TLDR;
Ever wonder why some teams thrive through chaos while others crumble?
It’s not about micromanagement or perfect plans—it’s about trust. It’s about fierce loyalty.
In this powerful episode, I, Michael Hunter, and DocuSign’s Director of Engineering, Wes Clines, decode the true essence of an uncommon leader.
Wes shares his battle-tested “hacks” to transform teams through transparency, consistency, and non-negotiable, genuine communications.
More than just theory, this conversation offers a peek into a leader’s essential toolkit, showing you how to move beyond management and truly begin to lead.
Discover how investing in genuine connection, embracing imperfection, and fostering open dialogue creates a culture where people don’t just perform—they’re empowered, resilient, and ready to follow you anywhere.
Ready to transform your leadership and unleash your team’s full, untapped potential?
Tune into the full Uncommon Leadership Podcast episode now!
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Your learnings from the podcast:
- Transparency cultivates trust. Openly communicate “why” and how decisions are made to build psychological safety.
- A leader’s reactions to mistakes (learning over blame) can empower teams to take strategic risks.
- Prioritizing deep, 1-on-1 connections can help uncover individual talents, strengths, and weaknesses.
- Embrace continuous progress and learning from inevitable mistakes for sustainable team performance.
- Lead beyond management through genuine connection, driving higher output and retention.
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Want to get in touch with the speakers?
About Wes Clines:
Wes Clines is the Director of Engineering at DocuSign, leading developer infrastructure and tools teams. With a rich background from his 15 years at Microsoft, Wes is passionate about fostering authentic team cultures built on trust and open communication. Connect with Wes Clines on LinkedIn by clicking here: https://www.linkedin.com/in/wes-clines/
About Michael Hunter:
Michael Hunter is the founder of Uncommon Teams and the host of the Uncommon Leadership Podcast. He is dedicated to exploring leadership principles that empower individuals to lead with authenticity and impact. You can connect with Michael Hunter by clicking on this link:
https://uncommonteams.com/work-with-me/
Watch the Uncommon Leadership Podcast:
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Presented By: Uncommon Change
Transcript:
Michael Hunter
Whether you want more innovation, more easily, you’re feeling burnt out or overwhelmed, or you simply know that something isn’t quite the way you know it can be. You are not alone. I hear the same from leaders every day. On Uncommon Leadership, we explore aligning personal fulfillment with business success, creating authentic teams, and cultivating the resilience, adaptability, and ease necessary to move beyond simply surviving today’s challenges into thriving.
I’m Michael Hunter, and today we will uncover fresh insights into what it means to lead uncommonly. Joining me today is Wes Clines. Wes is the director of engineering at DocuSign for their developer infrastructure and tools teams. Prior to this role, he spent 15 years at Microsoft starting as an individual contributor on the .NET framework before joining the Bing organization and managing multiple teams.
Welcome, Wes.
Wes Clines
Thank you for having me. Excited to be here.
Michael
I am excited for this conversation. When did you first recognize Wes, that integrating your whole self, bringing that into everything you do, might be a valuable approach?
Wes
So I was thinking about this, and I think it all distills down to when I started at Microsoft, I got my second manager, which, as you might imagine, happens, you know, not infrequently at Microsoft.
And that gave me a little bit of context to kind of compare and contrast, both style differences, so to speak. And, you know, when my second manager, Tom came in, you know, it was a very stark change, both in transparency and authenticity. You know, basically under his leadership I got a little bit more of the full picture and I think I could derive a little bit more meaning and purpose out of my work, and that certainly was, I think one of the first things that I still to this day kind of think of as that turning point.
I mean, you know, this I think, was a year into my professional career, and at least at the time of Microsoft, I mean, still probably some truth to this day. It was a place that certainly emphasized high performance and achievement, but I think what Tom brought was a little bit of levity, to create a little bit more of a positive and a bit of a cohesive environment and team.
And when I take a step back and look, I saw kind of my own performance and even the approach that I took to, you know, my work fundamentally changed. And I, that was for the first time, I kind of internalized how that came about. And I think really being able to see how different managers or leaders interact, both with the team and other leaders, gives you a little bit more perspective on the different approaches on how various different people get things done and how that kind of rolls down to the team and how culture is derived from, you know, how these leaders interact and how these leaders manage down and up.
And that second kind of manager was, because Microsoft was my first job outta college, so I was still bright-eyed and bushy-tailed. And that was kind of the first time where I got a different side of, I guess, Microsoft at that point in time. And having a little bit more of a differential in leadership helped me, I think, recognize that different styles are for different people and they get different results just based upon kind of the person that you are and what you bring to the table and to a certain extent what you bring to the company.
Michael
You still seem pretty bright-eyed, Wes. I can’t tell how bushy your tail is, though.
Wes
I try to, you know, keep that out there. Right. I mean, I think that I’d like to think that I’m a positive person in general, and I like to keep things light. But still, you know, again, with a focus on, you know, we’re all here to do a job and, you know, you choose to spend it at a company, you’re not forced to.
And naturally, you wanna keep good people, and you know, keep them on their growth journey. And I think having a little bit more of a positive spin and not always having that, you know, deadlines are getting missed, you know, the world is about to fall down. Having a little bit of a different approach is something that’s kind of stuck with me, and I try as I might to bring that to bear.
But, you know, I’m not always successful. I think, you know, we always have a room for improvement there.
Michael
Thank goodness. It’s a lot easier to not be perfect when being perfect is pretty much impossible.
Wes
Yeah, no, I think it’s, you know, it’s always about, when I, went back to school to get my MBA and there was a professor there, you know, you don’t need to be perfect, just pretty good, pretty good’s, a lot closer to perfect than you might think.
And you know, when you’re chasing perfection, you are inevitably always in forever fall up short. And that can, you know, if you’re constantly, you know, getting data on yourself and seeing, you know, the absolute worst of your game, or even worse than that, seeing that in others and never having that, you know, positive side, it can, you know, spiral outta control.
And I think that’s a lot of times how teams, you know, become divided and not unified.
Michael
Yes. If we go back a second to your first manager and then Tom, your second manager, what’s an example of a situation that really showed you the difference between those two styles?
