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Getting Things Done in a System of Imperfect People with Wes Winham Winter

“If you are someone who needs to get a task done in a hurry, which is probably most of us, you have to treat the same person differently, depending on what the task is.”

In his first leadership role, Wes Winham Winler, now CEO and Founder of Woven, was the only software engineer at a startup, and it was his job to build a team. He was lucky with his first few hires, but struggled to lead them effectively. Over time and with some well-timed advice, he learned to leverage his team’s talents and give equal attention to the feeling side of leadership.

In this episode, Wes shares how he leverages his own strengths and weaknesses to be a better leader and get more done through delegation. Listen in to hear how to find the right tools for the right person and focus on the hard problems facing customers. It’s time to get more done and bring the power back to the people.

After You Listen:

Key Takeaways:

  • Take a more individualized approach to your people to better delegate tasks and communicate ideas
  • Keep yourself organized with reminders of smaller tasks to avoid last-minute scrambles
  • Bring the same sincerity of public forums to one-on-one conversations to maintain personal connections with your team

Things to listen for:

  • [02:19] Lightning round with Wes
  • [08:14] Listening to influential leaders
  • [13:23] How to achieve results through others
  • [25:02] The importance of being sincere in business
  • [34:24] Craig’s takeaways


[00:00:00] Craig: As a leader, I had a strict no hugging rule, and then one day I broke. This is Executive Evolution. I’m Craig Anderson and my mission is to equip accidental leaders like me with the confidence, competence, and calm to level up their leadership. Leadership isn’t all about goal setting and KPIs and outcomes.

In many ways, it’s a people game. We spend a big chunk of our lives at work and we’re not robots. Our people bring their skills and talents to our business, and they also bring themselves with all the rough edges and emotions. A quick story, as I said, I had a no hugging rule. My team knew it. They even made fun of me for it, but it was a very strict rule.

And then one day during an exercise with my leadership team meeting, one of my team members broke down into tears over a personal issue that she was dealing with that really came up during this exercise. And in that moment I knew that the person was more important than the rule. I reached over, gave her a hug and let her know it was gonna be okay, because that was the right thing to do in the moment because people are important to our business and people have feelings, and when we tend to those feelings, we can be more successful as a leader.

My guest today is Wes Winham. He is the founder and CEO of woven. And there came a time in his career as an engineer that he realized he could get more from his people when he tuned into their feelings. So let’s bring on Wes and hear the story of his executive evolution. Before we jump into kind of our opening round of questions, why don’t you tell us just in a couple minutes here about woven,

[00:01:45] Wes Winham: Sure. Woven is the the first developer hiring platform built for senior engineer. . senior engineers are different. you have to treat them better. You have to move faster on them. we like to say senior engineers are not just three junior engineers stacked in a trench coat. It’s just not junior engineering, but more. And we assess and handle inbound and, bring in talent network that, uh, reflects what is different about senior engineer.

[00:02:12] Craig: That sounded great niche for you guys. So Wes, what we always like to do is to get to know you with three quick questions to kind of jump out of the gate. So if you’re ready to get started, we’ll jump right in. Question one, what is the best leadership book you have ever read?

[00:02:28] Wes Winham: the most impactful one for me is a classic, is how to win friends, influence people, that. special to me. Since then, I’ve, there’s like a, a combo of books I read. I, I think a lot of leadership is about how to get leverage for you personally, and that’s different for everyone. And I was, there’s a book called A First Rate Madness, which is about, it’s kind of about mental illness.

It’s about how John F. Kennedy, was manic depressive and, Winston Churchill, maybe the. And how they structured their, their day and how they used their strengths and weaknesses to get a lot done, to accomplish a lot. and there’s also a book called The Power Broker by Robert Carro, which is about Robert Moses, the guy who essentially shaped New York City, all of the parks and national parks and just, he just built a lot and made a lot of things happen in a time when New York City really needed it and it wasn’t happening.

all of these very flawed charact. But one of the things that picked up from those books is that all of these people had ways to get leverage for theirselves. So for example, Kennedy was famous for having a meeting and, like rattling off a memo to one, to an EA right after the meeting. And you would have this experience where you talked to Kennedy and when you drove back to your office by the time you got there, there would be a memo waiting for you to.

