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1193: How to Build a Team That Can Thrive Without You with Bill Flynn

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Bill Flynn shares his strategies for building a team that can lead, decide, and thrive without you.

You’ll Learn

  1. Why you shouldn’t play the hero
  2. How to build a self-sufficient team
  3. How to delegate authority, not just tasks

About Bill

Bill Flynn has collaborated with Alan Mulally and Amy Edmondson, pitched Steve Jobs, accomplished much, failed often, and learned many useful lessons from thirty years of studying the science of success. He is best described as a pragmatic Simon Sinek; an optimist and an operator.

Bill embodies his core purpose – simplified servanthood – by spending each working moment to help create a compassionately productive society by enabling enlightened leaders to focus on the few things that truly matter to their teams and key stakeholders. For having a great business is one way of making a better world.

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Pete Mockaitis
Bill, welcome!

Bill Flynn
Thanks, Pete. Glad to be here.

Pete Mockaitis
Well, I’m excited to chat about your latest, The Hero Trap. Could you kick us off with a particularly surprising or extra fascinating discovery you made while putting this all together?

Bill Flynn
Well, what I found out is that when you get promoted to run a team or run an organization or division, department, whatever it may be, everything that had got you there, all of the successes, rewards, recognitions for being the decision-maker, the hero, the person who won the deal, came in at the last minute and saved something, whatever it might have been, work against you when you are now leading a team.

Being the hero is not your job when you run the team. It is to make the team the hero. And it is a sort of insidious situation because you’ve got decades probably, at least 10, if not 20 or 30 years, of reinforcement from when you’re young, in school, wherever.

And then if you actually get to a point where you say, “Hey, you know, this isn’t working for me. My life has been taken over. The hours and time that I have to spend doing this because I have to be the one who has the answer.”

You know, you can’t eat dinner, you can’t go home, and you decide that that’s not working for you, and you begin to pull back and let the team do more stuff, their first reaction will very likely be discomfort. They don’t want you to pull back because they have been acculturated, if you will, into this particular way of thinking where when something bad happens, you’re the one who comes in and fixes it.

So they sort of help you solve that as opposed to having the responsibility to do it themselves. That’s what I’ve learned.

Pete Mockaitis
Yeah, that’s well said. And I think that just the hero verbiage, really, I think grounds this whole thing in sort of the emotional stakes of what it feels like as opposed to very theoretical discussion, like, “Oh, as you enter a leadership role, you’ll need to begin delegating what you used to do.”

It’s like, “Okay, yeah, I’ve heard that before.” But when you crystallize it in this hero language, that really brings it home. Could you share some key stories that illustrate this?

Bill Flynn
Yeah, so I sort of experienced this myself, not that I was necessarily the hero in this story, but I came in and replaced the hero. I was brought in a number of years ago to help a founder sell his company, and he brought me in as his sort of head of sales and sort of the guy with the gray hairs, if you will.

And through that process, I helped him do that about a year or so after I started, he sold the company. But during that process, his co-founder, who was the person who wrote most of the code of the software that we were using, this was an email hosting company, was running marketing.

And he ran marketing like an engineer. And he did a Scrum in the morning and he gathered his four or five people, and sort of told them, “Okay, let’s do this today.” And then at the end of the day, they sort of debriefed. And he did that day after day after day.

And when I took over, I said, “I’m not going to do that,” for two reasons. One is that just wasn’t the way I did things. I’m more closer to a builder and an architect in my vernacular than I am the hero or the controller.

And, two, I didn’t have the skills to do that. I didn’t know how to write copy. I didn’t know how to do page search or a SEO at the level that needed to be done, so I couldn’t tell them what to do. But I could say, “Hey, look, you know, what do you think marketing’s job is in this company?”

And we had a discussion about that, and we came away with, “Marketing’s job is to help make sales easier.” So I said, “So all the things that we do, that’s our job is to make the process of actually turning someone into a customer a lot easier.”

“And you all have roles to do to contribute to that, and let’s discuss what that looks like, how we would measure, how well we do there, what are the areas of marketing that we want to make sure we’re excellent at in terms of cost and throughput and volume, etc.”

And I said, “Then go do your jobs, and then figure it out, and let me know when you need me to help sort of come in.” And I didn’t just sort of let him go. I certainly was involved in the process, but I was more sort of eyes-on hands-off type of thing. And when I first said this, you should have seen the faces in the room.

They hated me. I think the word is correct. And I was told later by them because, eventually, they came to appreciate what I did. I was told honestly, “You know, we just hated you because, you know, what are you doing? You sort of basically upended our entire existence at that time, and asked us to do something that we weren’t asked to do.”

But as time went on, and I supported them, they were very good at what they did, they knew what they were doing, there were certain things that I could do to help, but so they sort of ran marketing without me.

And what’s really nice about this story is one of them became my client years later in what I do now. And we’re still, we have a 20- some odd year friendship from that. And two of the other women that were in the organization used me as their reference for the next job. So for the next 10 years, I was the person they asked to be their reference for the next job.

So If you can get through that knothole of difficulty and despair, if you will, it usually turns out pretty well.

Pete Mockaitis
Well, boy, that speaks to a lot of things all at once, and I’m really digging it. Because, well, one, the fact that they hated you suggests that what they were doing before was working for them reasonably well, I would speculate, right?

It’s funny, if what they had before was terrible, and you came in with those fundamental, you know, big-picture first principle questions, “What’s marketing’s job here?” they might say, “Oh, finally, we can throw off the yoke of all of the silly junk we’ve been dealing with.”

I’m thinking about the book The Goal, about manufacturing. It’s like, “What are we trying to do here?” “Well, we’re trying to make some money, and the manufacturing supports that by, you know, efficiently, cost effectively, reliably, turning stuff through the manufacturing lines. So that’s kind of what we’re doing here.”

And so they had all these, you know, silly metrics that were just bogging things down and nonsense. So they were doing something that was working for them well enough, such that when you disrupted it, it was not welcome.

Bill Flynn
Yes. exactly. And what’s interesting is, and they began to see it as we added, we started to add velocity to marketing. because when you have to wait until it goes up through the top, that slows everything down, and he or she may not have all the answers. or if even the fact that you have to do that, slows everything down.

I gave them guidelines and guardrails, and I gave them direction at the high level, and I gave them safety. You know, I said, “Look, you’re not going to get everything right. You may make a mistake every now and again, but that’s okay because what we’re doing here together is new, and we want to grow this part of the organization, which means you’re going to make mistakes.”

“So what we’ll do is we’ll just work together and we’ll correct them, and next time we won’t make those mistakes.” And, again, they didn’t believe me. They thought I was setting them up for failure. I think that’s what made the difference for them. They saw that they could do things faster. And the metrics actually got better.

We increased the average order size because we did marketing to help sales, but we also had a website and we did online sales. So marketing was basically also a sales engine. That average order size went up. The cost per acquisition went down. So all the things that you really look for at a high level worked really well.

So they were competent and reasonable people, and they saw that. And once they saw those metrics going, it actually gave them energy and motivation to want to do even more. So I think that’s what you see when you go from good enough to approaching great.

Pete Mockaitis
And what I also dig, when we think about just the title there, The Hero Trap, you can feel like a trap for you in terms of, “Oh, my gosh, the sheer hours required of me to do all of these things is, it feels like a trap, like a prison.”

And also, it’s a bit of a trap in terms of, as you think about what universe of career possibilities might exist for you, you might say, “Well, I don’t know much about marketing, so I have no business leading a marketing team.”

But it seems like, “Au contraire, if we utilize some of these principles, you could be an effective leader of all kinds of teams in which your subject matter knowledge is somewhat limited.”

