me five, ten, fifty thousand more dollars, what else would I be able to do? Does it serve bigger clients, manage a bigger team?”

You need to paint that future so that your manager, again, see a theme here, can make a case to their own leadership about, “Why should we give this person more money?” It’s not enough that you want it or you feel you deserve it. That may be true and there needs to be a business case there. So that, combined with, instead of just saying, “I deserve this. I work really hard,” approach it from the standpoint of fairness.

We humans, we are wired for reciprocity. We want to make sure that people feel like they are being treated fairly or correctly. And so, if you can use language around that to say, “I want to make sure that my compensation matches the level that I’m performing at or is commensurate with the amount of value I’m bringing to the organization.” If you can use that sort of language, it makes it feel less like this request that you’re demanding, and again more like a trade.

Pete Mockaitis
Certainly. Well, thank you. Well, now, could you share with us a favorite study or experiment or bit of research?

Melody Wilding
In the book, I actually cite some of this research around micro-yeses. And so, if you can get a micro-yes, let’s say you have to give someone feedback, and instead of just diving into, “So, in that last meeting, I felt like you talked over me,” ask for permission first. Get a micro-yes, “Will now be a good time to talk?” “Yes, sure.” “Okay, I’d love to chat about that client meeting. Is that good with you?” “Yes, sure.” Get those micro yeses along the way so someone is a bit more bought in and not as surprised by what’s coming next.

Pete Mockaitis
All right. And a favorite book?

Melody Wilding
Difficult Conversations by Douglas Stone and Sheila Heen. Fantastic book, as well as their other book, Thanks for the Feedback. Both amazing books that really break down the nuances, the anatomy of how to have these difficult conversations.

Pete Mockaitis
All right. And a favorite tool?

Melody Wilding
I am a huge Oura user, so I have my Oura ring on here.

Pete Mockaitis
Oh, yeah. Mine is on my charger.

Melody Wilding
Yes, I probably have to charge mine today, too. But I’ve had it for years, and I just, especially since they have added the heart rate monitoring throughout the day, it is so helpful for me to see what spikes my stress when I go into restorative time. It’s just helped me manage my own schedule and my own energy much better.

Pete Mockaitis
And a favorite habit?

Melody Wilding
I am a go-to-the-gym-first-thing-in-the-morning person.

Pete Mockaitis
Okay. And is there a key nugget you share that really seems to connect and resonate with folks, you hear them quote it back to you often?

Melody Wilding
“You teach people how to treat you.”

Pete Mockaitis
All right. And if folks want to learn more or get in touch, where would you point them?

Melody Wilding
ManagingUp.com is where you can find all the information about the book. You can connect with me as well there, too.

Pete Mockaitis
All right. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Melody Wilding
Start today with having the alignment conversation, and that is a really simple entry point to begin managing up, to ask your boss, “What would success look like for you in the next three months? What does great performance look like in this role? Or, what metrics does your boss discuss with you?” Start there, and I think that’s going to establish a basis of trust and give you a lot of insight that will be really valuable.

Pete Mockaitis
All right. Melody, beautiful. Thank you.

Melody Wilding
Thank you.

Pete Mockaitis

Jay, welcome.

Jay Baer

Pete, thanks so much for having me. I appreciate it. Looking forward to it.

Pete Mockaitis

Oh, I’ve been looking forward to it, too. You are so fun, and you have so much good stuff. I have to pick and choose within the ocean of your wisdom where to dive in.

Jay Baer

Well, I don’t know about that.

Pete Mockaitis

And I’m going to go with two books, actually, Talk Triggers and Hug Your Haters. I kind of see them as two sides of a similar coin. You might conceptualize them differently. But just to orient us, for starters, what’s the big idea behind these two books?

Jay Baer

So, the big idea for Hug Your Haters is that people who are unhappy about you or your business are not your problem, ignoring them is, and that you can win the day by being disproportionately kind even to, and perhaps especially to, those who are unhappy. So that book is really about retaining your relationships, retaining customers.

Talk Triggers is almost the opposite. Talk Triggers is a book about differentiation and word-of-mouth. The concept is that word-of-mouth is and will always be the greatest way to grow any business, to accomplish anything. It’s also the most cost-effective, but individuals and organizations are often loath to do anything that stands out because they think it’s risky, or they just don’t have a framework for how to do it. So that book provides the framework. A talk trigger is defined as an operational choice that you make so that conversations are created.

Pete Mockaitis

That’s so cool. Yeah. And so, in terms of we’ve got great wisdom to be gleaned from haters, as well as for raving fans.

Jay Baer

Yeah, absolutely.

Pete Mockaitis

Or, soon to be raving fans, with a little tweak. And I’d love to hear your take, if we’re talking to professionals who, and some are maybe not customer-facing, client-facing, marketing-driven, how do you think some of these principles apply to these sorts of folks?