About the next steps. So he was just brutally efficient at, getting work done through other people. Robert Moses had the same setup where he actually had a car of people that would follow his car around the city as he was moving from meeting to meeting. And at any time he could stop. And say, I need this done.

You know, this was before the internet, and someone would get out of his car with instructions on the task and what to do next, jump in the other car and go, get something done. So these were like tactically people that were just very good at, like getting things done through other.

[00:04:28] Craig: and as you’ve kind of grown in your business and through your career, is that leverage a piece that you’re finding is helping you achieve your goals?

[00:04:36] Wes Winham: For me personally, it’s a thing that I need to remind myself constantly. My background is as a software engineer, and I just really love the work and the details sometimes. And if I don’t remind myself constantly to give away my, Legos, give away my toys, don’t do this myself, find a way to enable someone else to do this, or like pass on my context, then I get stuck doing work that I love and I fulfill on, but it’s low leverage.

And at the end of the week I’m like, oh my. the stuff that only I could do didn’t get done, and some stuff that honestly, someone else could do did get done. that’s my weakness. That’s why I try to remind myself of it. And when I do well, I do things like fire off a voice memo that’s like, fine, and it’s good enough to be a starting point, or I’ll spend time to drop context of a problem instead of diving into, solve the problem or write the problem myself.

[00:05:28] Craig: I love it. So yeah, really just figuring out how to best manage your time so you’re working at your highest level self as often as possible.

[00:05:36] Wes Winham: and just like very practical tools to do that because I think everyone knows Delegate, but like, delegate, like it’s easier said than done cuz the delegation always, , micromanagement is a bad term there’s a period where I did it really, I, I did lots of micromanagement.

My team hated me sometimes for it, but we got stuff done and then there was a period where I overreacted and I would give not enough context, too much freedom for the person. And now I’ve kind of settled back into like, more like a task relevant maturity model where for some people I can fire off an eight minute voice memo that’s, , it’s not very good, but because I’m working with someone that knows how to turn those into a piece of content that I can go edit, it’s good enough for other people.

We need to do a working session and just being like very aware of that, like the right tool for that person. So voice memos is a big one that’s leveraged for me at least.

[00:06:32] Craig: Yeah, that reminds me a lot of something. I talked with some of my clients about the situational leadership model where you’re kind of working with people where they’re at and in their own development. Every time you’re delegating a task to the. ’em, and it sounds like you’re very context specific based on the person that you’re working with

[00:06:47] Wes Winham: Absolutely. a mistake is to think of a leader as, you know, they have this level of competency and trust is the case that we all have. , we’re all spiky, right? We are great at some things and new at others, and I used to treat people as like, oh, this person, they get it. They’re super smart.

but if they’ve never done this thing before, at a high level, I need to interact with them. Like I would someone that was much earlier career and like being able to talk about that and, draw out that they haven’t done this before. So, hey, should we do a kickoff meeting together? versus, hey, this is a, a seasoned executive.

I can just trust them for everything. And the reality is, if you are someone who needs to get results on a hurry, which is probably most of us, you have. treat the same person differently. , depending on what the task is and what the project is.

[00:07:38] Craig: Yeah. That’s brilliant. And being able to read, that’s gonna make you so much more efficient and reduce the need to actually do that overmanaging and micromanaging you’re trying to avoid.

[00:07:46] Wes Winham: Yep. the rubber banding, we call it seagoing. I don’t, I can’t remember where we picked up the term. It’s like you, you swoop in on someone and you drop stuff on them, and then leave is just the worst. It’s like better to, I think it’s a little bit better for someone to be like, ah, why are they, you know, kind of up in my business side at the start of this project. And then, you get more freedom as you go rather than too much freedom in the start and you swoop in seagull and everybody feels bad about that.