Bill Flynn
Exactly. And interesting enough, so I used to be a Vistage speaker, and for those of you who don’t know, Vistage is a sort of peer-to-peer advisory organization, have been around for 60, 70, 80 years. And it’s mostly CEOs and leadership teams. It has a whole bunch of capabilities. And I would speak to CEOs, so I’ve spoken to hundreds, if not thousands of CEOs.

And I would do this exercise with them where I would have them fill out a three-by-five card for that particular role. And we’d put CEO or founder or whatever on the front. And on the back, at the top, it says, “Why do I get paid?” And it’s, “What are the key things, what are the key outcomes that this role, regardless whether I’m in it or someone else, gets paid?”

And I had people who ran, you know, pet stores and ball bearing companies, and software organizations, high-end technology, in the same room. And after I had them fill out the card, I would have each of them turn to each other, and they would read their card to each other, and they would help each other, you know, sort of helping them with the process.

And then after all this was done, I said, “So what was the thing that you noticed when you did this?” And, invariably, more than half the time, I would hear from people that say, “Well, you know, I run a pet store, and he’s the ball-bearing CEO, and our cards are remarkably similar because the key outcomes for that level of the company are basically the same.”

So I think, in some cases, you absolutely have to have some knowledge, some skill, minimum amount. There’s a credibility issue, of course, and competency issue, a minimum competency. But you don’t necessarily have to know everything to the nth degree. But you do know how to attract and build and develop teams. And that is a universal skill.

And as far as I know, Pete, and I’d love to hear from your take. I mean, I went to school. I have a business degree. I have a degree in marketing. I was never taught how to run a team. I wasn’t taught anything about teams, right? I was taught things very specific, very discrete things about skills and knowledge, but not about something that really matters to me.

It may be the most important thing on the people side of the business because teams get most of the work done. It’s rare that one individual is responsible for a large portion of the success of a company. So I think your comment is well made.

And if we can help people understand that being a great teammate is how you can be awesome at your job, not just being just great at the thing that you have been asked to do, but also be part of a great team, then you will be able to go very far, whether you want to go up an organization or wide or somewhere else. I think that’s a really important skill to have.

Pete Mockaitis
Well, I’m loving you already dropped a few of these very foundational questions, which I think are really illuminating. Can you give us some more of these favorite questions in your toolkit that really help organize and clarify what we’re up to?

Bill Flynn
Yeah, so one of the things, I work with individuals that lead teams. So I typically work with CEOs and then the leadership team, but I also work with people below that. And I’m a go-to person sometimes for these folks.

And when they come to me and they say, you know, “Here’s the situation. I’m trying to figure it out,” my first question almost always is, “Let’s assume that whatever you’ve done here is completed. How would you describe that as an ideal outcome? What would that particular thing look like?”

“And so give me details. Don’t just give me a word or two, but let’s walk through what that is. Because it’s a lot easier to go backwards from there than it is to go forwards from where you are.” So that would be something that I definitely work with, be it an individual contributor or a team leader or a CEO. It doesn’t matter. To me, that’s a vital question.

And that is also a question that goes across all sorts of parts of the company. For instance, if your job is to run a particular meeting, that should be the first thing you ask yourself, “What is the ideal outcome of this particular meeting? How would I describe a very successful version of this meeting?”

And then you say, “Okay, if that’s what I’m really trying to do, who are the people in the organization, regardless of title or whatever, that I must have in this meeting to give me the best possible chance of achieving that outcome?” Then you put together the agenda.

We hardly do those first two things. We just invite anybody. We don’t really know the end. If you do those two things, your meetings will go much faster, they’ll have much better throughput. The people in the meeting will be a lot happier because they actually have context and they understand what they’re trying to accomplish, why they’re there.

So those would be a couple of things, or one thing that I think can stretch across a couple of different areas.

Pete Mockaitis
I love it. Okay, so the ideal outcome and then going backwards, and then the subsequent questions. What are some others?

Bill Flynn
As a contributor to an organization, one thing that I learned, and I remember from your notes, I’m a big fan of Pareto, the 80/20 model. And this quote that I can’t find, so I guess it’s mine, but I’m sure I stole it from somebody, is “Few things truly matter, either in business or in life, but those that do, matter tremendously.”

Pete Mockaitis
Oh, yeah.

Bill Flynn
And your job as a parent or as a team leader or a team participant, whatever it may be, if you could figure out what those few things are, and it’s typically no more than five, and most likely somewhere between two and three, and you spend the bulk of your time and energy making those things optimal, that is the best time you could ever spend as an employee, as a leader, whatever it may be.

It’s easily said, more easily said than done, but once you figure that out, the world becomes a lot easier to navigate and to view, in my opinion.

Pete Mockaitis
Yeah. I think that’s so true. And I have found, like I love the book, The 80/20 Rule, or Essentialism, or The ONE Thing. And it’s funny, so these are books about, you know, productivity, effectiveness, getting more stuff done.

And I find that if I’m stressed, I actually pause to read or reflect on some of these ideas. It’s very liberating. It increases peace and it reduces stress because it’s, like, “I don’t actually have to deal with everything. I’ve got to deal with these, you know, two, three, four things. And they make all the difference there.”

I’ve taught on the 80/20 principle and, like, these things are not just a little bit more important or impactful. They’re 16 times as impactful. Let’s walk through the math, and it’s huge. So could you maybe give us a few examples of a domain, and the two or three things that matter a whole lot in that domain?

Bill Flynn
So, I used to run sales. And when I first started running sales, I wasn’t very good at running sales and I, again, sort of said, “Okay, what does selling mean? And how do I know when there’s a great salesperson?” And I looked at all the great salespeople I had worked with, and they were all different. Yet, one would say that they were successful.

So I said to my team, “I only have two rules as your leader of sales.” I said, “Of course, you need to know your product, you need to know what we do, all that kind of stuff, all the basic stuff.” I said, “But I don’t care how you reach your number. We can argue whether your number is fair or not, and I’m happy to do that. But once we sort of set your number for the month or the quarter or the year, whatever it is, my two rules are be honest and be responsible.”

“And, you know, honest was, I don’t want you to knowingly say something that is disingenuous or incorrect in order to win a deal. And then responsible is responsible to there are three constituencies that you need to be responsible to. You need to be responsible to the organization, you need to be responsible to the client, and you need to be responsible to yourself.”

“So if you are able to do those two things, again, if you want to make a thousand calls to get your number, or you want to make ten calls because you do deep research, whatever, or somewhere in between, if you want to focus more on your personality and relationships versus technique, I don’t care, as long as you’re honest and responsible. And we, as a team, we’re going to work together to make that happen.”

Pete Mockaitis
And how do you define responsible in this context?

Bill Flynn
Responsible, again, for those three things is you need to be responsible to the organization so that you know you’re not just closing a deal to get a check. You’re representing an organization. In many cases, you are the organization to those people, so you have to remember that. So the things that you do and say are reflective of everyone else behind you.

The second is you need to be responsible to the client. They’re going to be clients that want to buy from you. But if you do a good job of qualifying them and doing needs analysis, we may not be the right fit. And I would rather have you walk away from a deal that isn’t the right fit because, eventually, that client is going to be unhappy.

And if you do that a few times, you’re going to be dealing with those unhappy customers, which will take time away from you getting new customers who are happy. So you need to be responsible to them. And then, of course, to yourself, right? You want to make sure that the future version of you is very proud of the current version of you.

Pete Mockaitis
Okay, so responsible in the sense of you are owning their concerns and acting in their best interest. It’s, like, that’s yours. And you feel it, as opposed to that’s someone else’s issue. They’re going to have to deal with satisfying them somehow.