Jay Baer

I think universally, because it doesn’t matter whether your job is customer-facing, you are still customer-adjacent. This happens all the time. I was talking to a CEO the other day of a Fortune 100 company, you know, it’s many tens of billions of dollars a company, and she was saying that one of the things they struggle with is their actual customer service department, if you will, is fine. Like, they’re good and they’ve got good policies, and they got good software, it’s all good. But she was like, all the time, customers are contacting people who are not “customer-facing.”

They’re a manager, they’re an executive. All you gotta do is look on LinkedIn and be like, “Hey, check it out. Here’s where Pete works. Let’s just send that person a message.” So, you don’t get to decide whether customers can think of you as customer-facing or not. And the reality is if you carry the business card and you’re associated with a logo, you are customer-facing.

Now, whether you’re talking to 100 customers a day might be a different story, but I think the right way to think about it is everybody is customer-facing at some point. Consequently, wouldn’t you want to be really good at that? Like, wouldn’t you want to be really great at working with customers when they’re unhappy, and also be great at explaining to customers why you are the only solution for them?

Pete Mockaitis

Absolutely. And I also think about “internal customers” in terms of another person inside our organization relies on me, or our team for these reports, or this information, or this key enabling stuff, and so, yeah, you’re going to have some folks who are doing some talking about you and your team and maybe some hating about you and your team.

Jay Baer

Absolutely. And I’ll tell you, I ran a correlation study a long time ago on the relationship between sort of employee culture and customer experience. So, we looked at companies that were awarded Best Places to Work designations versus Net Promoter Score, which is a measure of customer satisfaction, and the correlation is almost the same.

So, what that means is that it is essentially impossible to be great at outwardly-facing customer experience unless you are first great at inwardly-facing employee experience. So, you’re exactly right, Pete, like you’re going to have workplace conflict, and how you handle that can really separate you from other professionals in your organization.

And also, some of the people who go on to the greatest successes inside organizations are those where there is a consistent story told about them. And so, there’s like sort of an earned wisdom about, “You know, when you work with Pete, what’s great about working with Pete is X, right?” And that same kind of value statement gets attached to you throughout your entire career, and that can be a huge, huge advantage as you’re looking to advance in that organization or even move along to a different. organization.

Pete Mockaitis

Boy, that’s so powerful, that notion that the customer satisfaction and employee satisfaction are almost the same with regard to correlation. And, in some ways, this kind of makes sense, like, to the extent to which you are a jerk who doesn’t care about people, customers, your colleagues, or a sweetie who cares a lot is, like, I could see like that’s one dimension there, but there’s also some particular practices associated with things that make for excellence on both these dimensions.

So can you lay it on us, you say that there are three things that customers or clients really, really, truly care about. What are those things and how do we deliver them well?

Jay Baer

Well, I know three things are the same that your colleagues care about, too. So, we can set the customers aside for now because these three elements of sort of your behavior and your interactions are important to everybody, disproportionate to everybody. So, what you’ve got to focus on in your career is being quick, clear, and kind.

If you can be quick, clear, and kind, and really be demonstrably better at those three things than other people, you are going to be on a rocket ship ride to success in your career, because, yes, there’s a lot of dimensions of success, there’s a lot of dimensions about being a good teammate, and a good colleague, and a good company, and a good friend, and all those, but if you can consistently overdeliver on responsiveness, on clarity, and on empathy, the world is your oyster.

Pete Mockaitis

Now, Jay, there are so many directions I could go with this, but first, let’s hear. I know you are a marketing genius, if I may, I’m just going to bestow that upon you.

Jay Baer

Thanks.

Pete Mockaitis

I’ve admired your work for a while, and you do a lot of research. Could you share with us, when it comes to quick, like there are eye-popping numbers associated with, say, if you have an inbound lead land in your lap, if you respond to them within minutes or hours, it’s like a crazy huge difference? Can you share some of those figures with us?

Jay Baer

Yeah, and we did a lot of research for my most recent book, which is called The Time to Win, and most people, and certainly most organizations, feel like they are fast enough. Like, “I’m getting to it as fast as I can, man.” But what they fail to realize is that people’s expectations for what constitutes fast has changed dramatically in a three-year period. So, yes, you used to be fast enough, sufficiently fast, but you’re no longer sufficiently fast.

Two-thirds of customers say that speed is as important as price. And to your point, Pete, about something landing in your inbox, check this out. Fifty-one percent, more than half, of all customers will hire whomever contacts them first regardless of price. So, if you’re shopping for a car, a sofa, a hamburger, a mate, a job, I did a podcast last week for the manufacturing sector, and one of the things we talked about was they struggled to hire and retain talent.