[00:08:12] Craig: Yeah, I love it. I love it. All right. Question number two, who is your leadership crush?

[00:08:20] Wes Winham: it used to be Elon Musk was my answer for this since like 2007, and he was, figuring out how to go to space and build electric cars. Now I think people read too much in into recent. You know, it’s, it’s no longer a useful example. I do think, maybe Robert Moses is the less politicized version of this.

Both very flawed people, but what I admire in them, so I, I’m autistic. It means I have some strengths and some weaknesses. Definitely some weaknesses, and I. , I see some of that shape in both of those people. And for Moses, he was someone who early in his career was an idealist, was great at the work in this case, a design, especially like urban design, architecture, just threw himself one of the work, love that and hit a level where, he realized that if he wasn’t able to help convince people, the people.

Were in power, in this case, in in kind of local, government. He was not gonna be able to achieve what he wants. And he edited this. there was this period where he basically got kicked out of his profession. Like he couldn’t get a job anywhere because he was unwilling or unable to play. to, play politics is probably the negative way to say it, but the positive way to say that is to think about the humans involved in the system and what their needs are, and.

What’s gonna be harder for them? So he was like drummed out of this profession in his early thirties where he could, it would be easy to guess that this promising person, uh, was gonna make no impact. And he had a mentor that really taught him about the nuts and bolts of how to think about getting things done in a system of, imperfect people who are working on limited information, who don’t always care about your goal. And he went from someone… I would say essentially inept to someone who, reshaped New York mostly for the better. Although, I think with a modern lens we can see a lot of things that heated wrong and could have done differently. But, it’s hard to argue with all of the parks that would’ve been private residences and.

All of the, the beaches that are now amazing, amazing public properties that just wouldn’t exist otherwise and would be otherwise some rich person’s, Beachside resort. Like he really did create good work because he combined like excellence in the actual planning and craft with, excellence in the ability to think how to navigate leadership, in kind of, The levers of persuasion and and power.

[00:10:55] Craig: and it’s a fascinating piece on kind of evolving leadership When you think about. You know you’re very good at something and then you hit a wall because now you need a new talent to get to the next level. And he kind of hit that wall and had to, fortunately had someone in his orbit who came in and showed him how to make that next leap.

[00:11:14] Wes Winham: to his credit, he listened to that person, but also he was kind of at the end of his rope. So, yeah, I think he, he got a little lucky that someone’s willing to take him under his wing and teach him that new skill at a time when, he wasn’t listening for years and years before that just really took that bottom me out to be open to that learning.

So hopefully we were all open to that learning before completely bottoming out.

[00:11:36] Craig: Yeah, it’s really two lessons for the new leaders who I really target this podcast to. You know, be open to that feedback when you get it. But for the more experienced leaders, just think about the change you can make by taking that person under your wing and showing them how to kind of take their career to the next level. So it’s really both takes both sides to really make this work.

[00:11:56] Wes Winham: Yeah, it did take a mentor, willing to work with someone who is, kind of a jerk, like, uh, inconsiderate, right? There’s a lot of downside to being will willing to w work with that, young, uh, Robert Moses. but the, uh, the impact on that was, was huge.

[00:12:14] Craig: All right, and last question of our first round. In 10 words or less, how would you define leadership?

[00:12:20] Wes Winham: the ability to achieve results through others, I think is my favorite definition. I can’t remember who I stole that from, but I, I like that one a lot.

[00:12:28] Craig: it’s so true and it’s a kind of a re recurring theme is, is it’s making that transition from being really good at something yourself into a leadership role. Well, now you have to do it through other people, and you’ve gotta inspire through that vision. You’ve gotta give people the freedom and not do that seagull management that you talked about a few minutes ago.

[00:12:47] Wes Winham: that’s easy to fall into the Seagul. It’s easy to not, give away your Legos. I also think it’s easy to. , to not put in the time to become excellent at aircraft. I think that is pretty necessary, increasingly necessary. It kind of doesn’t matter what it is, as long as it’s important.