Bill Flynn
Right, exactly.

Pete Mockaitis
Okay, very good. Well, so now, zooming out a bit, you’ve got a framework – a controller, builder, architect. Can you walk us through that a little bit?

Bill Flynn
Sure. So what I found is that, either myself or other people that I’ve worked with and/or researched, because of this hero trap, the success paradox, we have usually a default identity. Most people, especially if they’re founder-led, you know, they’re a founder of a company, default to the hero, the controller model, because they were the ones who had the answer, they had to do the research, they had to do all the work, because that’s what got them there.

Eventually, the company grew and got successful, hopefully, and that became more and more of an issue for them. But also, what does happen, and I’ve seen happen, is when pressure hits, that’s their default regardless of the size of the company.

So if financial pressure hits or some other type of pressure hits, they’re going to default to getting in there and solving the problem, as opposed to stepping back and saying, “Okay, how do I help my organization do this?” So that’s the issue that I found in general.

And I was saying, “Well, is that the best way to do things?” And I came up with this framework which says you actually have the option of three different identities. The controller, which by the way, Pete, is okay. It’s not a bad identity. Sometimes you need to jump in and do the work and make the decision, etc.

But if you just stop there, that’s where we get back to you don’t get to go home at night. You know, the nights get longer and you get a call at 3:00 o’clock in the morning because something was broken in Japan, and you have to fix it or whatever. But you can’t just stop there. You have to be moving towards architect.

And the next step is builder, and the last is architect. So if I were to synthesize this, controller is, “I do.” The builder is, “I teach how I do.” And then the architect is, “I build systems so I’m not necessary to do either of those two things.”

So if you are the hero and, let’s say, I’m sure in your situation, you’ve probably come in and you’ve had to, like, fix something. Maybe there was an angry client or some system broke, and you had to come in and just make it happen because there was urgency to it or whatever.

Your next step is to say, “Okay, let me teach my team how I did that. Let them understand how I think through these kinds of problems.” You probably have an innate heuristic or whatever it is, you know, some sort of rubric that you use to walk you through a process.

And if you teach that to them, the next time that particular thing comes up, then they will know how to say, “Hey, this is what Pete would do.” And if you’ve read Turn the Ship Around, this is sort of what David Marquet was talking about in his example when he took over the submarine that he didn’t know how to run.

So he basically told people, “I need you to tell me what you intend to do, and I will just sort of say go ahead, because I don’t know how the ship works, but I will teach you how I think. I’ll teach you how. I need to keep us safe. Here are the things that I need to do.” So when they’re doing that intent model, they’re using his thinking to do that.

Now that works for a long distance, but when you really are in a situation where you want to fire yourself from the day-to-day as much as possible, you need to build systems so those people can take that knowledge of yours and use their own brains, be it individual or team, to look at things that you haven’t prepared them for.

So, for instance, you might have taught them a particular way of thinking, but the next thing that comes up is there’s a slight deviation from it, and it doesn’t look and smell exactly like what you just told them. So what will happen if you don’t teach them the systems, then they have to come back to and you have to sort of solve that one a little bit differently.

But if you put the systems in place and you create this architect model where you’re building people who think for themselves and can leverage the system, they won’t even come to you at all, or they’ll come to you and say, “Hey, this came up. It looked a lot like the thing you taught us a year ago, but this was the change. We’re going to do this because this is how we looked it through. Are you okay with that?” And you’re like, “Go ahead, give it a go.”

That’s very different than, “Hey, the problem came up and we don’t know how to solve it. Can you help us fix it, or fix it for us?” So those are the three models: controller, builder, architect.

Pete Mockaitis
Okay. Well, can you give us a real-world example of a domain in which we’re approaching it as though we are a controller versus builder versus architect?

Bill Flynn
Sure. And I can use an example from one of my clients. I had a client for many years that grew tremendously quickly, over many years, grew 40%, 50%, 60% a year and continued that pace. And then things started to slow down. And the leader couldn’t figure it out.

And what he would do is he would insert himself into the process. So he may have said, “I want to hire these people, and I want to be the one who makes the final decision, or this is what I want us to do to fix that particular thing.” He would literally put himself into that person’s role who reported to him, head of sales, head of marketing, whatever it may be, and just did their job for them, because, again, that pressure hit.

I have had other leaders who have taken what I’ve said and done the opposite, where one of my favorite sayings, which I already said, is, “Your job as a leader of team or teams of teams is to fire yourself from the day-to-day as much as possible, because your job eventually is to look out to the future of the business, or the team, not down into running it.”

And one of the folks that I worked with took that to heart and just sort of stepped away from his team, and they felt abandoned because he hadn’t set up the structure for them to be independent. He didn’t give them the guidelines and the guardrails that I mentioned earlier. He didn’t give them the direction. And they were very much struggling and were unhappy with his process.

So we had to work together and have him sort of step in and say, “Okay, you know, where are they disappointed? What are they looking for?” And he started to step back in and started to put the scaffolding in place so he could step back a little bit more than he did before. So those are a couple of examples that I’ve seen directly.

Pete Mockaitis
Okay. And you have made a point that, when you’re delegating, it’s not just about delegating tasks, but delegating authority. Can you share the distinction and some examples?

Bill Flynn
Yeah, so this happens a lot, and I bet your listeners have either, unfortunately, did it inadvertently or had it done to them is, you know, you’re delegated a particular thing, and then you go ahead and act on it, do your best, and then the leader comes in and either undermines you completely, and just says, “You know, we’re doing it this way. We’re not doing that way. I didn’t really like that.”

Or, you know, challenges you in front of the group in such a way that your authority to that particular delegation was minimized, if not eliminated. Another example that I like to give is, let’s say you’re given the ability to run a meeting, right?

So the leader says, “Hey, I want you to run today’s meeting.” And you finished the meeting, and it went okay. And the leader, as they’re leaving the room, says, let’s say I was the one leading the meeting and you were my boss, Pete.

As you’re leaving, you say, “Hey, Bill, can you follow me back to my office as I have some feedback I want to give you on this meeting?” And then I’m following you back to the office, and as I’m walking behind you, I’m catastrophizing. And I’m thinking, one, you know, “What happened? Am I in trouble? What is everyone else who was left behind in the room thinking about me? Where is my status within the organization because you just sort of threw this out there?”

So by the time we get to your office, and you sit behind your desk, which is a status symbol, and a protection of you, right, because you’re physically behind something, and I’m sitting in a chair, completely exposed, so my lizard brain is on fire, and my heart is beating.

I’m probably sweating a little bit. Maybe my vision has narrowed. And no matter what comes out of your mouth next, I’m probably not going to remember it because my brain is already saying, “Run like hell. Get out of the room. This is an existential event.”

Because our brain isn’t very good at distinguishing between a social threat and a physical threat, so all the parts of our brain light up are the same. So what you could’ve done differently to, hopefully, get the same outcome was you could’ve waited till everyone left, sat down next to me, and said, “Hey, Bill, how do you think that meeting went?”

And if I’m not delusional, I’m going to say, “You know, I think part of it went pretty well, and some of it, some of the parts I was a little comfortable with.” And you say, “You know what? I agree. Let’s do this. Put some time on my calendar this week, and I want you and I to get together.”

“And I want you to bring two or three things that you thought went really well in the meeting that we can maybe brainstorm and even improve and make them better. And I want you to bring one or two things that you didn’t think went very well, and I’ll do the same thing, and we’re going to work together every week until you and I agree that this is the best possible version of this meeting.”

