Delegation Archives - How to be Awesome at Your Job

Pete Mockaitis

Kelli, welcome back.

Kelli Thompson

Oh, I’m so excited to talk to you again.

Pete Mockaitis

Me, too. Well, you’ve been talking a lot about shifting from a doer to a leader lately. Tell us, why, of all the topics you could research you’ve chosen this one?

Kelli Thompson

Yeah. Well, I think the things that we need most in our lives, what we’re most guilty of, sometimes become our most common topics. I mean, I don’t know, tell me where I’m wrong. But I just found myself always, and I don’t think I’m alone in this, Pete, in corporate America, I think a lot of times we promote the best doers. And I remember seeing this not only as a leader, I remember experiencing this myself, I remember I experienced this as an HR person. I think we say, “Okay, Pete is the best we have at producing these widgets. He’s amazing. He’s so fast. We should make him a manager.”

And so, I think sometimes what happens in this, we promote this person and we think this magic transformation is going to happen overnight, that tonight you’re going to bed, and tomorrow you’re going to wake up, and go, “Ooh, my new title, my new salary, I’m going to be comfortable delegating, coaching, having hard conversations, and really stop doing all the doing,” when I think, we don’t realize how payoff we get from doing.

Doing feels good. You can check a box. You get a gold star. We were raised our entire lives doing, “Oh, we’re so fast at this,” “You’re so quick,” etc. and it just feels good. And I think, even as a parent, I really have struggled with this, asking myself, “How much am I doing for my child?” So, I don’t think this has leadership implications or work implications. I think, as parents, we see this, too. We see somebody do something that that’s not how we would do it. They do it slower than us. It’s, like, really painful for us to watch. And so, we jump in and we do.

And even now, running my own business, it’s been really hard for me to let go of all the doing. But the problem is my business can’t grow if I’m doing all the doing. And so, I’ve had to hire a lot of help in the last 18 months, and so this topic has never been more important to me, or more relevant to me, in raising a teenager who’s gone off to college, but then also really learning the hard work of letting someone else take care of things for you and do it in their own way.

Pete Mockaitis

That’s really resonant. And as I’m thinking about my kids who are four and six, and then one super young, but it’s like they are capable of cleaning, and yet it is so much harder to ask them 20 times, sometimes literally 20 times, to pick up sort of maybe three key items. It might require 20 requests because they get distracted and they have imaginative play fun, which is adorable, and I sort of hate to put a kabash on that too much but sometimes it’s just not that quick.

And so, it’s like if I actually want the place clean fast, doing it myself is so much faster and less aggravating than asking many, many, many times, as opposed to asking them repeatedly. And so, yes, I could see from an emotional payoff perspective there’s a wide array of tasks in the world of work that would probably feel a whole lot better to just do yourself than to delegate and coach and to feedback-refine through other people to get done.

Kelli Thompson

Absolutely. And you really hit on something important because these are the things that I hear with leaders today, especially folks who are moving into kind of that first jump of leadership. So, they’re moving into team lead, maybe a manager, senior manager, director, is they say things, like, “Kelli, I don’t have time to delegate. I don’t have time to explain this to anyone.” They might say things like, “Kelli, I can’t delegate because people just make too many high-impact mistakes. I have company coming, and so we cannot make any mistakes in this presentation.”

The other thing that I hear a lot is when leaders say, and I remember feeling this, too, and even as a parent, “It makes me feel guilty. I feel guilty that I am delegating this.” It’s almost like I feel like I’m shirking work. But one of the things that I like to remind folks and offer them to consider is that people will make mistakes, expect them. Yes, it is normal to feel all sorts of uncomfortable feelings when you’re delegating because society has told us that our worth oftentimes is tied to our productivity, and, yes, people don’t do things the way that we would do them, and, yes, it can take some time.

But those things are going to be exacerbated when you are delegating and you’re waiting to delegate when the stakes are too high. So, I just want to talk about the overwhelm cycle. So, like, what tends to happen is, let’s just say, we are working on a project, we get more projects put on our plate, and we want to say to all the things because maybe we are in this belief that, “If I say yes to everything, I look capable and confident.” Well, then we get overwhelmed.

And so then, we delegate sometimes out of panic. Even as parents, right, it’s like we hoard and we hoard and we hoard, and, “Oh, my gosh, company is coming in an hour, and I’m delegating out of panic.” And so, when we delegate out of panic, lots of times we’re delegating when the stakes are way too high, when mistakes can’t be made, when it will take a long time to explain something to someone because the project that you’re trying to delegate is just huge.

And so, what happens is the stakes are high, we’re panicked, we delegate, and people make mistakes. Of course, they make mistakes because that’s what we do the first time we try something. And then when people make mistakes, as leaders and as parents, we get frustrated that people make mistakes, and we say, “See, I can’t delegate. I have to take this back. I have to jump in and fix it.” And so, we jump in, and we fix it, and tell ourselves a story, “See, I can’t delegate because nobody can do things as good as I can,” and the whole overwhelm cycle starts again.

So, one of the things I’d offer leaders and parents is to start delegating while the stakes are low. So, I can think of a time where I delegated out a presentation that needed to go to senior leadership, way, way, way too high of stakes because the people made mistakes. They didn’t put the slides together the way I would’ve done it. And so, what did I do? I took it back. And so, I had to learn to say, “Wait a minute. You don’t delegate out a whole presentation. You delegate out one slide. One slide that perhaps the person has expertise or experience in, and you coach them on the delivery of that one slide.”

And we should just hope that people make mistakes because if you’re delegating when the stakes are low, there’s low impact. In fact, those mistakes can be used for learning. When there’s a mistake in that single slide, we can have a coaching moment about it, we can start to talk about it, we can start to talk about delivery and presentation and those sorts of things.

And so, my challenge for you is to really think about, “How can I start to delegate when the stakes are low?” And if you are panicked about someone making a mistake, mistakes are still too high, let’s cut in half. Because here’s the thing, we’ve all learned through making mistakes, and that uncomfortable learning and growth moment, and I think lots of times we feel guilty that we’re dumping or shirking work when, in fact, the opposite is true.

And Gallup research shows us that one of the number-one things that keeps people engaged is the ability to learn and grow on the job. And so, if you’re hoarding all that work, you are not allowing people to learn and grow. And so, how can we create those safe spaces for people to learn and grow, and that’s what’s very low-stakes delegation, so that they can build their rep and confidence? So, when the stakes are high, we’ve got some reps under our belt.

Pete Mockaitis

Well, Kelli, can you tell me, really, what’s at stake for someone who’s an emerging leader who has done a smidge of delegating and coaching, and it’s like, “Nah, this isn’t working so well for me,” so they haven’t really embraced it, and they are continuing to do a lot, maybe 80% plus of what they were doing before? They started taking on the leadership responsibilities as well. Like, just how bad is it to keep on rolling that way if it’s comfortable, and you know you’re awesome at your job?

Kelli Thompson

Yeah, honestly, that, I think is the biggest hurdle is you are, you got promoted because you are awesome at your job. And so, when you get promoted into leadership, guess what? Because you’re awesome at your job you get more projects because they hope that you continue to be awesome at your job. But now, you not only have doing responsibilities, especially if you’re a working manager, but now you also have to hold team meetings, coach your team, develop your team, think strategically, plan for the future.

And so, what I see happen sometimes, and I think what the consequences are of this, is these leaders keep saying yes to these things. And then they often get told, “Well, you’re not being strategic.” “Well, because I haven’t left any time to be strategic because I’m still doing all of the doing.” The other thing that I see happen is burnout. More than ever with my own clients, lots of times they’re coming to me because they are so burnt out.