I suppose if you are. I don’t know, the best stationary designer that’s, uh, well, I don’t know, maybe the, the folks at Hallmark. That’s really the thing that, that gets you to the executive theme is being an amazing stationary designer at Hallmark. But, so I’ll, I’ll just say it’s gotta be, you know, gotta put the time in to be excellent at some craft.

[00:13:23] Craig: Yeah. And that’s, that’s some of the things that I talk about is this idea of accidental leaders, people who are really, really good at something and they’re successful, and suddenly now they’re in charge and they’ve gotta figure out what’s, how do I transition now from being really good at something?

To getting that really good something done through others You now have to get things done through other people, but still have that passion that you felt when you were doing the work yourself.

[00:13:48] Wes Winham: that was my story. I was the only software engineer at a startup. Things started going well, so we needed to build more stuff quickly. I guess that was gonna be me that was gonna hire and, manage the team cuz there’s no one else there to do lucky with the first few hires.

Was able to bring on people who were fairly self-managing and at least, at least of a personality type where we could be very, very focused on the work. And they were, I would say, pretty forgiving in retrospect of my inability to let go of some of the decisions. and looking back, Common failure mode for me was someone would come with something that was like 90 or 95% correct.

And I had something that I would thought was like 97% correct. And they would walk away from that conversation with the impression that they were very far off and now they needed to do Wes’ idea. And that just I, I could never forget why that kind of didn’t work. I was like, why is this? Slow or like, I thought we agreed on this, like why it feels like, you know, something’s off.

whereas what I’ve learned now is if we are, we’re 3% off from being a hundred percent right. I need to focus in that conversation, in that interaction. And the most important thing is giving them support for their idea first, and then we can come back and talk about the 3%. Once it is very clear that this is their idea, this is their proposal.

Now, if they’re 50% of the way there, that’s not the right tactic. there’s some coaching, coaching questions. probably that’s a sign that I didn’t provide enough guidance upfront and I should’ve, we should’ve started together. But that case where someone was like almost there and I would talk about the 3% variance and that’s what stuck in their mind and things would get much slower.

And that was a pattern that hit me over and over. Cause. , I love the work. I read about it all the time. I read people’s postmortems on how their software projects failed. I had built a lot of things, before my career even started just trying things out. So I’d learned these lessons and I’m like, oh, oh man, if you do it this way, if this, this field is a, uh, you make it a boo when really this should be an enum, it’s gonna be really hard to migrate down the field, like, you know, technical details.

And that’s what they walk away from. be less motivated to go do Wes’ thing.

[00:16:14] Craig: as you said, this was probably your first leadership role, so how did you learn that lesson? that I need to not focus on the three and focus on the 97. Was there a precipitating event? Was there someone who, who kind of interceded for you? How did you figure that out?

[00:16:29] Wes Winham: It took years. I worked with a new product manager who gave me that feedback is like, it was, she, she was particularly good at I think like, emotional reflection and like having hard conversations.

How so how you’re feeling. And I’d mostly worked with engineers at that point who, you know, there’s a, uh, we all have feelings. Feelings matter a lot. They are driving a lot of what we like to describe as facts. And if you are unwilling or unable to talk about the feeling layer, then sometimes it’s just like a fact layer that doesn’t make sense.

It’s like, okay, you don’t like this proposal, this architecture proposal. But the reasons you gave are like obviously dumb. So like you’re not dumb. I don’t know what’s going on here, but I’m not gonna pay attention to this. versus. It feels like you talked about this proposal as just like very, very bad.

So I’m not, you know, that’s, that’s surprising to me. I kind of feel bad about it and then it’s, it’s like, oh, once someone points out that they’re feeling bad, it’s not that the advice is bad, the feedback is wrong, it’s that they’re feeling bad. That was kind of an unlock to me as like, okay, it’s not that I am.