Both were trying to get the same outcome, but the way it was done was a difference of authority, if you will.

Pete Mockaitis
Certainly. Yeah. It was like we’re collaborative team partners achieving an outcome together as opposed to, “I’m the boss and you got to shape up.”

Bill Flynn

Exactly.

Pete Mockaitis
Okay. Well, tell us, any other tweaks or pro tips you recommend, like shifts that make a world of difference?

Bill Flynn
So from what I can understand, most of the listeners that you have are, they may or may not be running teams. They’re probably an individual contributor. There’s probably not CEOs at all.

Pete Mockaitis
There might be, like, 40 of them out there. Howdy CEOs, we appreciate you.

Bill Flynn

What you want to do is the best way to make yourself promotable in most organizations is thinking about how you can be the best possible teammate to the group, right?

What value do you bring to the organization and to the team? And then how does that fit with all the other folks on the team? And how do you make sure you work together and make sure that you understand that they’re all bringing their own perspective, they’re bringing their own experience, and that will make your contribution even better?

Unless, of course, the person that hired everyone hired exactly the same person, just five of them, then that’s difficult. But most don’t. We’re at least going to bring our different experience to it. When you become a better teammate, you’re seen differently by people on your team and by others.

And if that’s what you want, if you’d like to run a team, etc., you can. This is exactly how I acted. I eventually became the general manager of a division of a company. I’ve not been a CEO myself. And I was one of those unusual people. I was usually the number one and number two sales rep in most of the organizations I was at.

And, usually, the mistake is to promote that person and they run the team. In my case, I guess I was a little bit different because I came at it differently. And I always thought about myself not as the best salesperson, but one of the other salespeople here. And I still can learn from everyone else, right?

There are so many steps in a sales process from awareness and interest generation, qualification, needs analysis, closing, negotiation. There are all sorts of skills that, you know, I could get better at. And I acted that way. So when I was promoted, it was not a surprise.

And it was not something that most people had an issue with as well, because they saw me that way as I developed myself through that particular organization and my career. That would be something that I would definitely tell the 33-year-old on average individual contributors.

That if you’re looking to do that, whether you’re looking to lead a team or not, but just be recognized as someone who’s valuable. To me, that would be something I would highly recommend that you think about is, “Am I being the best possible teammate today? Am I working hard not only to be a great individual contributor, but making my other teammates look great as well?”

Pete Mockaitis
And I think that’s so essential to proactively prompt yourself, interrupt yourself, get that in the groove, because, otherwise, it’s so easy to just get sucked into the endless to-do list and hustling to achieve the thing.

I found that it really does take a moment of stopping, pausing, considering. It’s like, “Oh, you know what? Hmm, this person over there, that just happened for them. And so they’re probably feeling this or needing that. And so, well, hey, I can offer something there.”

I just recently had an experience. It’s like, “Oh, man, someone got some bad news. Oh, I should probably give them a call. They might like that.” And then I heard from a third party, it’s like that meant the world to them. It totally picked them up.

And it’d be very easy to say, “Oh, shucks, I’m behind. I got to hustle up and get out the door.” But, yeah, I think that’s a great tip is to proactively ask yourself that question because, otherwise, it won’t bubble up and you’ll overlook many little opportunities that can make a big impact.

Bill Flynn
Exactly. And I think what you’re saying is the word little is important. You know, if you did this, it probably took 30 seconds to a minute to just say, “Hey, you know, I was thinking about you. I heard about this, and I can’t imagine how you’re feeling. I’m here if you want to chat, whatever it might be.”

And most of the time they’re not going to take you up on it, but they’re going to remember that you did that. And if you just do that, you will be putting credits in the bank, and then there will be a time where you’ll need something.

And if you do that well enough, my suspicion is you won’t even need to ask someone. They’ll just do it, because they’re going to say, “You know what?” Just like in the military, they say, “Why would you do that? Why would you put your life on the line for this other person?”

And the answer is always, “Because he or she would do it for me.” And if you can have that sort of esprit de corps in an organization, the velocity and the production and the satisfaction and fulfillment of that group of people will be off the charts.

Pete Mockaitis
Beautiful. Well, Bill, tell me, any final top tips you want to make sure to put out there before we hear about your favorite things?

Bill Flynn
When you hear that little voice in your head, especially, again, if you’re highly competent, you’re probably the top person in the group for certain things, if you find yourself saying to yourself, “It’s faster if I just do it myself,” that is a bit of a yellow, if not a red flag, that will probably work against you eventually. In the short term, it will not.

And this is the insidious nature of it, right? You will be celebrated. You will get an endorphin rush, a dopamine rush. It’ll feel great. And what also is interesting is if you start to do it the other way, because what you’re doing feels, it’s not only self-rewarding and egocentric, but it also feels like caring, so it’s hard to sort of walk away from that.

But if you hear those words, right, “Faster if I just do it.” That should be something that ticks in your brain and says, “You know, maybe I’m trying to be the hero a little bit too much here,” and stop yourself, and say, “Okay, am I the person who absolutely has to do this?”

First is, “Am I actually the right person to do this? Do I have the expertise, skills, knowledge, abilities, etc.?” And if you’re not and you’re just trying to sort of look better than someone else, then that’s a whole other problem.

But if you are, you know, it’s also you want to say many hands make a lighter load, or something like that, right? It has other benefits as well. So that would be my sort of last tip that I would say, if that little voice in your head says that. Listen to it and think of an alternative.

Pete Mockaitis

Beautiful. Well, now could you share a favorite quote, something you find inspiring?

Bill Flynn
This is probably for the future version of the people who are listening to your podcast. I have come to believe very strongly that great leaders create organizations that don’t need great leaders.

Your job is to create a situation when you’re no longer in that position, that when you leave, either to be moved up in the organization or out of the organization, or wherever else, that the person that takes over from you, there is little or no disruption from when you leave to when they take over.

So if you can create that environment, then I think that’s what we should applaud as a great leader, as opposed to, again, the hero that came in and saved the thing. And I think a really good example which would have surprised me, is Steve Jobs and Tim Cook, right?

When Tim Cook took over, the world said, “Oh, my God, Apple is going to fall apart.” It did not. It grew at a record pace outside of it. And, again, Tim Cook, completely different kind of leader than Steve Jobs, but to his credit, Steve Jobs set up that environment.

I think, in an interview once, he said, he was asked what his greatest accomplishment was. And he didn’t say a product. And this is a product guy, right? He loved products. He loved making things. He said, “Apple University.”

He said, “I created an environment that will build great Apple folks. And whether they’re here or somewhere else, we’re teaching them all the things that we know.” He said, “That will be my greatest legacy.” And even though it’s sort of behind the scenes, I think he’s right. And Tim Cook is a good example, and we’ll see how this next leader does as well.

Pete Mockaitis
And could you share a favorite study, or experiment, or bit of research?

Bill Flynn
So the research that I cite often is the stuff that Marcus Buckingham did, and I think he talked to, I think, it was a thousand different people in 19 different countries. And he asked them, “How many of you are on a team?” And it was 80 something percent.

And then he said, “How many of you are on more than one team?” And 60 some odd percent of those people said they were on more than one team. And then, “How many are you are on more than that?” And there was another 50% or so.

So the research shows that teams are the most important human component of any organization, of almost any organization. And being a great teammate and running a great team is probably the most important thing.

And he’s not the only one. Amy Edmondson has done similar research. There have been some other folks who’ve done similar research as well, that teams are really the thing that drive most success of companies, etc.

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

Bill Flynn

“Your job is not to run the company. It is to create the future of the company.”