And when we do a little bit of a calendar audit, one of the things that we see is they are still holding onto and attending meetings that their team members are in. They should’ve stopped attending that meeting six months ago. They’re still hanging on to work projects that are no longer a development opportunity for them. They still just keep doing them because it feels good and they get the rewards and the accolades but they’re exhausted because they’re still doing all the doing, they’re still saying yes to all the things, and they haven’t delegated down.

The real impact, though, and where I see this, especially with the clients that I coach, because they’re coming to me wanting to accelerate in the organization but, unfortunately, it becomes really hard to accelerate in the organization when you continue to hang on to old projects. So, let me just kind of give you an example of what happens. So, they hang on to projects because they are the expert in what they do. And lots of times, that first promotion into leadership, we are managing people in which we have also done the work.

And so, you know what that means, it’s so easy to jump in and do and help and all the things, but as you promote, want to get promoted into leadership, guess what’s going to happen? You are going to start to inherit teams in which you have never done the work. And we see that with senior leaders all the time. They manage teams in which they’ve never done the work. And so, lots of times there’s a crisis of confidence that happens because, before, they got all their confidence and leadership expertise because they knew the work. But now they’re managing teams in which they don’t know the work.

And so, they have to learn how to lead in a whole different way, and that’s why delegation becomes so important. One, because you’re going to need to learn how to expand your leadership team to coaching people in which you’ve never done the work, so you can’t do anymore, but now your job is to coach, to motivate, to inspire, and you can’t do that if you are still hanging on to all those pieces of work that you know how to do, and you can jump in and do it better, faster. It becomes a real kind of skill and confidence crisis as people want to accelerate in the organization. And lots of times, it can really keep them stuck if they’re unwilling to start to delegate when those stakes are low, and test and trust people.

Pete Mockaitis

Kelli, that’s powerful and what a compelling case there. So, when you’re doing the stuff that you need not to be doing, you’re going to burn out, you’re not developing. It might feel good in the moment but developing also feels really good. So, you can just trade it for another source of work pleasure if you’re doing the stuff that is development-y instead of not development-y. And then, ultimately, you’re going to capped in terms of your career progression. It’s like, “Oh, I guess you just don’t have the capability to lead folks doing work that you have not done before because you’re not sort of inching in that direction.”

Okay. So, I’m also curious, could you tell us a hopeful story of someone who was struggling with these very common sorts of challenges and then did some things differently and saw some cool results?

Kelli Thompson

Yeah, so I’ll just throw myself under the bus here. So, I remember early on in my career, I went to my leader, and I said, “Hey, I want to develop my executive presentation skills.” I was that leader who was managing a team that I hadn’t done the work but I had gotten a few other teams, and so I’m thinking big picture, “I want to develop these presentation skills so I can continue to accelerate,” all the things.

And my leader, she was awesome, she goes, “Oh, that sounds great.” She goes, “You know what, all those slides that I have you prepare that I present to the C-suite every month for the month review, I’m gonnahave you come and you just present them.” And I’m like, “Oh, yeah, that sounds great.”

So, I go ahead and I prepare my slides, like I’ve always done, and we go to the top floor of our building, and I’m meeting with the CEO of the company, my boss, my boss’ boss, I think the CFO was there too, and I start presenting, and so far, so good. They’re asking me questions; I know the answers.

Well, what I didn’t know was she had prepped them ahead of time to let them know that I wanted this development opportunity, and I did not know this at the time. But they started to have a little fun with me, I think, and they started to ask me questions that, quite frankly, I didn’t know the answers to. Now, these questions were next-level questions that the senior leaders should be able to know and answer about sales, and revenues, and ratios, and all that sort of stuff.

Pete Mockaitis

“Kelli, how is this going to drive long-term scaleable synergies and keep going on?”

Kelli Thompson
Yeah, it was like that. And so, if you’ve ever been in a meeting like that, like let’s just pause and picture. Like, I’m stammering, my neck is red, I’m pitting out, I’m feeling like a complete idiot. It is so uncomfortable. But I know we’ve all been in meetings like that. And I don’t know who it’s worse for, the person, like me that’s sitting and stammering, or my boss, who is watching the train wreck go down in action.

And I think all of us watching the train wreck, and I know I’ve done this as a leader, have jumped in, interjected, saved the day, answered the questions, but she didn’t. She just sat there silently and gave me space to struggle through and answer the questions. She only answered questions when they were directed at her directly.

And so, the meeting finished, and we get in the elevator and we ride all 40 flights down, and she looked at me, and she said, “So, how do you think that went?” And I’m like, “Oh, my God, it went terrible,” and all the things. She goes, “You know what, Kelli, I prepped them a little bit. They were having a little fun at the end.” She goes, “But those questions are things that you’re going to have to learn how to answer.”

So, she goes, “I have a question for you. Who do you know that always seems to present well in front of senior leadership with those types of high-level questions?” And I actually named off a few people who I really admired. She said, “Great. I want you to go to them, and I want you to find out how they prep. And I want you to incorporate some of those methods so that you can do this again next month when I ask you to do it again.” And I was, like, “Oh, my gosh.”

So, I think we learn a couple of things from that. One, had my manager jumped in to save me, all I would’ve learned was that I only need to prep to a certain amount because, at any point, if this gets too uncomfortable for me or her, she’ll jump in and save. And so, when we do that to people, I know I’ve done that to people, they’re like, “Eh, I only got to do about this much. My manager will come in and take the rest,” and that really limits someone’s development and their learning because we never allow people that uncomfortable space for growth. So, one, she did not jump in and save me.

Number two, she did not tell me what to do. She just said, “How do you think that went? How do you want it to go? Who else do you know that does this well?” Well, she gave me my problem back, she’s like, “You go talk to them, you go figure out new ways, and then let me know how you’re going to present differently the next time.”

And so, she really let me own that discomfort and that struggle. And while it didn’t feel good, she still provided a lot of empathy, “Hey, we’ve all done this the first time. This is totally normal. They were testing you a little bit, so you can relax. You didn’t kill your career.” There’s lots of empathy and compassion but there was also this, “Hey, you have a new problem to solve, and how are you going to go about that for your own personal development?”

Pete Mockaitis

Oh, that’s beautiful. Thank you, Kelli. Well, now can you share with us what are perhaps the mindsets we need to adopt in order to pull this off effectively? And I think the answer to that is mistakes is to be expected, but you have more.

Kelli Thompson

There is. And so, maybe you can ask yourself these questions. I have found in my own life and in all of the hundreds of clients that I’ve worked with, there are four mindsets that keep us saying yes instead of saying no. And when I say, say yes, it’s doing all the doing, saying yes to all the things. Mindset number one is kind of a capability mindset. It’s this belief that, “Oh, if I don’t say yes, people are going to think I’m not capable.”

Then there’s sometimes a people-pleasing mindset, and it’s this, “Oh, gosh, if I don’t say yes, people are really going to be disappointed in me. They’re going to be really unhappy.” We say yes to keep people happy. Then there’s mindset number three. These are our responsible-caretaker mindset folks, where they’re like, “I have to say yes so that I look responsible and people know that I support them.” And then the fourth mindset that I often see is of, like, a perfectionist mindset, “I have to say yes so that I look perfect, and then I’m going to stall and stall and stall in this until it is perfect.”

And so, I think, sometimes, just by recognizing what’s happening in that moment can bring a little bit of self-aware so you can pause, in that way when your leader comes to you, and says, “Hey, can you take on this massive project?” or when you think about continuing to do the things instead of delegating, it’s like, “Wait a minute. Why am I hanging onto this project? Why do I feel that I’m the only one that can do this?”

I know for me, personally, capability mindset was a big thing, “If I delegate this and I delegate all this work, people are going to think I’m not capable, and that’s going to show up in my performance review, and my manager is going to be upset, and then I’m going to get fired,” we go down the whole spiral. So, maybe just really think about what is that mindset that keeps you saying yes, and then ask yourself, “Could the opposite actually be just as true?”