Not getting my point across about the work or the proposal. It is, I am, do it in a way that is, uh, resulting in people feeling bad, and that’s a lot more actionable, right? So I don’t have to change my proposal. I have to change what order I say things or I need to make sure and spend more time on the agreement points early.

Or I need to stop and ask a question and make sure they, they realize that we’re 95% aligned before I dive into the feedback. I had misidentified the problem and getting that feeling level feedback from someone explicitly was kind of eye-opening.

[00:18:21] Craig: I bet. And you would even think in a world of engineering, right? This is an, this is a world of facts, so where would feelings even come into the equation? But we’re also all human

[00:18:31] Wes Winham: Yep.

[00:18:32] Craig: and that human peace is what’s really keeping us up at night, not the facts. And you found a way to tap into that. through this one person who was just super helpful with that.

[00:18:42] Wes Winham: Yeah, and it was, it was a moment where I like unlocked a lot of like previous things that didn’t make sense. Like we have one engineer I worked with who was, just a pattern, which he was always resistant to initial. and it, it almost felt like he was coming up with random reasons. While it was bad, that just like didn’t make sense.

And I was like, what is going on this? why does it take this person so long to think through the problem? And no, that was just a personality characteristic. they’re just somewhat, we all have like a, a slider on how open wear to change his slider was all the way to one direction. and this might be obvious to everyone else, but I do, um, a model that’s worked well for me is I’m not great at intuiting.

Personality traits and characteristics and like just intuitively adapting. So I kind of think of people as walking around with like sliders, like settings, on key points. And one of those is like openness to change and just having a mental model of like, all right, of the people that are on my team and like maybe the next level down, who are the folks that are.

Resistance to change. How can I not give them proposals cuz it will drain them? until I’ve talked to the people who like, like change to run those ideas by them first and then, we can come with something more polished. And again, this is probably obvious to everyone else here, but that was not at all obvious to me that cuz I love change.

It’s like, I love entrepreneurship, leadership, like doing new stuff. It’s super fun. That’s just like how I’m wired.

[00:20:07] Craig: so what I hear you saying in all this is just like with Robert Moses, there was a point in time where he started to realize through that mentor or whatever mechanism that that people aspect really came in.

And for you, it’s kind of putting people on these sliders. Once you’ve started to kind of see that piece, tying into kind of that emotional piece or the feeling piece as you said, what difference did you see in how the team reacted to you when you were able to tap into that?

[00:20:32] Wes Winham: For me, like my, my experience is we got to have more conversations about the hard problems facing our customers or hard engineering architecture problems or product flow problems. We started to have conversations that were more. , like it’s hard to solve any of those types of problems. Like, what characteristics do you look for in an executive hire?

You need to get feedback from your board. And for me, sometimes I would be, I would have those conversations, but I felt like, ah, didn’t feel like we were all talking about the problem, when in reality we were all like, we’re all doing like lizard brain things like, okay, is this, oh, these executive characteristics are what we’re talking about.

Is this a reflection on me? So do I need to advocate for a thing that’s kind of like me, otherwise that’s kind of like, it’s kind of a threat, right? And it’s just like you have a conversation and you’re like, oh man, that was not as good as it as it felt like it should have been for like the caliber of people have in the room.

So just feeling like, you got to have more of your brain focused on the really hard. Problems for your customers or, or the businesses facing. And that feels really good. But honestly, I would say, you know, half of the time it’s, for me, it’s noticing, it’s that moment where I notice I’m confused. I’m like, okay, that didn’t quite go.

It’s not going the way I thought. And for me, like. , like some people will just like get better at it naturally. I, I, I talk to some people and it’s like, oh, that preamble they just gave to start that meeting. I should totally steal that and do that more often. Cause that’s gonna set people in the right intention upfront.

It only took 20 seconds. some people need to hear it. And what I actually do is I’ll. Farther down the problem, and I’ll realize, all right, something’s not going right. And then I kind of run through my checklist of like, all right, what are people feeling right now? And then I’ll remember to go back and usually can, you know, can save it at this point.

but for me it’s mostly like noticing, when things are going off the rails and having a toolkit, to kind of address it. Like running through my model of, the sliders for people in the room and what they might be.