And, again, back to neuroscience, we cannot focus on two things at the same time. We context-switch. And I said, “If you’re indispensable, if you have a long line out your door, you’re not going to be able to look out and have time to do that.”

“So your job as you move up in the company and, especially to running teams, always be thinking, ‘How can I be doing less? How can I fire myself from the day-to-day so I can spend more time creating the future either of the organization or the department or the division or the team?’”

So you’re making sure that you’re spending the best part of your time is making the whole better than just the individual.

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

Bill Flynn
My website is probably the best place to go. My books are on there. You can download my latest book for free, and The Hero Trap will also be on there if you want to pre-order it. There’s all sorts of other resources and things I have on there. And that’s called www.CatalystGrowthAdvisors.com.

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

Bill Flynn

Yeah. Fight the feeling to become indispensable. So keep that in the back of your mind.

Pete Mockaitis
All right. Bill, thank you.

Bill Flynn
Thank you, Pete. Appreciate it.

1192: How to Tackle Difficult Conversations to Build Stronger Relationships with Kerry Siggins

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Kerry Siggins shares her practical framework for navigating conflict, managing emotions, and finding common ground.

You’ll Learn

  1. Why avoiding conversations often does more harm than good
  2. The SHARES model for effective feedback
  3. The hidden assumption harming your conversation

About Kerry

Kerry Siggins is a sought-after international speaker and the author of The Ownership Mindset: A Handbook for Transforming Your Life and Leadership. Her work focuses on leadership, communication, accountability, employee ownership, and building high trust cultures.

Siggins also brings her work directly into organizations through The Talk With Trust Leadership Experience, an immersive and interactive leadership experience designed to help teams practice courageous conversations and build stronger communication habits in real time.

Whether speaking to executive teams, companies, conferences, or leadership groups, Siggins combines operational credibility, emotional intelligence, and practical leadership insight to help organizations create cultures where people feel empowered to communicate openly, take ownership, and grow together.

Resources Mentioned

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Pete Mockaitis
Kerry, welcome!

Kerry Siggins
Thank you, Pete. I’m so glad to be here. I can’t wait for this interview.

Pete Mockaitis
Oh, boy, me, too. Well, tell us, Kerry, what is something fascinating and counterintuitive you’ve discovered about us humans and tricky conversations?

Kerry Siggins
Tricky conversations, yes. Well, I wrote a whole book on this because I hate having hard conversations. I’m a recovering people-pleaser, and I found myself avoiding difficult conversations because I was always worried about the consequence of having that conversation, “I’m going to make this person mad at me,” “They’re not going to like me,” “I’m going to damage the relationship.”

And what I’ve learned is that when you don’t have that conversation, you’re actually avoiding consequences that are far worse. And if you want to build trust with people, you need to have those conversations. You need to trust enough in yourself and in that relationship to be able to lean into it.

And if you don’t, truth withheld, usually makes things worse in the end. So that is what I’ve learned is really digging into, “What consequences am I avoiding? And what consequences are there going to be when I don’t have this conversation?” And that helps give me the courage to go say what needs to be said.

Pete Mockaitis
Intriguing. Far worse consequences, could you give us an example story here?

Kerry Siggins
Yes. so I just had something recently happen of an employee who was a great cultural fit, came into a role, she was struggling for a bit, I really wanted it to work out. I was trying to help her and I would see these little improvements. And so I was like, “Oh, I think we’re getting there. I think we’re getting there.”

And what I didn’t have was a bigger conversation around, “If these things don’t get fixed, if I don’t see market improvement, then there’s going to be bare consequences. Like, maybe this isn’t the right fit for you.” But I kept just hoping that she would get it, hoping things would turn around.

And then, ultimately, when they didn’t, I had to have a different conversation. And that was, “I don’t think this is the right fit, this role is the right fit for you.” And she was so upset with me because she was like, “Why didn’t you just tell me that from the beginning? I didn’t realize that my job was on the line.”

And I realized that I was avoiding having that conversation because I believed in her, I wanted her to succeed, I didn’t want to demoralize her. And if it didn’t work out, then I was going to have to take something on. I was probably going to have to take her direct reports.

And so I was avoiding these consequences, couching it under, “I’m just giving her more time. I’m just giving her a shot.” And she felt really blindsided when I actually told her, “Hey, this isn’t working,” because I didn’t have that direct of a conversation. And trust broke down.

And so that is an example of something that we all do as leaders in trying to help people who are struggling, but not just coming right out and saying, you know, “There are serious consequences if this doesn’t…if we don’t see a turnaround.”

Pete Mockaitis

Yeah, well, I think that’s a really good nuanced distinction piece there in that you shared a portion of the key messages that needed to be shared with regard to, “This is what’s not working and needs to be adjusted,” but not the entirety of the messaging, which was, “And, in fact, this is so important if you don’t fix it, you’ll have to leave.” So that is the harder part to say.

Kerry Siggins
It is, and I didn’t say it. I didn’t want to say that. And then, ultimately, that’s what happened. And then that person was blindsided and it completely breaks down trust because, like, “We’ve been having these conversations for six months now. Why didn’t I know it was so serious?” And I had to say, “You’re right. And I’m sorry.”

And it made me feel like a really crappy leader because I know better than that. But it was one of those things that just snowballs. And the next thing you know, you’re like, “Oh, my gosh, I haven’t been having the conversation that really needs to be had. And now I’m going to blindside this person. Why didn’t I just have that conversation the first time?”

It would be so much easier if the expectations were clear and the consequences were clear, then somebody has a choice, right? At this point, though, I took away that choice of, “Can I really step up into the role?” because I wasn’t having the full conversation.

So, truth, when you come right out and you say it and you just put it on the line, it gives people options, it gives people choices. It doesn’t mean that it’s always going to work out, but truth delayed, it usually is hurtful.

It usually damages relationships because that person feels like, “Why didn’t I know this? I could have done something about it. I could have done something differently if I would have known.”

Pete Mockaitis
Okay. Well, so great perspective there in terms of you are avoiding something in the short term, but it could be far worse in the long term. Alrighty. Well, tell us then, what are the best practices for finding the courage, for finding the words to go ahead and go in there in conversation?

Kerry Siggins
So I think the key is preparation. And it doesn’t have to be this long preparation, but, oftentimes, we go into conversations that are difficult and we haven’t really thought through, “What am I trying to get out of this? How do I make sure that I have accurate information? How do I get the other person’s perspective? How do I make sure that there’s a path forward so that it’s clear what expectations are going forward? And how do I stay grounded in this conversation?”

We just go in and we wing it. Or, maybe we spend a few minutes, like, writing down what we’re going to say. But if you have a process to prepare for these conversations, it makes all the difference in the world.

And that’s why I wrote my book, Talk with Trust, is that I have this model that I was just using intuitively. And then I had someone tell me, “You’re actually really good at having these difficult conversations and, like, making people feel good when they walk out of your office. How do you do it?”

And so I started to think about it and I was like, “Oh, I have a process that I do,” and that’s what is in my book Talk with Trust, which is the SHARES model. So the secret is going in with preparation and always seeking to understand, always going, “What is your perspective on this? What is going on?”

Help people stay in dialogue, and it’s so much more productive than you just coming in hot, giving the feedback, and then letting the person go. They don’t feel seen, they don’t feel heard, they don’t feel safe. And that’s our job as leaders is to be able to have the difficult conversations, but do it in a way that builds relationships.

Pete Mockaitis
Okay. Well, so the SHARES model, let’s hear it.

Kerry Siggins

So the first S is specify your ideal outcome. So that is, “What do you want from this conversation? What behavior change? What outcome do you want? What do you want the relationship to look like?” Know that going in because it helps keep you grounded, especially if things do get emotional.