I know one of the things that I learned in my own life, and I know my clients have learned, is that sometimes when I say yes to too much, people actually start to question my capability. Why? Because I’ve said yes to too much. My quality suffers. I turn stuff in late. I don’t get back to people when I promised them. And so, now all my fears of looking incapable have come true.

And so, I think that would be the first place that I would really start is just to go, and we’re going to be like, “Why am I keeping this? Why am I taking this on? Why am I saying yes when I should be delegating and coaching others?” And so, something to take a look at.

Pete Mockaitis

That’s powerful. And it’s funny, when you said when you say yes too much, people’s perception of your capability declines. And where I thought you were going to go with is if there’s a restaurant that has everything in the buffet, like, “Oh, we got pizza, and French fries, and, oh, burgers, and sushi, and Lomi,” it’s like, “Hmm, yeah, I don’t know if you’re actually capable of making all these items well. I actually sort of have less faith in this restaurant as being able to do that.”

So, is that also a phenomenon that happens in the human work perception of each other’s skills domain? I imagine it would. What’s your experience?

Kelli Thompson

Oh, absolutely. So, I often call this rust-out. It’s a type of burnout. And so, you’re right. What can happen? “Because I’m people-pleasing, or I want people to see that I’m capable and responsible so I’m going to say yes to all the things. And now, all of a sudden, I’m running a project, and I’m quasi-managing a sales ops team, and, oh, yeah, why don’t you add in a little bit of training team to that or HR,” right? You have all of these things on the buffet. So, you’re just very mediocre at all of them.

And one of the things that I’ve noticed, and I even notice this for me, personally, especially in running my business because you kind of have to do the buffet of all the things, is those create a ton of energy leaks because my hunch is, and I work on this with my clients, there’s something that probably just totally ignites your energy.

Same with you, Pete, right? You probably do a podcast because you geek out, and it’s exciting, and people know you for it, and every time you come, you’re like, “Yes, this is going to be so fun. We’re going to have a great conversation.” That’s the type of energy that you want to bring into your work because it builds your brand as a leader, is you become known for something.

And so, when you start saying yes to all of these things that are outside your genius zone, at least in my own experience, I face a lot of what I call energy leaks. I was spending my time and energy on things that absolutely drained my energy. And that sort of energy drain creates rust-out. And I call rust-out as not using your talents. You feel rusty, you feel tired, and it’s actually a type of burnout.

And so, I love that you brought up this restaurant that offers too many things on the menu because they’re not known for anything, they’re not doing that one thing that they can do in their genius zone and offer excellently so they become known all over town as the place to go for that thing. And I don’t think leaders are any different. I think it’s so important to find that genius zone. What is it that you’ve been put on this Earth to do? Where do you make the biggest impact for your organization, drive their most revenue, save the most money? And how do you delegate everything that isn’t that?

Because my hunch is, if you’re doing work that’s not in your genius zone, you are robbing the people around you and below you of doing work in their genius zone. I can’t work in a pivot table. But you know what, I’ve got somebody on my team that excel in pivot tables, and numbers is their genius zone. Why would I rob them of that and do it in a mediocre way that just burns me out at the end of the day?

Pete Mockaitis

That is beautiful. And it’s so true in terms of, I think, we can all think of tasks that, really, we’re fired up to do, and tasks that we really, really, really dread doing, and then afterwards we just feel not great.

I also like what you had to say with regards to when you delegate, mistakes are to be expected. And this brings me back to one of my favorite conversations, Episode 528 with Aaron Levy, is that we have an expectation of iteration on certain things, and other things we don’t, and that’s really intriguing. It’s that if you look at that where you have it.

And it’s funny, I’ve been working with a composer to redo the music here – Shoutout to Breakmaster Cylinder – and it’s been really cool how we’ve been going through a lot of iterations, and I don’t mind. I actually really appreciate Breakmaster Cylinder for going through that with me, I appreciate that patience, they’re like, “Hey, here’s the eighth version. Tell me what you think about these things.”

And yet there are other times in which if it doesn’t come back perfect the first time, I’m really annoyed and irritated, and so I’m like, “What’s that about?” I think it has more to do with me than the person who is sending me something. And I think that’s just an intriguing area to explore within our own psyches, is, “Where do we expect mistakes and iterations? And where do we not? And why? And is it fair?” Can you help us sift through a little bit of this mess, Kelli?

Kelli Thompson

Yeah. So, I learned this lesson the hard way, as all hard things are learned. First, when I switched jobs, when I switched careers, and switched industries. And the second time I learned it was when I launched my own business. And so, I remember switching, I moved from banking and I went into, like, a healthcare tech startup.

And in my first 90 days, and I see this a lot with my clients, too, I think there’s this expectation, like, “I’m going to go in, and I’m going to knock their socks off, and I’m going to do all the things and achieve all the results in 90 days or less,” and it doesn’t happen that way. And, in fact, a lot of times you kind of push people the wrong way. People are like, “Gosh, who’s this person coming in and pushing their agenda?”

I had to learn a different way. I had to learn that, actually, your first 90 days should be about learning, “How much can you learn? How much can you ask? How curious can you be?” And when I was working for that tech startup, I had a gift that I didn’t I was going to give me a reading The Lean Startup.

Pete Mockaitis

So good. Eric Ries. Shoutout in the show notes. Link it.

Kelli Thompson

It’s so good. And if you don’t have time to read it, just watch the YouTube summary. You’re going to get everything you need. When I started my own business, I totally had a, “If I’m going to launch this, it better give me all the results I want.” But, thank goodness, I had read that book because I had to change my mindset, that when we try something, when we test something, when we delegate something, our goal should not be results. Our goal should not always be revenue, or perfection, or excellence. Our goal should be learning.

Because if we can go in with that curious, iterative, experimenter’s mindset, Pete, it’s the only reason I’m still in business five years from today, and I haven’t totally burnt myself out, or had unrealistic expectations. But it’s just way more fun. It is just so much more fun to be, like, “I’m going to just test this and just see what happens, see how the world responds to it.” Like, when your only job is curiosity and learning, it is so much more fun. It is so much more freeing.

Like, I know so many people who beat themselves up and it does, it causes depression, burnout when they launch something, and they expect it’s going to be perfect on that first iteration. Like, what a pressure to put yourself under as a leader, and what pressure to put people under us. So, I just find, personally, it is way more fun, and it is so much easier to be a leader for the long game, or be in a business like mine for the long game, when you are just thinking about iterating, and testing, and learning, and just seeing what the world gives back to you.

Pete Mockaitis

It’s so true. And I recently did a keynote speech to a bunch of creators, and it was really fun. And I sort of shared, “Hey, here’s ten of my creations, from books to podcast, to whatever, and you’re going to vote in advance. Was it a hit or was it a dud? And then I will tell you afterwards, and then what lessons I learned.” And so, it’s kind of a fun format we did.

And it was intriguing that, as I took this stroll through memory lane, the majority of the things I created were a dud, particularly the first time around, and then I took some iteration, or you scrap it, like you learn something. And one of the biggest lessons learned is just about sort of validating a concept before you build it. There’s some more Lean Startup action for you.

But what was really cool, some of the audience – shoutout to Jonathan Blevins – said, “You know, this was so encouraging because I’m embarking on this thing, and I put all this pressure on myself, like, this really has to succeed, it really has to succeed. But, no, it could fail and that can be fine.” And it really can.

And so, I loved what you said, in that world of delegating, is you want to give people those opportunities where they can fail and it can be fine because you’ve got some buffer in the deadline, you got a review step before it reaches the super CEO, or the clients who have a huge account with you, or whatever. Like, one way or another, it’s okay to fail, and, in fact, it might even be enjoyable, in so far as you come up with some new learnings and insights and aha-s along the way.