Wes
There was, I will never forget this interaction. Not that it was super negative, but it’s always kind of stuck with me. So, you know, like any engineer would, or at least what I think an engineer would do, you know, fresh outta college. You know, I’d never had any formal computer science training, so that’s probably, you know, more, a little bit more descriptive and you know, kind of intuitive.
But the; I think the thing that really stuck with me was I had at that time really tried hard to kind of catch up. I’m working with some of the most brilliant people that to this day I’ve ever met. Like everybody is super smart. Like it was a great place to be, but I found myself really putting in a ton of effort, both in, you know, intention and to a certain extent, hours.
I think that there were three or four times where I just didn’t leave the office overnight, ’cause we were trying to get things done and obviously, as you might imagine, you can only do that so long before you kind of crash and burn. Right? And I had taken my foot off the gas a little bit. I was still, to be clear, still putting in full days and getting things done, but certainly not at the velocity that I had been when I was more or less burning myself out. And I think, I wanna say it was around midyear or maybe kind of in between midyear and annual, one of those two things. It might have been like three-quarters of the way through the year, I think. And I was in a one-on-one, and we were kind of going through, kind of my performance, just a little bit of a check-in.
And, you know, out of nowhere he’s like, Hey, you know, I noticed that, you know, your throughput isn’t as much as it used to be, like when you first started out, you know, and that I, vividly remember sitting in, you know, the chair in his office thinking like, did I fail here? Like, what’s going on? And, you know, I didn’t really say much at the time, but, you know, I, like most of the focus, I just wanted to finish the conversation and get out of there.
Right? Because it was the first time I’d ever heard really anything. I don’t know if I would say negative or perhaps constructive in my life. And I’m like, okay, great. I’m gonna figure out a way to, you know, just hammer this out, right?
And, you know, improve. And then, you know, I think it was later that night when I was kind of thinking through that feedback and trying to process it. And when I take a step back, it was, he had no idea that I was staying at the office many, times over through the night, working through the night to meet deadlines.
And I think historically growing up, it was one of those things where, you know, just, you know, bite down, hang on, and just try to power through and not giving that context, right? And so when I got that feedback, I mean, technically speaking, valid, but it was one of those things where, I don’t think he understands how much I’m putting in this.
Is that, is my level of effort now bad? And, you know, I was just kinda left in the lurch and, you know, I would say the quality of the feedback wasn’t particularly great. But when I switched managers, or this manager left the company and we got a new manager, and I was explaining this kind of situation through him, or to him, excuse me.
The way that he kind of works with me through, it wasn’t so much focused on my performance relative to my performance, but performance relative to expectations, right? He is like, No, you are doing great. Like you don’t need to change anything. I wish I could clone you three times over, which very different types of feedback.
And I think in that first one it just, I didn’t really understand. You know, there were not enough hours in the day to make this manager happy or, you know, deliver to him what he needed to deliver to his management chain and leadership. And you know, when, you just see one side of, okay, there’s a whole lot of delivery and then it drops off.
I mean, certainly that’s something to, you know, ask about. Right? But it wasn’t, Hey, you know, what’s going on? Like, are you struggling? Like, how can I help you? It wasn’t from that sense of how do I help you get back on track? Or perhaps was the track that you were on sustainable? Most definitely was not. And when, you know, taking that transition to Tom, my second manager, you know, he really took the time to kind of figure out, you know, what was going on.
He made it relatable to himself, like when he, you know, was first starting out and things like that. And so, while the focus still was on the delivery, the what went into that and how it was, you know, affecting me as a person, me as an engineer, and honestly, how I felt about Microsoft culture at that point in time.
I think this was 2007, I want to say. And it took, you know, probably that next whole year for me to truly understand, okay, no, I might have, you know, bouts of great performance and then I might not like, you know, we’re not robots and, you know, it’s a little bit of a roller coaster. And his point was, you know, we don’t like roller coasters.
We want just consistent things. And you know, it’s not a straight line, but don’t kill yourself, but still focus on, you know, delivery. And I think juxtaposing those two experiences and that those two types of feedback, I mean, it was very clear that, you know, Tom brought everything about his experience to the table and, you know, he would relate to his own personal failures.
I mean, here’s what I’m good at, here’s what I’m not good at, right? And, leaning into it versus trying to hide your weaknesses away in a closet and, you know, not deal with them. Like, Hey, this is not done. Why is it not done? And kind of being, you know, on the verge of militant and regimented versus let’s understand, you know, qualitatively what is going on and how do we fix it.
So, you know, there are a lot of learnings in those first two years, and I think I got, you know, really the both sides of that fence early on. And that’s certainly kind of stuck with me, you know, in my own growth journey. You know, even transitioning from IC to management and leadership and things like that.
Michael
It sounds like manager number one made an observation about a concrete fact. And then didn’t go anywhere else, didn’t ask any questions, curiosity-based or otherwise, about why that was. Didn’t give any context on whether this was good, bad, or indifferent. Left you to assume that it was bad because he was asking. He had no idea what to do with it or how to change in a way that would make him happy, whereas manager number two gave you the context, asked those curiosity-based questions, helped you understand where you were relative to what you were being, what you should have been evaluated on.
Who knows what the first guy was evaluating on because he never told you. Right? Job ladders are there to give guidance as to what you should be being evaluated on. It sounds like that’s what manager number two, Tom, was doing. And so, of course, you felt more heard, more seen, more appreciated, and way more willing to go above and beyond when that was necessary.
Wes
Absolutely. You know, I’ve always kind of internalized, like, I just internalized this basic metric. Hey, would your team follow you into the dark? Right? When I sum up, hey, am I being a good leader would, and it’s, you know, it’s not just about, you know, blind faith, but more often than not, if there are things people are scared of, you know, whether it’s a, challenge, you know, internally, you know, we call them big bets.
And it’s not abundantly clear how on earth are we gonna get all this work done? Do they have faith in me to understand, hey, I’m going to drive that clarity, give them, you know, to a certain as objective metrics as I can and not just tell them to do things, but it’s kinda like leading from the front. Help them, here’s where things are going wrong and here’s why, and here’s kind of my experience.