I’m like, well, one of the reasons that’s so is they put out a job description, and they get some resumes, and then they don’t get back to anybody until they have a sufficient stack of resumes and begin to analyze them. Meanwhile, that person hasn’t heard from me for three weeks and took another job.

Pete Mockaitis

Yeah, that happens. It’s true.

Jay Baer

It’s just about response time and cycles. They’re not nefarious. It’s not like they don’t care about those candidates. It’s just that they haven’t tuned their processes to understand that even though we’ve been saying the words “Time is money” for probably 100 years, it was never true. But it is true now. The relationship between responsiveness and revenue is inescapable now. And you either are good at that, or you are literally losing money, friends, colleagues, every day.

Pete Mockaitis

That’s powerful, and it’s true. I’m thinking, I recently acquired a company, my first one, which is pretty exciting.

Jay Baer

Congrats.

Pete Mockaitis

Ooh, I feel like a deal-maker, a titan of industry.

Jay Baer

Doing some of that M&A, baby.

Pete Mockaitis

And so, I was like, “Oh, man, I’ve never done this before. I should probably have a lawyer and accountant who really know what they’re doing. That’s probably important,” So, I thought, “All right. So, it’s very important for me to select an excellent accountant and lawyer.” And what did I do? I totally went with the first person who got back to me, and said, “Yeah, I can do that.”

Jay Baer

Yeah, and it’s because we interpret speed as caring. We interpret responsiveness as respect. It doesn’t mean it’s true. It’s just how we internalize it. So, if you hear back from a potential attorney in four hours, you feel one way about that individual or that organization. If you hear back from them in two days, you feel a different way entirely, and that matters. It has nothing to do with their competency as attorneys.

But you’re like, “Well, this is going to be a better relationship because they got back to me right away, therefore, they must want my business. They want to work with Pete. They want to be part of this project.” Now, does that mean it’s actually going to be better? No, but we can’t help it. It’s psychology. It’s our need to belong. And when you get back to somebody faster, what you’re actually saying is, “We belong together.”

Pete Mockaitis

That’s good. Well, so now let’s zoom into the interior of an organization. Folks like to have their emails and their Slack messages responded to quickly. And you know, hey, we had Cal Newport and other folks on the show, talking about deep work and the importance of focus, and so in many ways the advice, current, more so often in many of these interviews is, “Hey, you know, don’t non-stop be responding to your emails and Slacks, but rather really take some time to have that focus, deep work, high-value, strategic initiatives. Do that, good professional, as a differentiator for your value.” And so, yeah. But at the same time, people love quickness, Jay. How do we navigate this tension?

Jay Baer

Yeah, I don’t believe in deep work during the day. I feel like what you’re doing is telling everybody else that your time is more important than theirs, and I feel like, eventually, that’s going to be a detriment to you and your career. I do deep work outside office hours. I do deep work at night and I do deep work on weekends. Does that hurt my work-life balance? Damn right, but I answer everything instantaneously and have for 30 years, and it has certainly served me well.

And I’ll do deep work later, and I will be as responsive as possible from 8:00 to 5:00, and that’s just the way I’ve always done it. And I think, largely, the research on human behavior bears that out as a very successful system, but I do understand how it can be a problem for people who are like, “Look, I’m not going to do two hours’ time on task from 5:00 to 7:00 o’clock at night.” I get it. I understand. That’s a choice you’re making.

Pete Mockaitis

Understood. So, at the same time, though, there are occasions where, hey, you’re doing a podcast interview here and now. I mean, you’re not emailing or Slacking in this moment but I’m imagining…

Jay Baer

You think that I’m not, but I’ve actually checked email twice since we started talking.

Pete Mockaitis

Is that really true? I had no idea.

Jay Baer

That’s 100% true.

Pete Mockaitis

You’re very slick. You’re very slick. Although, you didn’t respond though, right?

Jay Baer

I turned off my microphone and I typed an email a minute ago when you looked away.

Pete Mockaitis

I can’t tell if you’re joking or you’re not.

Jay Baer

I’m not joking. Why would I lie about it?

Pete Mockaitis

That’s impressive.

Jay Baer

I’m not joking.

Pete Mockaitis

That is impressive. Okay. Well, no, it’s fun to get multiple perspectives and varieties of counterpoints here. Because, yes, you have achieved towering success in your fields, which are pretty darn competitive, if I may add, you know, speaking and marketing and book writing, and you’re crushing it.

Jay Baer

Well, I mean, look at it this way. If somebody sends me an email, and says, “Hey, I’d like to maybe think about having you come do a keynote speech for our organization,” to me, the best way to do that is to build a life and a team and a system where we can respond to that within two minutes because I don’t want them to ever send anybody else a second email.