The H is have your facts and feelings ready. You need to be able to have observable facts. People want that, “Give me an example.” You need to be able to state that, and you don’t want it to be your opinion, right?

You can say, “You were late for a meeting,” that is an observable fact. “You were late to this meeting because you don’t care about the team,” that is your opinion. And then the feelings piece of it is really important because they need to understand the impact.

So, “You’re late for this meeting, and the impact of the team is that we’re waiting for you, and it’s really frustrating for people. And then we have to go back and repeat what we had just talked about. That’s not working for the team.” So you have the observable fact and the impact. So people really understand what’s going on when you’re trying to give that feedback.

The A is my favorite, it’s articulate your experience. So we’re taught to use I statements, “I feel,” “I think,” as a way of owning your perspective. But, usually, the statement that comes after “I feel” still is a judgment, “So, Pete, I feel that you were disrespectful.”

And it’s like, “Whoa! Wait,” you know? So that sets people back. It creates defensiveness in people. But when you articulate your experience, and you say, “Hey, Pete, in this situation, when you said X, Y, Z, I experienced that as disrespect. And a story I told myself is that you don’t respect me. But I want to own that that’s my interpretation. Can we talk about this?”

Now you’re owning that it is the story that you told yourself, and you open it up for the next one, which is reflect with questions and dialogue, “Okay, is the story that I’m telling myself true? Is that what you intended? What was going on?”

When you have questions, it allows the other person to be in dialogue, where you could say, “Oh, Kerry, no, that wasn’t what I meant at all. I’m really sorry. I have X, Y, Z going on in my life and I was distracted.” Or, you say, “Yeah, Kerry, actually, I do respect you, but I am struggling with you right now because X, Y, Z happened. “

And now, all of a sudden, you’re in dialogue and you’re really understanding what’s happening. And that is such an important piece of creating psychological safety that the other person gets to be able to share their own experience, too.

The E is endorse a path forward, which is make sure that you have an out, like what success looks like, “What do you want from this?” So you have your outcome, “I need this behavior changed. Now, how do we get there?”

When you come and give someone feedback, especially an employee, and you don’t have a path forward and you just expect them to go do it, a lot of times you’re going to be disappointed.

And a lot of times when you’re giving somebody feedback, you’re giving that feedback because they’re struggling and they probably need help designing a path forward, getting to that successful outcome. So our job as leaders isn’t just to give them the feedback, but it’s also to be able to have them, help them see a path forward, a way forward.

And then the final S is stay emotionally grounded. And this is the thread that goes through all of these things because, oftentimes, when we’re giving feedback, we can feel emotional, we can feel upset about something, and then we might show up emotionally charged, which makes a person defensive.

Or, we may be grounded, but the other person gets emotional. And, oftentimes, we want to either fix it or we get defensive ourselves, we meet them where they’re at. And our job as leaders is to stay grounded. And so that’s the final S in the SHARES model.

So this is a whole process that you can walk yourself through to be able to have a difficult conversation in a way that builds trust rather than just winging it and hoping for the best.

Pete Mockaitis
Okay. Lovely. And how do you stay emotionally grounded if you are frustrated, annoyed, enraged during the course of the conversation? How do you stay grounded?

Kerry Siggins
So the biggest thing that I do is take a deep breath. When you take a deep breath, you calm yourself and it calms the other person, too. And as leaders, we have to hold ourselves accountable to managing our emotions. But it’s not always easy to do.

So if I am in a meeting with somebody and it gets heated, I put my feet on the ground and I just lean forward like this and I just take a deep breath. So I’m just going to pause for a minute, right? There’s power in the pause.

And I remind myself, “What is the outcome that I want? The outcome is that I want this relationship to be better. And so what do I need to do right now in this moment?” And taking that breath or two deep breaths is enough to help you reground yourself in that moment.

If you can’t, if you feel yourself getting angry and you’re going to say something that you are going to regret, I, 100%, think it’s okay to say, “You know what? I need time to process this conversation. I really don’t want to. I want to be thoughtful in what I want to say. And so can we circle back in an hour or back tomorrow?”

I did this when I got some of the toughest feedback I’ve ever received in my life. Several years ago, my VP of operations, who was my right hand man, told me that I was erratic and hard to work for. And my initial reaction was, “Get out of my office. If you don’t want to be here, you don’t have to be here. You can go.”

But I didn’t want to react that way. I wanted to understand what he was saying, but I was emotionally charged in that moment. And so I said to him, “Well, that was a lot. and that really stung. And I want to be able to have a conversation about this, but I can’t do that right now. I need to go process what you just said. Let’s circle back tomorrow.”

And if I would have had my initial reaction, it would have been really bad. By giving myself, you know, 18 hours to calm down, to process, to be thoughtful in the conversation that I wanted to have with him, the next day, it changed the path forward.

So there’s really important power in the pause and just saying, “Hey, I need a minute.” That’s okay. It’s okay.

Pete Mockaitis
Okay. All right. So you’re pausing and you’re breathing. Understood. With regard to the endorse a path forward, It’s funny, I really like the use of the word endorse, and not just because it makes your acronym work, but because it’s not the same as dictating, like, “And this is what you need to do, pal.”

Kerry Siggins
Exactly. Yeah, it encourages a shared path forward, and I think that that’s really important.

Pete Mockaitis
And so could you, perhaps, give us some examples of how a full conversation cycle might unfold here?

Kerry Siggins
Sure. So I’ll give you an example why this is so important and why I put this into the model. I’ll give you a story of me in my 20s. So I had been in a sales role in my early 20s, really successful, left that company, went to another one, similar role, and, all of a sudden, I was struggling.

I wasn’t getting in front of decision-makers. I wasn’t closing deals. Everything that I had done in the previous company wasn’t working. And my boss called me into his office and he said, “You know, Kerry, we’re not seeing the sales numbers. And looking through your call logs in Salesforce, you’re not getting in front of the right people. You’re not getting in front of the decision-makers.”

And in my head, I was like, “Yeah, I know. Duh!” But I was like, “Yes, I get that.” He’s like, “So I need you to put together a plan and come back to me by the end of the week of how you’re going to change your approach,” and excused me from his office.

And I was so demoralized because I knew I wasn’t successful. I knew what was working in the past wasn’t working now, but I needed help. But there was no conversation about, “Hey, let’s brainstorm. Why don’t you role-play with me? I’ll be the client, you be you, and let’s walk through how you’re approaching this. Let me go on some calls with you to see.”

There was no collaboration or curiosity around how we do this better. And I left eventually. I left the company. And if he would have said, “Hey, I know you’re struggling. I want to help you. You are responsible for you,” because that’s what he was doing, he was creating accountability.

“But let’s do this. Let’s talk about how you can be more successful. Let’s get you some coaching. I’m going to go on a ride with you. You know, I would like to see a list of decision-makers. Let’s brainstorm this together,” I would have walked out going like, “Okay, I have a plan now that I can go execute to,” and it would have changed the entire experience.

So I think it’s really important to say, “This is what success looks like. Now let’s come up with a plan to help you get there,” and not just put it all onto the employee. They’re struggling for a reason.

So brainstorm with them, “What is it that you need? What are you trying that isn’t working? What roadblocks do you have? Do you not have clear expectations?” Those types of questions can help you put together a plan that when that employee leaves your office, they know what they need to go do. And then it’s up to them to do it.

Pete Mockaitis
Yeah, I think that’s a real nice illustration of, perhaps, extremes. One could be, quite simply, “Do X, Y, and Z, and that’s it. You know, here’s the answer. I dictate, I direct. And I pontificate, and that’s that.”