And you know, the feeling that you’re feeling or the feedback you’re, that you’re getting is not unique in this world. You’re not alone. Right? And we can talk about imposter syndrome all day, but you know, these are valid feelings. There are valid curiosities and concerns, and they can be worked through.
You know, the sun’s gonna rise again tomorrow, and we can just work through it. But I think it’s that sense of togetherness and purpose to a common goal that really, I think, creates that team culture, you know, and allows leaders to actually lead versus, you know, manage.
Michael
So, what are some concrete things that manager number three, Wes, does to help your people feel seen, heard, and appreciated right from the start?
Wes
Right. I would say I was having this conversation with one of my directs, I believe in a one-on-one, the other day. And you know, I think for me it starts with transparency, right? We always talk about how we arm people and empower people, but do people understand the lens through which their actions, decisions, or whatever it might be, will be evaluated and or judged, right?
You know, to your point, like there’s a career ladder. Like here’s, you know, how you get to the next level. Here’s level expectations, and again, leaning into it and being transparent and conquering those things head-on. Like, here’s how I make decisions, here’s how I handle mistakes or incidents.
Right. And you know, here’s kind of the way that I work and being very transparent about that, right? One of the topics I was talking about, I think it was a couple weeks ago was, you know, I tend to catch up on work late at night. A lot of meetings during the day. It’s nature of the beast. And I’ll follow up with stuff that people need from me or things that they’re concerned about.
And generally speaking, that goes well into the night and early morning hours. And you know, one of the things that I am very, explicit about is if I ask you a question at, or if I, you know, I may ultimately, it is a question if I ask you a question at midnight in Slack, number one, I’m not calling you, I’m not texting you.
I do not expect an answer at all until whenever the next business day is. And that’s something that I hold dear. I know, you know, that’s something that I probably should, you know, be better about. Like the, I think that there’s the send later function. Most of the time I forget about it. And you know, that’s on me.
So that, you know, they’re not trying to like waking up at three o’clock in the morning seeing a text for me and you know, feel feeling this need or pressure to answer. But, you know, kind of getting back to it, I think a lot of it comes down to how transparent are you about what it is you’re doing, what the team’s doing, what your perspective is, both the good and the bad, and how, you know, your team or teams fit into that, you know, decision making criteria, but also transparency on its own isn’t enough.
And I think the second part of that is, you know, being very consistent in those things, right? So, if here’s how I make decisions. If I change how I make decisions, you know, that’s definitely inconsistent. And that starts to give rise to, Ooh, is he gonna like this or is he not? Right? And being consistent about how we handle mistakes.
You know, mistakes happen. And I always say. At some point in your career, you’re gonna cause a Sev 1 or a Sev 0. It’s gonna happen. There’s very little that you can do to stop it, right? But here’s how I handle these things. Like, yes, there are mistakes. I don’t need to remind you about it, ’cause chances are, you know, we all have a sense of pride in our work.
And you know, if something that you check in or deploy ends up causing an incident, you’re naturally gonna feel bad about that. I don’t even need to remind you, right? And we’re gonna have all like, we’ll diagnose the incident and all this other fun stuff, and you will naturally learn, right? And all of this is, these words need to be backed up by actions, right?
You have to, when we go through incidents, I’m expecting people to look at me and see how I react to those things, right? Again, it’s all learning. And when those words are backed up by action, we are or at least I am, consistent in the things that I do and reasonably transparent about the things that I can absolutely be transparent about.
That all kind of leads towards a culture where we all tend to know exactly what we’re doing. We know why we’re doing it. I think, you know, the why always matters, and the way that I do things is very consistent and doesn’t change, not in the sense of it’s inflexible, but you always know what to expect and aren’t scared to share bad news, right?
You’re not scared to say, oh, we had an incident. Oh, you’re not scared to make a mistake because it’s going to be a learn, like you’re not scared to make a decision because you know how I would evaluate them. And so, you know, that feeling of, and I guess we would call it psychological safety. Like I want people to feel safe, and I’m not gonna go bite their heads off on a decision that they make.
I might not be happy about it. Right. And that’s okay, but that doesn’t make them a horrible dev. Or less of a person or feel that like they should be scared to come to work the next day. Right? We all make mistakes. To your point about perfection earlier, nobody’s perfect. I certainly am not perfect. I have created all kinds of incidents in my career and I have learned from every single one of them, and that has shaped, you know, how I have developed in my own growth journey.
I’m no different than anybody else. I just might be older. That’s about it.
Michael
So it sounds like transparency and consistency are two tools you use to build cultures where your people feel safe and empowered to bring their unique talents to everything that they do. What else is in your toolbox that helps you build those cultures?
Wes
I would say that probably the next most important one is, it’s time.
You know, I have one-on-ones with everybody that reports through me. Perhaps not as often as I would like, but you know, again, when we think about, you can be transparent, you can be consistent from a distance, right? And you know, probably the next biggest tool in that toolbox is minimizing that distance.
And I don’t want people to feel like that I’m not approachable, like I’m sitting in some ivory towery throwing decisions out, you know, for them to go pick up. Right? It’s by minimizing the, you know, distance between myself and, you know, certainly my directs or my skips or so on and so forth, that oftentimes gives me a lot more perspective in what they’re going through based upon some of the decisions that I’ve made.
Right? So when we talk about not being perfect, I’m certainly not the most perfect leader on the planet by any margin, but without that feedback loop, you’re not building a culture of being able to speak up or manage up or, you know, deliver bad news, whether it’s to, you know, their direct line manager, you know, their skip or et cetera, et cetera.
And the more often that I talk with folks and you know, oftentimes it’s, you know, sometimes it’s about very personal things. Sometimes it’s just, you know, kind of shooting the breeze. The other times it’s like, Hey, you know, I’ve, seen this and, you know, observations and kind of digging into it and kind of having that perspective that my first manager certainly did not in that inquisitive nature, but being able to kind of tie in all of the things that, you know, we’ve just talked about, but also hearing it from me directly, and not just by observing me, you know, in our, you know, Q1 status or you know, like our all hands or things like that. It’s getting to know these people on an individual basis and understanding more about them, because again, as I’m sure you know, you’ve noted and, you know, talked to other folks as well.