[00:22:50] Craig: Yeah, and it sounds like that’s really helped you, as you said, now that you’re paying attention to those things, it sounds like maybe there’s more openness in your meetings. People are talking about customer experiences versus just the facts, and it seems like you’re really able to tap more into maybe those success characteristics around your customers, even through this change.

[00:23:09] Wes Winham: Yeah, we can talk about, uh, success characteristics with customers. Like people are bringing data and problem solving tools to the equation rather than being stuck in like that. , you know, we, we have a new idea or new topic. the first like step is to evaluate it as like friend or foe.

Is this a threat? And if it, uh, if it triggers any of that, is this a threat to me personally or things I care about? Then you’re getting nothing from that person for the actual problem of like identifying characteristics of your most successful customers or, whatever your craft is at the time. If it’s marketing and ICP definition, you’re getting nothing from that person. In that conversation, they are thinking, oh, we’ve already done ICP work. I was involved in that project. The fact that we’re bringing that up again is that because I did bad work. Does Wes think I’m bad at this?

Uh, like, oh, why is that? Person from sales in there. I think this is more like a marketing territory thing versus starting the meeting. Say like, Hey, I know we did market, uh, ICP definition nine months ago. It worked pretty well. this is really important though, cuz the world has changed in the last nine months.

We’ve learned some new things. So we’re ringing in some new people to incorporate new facts. And it’s like, okay, now I. , took the threat. Someone might be feeling about judgment on their prior work, encroachment on territory. And with that preamble if I’m smart, I have diffused the most common like fear response people would have.

In reality, I’m not always smart and I’m just like, man, I’m not hearing anything from Casey. And then I’ll like through. Something in, in the middle of the interview where I can ask someone about that or, maybe give a leading question about like, you know, when you were here last time, uh, when we did the I CCP definition, you know, what was kind of different about the world. It’s better to do as a preamble, but it’s okay to notice, notice you’re confused and do it as a question as.

[00:25:02] Craig: Yeah. Yeah. So that, you know, and you said it took you 10 years to figure this out, but once you did, it’s really made some big changes. as you think about your role today as the CEO and the founder of Woven, what are some of the other things that you’ve taken away that have made you a more effective leader today? As you’re growing.

[00:25:20] Wes Winham: I think that I have, I have kept on leadership is, my, my boss or c e o at, but my last job was really good at thanking people for specific things, and it seems small. Or at least it kind of, it, it seems small to 23 year old me. It’s like, that’s my job. Of course I’m gonna do that. I don’t thanks for that, but I was also like, you know, if I get honest with myself, it kind of felt good to hear that from the CEO e o, and he did it. everywhere he did it, really specific, like, you know, I appreciate you getting that to me early. Or like, the headline on that was great or like, or, you know, just like very small affirmations for things you did well.

And I just saw it impact the team and everyone around him. So that’s something I started to model and I think I’m, I am decent at thanking people for things they do and. being polite in asks, I think is kind of underrated, especially in text mediums where your tone doesn’t come through. So like, being really specific would please and thank you and emojis. I think, it really makes an impact. And, this slack first world where body language and and tone are,not coming through.

[00:26:32] Craig: Yeah, just imagine somehow through our interaction with the mouse, people could perceive our body language in Slack. so building that in, again, this becomes more of the people side of leadership or the, the feeling side of leadership. Keeping that so it doesn’t seem disingenuous, cuz a lot of times you have leaders who in the big public forum will thank people and it’s very, expansive and you. Seems very meaningful, but then in the one-to-one interactions, it’s not there. Do you see that creates kind of a dissonance for people when, when you’re working on that level and, and how do you make sure you always feel like you are being authentic or that they feel you’re authentic?

[00:27:11] Wes Winham: So the idea is you. you might give general thanks in public forums, but not kind of have the same focus on thanking people in like private forums in one-to-one.