And then there’s the other extreme, which we saw you demonstrate from that manager, it’s like, “Give me a plan.” It’s like, “Okay, it’s all on you to generate the thing.” And, in a way, that’s nice. You’re not being micromanaged, but it’s not so nice, it’s like, “Do you care? Are you in this with me? Are we a team?”

So, yeah, I like that a lot in terms of being collaborative and helpful but also saying, like, “Yes, that thing you said, this is the one that I endorse,” because it’s quite possible that you could come back with a plan that was no good.

Well, so you said at the very end of the story, you left the organization. But maybe before that, tell us what happened when you came back with your plan?

Kerry Siggins
I came back with my plan, and he told me, “I think that this is okay. You need to do these three other things.” And so he dictated it, but I was actually grateful for it. And, at that point, though, I was already planning to leave the company.

And so I only gave it, like, I didn’t put very much effort into it because, at that point, I was like, “This isn’t going to work.” And so I think I quit, like, two weeks, two or three weeks later, like, “Okay, this isn’t working.”

So, by that point, I was pretty frustrated and I could see the writing on the wall. I was either going to quit or they were going to fire me, and I was like, “Okay, I’m just going to quit.”

So he gave me some feedback on it and then gave me, like, three additional things to add to the plan. But neither one of us were very invested in it at that point. So it didn’t really matter.

And it’s really interesting that that part of the story doesn’t stick in my head, like, how frustrated I was when I walked out of his office with no support. Yeah, good question. I got to think about that, like, “What did I do?”

Pete Mockaitis
I think we’re considering these things and we avoid the discomfort, the unpleasantness, there’s fear, all kinds of uncomfortable, you know, going maybe the back of the neck and your belly or wherever you feel it.

I’m curious, how much of our fear or perception of risk about whatever terrible consequences we imagine by going into these conversations, how much of that is real versus just entirely just a goblin of our imagination?

Kerry Siggins
I mean, it depends is the answer. You know, the better that you know the person, I think the better read you can have on the situation. But I found that almost every conversation that I had going in with a perception of how it was going to turn out, something was inaccurate about it, because you just don’t know, right?

We’re so sure that we know how things are going to go, that what people are going to say, how someone is going to react, and I always find myself surprised at what I learn in those conversations.

So, sometimes, I’m like, “This conversation is going to go really poorly.” And sometimes that is true. It does go really poorly because I know that person and they don’t like feedback and they’re going to get defensive and I have to give them their response.

But it’s almost not always as bad as I thought it was going to be. Sometimes, it was worse than what I thought it was going to be. But because I try to stay in dialogue and create that curiosity around, you know, “What are your experience? What do you feel? What happened?” I always gain some type of insight.

So I’ll give you an example. I had to have a conversation with an employee. She didn’t report to me, but something happened and it involved me. And so I debated on giving her feedback, “Should I give it to her or should her boss give it to her?’ And I was like, “You know what? I’m going to give it to her because I’m the one who is part of this story.”

And I, honestly, thought like, “I’m going to fire her. She’s probably going to get emotional. And like what happened was a breach of confidentiality. And so I’m probably going to let her go, but I’m going to ask, I’m going to seek to understand. I’m going to use my SHARES model.”

And so I did. I had the conversation and she immediately owned it. And I was expecting her to deny, to try to figure out how to deflect, and she just came in and she owned it, which changed how I felt about it.

People make mistakes all the time, and when you own it, for me at least, I’m so much more willing to be forgiving and to help that person through it. And so she owned it. And so I was like, “Okay, I don’t think I’m going to fire her. But this is all in my head. And I could see that she was just really scared.”

And I was like, “Why don’t you just tell me what was going on with you at that time? I’m trying to understand why you made the decision that you made.” And she told me this, like, really personal story about something that was going on in her life.

And I realized that she made a huge mistake, she didn’t handle it well, and she needed help. So the conversation went like I thought it was going to, in fact, that she did get emotional.

It didn’t go the way that I thought I was going to fire her because she did own it. I didn’t expect her to own it. And I learned something really important about her that helped me help her get some help. And at the end of the conversation, she gave me a big hug and she was like, “Thank you so much for not firing me, and thank you so much for listening to me.”

And six months later, she’s thriving. We were able to support her with this personal thing that was going on. And so that surprises me, right? And so part of my expectations were accurate and part of them weren’t. And because of the way I handled it, I now have a personal, a better relationship with her that I wasn’t expecting to have.

Those kinds of things happen all the time in these conversations, but we have to seek to understand. We’ve got to make sure that we just don’t come in hot, say what we need to say, and do not give that other person a chance to be able to talk through it with you because there’s always going to be something that you learn.

Pete Mockaitis
And I think that’s great advice when you’re on the receiving end of these conversations as well, that owning it is the right answer.

Kerry Siggins
Yes. Always.

Pete Mockaitis
Like, you were expecting, “Okay, well, she’s going to get defensive, then I’m going to fire her. That’s how this is going to go.” So, one, you were surprised that that did not happen. And I suppose, I was also recently talking to someone who was in a position of, you know, thinking, “Oh, I might need to fire someone shortly.”

And I said, “Well, you know what, I’m going to raise the concerns with her and we’ll you know see what happens.” And I was so struck by how, and maybe I’m just, like, spoiled because I’ve had over a thousand of these conversations with experts on workplace matters, such that he had some thoughts about what he noticed and what he would like to see differently.

And she just, basically, you know, argued that he was wrong, that he was mistaken in his perception. And I was just like, “Oh, that’s just the wrong answer.” It’s like, “Even if you believe it,” I was like, “It’s so the wrong answer. I think ChatGPT or Claude could have told you what to say. And it, off the shelf, no knowledge of deep context could tell you the right words or words that would be far better than those words.”

So there’s that. You’ll be surprised. And, yeah, owning it just always goes better.

Kerry Siggins
Always. Always. Always. Always. The cover-up is always worse than the crime. Nobody wants to work with a victim. Nobody wants to work with somebody who is defecting or blaming. And we do it because we’re protecting ourselves, right?

When we deny, blame, say that, you know, argue with somebody about why they’re wrong, it’s because they’re brushing up against what we believe about ourselves and we feel the need to defend who we are.

But my philosophy is that there’s always something to own in every piece of feedback that you ever receive, even if it’s just perception management. So, like, this woman didn’t, you know, didn’t agree, but it’s the other person’s perspective.

So it’s their perception. So maybe I should be curious about why they have this perception so that I can go, “Huh, okay. Is this just an image management issue, a perception management issue? Or is there actually something that I should dig deeper?”

And human nature is that we want to be right. And that’s why we argue, “I want to be right. I would much rather be accurate.” And so when I feel the need to protect my point of view, I pause and say, “Do I want to be right or do I want to be accurate? I want to be accurate.”

So I should stop and listen and ask more questions and make sure that the way that I’m seeing this is actually correct, because if it’s not, I might make a decision or I might continue to do something. And based on this idea of, like, “I’m right” versus “I’m accurate.” So it’s a great tool to just pause when you feel yourself getting defensive because it’s usually we want to be right.

Pete Mockaitis
All right. Well, Kerry, tell us, in your experience, what are some top do’s and don’ts that you’ve seen over and over again that make all the difference?

Kerry Siggins
So the number one do is prepare. Always prepare, even if it’s five minutes, you can just use the SHARES model, just quickly jot down, “What outcome? Here’s the facts. Here’s my feelings. Here’s the five questions I’m going to ask. Here’s the path forward that I would like to see.” Collaborate, collaborate, collaborate. Like, you preparing is so important.