You never want them to say, “Well, we didn’t hear back, therefore…” and you don’t know how long their fuse is. When do they say, “I haven’t heard back from Jay”? Is it an hour? Is it four hours? Is it a day? Is it two days? I don’t know. I do know a little bit because I’ve done the research on it. But our SLA in our organization is we respond to everybody within 59 minutes, unless there’s like some weird extenuating circumstances, like that’s the deal, right? And, usually, it’s more like two minutes.

And, obviously, we’ve got to sort of build our work style around that, and I am better than most at being able to record a podcast and type an email with one hand, but you train yourself to be able to do that over time.

Pete Mockaitis

And it sounds like you also have teams and systems and processes enabling that.

Jay Baer

Yeah, of course.

Pete Mockaitis

It’s not all Jay email all the time.

Jay Baer

No, and I’d have to tell you, all of this is going to get so much easier because, in the near future, i.e. today, you’re going to be able to just say to Microsoft Copilot, Google Genesis, Meta, whatever AI suite you’re going to use, you just say, “Hey, send a three-paragraph email to Pete asking about what time the podcast taping is going to be and what he prefers in terms of promotional graphics.” That’s it. The email will be created and sent.

Pete Mockaitis

All right. So, quickness, it sounds like the takeaway is do it. Any other nuances to that?

Jay Baer

Hey, I’m not saying it’s good. I just want to point this out. I don’t love it either, man. I don’t love having to write proposals from 7:00 o’clock to 9:00 o’clock at night or whatever the circumstances are. I don’t love it. I’m not saying this is a net positive, either for me or for society. I am saying it will make you a better professional, and it will help your career, and it is the trend that we’re all going on.

I don’t think anybody, Cal Newport, nobody else is going to say, “Hey, you know, I’ve been looking at the trends and it sounds like we’re going to start doing things more slowly.” Like, I don’t think that’s going to happen. So, you either lean into the skid or you end up in the ditch.

Pete Mockaitis

All right. So, quickness, takeaway, do it. Let’s talk about being clear.

Jay Baer

Yeah. Well, look, people hate to wait. We just talked about that. The thing they hate the second most is to be under-informed. This is also something that has been changed over the last few years because, until then, we were under-informed all the time and we were okay with it. We didn’t have any choice. So, the other night, my wife and I were watching TV, and Cher comes on, and so I say to my wife, “Hey, how old is Cher?” She’s like, “I don’t know.” So, we’re like, “Siri, how old is Cher?” Cher is 78 years old, as it turns out, which is kind of impressive. A-plus plastic surgeon for Cher, for sure. A-plus, like incredible.

But then I thought, “Okay, what would it have taken, pre-internet, to figure out how old Cher was?” And I was like, “Okay, you’d have to get in a car, drive to a library, meet with a reference librarian who would maybe have a book on actors and their birthdays or something, and then you’d look it up, and then you’re like, ‘Oh, Cher was born in whatever.’” And so, it would take, I don’t know, a couple hours to decide how old Cher was. And, of course, nobody would do that, no employed person would do that.

So, we used to say, Pete, you might remember this, back in the day, we used to say, “I don’t know,” and people were totally okay with that. That was literally an acceptable answer to almost any query. You could just say, “I don’t know,” and that was fine. We just went about our business. But now you can’t say that because you can know, you can figure it out. So, we’re now in this era where when people are under-informed, where there’s an information asymmetry, where you know more than they do, it creates a ton of anxiety.

So, one of the best things you can do is to literally over-inform your colleagues about what’s going on, what’s going to happen next. Like, be the person who always knows exactly what the next step is, and is always telling other people what’s going on. Because this sort of black box, like, “We gave a thing to Pete. And I guess he’s working on it, but we haven’t heard a status report.” Like, all of that creates a lot of anxiety and really hurts you as a professional.

Pete Mockaitis

It really does, and I’ve been on the receiving end and probably delivering end – sorry, everybody – of that. And so, can you maybe give us an example of what is a disappointment, yet all-too-common demonstration of clear, like, “Not clear enough but you see it all the time,” versus what is exemplary clarity that we’d love to receive?

Jay Baer

I’ll give you an example of exemplary clarity because it really surprised me, and it sort of turned a negative into a positive for me. So, as you may know, my side job is I’m the number two tequila influencer in the world, and I was combining jobs, and I was drinking tequila while shopping online recently, and I don’t recommend that for this reason.

I bought a pair of leather sneakers, and they were super cool, very happy with them. And then I immediately got the confirmation email that said, “Okay, we’re going to make your sneakers. Expect them in eight weeks.” That was a surprise because I thought that the sneakers were ready to be shipped that day. I didn’t know it was a “make a sneaker” thing. I thought it was like, “We have these and we’ll send them to you.” And I was like, “Oh.”