[00:27:22] Craig: Yeah, you’re kind of scripted to thank people in the big town hall meeting, but then when you’re interacting with people, you’re more the seagull guy, right. Then, you know, do you see that dissonance, especially kind of in this world of, and again, I, this is such a stereotypical thing, but you always think of, the engineering piece is not so much focused on that.

So how is that working in your world?

[00:27:43] Wes Winham: Yeah, I definitely believe people notice that, especially if your public scripted thank you does not demonstrate understanding of the specifics of someone’s work, like you can’t thank someone for a piece of marketing content that you haven’t read in and possibly even complimented a specific piece of, I think it just really land, a bad habit I sometimes have is like, for very quantifiable positions like SDRs, I will sometimes compliment. Hitting a number. And I think that, I think congratulations, I think is, is one thing, but like complimenting and thanks for hitting a number, I think is not a good move.

And I’ve moved away from that cuz I got a couple, a couple really good pieces of, of feedback that it felt like when, that was my primary source of compliment, that they felt like a number, a machine to hit a number. So what I’ve switched to do is complimenting. Controllables for those sort of like roles where the job is really hard, you have to do this much work and you get outputs. So complimenting their like behavior where I see it rather than, the fact that they hit quota, for example.

[00:28:56] Craig: Yeah. And it seems, Wes, you know, as I think about this, you’re the founder, you’re the ceo, you’re dealing with investors, you’re dealing with clients. You’re dealing with all these moving pieces. Yet you’ve trained yourself to really be focused in on people. How are you finding the time in such a busy world to make sure you’re emphasizing that.

[00:29:19] Wes Winham: I would say I recognize how important that is, but I feel like I’m failing at this every day. That’s what my, feeling is. , the people matter more than I’m allocating time for. So I can tell you, like, I don’t feel like I am succeeding here, but I can tell you what I do. So for me, I have this problem where I feel like I think about what’s in front of me and I kind of don’t think about other things and I need lots of reminders to remember.

I’ll forget that my birthday’s coming up until it’s like a week away. Like, I don’t think of it. it’s not like I’m thinking about myself. I’m like thinking about nothing. I’m thinking about this book. I read about how they, the atomic bomb project worked and how many things had to go. You know, I’m thinking about stuff like that.

Um, so I have to come up with like specific reminder. Specific rituals and cadences to do this. So I literally have a Slack reminder that goes off once a week and it says, how many one-on-one reach outs did you do this week there was part of me that like, feels icky for needing to do that, but part of me is also like, you know, I, I think I should get credit for having set that and for listening to it and, taking, five minutes to go send some, some slack messages to people.

As I think about ’em, it’s probably pretty common, but in our all hands we have a high fives and kudos section. We compliment people on hidden milestones and also living our values. And I take, care to set a timer when I do my five 15, which is like my 15 minute update to put folks on our team on what I did this week to also use that time to brainstorm some high fives and kudos.

So I always have two or three and I use them strategically. So I go last and I figure out I probably have more than I, more than three. But I look for the ones that wouldn’t otherwise get called out so that folks are getting recognized, on things that maybe are less visible. those are probably, and then, 5 15 is actually a pretty good one is that probably worth explaining what a five 15 is?

[00:31:16] Craig: Probably. Yeah. Yeah.

[00:31:17] Wes Winham: it’s a text update. There are many like it, this one is just, the idea is you spend 15 minutes writing about your week highlights and challenges and observations or is the, the, the format I use and I also rate my week one to 10 with kind of headline, and then it takes you 15 minute, right? You post it in Slack or. and then other people are doing your theirs and it takes you less than five minutes to read. So for me, when I see those, I’ll go through and like try to make one comment on those. So it like is a forcing function for me to think about someone’s work to. Try to add something that’s, like non-critical there, and go on. we also do quarterly reminders for personnel exercises where we identify folks who are doing really well, and that just reminds me to go do things. I, I feel like I need reminders over and over. So that’s kind of what I’ve built up. I scrape by with systems