You know, you can’t manage the everybody exactly the same and if you’re trying to build that culture and you’re trying to get the most that you can out of them, you naturally have to take everything that they are and figure out ways to blend it in. And if you don’t know what their strengths, their weaknesses, the unique things, the things that make them unique that they can bring to the table, you know, you’re going to be missing out on a whole lot of interesting opportunities that might not otherwise present themselves.
You know, whether it’s a specific, you know, Hey, I’ve used this tool before. Here’s how we can integrate it. Great. Here’s how we’ve handled incidents at, you know, Google or Meta or any of the other places folks have come from by just sitting there and listening and taking action, right? Like, you can tell me all these things, but if I don’t really internalize it and put it to use, you know, kind of what’s the point?
It becomes more of a checkbox. And so, you know, those skip-level one-on-ones and hearing their stories, figuring out what makes them tick and how do I best position them, their team, for opportunities that leverage those skill sets. And how does that make them feel like they can bring all of this to the table, even though, you know, that might not be something they have traditionally been responsible for.
So, you know, there’s a lot of different things in there, but you know, certainly the transparency, consistency, and you gotta know the people, right? If you’re not having one-on-ones with them, start. It takes a lot of time, but it’s time very well spent.
Michael
How do you balance taking all the time to get to know your direct reports, their direct reports, however far down that chain you go?
Which could be a more than full-time job, even with just two levels.
Wes
Sure, definitely.
Michael
With all the other stuff that you’re responsible for as a manager and as a leader.
Wes
Yeah, that’s, I mean, honestly, those are existential questions that I continue to ask myself to this day because, you know, you’re definitely right.
I think on one hand, naturally, stuff just has to wait until, you know, nine o’clock at night when I can actually do it. Right. And that’s a lot of just kind of spending time writing feedback for, you know, annual or, you know, doing big plans, writing specs, or one pagers. Those are things that unfortunately tend to, you know, limit themselves to when the sun is not in the sky and your days do get filled up with meetings and kind of, the way that I look about, I have a, spreadsheet of, I think it goes across, I think it’s an entire quarter, right? It’s like Monday, Tuesday, Wednesday, Thursday. And I have chunks of time that I reserve in there for, you know, generally speaking, important things. And I have one slot, I think it’s every day at 10:30 AM. I almost certainly every single day of every, year have a one-on-one at 10:30 with somebody.
And so I kind of have these blocks of time where I know I’m just having one or two one-on-ones so that I can get to all my folks, generally speaking, once a quarter, give or take. Now, if you’re the CEO, clearly that’s not going to, clearly not going to work, right? And so one of the things that I’ve kind of learned from my manager now is, you know, the concept of team on ones right?
It’s where, and you know, it’s just, you know, the skip and, you know, one of the teams without the, team’s, you know, engineering manager there. And part of it is, I mean, I know it sounds like, oh, let’s debate the, you know, your manager’s performance and things like that. But it’s more for the purpose of understanding. Hey, what’s going on?
Like, what is working, what’s not working? Like, are the things that I’m communicating through to your manager getting to you? Is there a disconnect somewhere along the line? And that’s, you know, to a certain extent, something that’s kind of going on right now, and certainly something that I need to address.
But the nice thing is I know about it, right? And if you don’t, you know, take the time. And unfortunately, there’s no shortcut. Like you have to communicate, you have to spend the time to build those relationships to understand. Now whether that happens four times a year for your skips, and so on and so forth, whether you do kind of the batch processing, so to speak, with the team on ones, there’s a couple of different ways that I’ve found to be successful, depending upon what you’re going to get.
But, thus far, I’m, kind of at the brink where if we continue to add, you know, new people or new teams, I’m gonna have to rethink some of this kind of to your point, but regardless, even if it’s, you know, once a year right, having the ability to have that conversation.
And I don’t come up with the agenda. It’s 100% up to the; if the IC wants to talk about, or the EM, for that matter, why the sky is blue? I mean, that’s your prerogative, right? It doesn’t seem like the best use of time, but you know, that’s their time and I am here to honor their time. I’ve never talked about why the sky is blue, just for the record, but it’s, it gives everybody a chance to talk through the things that are most important to them. And they may not have anything to do with work, right? Hey, in a couple months, like, you know, my fiance is moving to so and so, and you know, I would like to go remote, or Hey, you know, my, you know, I need to go travel to take care of a family member, right?
Those are the things, you know, that come up relatively often that, you know, if I didn’t have that conversation, I would be asking, why is this person out for a month? Like, we’ve, gotta get that done. And kind of to your point, like that starts to kind of invite some rushes to judgment and perhaps some label that might completely be true.
I think it is super honorable for somebody to go, you know, take care of their parent while they’re sick and things like that. And those are things that I certainly want to support because chances are that’s a good person. Who’s, you know, innocent. They’re not choosing, I mean, they’re choosing to do this, but you know, they were kind of thrust into this position and by no real fault of their own or anybody.
And without getting that context and having those connections, how deep or maybe perhaps superficial, if nothing else, you know, I, as a leader, am aware of kind of what’s going on and, you know, I can address things as and when they need to. And, you know, we can work together to find, you know, a good result.
Because over time, when you build up enough of those things, eventually you get to that point where going back to, you know, kind of the previous analogy, I will follow this person to the end of the earth because they are amazing. They all have a fundamental insight onto me, you know, my needs as a human, not just, you know, an IC, you know, writing code.
And I have full confidence that, you know, come whatever challenges may, this person is going to be, I know exactly how this person is going to react, and we’re gonna get through it together. Right? ’cause it is a two-way street.
Michael
How do you know when you know enough about a person?
Wes
Oof. That’s a good question.
I don’t know. That’s a, I haven’t really thought about that. You know, I think a lot of it is when I, you know, kind of think back to the friendships that I have, like outside of work, that have nothing to do with work and the sheer amount of time we have spent together. Right? I mean, if you added it all up consecutively, it’d be weeks and weeks and weeks and months.
And, you know, obviously as you grow older, like, you know, you don’t have as much time to do those things. But when you have those seeds, then the kind of touchpoints or checkpoints don’t need to be infrequent. Like when I talk to my friends, I can pop in and say, you know, Hey, what’s going on? You know, I saw something funny or whatever.