So, then I thought about canceling the order, but I was like, “No, I really do like these shoes. Like, I can wait a couple months. I’ll survive.” But then, every single Wednesday, Pete, for eight weeks in a row, I got an email from my account manager at the sneaker company, saying, “Hey, this week, your shoes are going to the tannery. And this is Manuel. He’s our tannery guy, and he’s been doing this for 20 years. And here’s a video of Manuel doing his job. And then, next week, it’s going to go to the stitching people, and that’s going to be Sheila. Here’s Sheila’s workspace. Here’s what she’s all about.”

So, literally, it was like a week-by-week documentary film of how these sneakers were going to be made. So, the entire time, there was never any question as to, “What are they doing for two months?” Like, I knew exactly what was happening every week, and I could kind of follow along. It was an amazing, amazing experience. And I think we can take that same idea into our own workspace. And every time we’re working on a project, every time we’re collaborating with colleagues, just make sure that, wherever possible, you are over-communicating.

And I’ve done a lot of research on this, Pete. Here’s the way I like to frame it up. If it feels to you like you’re over-communicating, you’re probably communicating just the right amount. Because the truth is, it doesn’t matter whether they’re email, Slack, voicemails, puppet shows, Haiku, it doesn’t matter, whatever you’re creating for your colleagues, they’re not reading all of it. And if they are, they’re not letting it all sink in. Like, they’re skimming it like the rest of us do. So sometimes the best way to separate yourself apart is to just be the one that communicates more.

Pete Mockaitis

That’s really cool. And it sounds like the nature of communications is specifically in the domain of the status of stuff and what’s going on right now. Because sometimes people can feel a little bit of an information overload in terms of, like, you’re doing a report, or, “Hey, our recommended course of action is this. And it’s because if you look at the database, dah, dah, dah.” It’s like people often don’t want all that.

Jay Baer

Exactly.

Pete Mockaitis

But they do want to hear, “Hey, what is going on? What’s the deal with this thing?” And that reminds me of a story. One time, I made a boo-boo and I had a client…

Jay Baer

Hopefully, it wasn’t the buying the company part.

Pete Mockaitis

No, no, that’s been working out great. And I made a boo-boo and so I had a client who was rather upset. I put him in a pickle. And so, I told him, “Okay, here’s what I’m going to do. I’m going to reach out to everybody, and I’m going to have a helper also record the status of what’s unfolding with each of those people in this live Google Sheet, so you can see at any moment where do things sit with all of these people, and then I’ll be reachable via…” I was on a camping trip. “I’ll be reachable via satellite phone for dah, dah, dah.”

And they said, “Okay.” And then it was all said and done, they said, “You know, actually, everyone was really pleased with how you handled that.” I was like, “Oh, cool.” So, I was effectively able to get myself out of a tight spot because I was doing that. It’s like, “You could not have more information than this. The status of all of these people and the minute it changes at your fingertips, anytime you like.”

And I also love it when I’m coordinating a big project. I got a lot of ins, a lot of outs, a lot of what-have-yous, to say, “Oh, okay, this is exactly where that is,” so that I could see, “Oh, shoot, we’re getting hung up here. I better get some more help there, pronto.”

Jay Baer

Absolutely. I’ll give you another little life tip for this notion of clarity. This really helps. I’ve been doing this about two and a half years now in my personal life, and not only has it made me a better business professional, but it’s improved relationships with my wife, and my kids, and my friends, and my mailman. Like, I really want everybody to do this because I’m telling you it’s going to work. It’s called reply without answers. So, here’s how it works.

Today, if somebody has a question for you, a work colleague, you don’t know the answer, what do you do? You go look it up. You ask Julie in accounting, you check with the boss, you check with the customer, you Google it, you look in the intranet, like whatever, you do the stuff. And then once you have manifested the answer, you tell the person what they need to know. Yep. Stop doing that. Don’t do that anymore. Because the entire time that you are figuring it out, that person is slowly freaking out.

Pete Mockaitis

All right.

Jay Baer

So, if I send you an email today, so this actually applies to both clarity and speed, if I send you an email today and I don’t hear back for like, I don’t know, two days from Pete, I’m like, “Oh, wow, I didn’t hear back from Pete. Did that go to spam? Did I attach something that would have sent it to spam?”

Pete Mockaitis

“Did I offend him? Is he mad at me?”

Jay Baer

“Did I offend him?” Yeah, “Is he mad at me? Should I now send a call, or a text, or a ping, or does that make me seem sad and desperate?” We play all these mental games, and our own anxiety goes up and up and up. So, what you want to do instead is, if somebody needs something from you, you’re like, “Good question. Such a good question. I have to go figure it out. I’m going to do that, and then I’ll let you know.”