[00:32:10] Craig: Yeah, but when I think back to your earlier examples of some of the leaders that, you know, the leadership crushes with Kennedy and Moses, right? They built systems as well. It’s not a disingenuous system, right? That you’ve built. You’ve built, this is important to you, but it’s also not native. So you’ve created systems to make sure you’re doing the things that are important.I, I think it’s brilliant. It’s a great way to make sure you’re getting the things done. So we, here you are running your company, but there’s also that 25 year old leader that was you. I think you said you were 25 in that first leadership role. If you could step into a time machine right now and go back to that person who was just told they have to hire a team, what’s the one piece of advice you would share with.That would help them the most.

[00:32:56] Wes Winham: Okay, I gotta figure out what Wes would listen to, right? Because there’s a, there’s the thing that I need to believe and the thing that I need to hear are sometimes not always the same. And that, you know, that kid, had some opinions I would say keep reading how to Win Friends and, influence people every year.

Don’t stop doing that. And when you’re thinking about systems and the work, realize that people’s motivation, is often more about how much they believe this is their idea and they have control and autonomy than about whether they believe something will. So don’t make trade offs between feelings of autonomy and some, hypothetical better version of the week work. If you can help it.

[00:33:46] Craig: That’s perfect. I love that. it’s a great way to look at it. not only what would be the advice that would be helpful, but what is the advice 25 year old me would listen to, . Cuz that’s such a crucial criteria. Well, Wes, thank you for being on Executive Evolution today. If people wanna connect with you, learn more about you, where are the best places for them to

[00:34:04] Wes Winham: Sure. I’m, Wes Winham on LinkedIn, w I n h a m, and same thing on Twitter. I love questions. I love when people call me out when my, overly broad claims seem wrong. So please come, come to social media and disagree with me. I enjoy it.

[00:34:20] Craig: As always on the Executive Evolution Podcast, I like to break down some of the key messages from our guests in the areas of leadership. Confidence, confidence, and calm In our discussion with Wes today, let’s talk about confidence. Confidence is when, as a leader, you realize that when your team brings you 97% of the answer that they’re gonna be working on, as Wes talked, You let them go from there and build off that 97%.

You don’t worry about your own insecurities and focus on the 3% that you don’t see there. A Confident Leader focuses on the 97% effort that his team’s at right now let’s them get through that work. and then when you are bringing the project home.

That’s when you can address the 3% to really finish off the product. We also had a great conversation about confidence in our time talking about delegation. What I really loved about Wes’ realization with delegation is delegation isn’t just telling people to go do things. Delegation is meeting people where they are and getting them moving forward.

Whether that means I can leave them a 32nd voice memo and they can run with it from there, or if I know where they’re at in their own development, I’m gonna need to spend 15 minutes or 30 minutes in a conversation to get them up. And. So that’s a level of leadership confidence when you realize everybody needs to be met where they are.

And then finally, one of the things I really appreciated was how he brings calm into his leadership instead of worrying about am I getting enough touches in with my people and have I done these things? He has systematized something that he knows is very important for his business, but that’s not always top of mind for him.

So he has created systems through Slack and other operations like the five 15. That allows him to make sure he’s doing something that’s very important, but not always very apparent to him. And when you’re getting those things done, they’re not something you worry about in the middle of the night.

They’re something that you know is scheduled into a trusted system that allows you to be calm as a leader. So I really want to compliment Wes on his great exhibitions of confidence, confidence, and calm in our conversation today.

Thanks for listening to the Executive Evolution Podcast. Remember, leaders aren’t born, they’re made, and you can go from being an accidental leader and evolving all the way to the greatest of all time leader when you build out your confidence, confidence, and calm. I’d love to hear more from you. You can find me on LinkedIn, Craig p Anderson.

There’s a lot more content than just the podcast there. Would love to have you link up with me, engage. Let me know your thoughts on the podcast or any of the other posts that I made. We’ll see you next time in the Executive Evolution Podcast.