We just kind of pick up where we left off because we have that solid base. And so kind of relaying that back into the workplace, you know, when I take a step back and think about it, I talk to each person, I think four or five, well, each certainly skip like four or five times a year, one-on-one. And you know, I don’t know that you will ever fully get to know a person talking to them four times a year.
Right. And so to that end, like what I think about skip level one-on-ones specifically, you know, I don’t think that there’s ever a time where you can say like, okay, good. I know this person fully. I know you, I’ve got you like. We’re good. We don’t need to have this recurring meeting. If something pops up, feel free to schedule time on my calendar, which people do anyways.
But I think really what strengthens the organization and the culture is having those lines of communication defined, planned for, and when we get to that, you know, we all know, that both of us know, here’s what we want to get out of this meeting. Here’s kind of what we talked about last time. Here’s how, you know, the tips or feedback or whatever it is that they gave them.
Here’s how it’s working. It could be good, it could be bad. And so, long-winded way of saying, I don’t think you ever know enough about a person, right? Because again, people come, people go, and you know, if you don’t have those slots, I mean popping up stack a little bit, right? When we were talking about there’s not enough hours in a day, when people leave, I just hold that slot.
For like a to be hired. Like if we’re gonna backfill the position or somebody new comes in, I can just slide them right in there and not have to completely blow up my schedule. Right. And so, you know, it helps me have that reserved time for that person. We can talk about, you know, whatever’s bothering them both professionally and their lives and you know, how we go from there.
But gosh, yeah. I don’t think you ever really know enough about a person to really understand, you know, what they’re going through, what’s going on beyond, Hey, I’ve worked with you for 10 years and now I’ve moved to a team that’s adjacent to you to where we still see each other and great, maybe we don’t have those, you know, monthly, you know, biweekly, whatever, one-on-ones.
Like, I have one-on-ones with people that do not report to me anymore. Right? They did it one time. I mean, they’re very infrequent, right? But at the same time, it allows me to understand more about what they’re doing and you know, at least from a professional standpoint, hey, what are the things that you’re invested in?
’cause I’m not talking to your leadership chain at least beyond kinda like the high level, you know, company objectives. And so, you know, I think it is just lines of communication and the more lines of communication you have open, I think the better that you can align and advocate for yourself and your teams.
And so, no, I don’t think you ever really know enough.
Michael
I appreciate the structure you found everything on, Wes. I can see a quarter spreadsheet that you have on with all the time slots and who goes where, that gives you the ability to plan out at that larger scale that we can’t really keep in our heads or really see on our calendars on the computer.
It lets you do this deep interpersonal relation without stressing that things are getting dropped off because you know everything is there.
What you say that we can’t ever really know anyone enough really resonates for me. In part because if we, when we say, if we were to say I know someone well enough, what we’re really saying is I know someone well enough for all the things I’ve needed to know them in terms of, and we never know what’s coming that we’re gonna need to know something about
Wes
Exactly. Exactly. I think I couldn’t have said it better myself.
Definitely. I, and I don’t ever want, certainly, people that I manage or I lead to feel that, you know, this is a relationship that is business only, and the second that it doesn’t provide value to me, right, that we are severing those ties. Because fundamentally what I need is, you know, my goal is to get teams to deliver more value.
That doesn’t necessarily mean more hours or more bugs fixed or whatever. It’s, fundamental value. And by, I don’t wanna say severing some of these, you know, meetings that I do have with ICs and skip level ICs and things like that, or EMs for that matter. By severing that you’re basically saying either A, I have everything I need from you. I don’t, I have no use for you anymore. And I know that sounds bad, but to a certain extent, it can absolutely be internalized like that versus you know, kind of how I think about I need you, manager, or IC, or whatever it is to really understand what we’re doing here because I need you to execute. And I know that at some point you’re gonna need something from me, right?
You need to be a servant leader. Like I want to unblock you to do your best work. And if we’re not having those conversations, whether they’re casual or in a one-on-one, it doesn’t really matter truly. But if you’re not comfortable sharing those things with me, you don’t have the time and space to share those things with me, how on earth can I have an effective team or teams or organization to execute on these business goals objectives of the day, year, whatever. And moreover, than, or more than that is, are you going to be here for the long term or are you seeing me as like, okay, this person has no real use for me. I’m gonna go look for another team, right?
Or look for another company. Right. Whatever that is. And if you’re, if somebody leaving a team and they’re leaving to a different company, hey, that’s great. It happens all the time. But I want you to leave for like, Hey, here’s an opportunity. And it’s not because, you know, I don’t like Wes or I don’t like my management chain, it’s just, hey, it’s a different opportunity that I’m interested in, you know, happens, right?
I’ve left teams before, not because, you know, they’re horrible managers or anything. It’s just a different opportunity. And I never want people to feel that, you know, their utility has been used up and they need to go seek an opportunity. They have no room for growth.
Michael
So it sounds to me that the, a way, maybe the way you help your people feel, seen, heard, appreciated, welcomed, is you give them a foundation for interacting with you. You tell them, I am gonna do my darnedest to understand who you are. That can never be enough. Your responsibility, your, a primary job I am giving you here today is to tell me what I need to know to help you.
Because at the end of the day, my job is to help you do your job. And if you can’t do your job, then I’m not doing my job.
Wes
Exactly.
Michael
So it’s great that people feel seen, heard, appreciated, valued, loved, wanted. What’s the business value of creating these cultures?
Wes
You know, I was thinking about this kind of in the context, I think to the first question you asked. Right? When my first manager, you know, left and, you know, I got that new manager and I could start, you know, I was a little bit more, I would say, I don’t know if I would say valued, but I felt more comfortable in my role that I wasn’t fundamentally failing and that, you know, hey, you know, you’re doing just fine.
Like, just communicate better or, you know, whatever that, I can’t exactly remember the exact contours of the feedback, but it was something along those lines. You know, when, as a leader now, I’m going through that myself. My output in my investment in my team was significantly higher, kind of in the new world order, so to speak, with my second manager.
So when I think about the business value, I think you’re naturally going to get more out of people simply because they’re not afraid to make mistakes, ’cause if you’re not making a mistake, you’re probably not learning, right? So that’s one. Two, they’re not afraid to, you know, be wrong or, you know, share a difference of opinion or, you know, disagree, right?