So, the first response is instantaneous, and all you’re saying is, “I got it,” and then you give them what they need. Two huge things occur. First, their perception of how fast you are goes up dramatically, but, second, their anxiety goes way down. Because we studied this exclusively in the research I did for the most recent book, time to response is more important than time to resolution.

This is why, Pete, if you call the phone company, the cable company, whatever, they will say two things. First, they say, “Calls will be answered in the order that they were received,” which always makes me laugh because I think, “What was the second option?” “Calls will be answered by height.” Like, “What did they discard as the backup option?” I’d be like, “Why do you have to tell us that?” I love that.

And then the second thing is, okay, “Estimated hold time like 11 minutes.” So estimated hold time 11 minutes is the automated version of respond without answers. As soon as you say “I got it,” it takes it off of their mental to-do list and puts it on your mental to-do list, and that changes their relationship dramatically, and creates so much clarity around what’s going to happen next.

And here’s the secret tip, Pete. It actually buys you more time to respond. Because once they’re like, “Oh, Pete’s working on it,” then they’re not losing their mind. They know you’re on it. So, does this mean you’ve got to reply to everybody twice? It does. But the first one, you’re just like, “I got it,” right? And then you go figure it out, and then you respond. Do this. Implement it in your life. I’m telling you it’s going to change your relationships.

Pete Mockaitis

All right. Now, let’s hear about being kind.

Jay Baer

Look, I wouldn’t have even talked about this a few years ago, this idea of empathy and kindness, because there is no point to it. So, I’m a seventh-generation entrepreneur. My son’s an eighth-generation entrepreneur. My family’s been self-employed since like the 1850s, and the number of conversations I had with my dad or my grandfather about treating people with kindness, respect, dignity, and empathy, literally, never in my whole life beat, not once ever, because it was just the default setting.

Like, that’s just, you know, like it wasn’t that long ago. It’s hard to remember now because we’re in an era of empathy deficit, but it wasn’t that long ago that we treated everybody with respect and dignity and kindness and humanity all the time. It was the golden rule era, like it wasn’t that long ago. But somewhere along the way we kind of lost our way, and now you know everybody’s always kind of angry and at loggerheads, and the sort of level of discourse has dropped dramatically, and it kind of makes me sad, actually, as a person.

But I’m telling you, as a professional, if you can be the hyper-polite, hyper-courteous, hyper-understanding, hyper-kind one, man, it stands out now like it didn’t used to because it is such the exception in the workforce. Be that person. And I want to make sure we define what empathy means here, Pete. It doesn’t mean that you do whatever. It doesn’t mean that the other person’s right and you’re wrong.

Empathy is defined as the ability to understand and share the feelings of another person. What it means is that you’re the person inside your organization who can walk a mile in somebody else’s shoes and behave accordingly. You understand how this colleague is feeling and you change your own behavior accordingly. In an era that’s going to be defined by robots, the most empathetic professional is going to have a massive advantage over everybody else in the organization.

Pete Mockaitis

Jay, I’d love it if you could give us again a demonstration, illustration of what is typical insufficient empathy and the counter example of “And this is what would really be optimal”?

Jay Baer

Well, I think sometimes, when people believe they’re being empathetic, they’re actually being obsequious. They’re being fawning, or just, everybody’s been in that situation where somebody is so supportive that it feels saccharine and artificial, and that’s not what I mean. An empathetic leader is somebody who treats everybody on their team differently, not the same.

And there’s this business wisdom that says, “Treat everybody the same. Be a very consistent manager.” That’s terrible advice because everybody on your team has different needs, different circumstances, different scenarios. They’re motivated by different things. If you’ve got 10 people working for you, you should have 10 different management styles, and you should be adopting your management style to what that person needs at that time. That’s what empathy means.

People think that being an empathetic leader means having good work-life balance and taking people to the happy hour, whatever. No, no, no, no, no. It’s about looking at every situation and every circumstance and using your own innate humanity to make the best possible decisions for that person at that time.

Pete Mockaitis

Okay. So those are the principles we’re working with. And so, I’d love it if there’s an example that comes to mind for you in terms of, “Wow, that was super empathetic and I loved it,” versus, “But, usually, I get something much lamer.”

Jay Baer

Well, my favorite example, and it has, fortunately, not happened to me personally, but I think people, some folks will know the tale, is Chewy.com. Do you know this story, the Chewy.com pet supply company?

Pete Mockaitis

The pet food website.