Can you give us some more practical tactical approaches for setting up that kind of safe delegating environmental vibe?

Kelli Thompson

Yeah. So, let me do it from two sides here. Side number one, I just want to continue to reiterate, delegate when the stakes are low. Okay, so let me give you an example from my own life. I didn’t go out and write my book, Closing the Confidence Gap, because it was the first time I’d ever talked about those concepts. Like, “No, we’re not going to go and put that out in a book.”

That book came from years of conversations, curiosity, asking questions, talking to people, and, quite frankly, putting information out. Like, I love sharing content on LinkedIn. I think it’s fun. It’s a good place to iterate and test, “I’m going to share this idea and see if people react to it.” And you know what, the more kind of people engage and react, I’m like, “Okay, I might be onto something. I can expand this and grow it.”

And sometimes, I’ll put stuff out and it is a dud. And so then, I have to ask myself, “Okay, was it tone? Was it too much? Was it too long? Is this idea not resonating right?” It’s really like a lab. And so, I wrote the book through lots and lots and lots of iteration and testing in low-stakes environments. Like, LinkedIn is a low-stakes environment to test ideas. But then we refine those ideas with people and with audiences, and I might share them with a small group, and then it gets into a book.

So, I want you to think about that at work, how we are constantly testing low-stakes environment where we can learn and it feels fun to learn, but I want to flip this and I want to put it also from the person who’s, like, “But, Kelli, I am not a manager. I’m awesome at my job. And because I’m awesome at my job, guess what, everybody wants me to do all the things.”

I want to share with you a tactic that actually my business manager did to me just about a month ago, because, as leaders, I just want to normalize, sometimes we get really excited about things. We read things, and we’re like, “Oh, I’m going to have my team work on this right away,” and we forget everything that we delegated to them the last three months.

So, that was me. I got all jazzed about an idea. I think it was some sort of competitive analysis, and I emailed my business manager, I said, “Hey, Kristen, I just thought about this, and we should do this this week.” And she so beautifully said, “Kelli, here are the three priorities that you gave me in the last month to work on for the business. Would you like me to stop one of these priorities so that you can focus on this one that you came up with today?” And, of course, she was very nice, she was very tactical, and I laughed, I was like, “Well, she’s read my book, and she used my technique on me.”

Because I think, sometimes, we forget, as leaders, what we’ve told people, what people are working on that maybe we forgot to tell them to stop doing, we’re like, “Oh, I forgot to tell them that’s not a priority anymore.” So, I think if you’re an individual contributor who’s awesome at your job, and you don’t want to be burnt out, just have a very intelligent conversation with your leader, and say, “I love that idea. Here’s the three things I’m working on this week because you said they were a priority, and they’re due by the 15th of the month. Is this still the case? Is this still a priority? Or, would you want me to pull one of these off the list so that I can put that one on?”

Like, let’s just have a priorities conversation because, that way, we’re not getting overworked, we’re not getting overloaded. And for somebody who has no one to delegate to, I think it’s a good way to manage up some of those delegation opportunities.

Pete Mockaitis

Beautiful. And tell me, when you’re engaged in some of the coaching, the follow-up, the accountability, the hard conversations, do you have any top do’s or don’ts or favorite scripts you like to use in the course of these conversations?

Kelli Thompson

I like to think of the four P’s. So, when you’re delegating something, talk about the purpose, “Why are we doing this? Why am I asking you to do this? Like, what is the bigger picture?” The second thing that I want folks to focus on is the second P, which is people, “Who is involved?” And when you think about people, “Who are the decision-makers? Who needs to be consulted in your work? And who just needs to be informed?”

And so, that’s a really good conversation to have when you’re delegating something because, then, you can say, “Who is the decision-maker here? Is it you, Pete? Or, is it still me? Do you still need to bring things to me? Or, are you capable of making all the decisions about this project? Who do you need to consult? What stakeholders do you need to talk to before you move forward on any progress? And then when you made these decisions, or you’re doing this work, who do you need to keep informed?”

The third thing is the process. So, I think this is a good conversation to have to say, “Okay, here is where, perhaps, you need to follow some standardized processes.” I used to work in banking, so there were just some rules we had to follow, like, “Hey, here are some rules you have to follow here to get this done, but here’s where you can have leeway.” I think it’s great. Instead of just saying, “Hey, do whatever you want.” I think that can cause a lot of panic in folks. So, let’s communicate what processes or systems do we need to follow here but where you can have a little bit of creativity.

And then the last P is performance. I see people miss this one all the time. I struggle with this one. But be specific about what great outcomes look like, meaning, “What does success look like in this project? Are there ratios we’re trying to achieve? Is there a certain revenue number we’re trying to achieve? Is it a certain number of signups, or money saved, or risks reduced?” Whatever that is, but be specific so that you can communicate to this person.

And I think about, like in my own team, when I’m talking, my business manager helped me implement a customer relationship management system. And so, when I delegated that to her, I said, “We will know we have been successful in choosing the right system because it will do, A, B, and C.” Like, be clear about that so that people aren’t just assuming that they know what the results look like, but we actually have a conversation about what looks like success.

Pete Mockaitis

That’s lovely. Well, Kelli, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Kelli Thompson

I would say, in terms of delegations, I think sometimes, we do, we feel it’s hard. We feel uncomfortable Sometimes we feel guilty. It’s hard sometimes watching other people struggle. It truly is because it evokes feelings in them and in us because sitting in discomfort is not something that we, as humans, enjoy.

But I would really just encourage you just to pause one moment longer. When you’re watching somebody struggle, when you’re watching your child try to clean the living room or use the vacuum, before you jump in, can you pause just one moment longer to allow them to work through that discomfort because that’s where all the learning happens?

Pete Mockaitis

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

Kelli Thompson

Because I love to play the long game. I’ve been really reciting this quote back to myself, which is, “Consistency isn’t sexy but it works. Just showing up every day, playing the long game keeps you from burning out.”

Pete Mockaitis

And a favorite study or experiment or bit of research?

Kelli Thompson

So, every year, I love the McKinsey and LeanIn Women in the Workplace Report. It comes out every year, usually November-ish of every year. And the one I’ve especially been focusing on is this, is that first promotion that happens. And so, what they find is that the talent pipeline breaks down because, for every 100 men that are promoted, 87 women are promoted. And as those job roles continue to accelerate in the organization to the C-suite, it gets less and less and less and less.

Pete Mockaitis

Okay. And a favorite book?

Kelli Thompson

My favorite fiction book I read in the last year was Lessons in Chemistry by Bonnie Garmus. It is fiction but it does read like nonfiction when it talks about, again, women’s role in the workplace in which it takes place. But the book I waited way too long to read was, Never Split the Difference by Chriss Voss.

Pete Mockaitis
Oh, yeah, we had him on the show.

Kelli Thompson

Yes. And so, I won’t give too many spoilers but I will say that that is not a negotiation book. It is an emotional intelligence and empathy book, and I highly recommend all leaders read it.

Pete Mockaitis

And how about a favorite tool, something you use to be awesome at your job?

Kelli Thompson

I don’t know what I’d do without Calendly. It makes everything so easy, so much less back-and-forth.

Pete Mockaitis

And a favorite habit?

Kelli Thompson

My favorite habit is to lift weights almost every morning.

Pete Mockaitis

And is there a key nugget you share, something that really connects and resonates with folks; they quote it back to you often?

Kelli Thompson

“Confidence is a side effect of taking action.” I think, all too often, we wait until we feel confident to take action, but it’s after we take the action that we actually feel the confidence.