A little bit of disagreement’s healthy, you get better designs and all kinds of things, right? And so when you bundle all this together, you ultimately get more output. If you’re talking about business value things, generally speaking, get done faster, number one. But the second part of that is you’re not burning people out left, right, and center to where they feel like, okay, I’m just mentally exhausted. I need to go take a two week long break and then now we’re all trying to scramble how do we structure or shift or perhaps delay deliverables or milestones to kind of fit this person who we just burned out.
Right? So, you know, I don’t know that there’s, I think it’s hard to objectively say, this is clearly the value, but what I have seen is we get more out of people. Turnover is significantly less, trying to hire, you know, quality people quickly, very difficult to do. Right? And so when you’re kind of on a trajectory where things aren’t going well, you know, people are unhappy and they’re leaving well, the business objectives don’t change just because, you know, somebody wanted to leave to go to Microsoft or Amazon or any of these other places.
And so, by virtue of the fact that you’re kind of creating that space and that culture where the person that you are, is fundamentally welcome into this team, or they’re going to be comfortable, they’re going to be happy, and things just naturally flow. There’s, you know, not really a lot of, you know, workplace drama.
There’s not a lot of, you know, backstabbing, at least kind of like on, you know, like the old Microsoft where like, Hey, for me to get a promotion, I gotta make you look bad. And things like that. That stuff just tends to fall by the wayside. And, you know, we’re focusing on how do I make myself as productive and impactful as I possibly can, because I don’t have to worry about all these other things.
I know exactly how Wes is going to react to this, or if I presented them with this, you know, problem, right? And the options that I have, I know exactly which one he’s going to pick. So basically he’s just, yep, that makes sense. Here’s what, and it’ll probably gimme some type of feedback. So I think it really comes down to you get more performance because people aren’t scared.
They’re not worried about what somebody else is going to think. Right? There is a little bit more of a bias for action and you know, less turnover. Right? I think the turnover is a huge one, especially in this day and age. You know, hiring people is tough and if you have less turnover, you know, you don’t have to like, okay, well this person left the company, shoot, they were working on some very big project, not great, but understand why they left.
So now we gotta figure this out. So I think all of those kind of in conjunction are really what deliver the true value to a business and an organization. But, and then the other thing is, you know, the, more alike that we see ourselves, like as people, not just as ICs, managers, leaders, right. Despite the different levels or roles or expectations.
You know, the faster that we can get to the root of those issues get in alignment and, you know, communicate both good and bad. You know, you’re kind of greasing the wheels of business so that they can spin faster or not run as hot or just fundamentally keep the train on the tracks and keep moving.
So, you know, that’s kind of how I think about what happens to the value when you’re able to bring everybody’s kind of whole self, personality, strengths, weaknesses into the fold. You know, identify it, talk about it, address it, and we can get onto bigger and better things because like, Hey, that’s cool.
We’re fine with that. Don’t worry about it. Let’s just focus on this specific objective.
Michael
Yes. So there’s, you know, everyone’s strengths and can arrange work to give people what they love doing. You know, everything people don’t love doing and you can arrange work so they don’t have to do that because there’s probably something else on the team that’d be happy to pick that up anyway.
Wes
Yeah.
Michael
All the energy that people would otherwise be spending griping about the work they’re doing that they don’t wanna do. Lusting after the work that they’re not getting to do, that they would love to do. And trying to navigate all of the office mechanics and politics and squishy, squishy people stuff.
That they’re worried about how things are coming out. All the energy can go to doing that work that they love doing.
Wes
Definitely. And you know, I wanted to kind of, you know, you had mentioned, you know, the things that you don’t wanna do there. I mean, there’s always work that people don’t want to do.
I always call it kind of eating your vegetables. It’s like, I want you to have as much dessert as possible, but hey, we gotta eat these vegetables too. And, you know, again, being transparent about, you know, hey, I’m, you know, we can’t all do everything that we lust for all the time. I wish it worked like that, believe me.
But, you know, the business has needs and these needs have values, et cetera, et cetera. But I think people are understanding, like, Hey, why am I having to do this right? Why can’t this other person do this? Or why can’t this other person do that when it’s all out for the world to see? Right? Like, hey, they’re busy on this thing.
Not that I have to, you know, explain that, right? ’cause it’s right there. But you know, everybody at some point is gonna have to do something that they don’t want to do. Whether it’s picking up the slack or helping out during an on-call rotation, right? But when you have that sense, when you have that culture truly, that team-based culture is like, I want the team to succeed, and if the team succeeds, chances are I am succeeding as well.
You know, to your point about the office politics and, you know, mechanics. People genuinely speaking, not only care about the team, but care for one another enough to lend a hand, you know, eat the vegetables and do all the, you know, rote tasks that perhaps people don’t want to do, or they do them, they do the rote tasks enough to where they figure out a way to automate it, right?
Which is even better, right? Everybody loves automation. And so, I think having that shared sense of understanding of how decisions are made and you know, to a certain extent how work is assigned. Whether it’s, you know, hey, a FIFO, I just go pick a ticket off of a queue. Or if we’re talking about more organized, you know, business plan, which is kind of where we’re executing on right now. People are generally more receptive when they understand the why and the fact that this is not something that they’re gonna get stuck with forever.
Like maybe it’s two weeks, maybe it’s a week, I don’t know. But I have found that people are okay with perhaps not the most glorious of work when they understand the value to the business and why it’s important. And when you have a culture that values the team over me, those are easier conversations than, in organizations where that has not been the case.
Michael
Yes. And on top of all of that. When you understand what lights a person up. Almost always there’s a way to engage that, to find that in the thing that they aren’t excited about doing. So we still may not be absolutely excited about doing it, but they’re less unexcited about doing it.
Wes
Exactly. It’s about minimizing distaste rather than maximizing happiness. At least in this specific instance.
Michael
Maybe we spread some ketchup or mustard or whatever the spicy spice you like on those vegetables and it’s a little more palatable for you.
Wes
Sure. Absolutely. Absolutely. I like that analogy. I’m gonna, I’m gonna have to use that next time.
Michael
Pull half the ranch, for much of America.
Wes
There you go.