Jay Baer

Yeah. So very successful business, growing like crazy, and, look, it’s a good company. They’ve got good products at a good price, but they don’t have a different mousetrap. They’re selling pet supplies. But they are rooted in empathy. Rooted in empathy. It’s like a core value of the organization. So much so that if you, unfortunately, lose a pet, the pet passes away, in some cases, you might send a live chat or an email to Chewy, and say, “Hey, I’ve got an unopened bag of dog food. I’ve got this rawhide bone I never got a chance to give the dog. Can I return it to you?” And they always respond and say, “No, no. Please just donate it to a local pet shelter.”

But then they will find a picture of your pet in social media, they have a staff of 1,011 freelance oil painters working for the company. They will paint an oil painting of your deceased pet. They will FedEx it to you for delivery the next morning with a handwritten condolences note, and you open this box, “Where did this come from? Chewy.” And it’s from the day before, an oil painting of the pet you just lost with a handwritten note, “So sorry for your loss. Thank you for your business. Chewy.”

And there’s a video on TikTok or Instagram, etc., there’s just video after video after video of people bawling their eyes out because the simple kindness and the empathy and humanity that that brings with it. And the question I always have is, “In a situation like that, if you choose to get another pet someday, what are the chances you spend even a penny with any other provider of pet supplies ever in your life?”

Like, minus 50%, I think, is the actual answer. So, it is such a smart business decision and it’s proven to be true in their results. You can use empathy as a unique competitive advantage, both at the company level and certainly at the individual level.

Pete Mockaitis

That is powerful. And it’s intriguing because, okay, pet owners love their pets, and when pets die, it’s very sad. And that’s sort of like emotionally just true and simple and clear. I’m thinking about, and of other businesses that feel far less personal, like podcast production. It’s “How might that be utilized?”

Jay Baer

And some of this is even just something simple. Like, you don’t need to get an oil painting of the podcast host, although, hey, you know, we will take one. A lot of times, what triggers empathy, or lack thereof, is just the language that we use. In many cases, I talk about this a lot in the Hug Your Haters book, especially when somebody needs something from you, or, even more especially, if somehow you have been deficient, you’ve been slow, you’ve been inaccurate, something has gone less than ideal.

What happens in many cases, and it’s not nefarious, it’s just a natural human reaction, we will try to information ourselves out of the jam. So, we’ll start to say, “Well, here’s exactly what happened,” and you start to prosecute the case, and a lot of times we fall back on very specific details and jargon, and it becomes a very stiff, formal response. And I’ve certainly done that, and people have done it to me, especially in a colleague setting where you’re, like, you feel attacked, and so the way you prevent that attack is to put up a shield.

And that shield is very stiff, formal language that uses a lot of sorts of terse and mellifluous phrasing, and so you’re trying to information yourself out of it. The better way to go is to just lean into the empathy first, and just say, “I’m sorry that sucks.” Like, “We’ll make it better.” And so, it really is, sometimes in a colleague setting, it comes down, Pete, to just the words and the language you use when things are going less than ideal.

And the more empathetic professionals, actually, there’s almost a reverse correlation, so the stickier the situation, the more casual and personal their language. Whereas, what most people do is the stickier the situation, the more stilted and formal their language.

Pete Mockaitis

That’s good. That’s really good. In terms of the psychology emotions at work, it’s like you feel attacked and so you’re naturally like, “Well, let me explain why. In fact, I’m not bad. There’s a reason that this thing occurred that you don’t like.” And so, to really just be able to take a breath and shift out of yourself for that moment to do this.

Jay Baer

Yeah, I used to do this exercise in workshops, like the 13 words you should never use in that situation. And it’s things like division, department, per, “Per my last email.” If you’re dropping the “per,” then you know you’re falling into that sort of formal defensive language trap. Like, “heretofore,” that’s a good one. Like, all of these kinds of words that you never use unless you’re in, like, sort of this passive-aggressive kind of conflict thing.

And you see it all the time in tools like Slack. It does tend to drive very short, choppy interactions, which sometimes don’t have as much nuance as might be ideal in that kind of situation.

Pete Mockaitis

That’s powerful. Well, before we hear about some of your favorite things, can you give us any other quick do’s and don’ts for having folks rave about us word-of-mouth style?

Jay Baer

The biggest opportunity for word of mouth is to understand that competency doesn’t create conversations. Being good, even very good, at whatever doesn’t cause people to tell others about it because that’s what the expectation. They expect you to be good or very good. So, we talk about different and we ignore same.

So, if you want people to talk about you and tell your story, either in the workplace or outside the workplace, you need to do something different, and you need to do it different consistently. This is why, and this is a poor example, but it’s one that people will be able to recognize, this is why some professionals are like, “Look, Jillian always has the purple hair.” Now you may or may not like the purple hair on Jillian, but as a word-of-mouth device, it’s actually a sound strategy.