Pete Mockaitis

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

Kelli Thompson

You can go to my website, www.KelliRaeThompson.com. I’m Kelli with an I, and then R-A-E. The two places I hang out on social are LinkedIn. So, find me at Kelli Thompson, or Instagram @kelliraethompson.

Pete Mockaitis

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

Kelli Thompson
I would say find that one thing, one tiny thing, even if it you don’t manage people, I bet you can do it in your personal life. What’s one low-stakes item that is draining your energy that you can delegate, either to your children, to an outside company, or to somebody on your team?

Pete Mockaitis

Beautiful. Well, thank you, Kelli. I wish you many successful delegations.

Kelli Thompson

Awesome. Thank you.

Pete Mockaitis
Aaron, welcome back to How to be Awesome at Your Job.

Aaron Schmookler
Thank you for having me, Pete. It’s exciting to be talking to you again.

Pete Mockaitis
Well, I’m excited too. And I was taking a gander at our last conversation. Fun fact, in the transcript of Episode 497, the phrase “Tell me more about that” appeared 13 times.

Aaron Schmookler
Oh, fun that you counted.

Pete Mockaitis
Well, I could just do Control-F find. It’s funny because I think we’re both such fanatical fans of the phrase and how useful it is for a variety of purposes. And, listeners, I recommend you check that out. It may transform your lexicon forever. But I’d love to hear, over the last three years, have there been any interesting stories or discoveries or saves of that day that have emerged with you trying out our favorite phrase?

Aaron Schmookler
Boy, I’m sure that there have been countless times that that has come up. I had already experienced the time when somebody called me a jerk or some other less kind, less family-friendly term, and I said something to the effect of, “Well, clearly, I’ve rubbed you the wrong way. Tell me more about that.” And that turned the relationship around.

Since then, I’m sure it’s helped with the health of my marriage and with my daughter. I’m sure, also, that it’s helped with my business partners and with my clients. It’s such a natural and consistent part of my lexicon now that I don’t think that I have the dramatic stories that I might’ve had when I first started to employ that phrase as a tool.

Pete Mockaitis
Yeah, I hear you. Well, it has continued to serve me well also, particularly when I just need a beat to think, to orient, to, “What the heck is going on right now?” as well as, “I genuinely don’t understand what you said,” and it’s much more friendly than, like, “What the heck are you blathering on about now?”

Aaron Schmookler
“What? That doesn’t make any sense,” is what I’m often tempted to say.

Pete Mockaitis
Okay. Well, good to know. So, now, I’d love to chat with you about delegation. You sent me a beautiful proposal. Thank you for that. And I thought that’s exactly something that we should talk about, so let’s do it. Can you kick us off with any particularly surprising or fascinating or extra counterintuitive discoveries you’ve made about delegation in your 30 years of working with different folks?

Aaron Schmookler
Well, I’ll skip to the end and say I love the book Who Not How. And I’m trying now to remember the name of the author, but “Who Not How,” the premise or the thesis of the book is, essentially, “Stop trying to figure out how to do it. Somebody already knows and they can do it better than you. So, figure out who should be doing this instead of how you are going to do it.”

Pete Mockaitis
I love that so much that I was frantically Googling in the background. It is Dan Sullivan. I believe that’s the strategic coach Dan Sullivan.

Aaron Schmookler
That’s the guy, yeah. Thank you.

Pete Mockaitis
Who’s got a wealth of goodies that I’ve enjoyed.
Who Not How, I think that really holds true. And I am astounded at how people can often do things so much better than me. Maybe I shouldn’t be astounded. I should just expect that by now, having learned it so many times. Where I thought, I’ve got a rental property in Chicago, and I thought, “Okay, I’ve checked out the BiggerPockets podcast, okay, I’ve got a little bit of sensibility associated with finding a bargain and renting it out and making it look okay.”

And then I get a property manager who just, like, ran circles around me in terms of, “Oh, yeah. Well, that’s actually a two-car garage so you just got to paint a really good line in there.” I was like, “Oh, but it’s kind of tight.” He’s like, “Welcome to every parking space in Chicago. Also, here’s how we can make them pay for their own water.” It’s like, “Whoa, you should be doing this and not me.”

Aaron Schmookler
One of the things that’s coming to the top of my mind as you’re sharing that story, as a counterintuitive truth about delegation, when I’m training managers to delegate effectively, one of the questions that I ask them in kind of preparing before we got to the “What are our six-step model looks like?” is I ask them, “What holds you back from delegating?”

And, very often, I get responses like, “I don’t want to give people things that I wouldn’t want to do. I don’t want to just push the scut work off onto somebody else.” And the remarkable truth is all the stuff that I hate doing, somebody else loves.

Pete Mockaitis
It is remarkable and true. Hence, a remarkable truth.

Aaron Schmookler
Right. I thank God every day for inventing accountants, for example.

Pete Mockaitis
Oh, yes. You’re speaking my language, and I love accountants too. I hope I haven’t been harsh on them just because I dislike doing accounting work so much, but if it’s in the realm of bookkeeping or compliance-y things, today, we had to find a title for a car in order to renew a thing, I was like, “What? Is a paper I was supposed to have received in a mail and then held on to for a year? That’s really pushing my capability.”

Aaron Schmookler
As my friend Dave would say, “I resemble that remark.”

Pete Mockaitis
All right, so that’s cool. So, it’s who not how, and Dan Sullivan wrote a great book called just that, which is nifty. And some things we sure dislike doing, other people love doing. That’s cool and a blessing. So, then lay it on us, is there, maybe, a particularly inspiring story to tee this up and get us going, “Oh, yeah, I’m fired up to delegate”? Maybe there’s someone who’s overwhelmed and transformed their effectiveness and their stress levels with delegation. No pressure, Aaron.

Aaron Schmookler
I’ll tell a story from my own history. I don’t know if we talked before, Pete, about the fact that I come from a theater background, and my primary training there was as a director, but on the way, I was also a technical director. And one of the things that the technical director is responsible for is, at the end of the show, the very night that the last audience sees the show, as soon as the audience is out the door and those doors are closed, at that very moment begins what’s called strike and they start tearing down the set.

A lot of it goes, ridiculous amounts of the set goes into the trash, all the lights are removed, those that aren’t part of the regular repertory in the theater. And the technical director’s job at strike is, essentially, to make sure that it goes and that it goes off without a hitch. And the first time that I ever led strike, I remember standing on the stage, I’ve got my tools in my hands, I’m spending a fair amount of time working on the materials myself, and pointing and telling people, “Okay, go do this,” and giving them a single task to do, and people would be flocking to me.

I, eventually, had to put my tools down, and it was just so much work for me to try to direct 23, or something like that, people to go and do this task and then this task, and then this task, and then this task. I was so exhausted at the end of that night that I might as well have done the strike myself in order to have gotten that exhausted, and it wasn’t very effective. And we were there much longer than we should’ve been, and we made much less progress than we should’ve been.

So, I called up the last tech director that I remembered working for and really enjoyed, and I said, “What did I do wrong? What do I need to do better?” And he said, “Okay. Well, tell me about what you did.” So, I told him the story of the night, he said, “You are assigning things task by task. And then he said, “You got to break things down into objectives, what’s the result that you want to see, and put somebody in charge of that result.”

“And when somebody comes to you and says, ‘What do I do next?’ you say, ‘Go join Mary over there,’ or, ‘Go join John over there. He’s got this project and he’ll put you to work.’” And so, by delegating objectives, I was able to create mini-teams of my team. And the next time, we got more done than we had anticipated. We got out earlier than we had anticipated.

And so, just that one shift from delegating or assigning tasks, and this is a distinction that I was expecting to talk to you about by the end of our conversation, this distinction between assigning tasks and delegating end results, delegating outcomes, was tremendously powerful for me in an instant.