Michael
How do you help your people, Wes, find their way through all the change, uncertainty and overwhelm that seems to be all that life is these days?
Wes
So I think that goes back to some of the things I mentioned before, right?
In one-on-ones and skip one-on-ones. But more importantly, or I would say most importantly, is that it starts with listening. You know, we all have our biases and assumptions about what is or isn’t going on, or what the reasons for something is or isn’t. But when you try to perhaps empathize with a specific situation that is happening, everything starts with listening.
Like I listen far more. Wow, I can talk a lot, but I tend to listen far more than I speak simply because I want to understand, right? Because that’s kind of that first part. You gotta listen, you gotta understand, and then, I’ve found a lot of success, and this just kind of comes back to the whole, you know, bringing your whole self and being, you know, again, very transparent about both business, but also, you know, kind of my own personal experiences.
And there’s probably very little that, you know, my ICs or you know, my managers or skips or whoever it is, there’s probably an analog that I’ve come across, you know, in my own career, right? Whether it’s when I was an IC or you know, early on in my management career, you know, the challenges are generally speaking very similar, right?
Not exactly identical, but similar. And you know, I’ve found that especially when we’re talking about challenges, I almost naturally go to a time and place where, you know, I fell, I failed, excuse me, and how I dealt with that, right? And, you know, kind of, but again, you know, I’m not trying to make these things about me by any stretch of the imagination.
Hence why you gotta start with listening. But I found that finding, trying to find that common ground with, you know, whatever it is that people are, you know, upset about. Right. Whether it’s, you know, layoffs and uncertainty or, Hey, this team got a new manager and you know, I really need them to deliver something so that I can deliver my thing.
Right? And part of it is just understanding that yes, these are challenges, right? And if you’re kind of in that pocket where you’re a little bit uncomfortable, right? Seeing that kind of to your point about kind of spinning it a little bit, right? Kind of adding the sauces to the vegetables, so to speak.
When you come at it at a perspective of, okay, I hear you, you can, you’re, you know, uncertain about this, you’re worried about that. How do we turn that into kind of a learning or a growth opportunity, you know, whether it’s, you know, and one was probably a year and a half ago or so, you know, a peer team, you know, had a managerial change and that peer team was delivering something that, you know, one of my teams really needed to, you know, land some, you know, so some big changes internally.
And now there was, you know, I think, was it the manager? Yeah, it was the manager kind of brought up like, how am I supposed to, like, I’m very nervous about this. I was like, well, you know, the only real; I’ll tell you what I would do if you wanna hear that, right. But fundamentally, we’re never gonna know if we don’t just go talk, right.
Everything always starts with a conversation. Right. And so, you know, then I think I went into some examples, you know, kind of through my own career, but you know, fundamentally understanding that yes, this is something that’s uncomfortable with them. Turning it into, hey, you know, these are things that, you know, we, have to deal with.
This is not gonna be the last time this happens. Maybe it’s the first time it’s happened for you, but it’s certainly not gonna be the last. Let’s think about how do we attack the problem, right? Is it a problem that we need to solve? And how do we approach it to where you’re not feeling uneasy or uncertain?
Right? Is it a, you know, a lack of confidence? Is it, Hey, you worked with this person and they’re not, you don’t like working with this person, or whatever it is. And so, you know, just kind of drawing upon my own experiences and listening to, you know, what they have to say and what the root of the challenge is.
And then, you know, 99 times out of 100 it’s, Hey, let’s just take, you know, we’re worried about this giant boulder. Let’s, break that problem. Let’s break that boulder apart into some rocks and let’s focus on a couple rocks at one time. Right. And eventually, at some point we’ll be all past this, right?
’cause again, the world’s gonna keep turning. Business is gonna keep booming. You know, we’re just gonna have to take things one day at a time. And, you know, it’s like that old adage, Rome wasn’t built in a day, you know, like, Hey, it’s okay. Let’s not worry too much about it.
And, you know, again, we can work through it together. Right? And it’s not one of those tasks that, you know, an IC or a manager or whoever has to go solve. Like, Hey, we are in this together. We are a team. We can solve this together and work through whatever it is. And that’s been successful for me thus far.
Haven’t had any issues with it. So I’ll, keep on doing it. But, you know, again, it’s really just listening and understand and, having I think the mental wherewithal to know, even though I might have a similar experience, you know. To what they’re going through, or you know what the challenge is, that doesn’t mean it’s the same, right?
And so I bend over backwards to try and not say, Hey, here’s the solution, right? This is what I did because I’m so amazing. Like I don’t have all the answers and I’m very transparent about not having all the answers. But have you thought about this? Right? And just kind of asking more of those clarifying questions.
’cause more often than not, we’ll get to a point where I’ve just asked them kind of clarifying questions and broken it down a little bit to where they’ve kind of self solved whatever the issue is. Or at least have a, frame of reference to go attack something. And I’m just, you know, I’m just a sounding board at that point, right?
Which, as far as I’m concerned, is a success, right? Because I want them to kind of go through that on their own and arrive at their own conclusion so that they feel that, hey, the next time something similar or the same issue happens, they have, you know, kind of a little bit of a, playbook to draw from.
Michael
Yeah. Your experience helps you understand where they’re probably coming from. You employ your curiosity and you’re listening to discover where they’re actually coming from, and then you bring that experience back in to help you pinpoint places where they might need a little clarification, where they might be missing some options or opportunities that you can help them discover for themselves and you keep going in the cycle of experience feeds empathy feeds curiosity feeds, which goes into listening, and then it brings it back into experience, empathy, curiosity, listening. You’re a nice reinforcing cycle there.
Wes
Yeah. And you know, a lot of times, and I would say it is probably 50-50 split if I had to guess, you know, half the time it’s, you know, life experience, right?
It’s not that they’re concerned about something that has really nothing to do with work and maybe it is impacting, you know, their ability to kind of focus or concentrate or you know, whatever it is. But, you know, oftentimes, you know, I was kind of giving my perspective on, I think it was a housing purchase, you know, not too long ago, right?
They were like, that was the first time that they were, you know, contemplating, you know, buying versus renting and all those other fun things. And you know, far be it for me, I am not a financial advisor by any stretch of imagination. But again, you know, I went through that at one point too. I remember, you know, putting the down payment down and being like, oh my gosh, what am I doing?