The next do is make sure that you are grounded. If you are upset, it’s not the time to have the conversation. Don’t go into a conversation when you’re already angry. It is probably not going to go well because you are not in control of your emotions.

So pause. Take a day, take a night, take a shower, go for a walk. Whatever you need to do to calm your nervous system down to prepare to have that conversation, you’ve got to make sure you’re grounded.

My first don’t is don’t argue with the person. That almost never is going to get you anywhere. It doesn’t get you anywhere with your spouse. It doesn’t get you anywhere with your employees. It doesn’t get you anywhere with your boss.

And so if you feel the need to argue, it’s really good to just say, “I’ve got to pause. I feel like I need to defend myself here and I’m falling out of curiosity. And so I just need to ground myself.”

But whenever we start to go into our respective corners, that is when conversations fall apart and that is when trust falls apart. So when you feel yourself going into that corner because you want to argue a point, that’s a really good time to pause and just stop.

And then the other don’t that I would have is don’t assume that you are accurate. We humans think we have it all down, and we don’t. So seek to understand. Be curious. Don’t assume that your perception of what’s going on is accurate.

Pete Mockaitis
Well, I think that’s a tremendous lesson for all humans at all times. Yeah, don’t assume that your perceptions are accurate, I think, is a tremendous mantra, lesson, to hold firm. And I heard of that term recently, the cognitive bias is called naive realism, the belief that you see the world objectively, and anyone who disagree with you must be uninformed, irrational, or biased, coined by psychologist Lee Ross.

And I think that’s so perfect. It’s, like, I think that’s almost just like the air we breathe, the water we drink. It’s, like, “Well, yeah,” like you don’t even stop to question that you might be totally off base with your perception. So I love that.

Kerry Siggins
Yeah, we do. Just because you think it, doesn’t make it true. Well, I mean, let’s face it, like we are getting hit  with something like 11 million bits of information per second, and the brain can process something like 50. Your brain is filtering out the vast majority of input that it’s receiving in a given moment.

And so, of course, your perception of reality is not the same as the person next to you. They are processing different information. Those 50 bits can be completely different than your 50 bits.

And so it just comes down to science. Like, your version of reality is simply your version, and it doesn’t mean that it’s accurate, and it doesn’t mean that it’s the next person’s. In fact, it’s not.

Pete Mockaitis
Yeah, that’s dead on. And so when you talk about don’t argue, the notion of spouse, partner, sort of peers, or, you know, you’re the junior to manager, I totally get how not arguing there is great.

Now let’s say, though, you are the boss and, you know, you say, “Hey, I observed dah, dah, dah, dah, dah, dah, dah,” and then, yeah, I don’t know, the person, more or less, says, “Uh-uh.”

And so it’s funny, like, when emotionally, it’s like you’re hooked. It’s like, “Excuse me? Like, this is night and day. I observed this thing. How can you say, you know, the sky is not blue?”

You know, it feels very alerting when someone just, like, straight-up contradicts you, and maybe it just seems like a total unambiguous, unassailable, like fact, you know, rooted in truth and data, how do you not argue when someone just denies what you sure think is true?

Kerry Siggins
Yeah, that’s a really tough one. So here’s the difference. There’s a difference between arguing and debating. And arguing has this sense of emotion in it. And when you argue, people go to their corners and then they get more entrenched in, “No, I’m right,” “No, I’m right.”

And that does not mean, though, that you don’t have a healthy debate. So what I do when somebody says something to me that I believe is simply just not accurate, not true, does not in align with what I perceive it to be, I ask questions, “Okay, you know, that is absolutely not how I see it, but I want to understand from you. Like, where did you come up with that? Help me understand.”

That is such a powerful way to reframe it, “Help me understand,” because then, the person then is going to have to defend their point of view. And then it’s so much easier to say, “Okay, what you just said there, like that’s where I see it differently. Let’s talk about that.” So you can still have a conversation and you can still debate, but when you argue, that is when emotions rise and that’s when people go into their corners.

So when somebody comes back at me as the boss and says, “You know, I disagree with you,” I’m not going to argue with it. I approach it with curiosity, “Okay, tell me why. Give me an example. Show me how. Give me your thought process there.”

And, oftentimes, I can get them to my side because we just talk through it. And sometimes, I’m like, “Oh, you know what? I can see that point of view. I still might not agree with it, but I can accept that point of view.” Curiosity is the antidote to defensiveness, to arguing, to going into your corners.

So that’s how I approach it, is be curious. Because we as leaders, we don’t want to shut people down, we don’t want to make people feel stupid, even when somebody says something stupid, which happens all the time.

Like, you don’t want to make that person feel that way, right? They’re learning, they’re developing, they’re growing, they have their different worldviews. So ask questions and have a dialogue about it. It’s okay to debate. It’s okay to say, “I disagree with you,” but going back and forth and arguing, it’s going to diminish trust and it doesn’t feel good for anybody.

Pete Mockaitis
Okay. Good deal. Thank you. Well, now could you share a favorite quote, something you find inspiring?

Kerry Siggins
I love Brene Brown and, “Clarity is kindness,” is my favorite quote because I have to remind myself, like the example that I gave you of the very first time when I was dancing along the fringes of feedback, the tactical part of feedback, instead of the whole consequence.

I always need to remind myself that clarity is confidence, or clarity is kindness. If I am not being clear in my expectations, in the way that I feel, the way that I think, then how can I expect somebody else to be able to live up to those expectations, meet those expectations, somehow understand me better?

So my favorite quote is, “Clarity is kindness” from Brene Brown.

Pete Mockaitis
Okay. And a favorite book?

Kerry Siggins
I think my favorite book, I use it all the time, is, Good Strategy, Bad Strategy. It helps you define strategy so well. And I use it in all the boards I sit on with the CEOs, and I use it in my own company.

And so, as a CEO, you know, or as a leader, you need to define good strategy and have everybody aligned to it. And I think Good Strategy, Bad Strategy is the best.

Pete Mockaitis
Okay. And a favorite tool?

Kerry Siggins
I mean, ChatGPT, hands down. My life has been changed by AI. Oh, my gosh, I am so much smarter because of the power of that kind of information and automation at my fingertips. It’s amazing.

Pete Mockaitis

All right. And a favorite habit?

Kerry Siggins
Exercising. I love to exercise.

Pete Mockaitis
And a key nugget you share that seems to really connect and resonate with folks, they quote it back to you often?

Kerry Siggins
“Seek to understand,” that phrase is used here throughout my organization. And I said it probably 18 years ago when I started. I was like, “Well, I’m just going to seek to understand here.” And I think it is so powerful.

Before we go and spout our opinion, or get angry about something, if we just said, “No, I’m going to seek to understand,” it would change the dynamic of everything. So seek to understand.

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

Kerry Siggins
You can go to my website, KerrySiggins.com. Everything is there, my book, Talk with Trust; my first book, The Ownership Mindset, which is back here; my podcast, the Kerry Siggins podcast; and everything about speaking, advising, the company that I run, Stone Age, everything is there.

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

Kerry Siggins
Yeah, so I have this amazing Talk with Trust Leadership experience that I do. I can do it virtually and it is game-changing. The companies that I have worked with on it have changed the way that they have difficult conversations and how they lean into them and how they prepare for them.

And so if it’s something that you’re interested in learning more about, reach out to me because I think that there’s nothing more important than learning how to have difficult conversations. So much of the world’s problems come down to crappy communication, and not having difficult conversations well.

Pete Mockaitis
Okay. Kerry, thank you.

Kerry Siggins
Thank you. It’s been so much fun, Pete.