Pete Mockaitis
I love it, and it really does resonate. I am thinking about events. When you talked about striking the stage, like, “Oh, I did some theater stuff back in the day.” And some events, like putting on these, it was called HOBY, Hugh O’Brien Youth Leadership, sophomore leadership seminars for high school students, as well as my wedding. Like, one of my favorite things to do was carve out zones of responsibility for people.

And sometimes, I even like to make up new names. It’s like, “Okay, Michelle, you’re fantastic and I’m going to trust you to be the person who answers all of the guests’ questions that they would like answered when me and my bride would rather not be tied to our phones on our wedding day.”

Aaron Schmookler
There you go.

Pete Mockaitis
Because I’ve been on both sides of that equation in terms of, “Oh, I’ve got some questions but it’s not quite clear. Like, where do I go? What do I do? Can I do this at the wedding? I don’t want to bother the bride and groom but I kind of like to know.” And so, I was like, “Michelle, you are the director of guest experience. That’s your role. And we’re letting all the guests know, ‘If you have any questions, you call Michelle.” And so, that was really cool.

And for HOBY, we got someone who’s talented with design things but she didn’t want to be in charge of the whole programming thing, so we said, “You are the artistic director. If there’s any sort of color or logo or design or image that goes on a T-shirt or a booklet or a nametag or a door decoration, you are the master of that.” And she’s like, “Oh, sweet.” I knew it was fun for both of us because it decimates ambiguity, it was like, “Oh, that’s me.” It’s like, “Oh, lights? You say lights, Aaron, that’s me.” “Oh, did you say the huge backdrop? Oh, that’s me.” And you get to feel good when you own that thing.

Aaron Schmookler
That’s right. That’s right. And I’ve created an event recently that we called “I’m not participating in this recession.” And it was an event for C-suite folks to come to. I had a CEO, who had been the CEO of SOG Knives, to come because he had taken his company through some recessions. And one of the things that he shared with our attendees was that he likes to make people the CEO of their realm within his company because it just creates so much leverage for him to be able to say, “You handle this.”

And one of the things that I advise, when people are contemplating, “Can I delegate this?” is that if somebody can do a job up to 75% as well as you can, 75% is a good marker to say to them, “You, go take care of this.” Because if you can delegate to three people 75% of what you could accomplish, well, the leverage of all that multiplicity is tremendous.

Aaron Schmookler
Seventy-five percent of three things is much better than 100% of one.

Pete Mockaitis
Yeah, I dig that. And I think it’s really useful to note, “The thing that you’re delegating, is it super crazy mission-critical?” Like, there are very few things in this world, although there are some, in which if you do it a hair better, the rewards are huge. I’m thinking about maybe direct-response copywriting. I’m thinking about Google search engine optimization. I’m thinking about Olympic swimming. Hundredth of a second, like, gold versus nothing.

Aaron Schmookler
Yes, that’s correct.

Pete Mockaitis
But almost everything else is, “You can do this 75% as well? Well, then have at it, and away we go.”

Aaron Schmookler
Especially within our companies, part of the time and effort that we put in our companies is on the core competency of our company, “This is what we do. This is what we do different from other people. This is what we do better than other people. This is what you have come to us for. Everything else in our company is not that.”

Pete Mockaitis
That’s right. Bookkeeping, you didn’t come here. Or, invoicing. Yeah, that’s good. All right. Well, lovely concepts. Now, you actually have a pretty precise five or six, depending on how we’re counting, steps for effective delegation. Can you walk us through these?

Aaron Schmookler
Sure. And you’ve hinted at the idea that this is a six-step model with five steps, in a way, because step zero, I’m considering step zero because, though this is the first step in delegating, it is just you, all by yourself, getting yourself ready to go and do the delegation. And there are some questions for you to answer before you go and do that.

One, “What is the desired outcome? What do you want? What is the end state that you need to have accomplished?” In the military, they call this commander’s intent, “What’s the commander’s intent?” It sounds simple but it’s often very hard, and one way to get there is to think about, “Why do I want this done?” That will help you to conceive what is the end result look like.

So, then when you’ve got your end result mapped out, you also need to answer the question, “When do I need to have this result in hand? And, therefore, what’s a decent margin for failing?” So, if I’m going to delegate something to you, Pete, that I need on Friday by 3:00, if I asked you to deliver it to me by Friday at 3:00, I’ve set us both up to be in real trouble. Better that I should ask you for it by Thursday at noon so that we’ve got time to look it over, make some adjustments, figure out that we’ve got problems, resolve them before I need the thing.

The next question to ask yourself, and we’re still in step zero, is, “Who will be served by taking on this responsibility? And who is able to serve the purpose?” That’s kind of a two-part question. So, who is the right person because they’re going to be served by this? Maybe they really enjoy this kind of work. Or, when I have somebody working for me, I ask them, “Where do you want your career to end up? Where do you want your career to be a year, five years down the line? Okay, what skills and talents are you going to need to get there? Oh, well, this project is going to serve you developing that. So, that is a good reason to give this to you, also, because you’re going to be capable of serving the purpose.”

And then the last question to ask yourself, but still in prep, is, “What are they going to need to succeed? What’s the information that they’re going to need? What resources are they going to need?” And do not skip this one, “What authority, what decision-making authority are they going to need in order to succeed?” That’s step zero before you even begin to delegate, preparing yourself to be ready.

Pete Mockaitis
Okay. And then, I’m wondering, for those who have a hard time letting go, delegating, they might say, “Well, nobody is sufficiently qualified or able to handle this.” How do we respond to that?

Aaron Schmookler
Two things. One is, “Are you sure?” We talked already about that 75% rule. If somebody is going to be able to deliver 75%, then maybe it’s time to reassess what nobody looks like. The second thought that I have is Dennis Bakke wrote a book called Joy at Work in which he suggests that you push decision-making down. And in delegating, he says, “You can set parameters. Without withdrawing the authority to make decisions, you can set parameters.”

So, if I delegate to you, Pete, and I think you don’t have the judgment yet, I might say, “I want you to talk to Betty and Bob about everything that you’re considering before you make the decision. At the end of the day, the decision is yours, and I want you to have the benefit of their insights before you make the final decision.” So, that’s another way of cranking up people’s capability while leaving their decision-making authority intact.

And I’ve actually thought of a third thing to share, which is, “If they can’t do the whole thing, what parts of it can they do? What parts of it can you delegate and then maybe you retain the rest?”

Pete Mockaitis
That’s good. All right. I like that notion of the parameters. So, one of it could be, “If it’s you get the input from these people, another one could be if it’s over X thousand dollars or whatever, then you check in with me,” or, “If it’s concerning super client A, B, or C, I want to know about it. If it’s any dozens of other clients, have at it.”

Cool. So, we’ve got the parameters, so it’s not a sort of 100% carte blanche, “It’s all yours,” but rather, “Okay, here’s a slice of it,” and it may very well still be the vast majority, which is cool. All right, so that’s step zero. What’s our step one?

Aaron Schmookler
Step one, and this one is a little bit counterintuitive, is to ask somebody, to give them something to do without giving them any details. And this is counterintuitive on a couple of levels. When we’re training managers, some people push back on the idea that they should ask anybody anything instead of just simply telling them, “Hey, here’s what you’re going to do.”

And then the other reason that they push back is they say, “What do you mean with no details?” So, here’s what I mean, “Hey, Pete, can I get your help with something?” “Pete, may I give you a project?”