It doesn’t have to be your appearance, it doesn’t have to be your clothes, but even in your own set of colleagues. If there’s somebody who always wears whatever it is. I, not in this particular venue, but when I’m on stage, I always have a very bright plaid suit. It is my thing. Like, everybody knows it’s my thing. I’ve got 20 plaid suits. Meeting planners can pick out which color suit I wear on stage, I’ve got a whole, like, mobile app that they can do it with. Like, it’s my thing.

Pete Mockaitis

That’s distinction.

Jay Baer

Right. So, you just have to figure out what is your thing that you are going to do every day always that’s going to be just the device, the hook that people use to remember you, and it can be almost anything. And this starts to kind of meld over into the category of personal branding. So, what I always tell people is, “Look, your job is not interesting. It doesn’t matter.

Unless you’re like an astronaut or something, what you do for a living, nobody’s going to remember that. It’s your passions and your hobbies that people remember,” which is one of the reasons why in my bio, in my onstage introduction it says “Jay dah, dah, dah seven bestselling books, and also the world’s number two tequila influencer,” because everybody in the audience remembers that more so than, ‘Yeah, the guy wrote a book. Every speaker wrote a book.” But they remember tequila influencer.

And so, it’s understanding that everybody has something unique and memorable about them. It’s just giving yourself permission to put that out in front.

Pete Mockaitis

Okay, thank you. Now, could you share a favorite quote, something you find inspiring?

Jay Baer

“Remember, some days you’re the pigeon, and some days you are the statue.”

Pete Mockaitis
All right. And a favorite study or experiment or bit of research?

Jay Baer

I think that in the most recent book, “The Time to Win,” one of the things that really surprised me was that the most patient generation of all, like willing to give each other and businesses more grace in terms of response time, Gen Z, the youngest consumers.

And I think it’s because they don’t have as many leases on their time, might not have kids of their own, job might not be as pressure-filled, etc. They’re just like,  “Yeah, it’s okay. You can get back to me.” Conversely, the least patient generation, Boomers. Is this because Boomers have less time left on the planet? Maybe. That seems a little maudlin, but the numbers add up. They’re like, “Hey, I’m retired. I have nothing else to do other than wonder how come this email is taking so long,” and they start freaking out about it. So, I thought that’s kind of funny.

Pete Mockaitis

All right. And a favorite book?

Jay Baer

My favorite author, and there’s many, many books, is Bill Bryson, the travelogue writer. Probably my favorite one is his treatise on kind of small-town America. It’s called In a Sunburned Country. I love that one.

Pete Mockaitis

Okay. And a favorite tool, something you use to be awesome at your job?

Jay Baer

Right now, I’m really enjoying a tool called ManyChat, which I use in my tequila business to gather email addresses from fans on Instagram, sort of de-anonymize that audience. We do monthly contests with tequila brands, where you can win a custom Yeti cooler or some such.

And we use this tool, ManyChat, so that people just comment “cooler,” etc., on an Instagram post, and then it automatically harvests their email address, which we then use as a contest entry. It’s just a really slick piece of technology that bolts on top of Instagram and solves a pretty sticky kind of data problem for me. It’s great.

Pete Mockaitis

Awesome. And a favorite habit?

Jay Baer

This probably won’t be a surprise based on our previous conversation, I try to be at inbox zero every day.

Pete Mockaitis

All right. And is there a key nugget you share that really seems to connect and resonate with folks; they quote it back to you and retweet it often?

Jay Baer

I’ll go back to my second book Youtility. The thesis is this: helping beats selling. And that if you really focus on being as helpful and useful as possible, you don’t have to sell because people will sell you. And that’s certainly true at the company level, but especially for purposes of this show, Pete, I think that’s great advice for everybody.

Pete Mockaitis

All right. And if folks want to learn more or get in touch, where would you point them?

Jay Baer

JayBaer.com. J-A-Y-B-A-E-R.com is the main website. You can find me for all things tequila at TequilaJayBaer.com. And the books and the podcasts and newsletter and all that’s pretty easy to find.

Pete Mockaitis

And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Jay Baer

When you’re interacting with a colleague or a customer or anybody in the workplace, I think it’s helpful to take a second in every exchange, and just ask yourself, “What do they really need?” Because often we just take the initial interaction, the initial question as that’s the depth, but there’s usually a lot more going on beneath the surface.

And if we just take a moment, just take a moment to say, “What are they really saying here? What do they really need? Not what they’ve asked for, but what do they really need?” If you can give yourself permission to just take that extra beat and think about that, and then respond and interact accordingly, it will serve you well.

Pete Mockaitis

All right. Jay, this has been so much fun. I wish you many more delightful exchanges where folks are saying your name, and everywhere.

Jay Baer

We should do this with tequila next time.

Pete Mockaitis

Oh, it sounds fun.