And, you know, kind of to that point, it’s, you know, it’s a life experience that, you know, I’ve gone through and this person is now going through and, you know, if nothing else, it’s just a reassurance that what you’re feeling? Very natural. Felt it very much myself. And I’m sure every first time home buyer is gonna go through the same thing.
So it’s kind of that, you know, you’re not alone, there’s not really a right answer. And if you’re making a mistake for whatever, you know, for whatever definition of mistake you want to call it, you know, at the end of the day it’s a problem that can be solved. Right. You’re not going to die if you make the wrong decision or no decision at all.
You know, it’s, you know, again, all you can do, and this is something that I kind of beat, for lack of a better term, into, you know, my teams is hindsight is always 20-20. If you can say with a straight face that you made the best decision that you could for whatever it is, personal, work, whatever, given the information that you had at that time.
Don’t try to rejudge previous decisions because at that point, kind of, you know, full circle going back into perfection, you are measuring yourself against perfection and you will always, always come up short. And, you know, that’s something that has done me well in my own personal life, but also, you know, applying it to you know, strategic decisions or investments that we do or don’t make. Right? I wish we would have started this six months ago because it would be very helpful now. Well, what we knew six months ago from how many people we had, what the cost estimations were gonna be, how much it physically cost the business, what the business’s big bets were at that time, we made the right decision.
It’s unfortunate that between now and then there was a, you know, a big change or a strategic shift, but that’s okay. That’s business. That’s life. Things change. And if we have that, you know, mental model of dealing with change and have, you know, that support system, whether it’s, you know, at home with a family member or professionally with your manager, skip, a peer whomever, mentor mentee.
We’re all on a spinning rock in space at the end of the day. We’re all imperfect. We all make mistakes. And while the problem that you’re or uncertainty or change or whatever it is, is certainly you unique to you, it is probably not a unique challenge when you have a broader perspective. And so it’s trying to bring that breadth of perspective into, to make sure that they’re just kind of focusing on the problem, not trying to, you know, bring other things into where they feel the weight of the world and, you know, they start to shut down.
Because I’ve seen, I’ve had that happen, you know, in my career previously. And I think a lot of that experience is kind of formed the thought process that I have now. Right. Because it wasn’t going well, you know, Hey, let’s separate these things out a little bit. Let’s talk about this one.
Like why do you feel that way and being able to kind of attack them piecemeal versus trying to solve world hunger all at once? You know what I mean?
Michael
Yes. A long time ago, early in my career, a colleague told me, “At the end of the day, it’s all zeros and ones. If one of those gets in our post with another one, like it’s not a big deal.”
Wes
That is hilarious, ’cause I use, well, a slightly different adaptation of that. It’s, you know, there’s always that question of can we do it, right? And, I always, always come back at the end of the day, it’s ones and zeros, so it’s software. Yes, we can, we’re not asking about can, we’re asking about should. Right? Or if we don’t, what happens? What value does that bring? Of course it can be done, but at the end of the day, right, it’s a should question. It’s ones and zeros. Like we can make it do whatever we want to do, which is, that the right choice for the business? It’s all the other decisions that go into that one.
Right? That’s hilarious.
Michael
So Wes, what is the best way for people to connect with you if they would like to get more in with you on how you approach leadership or if they would like to choose manager number three and come work with you?
Wes
The best way is certainly on LinkedIn. If you search Wes Clines, I’m pretty sure I’m the only one on there, but I’m definitely the only one at DocuSign. That’s by far and away the best way to get ahold of me. Otherwise you can email me at wes.clines@docusign.com and I will do my best to handle the torrent of email that I get in a given day, but certainly LinkedIn is by far and away, the best way to get it, get ahold of me.
Michael
That’s great. And Wes, what would you like to leave our audience with today?
Wes
I would say to managers or leaders, I guess in general, always start with listening. You never know what somebody’s going through and you may not have the full story because they might not be comfortable. And taking specific and explicit time out of your day, week, you know, whatever it is to meet and understand people at a little bit of a lower level.
So that’s one. As for, you know, folks who are ICs, or currently ICs, I guess. Realize that, you know, management is a two-way street. You know, ICs certainly have a role to play here. I mean, obviously being a manager is important and there’s a lot of things that, you know, we are trying to deal with to the best that we can.
But also realize that, you know, your role is to, you know, communicate as well. And that is certainly a two-way street. You know, we can’t know what you don’t tell us. We can observe and, you know, kind of verify, but the best way to really make progress is to just have that conversation. And again, easier said than done, fully admit to that.
But that’s certainly something that, you know, I see ICs not doing probably enough. Not that it’s a bad thing, but I think you will get more when you are more even transparent with yourself and honest with yourself and you know, opened up because some great things can happen from that.
And the last one I would say is for ICs wanting to be going to management, which is a very common occurrence. Managing and leading are two very different things. You can manage a project or a workload, or whether it’s JIRA or any of the other software tracking vendors out there. Being able to manage a team is being able, is different than being able to lead a team.
Leading implies that there is a belief in your ability skill sets, and they are placing their trust in you to deliver something, whether that’s business value, a feature. You know, I mean, you could even extend that into like M&A. Like, Hey, I need you to get this deal done. Right. It’s a very difficult thing to learn and it’s not just a title, right? As much as I think certainly kind of going into it, I kind of had that mentality. It’s like, okay, now I’m just managing backlogs and people have to do what I tell them to do. And that is not it at all. And it is way harder than you would think and spend a ton of time on, you know, reviews and feedback.
I mean, I, guess that’s more feedback for the managers. I spend at least an hour writing feedback and I mean, per person. And by doing that, I have found that I can achieve a lot of growth on behalf of, you know, the people that report to me or report through me. It is a lot easier to, like, when you’re going into promo meetings and stuff like that, it is, you have everything right there ready to go and you can reference it from again, so, you know, spend a lot of time on your people, right. That’s really what it amounts to, and Listen.
Michael
That’s great. Thank you Wes, for being with us today.
Wes
Absolutely. Thank you for having me. I appreciate the time. This was great.
Michael
This has been great. And audience, let Wes and I know where do you wanna spend your time? Thanks and have a great day.