Pete Mockaitis
It’s so funny, like, when you asked me that, you’ve galvanized my attention but maybe in an anxious kind of a way, it’s like, “Ahh, what do you have in mind exactly, Aaron?” And maybe…

Aaron Schmookler
So, the maybe is important because the maybe is correct, and we’ll get to that in a moment. The galvanizing your attention is the biggest part of this. One is I’m treating with respect by asking for permission. And then I can’t count the number of times, somebody will poke their head into my office and simply start to ask me questions, and my attention is on whatever I’m doing, and I have no idea what they’ve said, it goes in one ear and out the other.

And with my attention deficit disorder, and I’m very much like this, and even neurotypical people are like this as well, we all need a basket to put things in. So, when you say, “Can I get your help with something? Can I give you a project? Can I give you a new responsibility?” I now have a basket to put all of the details that you’re going to give me in and create order for my brain, and that’s going to serve everybody.

And with respect to the anxiety that I’ve created, largely that’s because you and I don’t have a relationship where we’re doing this, where you know what’s going to come next. So, one of the things that I recommend to any manager or anybody who’s in a position to be delegating is to tell people in advance, “Hey, when I delegate to you, here’s what it’s going to look like. I’m going to go through these six steps.”

“And what this step I’m going to do before I even get to you, then I’m going to come and I’m going to ask you, ‘Can I get your help with something?’ I’m going to ask you, ‘Can I give you a new responsibility?’” And no is a perfectly good answer, and here are the other steps that I’m going to go through so that that anxiety is alleviated in advance by your knowing, “Okay, this is just step one in a five-step process.”

Pete Mockaitis
Certainly. And then I think you say no is the acceptable answer to, “Can I get your help with something?” I guess, also, maybe any number of context-sharing things, like, “Well, I feel wildly overwhelmed by this crazy important task that’s due in two hours, but what did you have in mind?”

Aaron Schmookler
Right. And if you tell me you have a crazy important task that’s due in two hours, I’m going to say, either, “Thank you for telling me, Pete, you’re not the right person,” or, “Oh, well, this is not pressing. Why don’t I come to you three hours from now to give you a chance to get that turned in and catch your breath?”

Pete Mockaitis
That’s good.

Aaron Schmookler
So, that takes us to step two, which is now we’re going to lay out the details of who does what by when, what is it that I’m asking you for. And there’s another podcast called Manager Tools, and one of the things that they suggest at this point in any delegation is that instead of delegating the task be done, delegate the reporting that it is done.

And I think that is just a brilliant insight to say, instead of, “Hey, Pete, will you do this?” to say, “Hey, Pete, please tell me by 3:00 p.m. on Thursday that this is complete,” or, “Please send me an email with the file of this report by 3:00 p.m. on Thursday.” So, you’re delegating the reporting because if I don’t know it’s done, it has no value to me.

So, delegate the reporting, “Tell me as soon as this is complete. Here’s the outcome I’m looking for,” the manager’s intent, what is the end state, rather than all of the meticulous details, “Here’s the deadline and here are some resources, here are some considerations, here’s the authority that you have.” When I say consideration, that might be you might be tempted. If I’m asking you to rent us a truck, I might say, “The last time we went to U-Hall, we had these problems, so consider looking at Penske and Budget before you go talking to U-Hall.” So, that’s step two, is to lay out what it is that I’m asking for.

Pete Mockaitis
All right. So you’re elaborating, so who does what, by when, to what standard, for what reason, with what resources. Can you elaborate a little bit on the standard? Like, how can we go about unpacking and delineating what is good optimal acceptable versus what is not?

Aaron Schmookler
So, you’re going to want to ask yourself the question of, “What do I need to see?” So, the standard for a truck might include it needs those rails on the wall that you can latch things to. The standard might include the budget. The standard might include the size of the truck. If I’m asking you to create a report, the standard might include margins for error.

Or, if I’m asking you to design something, the standard might be, “I want this to look opulent.” What are the ways that you can describe what it should look like, what it should feel like, what it should be like? And what are the questions that you’re going to be asking when you assess its success?

Aaron Schmookler
In other words, how do we know if you’ve succeeded at the end? Are there no grammatical errors? Are there no spelling errors? Does that matter? And perfectionism, when we talk about perfectionism, perfectionism is somebody insisting that they go beyond the standard, which wastes time, effort, and peace of mind.

Pete Mockaitis
Yeah, okay. Cool. Well, now, can you share with us the step three, negotiate?

Aaron Schmookler
Yeah. So, step three, as you said, is to negotiate, “I asked you if I could give you something. You said yes. And you said yes sight unseen, or maybe you said it depends, so you don’t know what…you didn’t know until now what I was asking for.” So, at this point, the negotiation includes asking the questions, “Okay, now that you know what I’m asking for, Pete, are you still in? Does this still work for you? Do you have what you need?”

“I’ve told you about these resources, I’ve told you about that authority, I’ve given you these tools. Is there anything else that you need that I haven’t thought of? Do you need help? Do you need people? People are some of the resources that you might need. And if you’re tempted to say no, and/or if you’re not sure how to meet the rest of your obligations, then we may be reallocating your other priorities and your other responsibilities.”

“I don’t have time to do that because I’ve got this.” “Oh, well, let’s delay the deadline on that,” or, “Okay, let me take back this thing that I was trying to delegate to you because, clearly, this isn’t going to fit on your plate,” or, “Let’s take this other thing off your plate and give it to somebody else so that you have the bandwidth to handle this.” So, the negotiation is, “Okay, what will it take to make this work if, in fact, it does?”

Pete Mockaitis
Okay. And then step four?
Aaron Schmookler
So, step four is to keep in touch, and this is very often an overlooked step because people say, “Okay, go do this. I’ll see you at the end.” Tools for this include if you’re a manager having weekly one-on-ones where you’re checking in with your direct report, or the weekly one-on-one is focused on your relationship in general where you keep touch, “How is this going?”

Or, if this is a longer-term project, you set, “Here’s the final deadline,” that there are benchmarks along the way, “Here’s how we know we’re on track. This is going to be accomplished three weeks away from the deadline,” “This is going to be accomplished four weeks away from the deadline,” “This is going to be accomplished five weeks away from the deadline.” So, you’re keeping touch of, “Are we on track at each of those benchmark locations?” And you’re checking in on the standards at those times as well.

So, you create a channel for reporting and keep in touch at least weekly, at least briefly. So, that’s step four, is to make sure that you’re keeping in touch.

Pete Mockaitis
At least weekly, that’s handy. And then you mentioned that fine is not a status report in terms of, “Hey, how are things going?” “Fine.” What more precisely are we looking to hear when we’re keeping in touch?

Aaron Schmookler
Here’s where the benchmarks come in, “Oh, well, I’m two days behind on this benchmark,” or, “I’m two days ahead. I’ve reached this benchmark even though it’s not actually due until two days from now.” So, that’s one thing. Or, a status report is, “We’re on track and, in terms of we’ve hit all the benchmarks, up until now. And there’s an obstacle emerging that I didn’t anticipate. Let’s talk about how I might get around this obstacle. Can I have your insight?” Or, “I’m going to need a $100 or $1,000 to level this obstacle that’s come up.” “The price of lumber has changed.”

Pete Mockaitis
Okay. And then step five, debrief?

Aaron Schmookler
Step five is after the fact. So, arguably, this isn’t part of a delegation model. It’s part of a checking in, and I think it needs to be there because I don’t consider it complete until we’ve learned what there is to learn from the process that we just went through, “What worked and what didn’t? What worked in terms of how our communication went? What worked in terms of my execution of what you delegated to me? What worked in terms of did our standard actually meet the need?”

“I delivered this entirely on standard. This is exactly what we designed and it still didn’t solve the problem that this project was intended to solve. So, what needs to change?” So, a few questions to ask here, “What do we need to keep? What do we need to stop, to just get rid of this entirely? This was completely extraneous. What do we need to add? What wasn’t there that needs to be there? And what do we need to adjust? We got the blue one, it was the wrong blue. Or, we got these but, instead of five, we need seven.”

So, what do we need to keep, what do we need to stop, what do we need to add, what do we need to adjust. And that takes us, Pete, through six steps if you include step zero to prepare yourself for the delegation.

Pete Mockaitis
Okay. And then maybe zooming out or cutting across all these steps, what are some of the top things that make all the difference for preventing disasters, disappointments, oopsies, and stressful moments?

Aaron Schmookler
So, I’ll start with perhaps the answer that people are going to like the least. I remember when I took my first advanced level biology class in college was a genetics class. And I sat down for the first exam, and I looked at the cover sheet of the exam, and what it said was, “This is one test in one class, in one part of your schooling, which is just one part of your life. Your performance on this exam, while it may be important right now, is not critical to the outcome of your life, so don’t fret.” That was the cover page of this exam.

And then I opened up the exam, and the first question was, “For ten points, what color is a Golden Retriever? Hint: Look at its name.” So, that story is intended, Pete, to illustrate that part of how you can prevent disasters is by chilling out, both because the things that you’re thinking of as disasters are probably not as disastrous as you think they are, and because fearing disaster makes disaster more likely. And so, one illustration that I love about this, I used to be a hang glider pilot.

Pete Mockaitis
Oh, cool.

Aaron Schmookler
And when you land a hand glider, generally, you’re looking for a big open field to land the hang glider in. And what happens more often than you would imagine is that there’s a big open field with one tree in the middle, and the hang glider pilot hits the tree in the middle. There’s lots of open space, and the hang glider pilot flies right into the tree.

And the reason is that in the fear and anxiety of not wanting to hit the tree, the pilot looks at the tree. And your brain is designed to take you where you’re looking. Millions of years of evolution have made our brains direct where we go to where we’re looking. So, if you’re looking for a disaster, you are much more likely to steer into it. Look instead for the clear open field, and you think, “Open field. Open field. Okay, there’s the tree, that’s where I don’t want to go,” and then you spend the bulk of your time and attention on, “Here’s where I do want to go. Here’s where I do want to go.”

Another part of the answer to your question, Pete, is to consider those benchmarks, and to really not get lazy about checking in with those benchmarks, and assessing along the way, as part of your keep in touch step, “Do these benchmarks still make sense or do they need to be reassessed? Are we still on target to meet the deadline? Are we still on standard? Are we getting further and further? If we start to fall behind, are we getting further and further behind, or are we finding that, over time, we’re catching up?” So, those are a few of the thoughts that I have about that question.

[39:21]

Pete Mockaitis
All right. And then when it comes to micromanaging, I think folks don’t like being micromanaged, and, on the flipside, managers are scared to be micromanaging. How do we make sure we strike this balance appropriately?

Aaron Schmookler
Micromanaging is about backseat driving. It’s about checking in so regularly that people can’t get into a flow. Micromanaging is about making decisions that other people could make. It is not about the frequency of your check-in, provided you’re allowing people to accomplish stuff and get into a flow state before your next check-in. People are so afraid of micromanaging in my experience. The tyranny of micromanagement is the fear of micromanaging far more often than the tyranny of micromanagement is actual micromanagement.

Pete Mockaitis
Okay. Well, so that’s reassuring and comforting. So, then any maybe pro tips or indicators, like, “Oh, you might be getting close to that line”?

Aaron Schmookler
Of micromanagement?

Pete Mockaitis
Yeah.

Aaron Schmookler
If you are tempted to take back the project that you’ve given to somebody, think twice. Taking back the delegation is often a piece of micromanagement. If you are trying to get marginal improvement by changing the decisions that they have made, you’re very likely micromanaging. And it’s important to think about… micromanagers are very often, what they’re trying to do is risk management, “I don’t want this to go badly. I want this to go as well as it possibly could. I want the outcome to be 100%.”

The risk there, the risk that you actually attain is demoralizing people, is losing the leverage that you have as somebody who can delegate, to get more than one thing done at a time. And so, if you are wasting human capital, if you are wasting people’s potential and fulfillment in pursuit of marginal accomplishment, you are a micromanager. It’s time to rethink your priorities.

Pete Mockaitis
Okay. Well, now, Aaron, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Aaron Schmookler
I’m glad you brought up micromanagement because that probably would’ve been how I would’ve answered that question. I think I’m ready for favorite things.

Pete Mockaitis
Let’s do it. Could you share a favorite quote, something you find inspiring?

Aaron Schmookler
This quote is often attributed to Goethe and it, evidently, is not his, and it’s not known where it came from. So, it is, “Whatever you can do or dream you can, begin it. Boldness has genius, power, and magic in it.”

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

Aaron Schmookler
there’s an experiment around something called enclothed cognition.

Pete Mockaitis
Oh, yeah.

Aaron Schmookler
And enclothed cognition is, essentially, enclothed, meaning the clothes that you are wearing, cognition, meaning thought. And so, this experiment took people and put them in a smock, like a painter’s smock, and asked them to do accounting work, like work on a spreadsheet, the kind of stuff that you and I were talking about we don’t really like.

And wearing a smock, they were worse than if they were just wearing their normal clothes at doing that task. And wearing a lab coat, they were better than they were at doing that task than if they were just wearing their normal street clothes. And by contrast, if they were asked to do something creative, like create a painting, then they were better wearing the smock than they were in their normal street clothes. And if you put them in a lab coat, they were worse at being creative and original and interesting in creating their art than they were…worse in a lab coat than they were in their street clothes. Fascinating.

Pete Mockaitis
Okay. And a favorite book?

Aaron Schmookler
Today, I’m going to name Never Split the Difference by Chris Voss. A very compelling book about negotiation.

Pete Mockaitis
And a favorite tool, something you use to be awesome at your job.

Aaron Schmookler
I love Calendly. I’m not that great at tracking administrative details, so being able to give somebody either a link to go and book time on my calendar, or Calendly gives you this one-off meeting thing where I can tell you, “Here are a bunch of times. Click one and you’ll appear instantly on my calendar.” Very, very useful for me.

Pete Mockaitis
All right. And a favorite habit?

Aaron Schmookler
“One more” is my favorite habit right now. There’s a lot to do in my life, as there is in all or our lives. And I might go to the sink that’s maybe full of the day’s dishes and start to wash the dishes and start to be tempted to go, “I’m feeling hungry. I want to go dirty another dish.” And I just say, “One more.” And one more will often get me all the way through all the dishes, or all the phone calls that I need to make, or any of those things. So, I have a habit right now of saying, “One more,” when I start to feel like, “I’ve got to move on from this.”

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

Aaron Schmookler
I’ve mentioned some of the manager training that we’ve been doing lately, and this is something that hits all managers, I think, where they live. I’ve had CEOs audibly kind of get hit, they sound like they’ve just been punched in the stomach when I say, “If there’s no consequence for consistently missing a job requirement, then that thing is not actually a job requirement. It’s something that you’ve put on your wish list and it’s a resentment-builder.”

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

Aaron Schmookler
You can find me on LinkedIn. I’m the only Aaron Schmookler on LinkedIn. And you can find me on all the work that we’re doing at TheYesWorks.com.

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

Aaron Schmookler
Yeah, I’ll stay in keeping with the theme of the day – delegate. Go delegate. Are you not good at it? Delegate it. Are you not interested in it? Delegate it. You don’t have time? Delegate it. Delegate it. Go delegate. There’s almost nobody that I know who delegates too much, but there are lots of people that I know who delegate too little. Myself included, by the way.

Pete Mockaitis
All right. Aaron, this has been a treat. I wish much luck and fun in all your delegations.

Aaron Schmookler
Well, thank you. Likewise, right back at you.