EP 85: Team Habits: Redefining Workplace Dynamics with Charlie Gilkey

Uncategorized Aug 18, 2023


Groups are a microcosm of life and the greater systems in which we live and work.

We learn so much about ourselves and others in groups. 

They refine our leadership and communication skills. They highlight our growth edges and our capacity for conflict. And they can bring out the best - and the worst - in us, sometimes at lightning speed. 

So many of us can recall frustrating and, too often, harmful experiences working in teams. Whether it’s a team member that drags everyone down without support or burdened systems, rules, and bureaucracies that stifle creativity and energy, the words “group project” bring up a lot of feelings.

What comes up when you think about your group or team experiences? And when preparing to join or lead a group or a team, what fears or concerns go through your mind?

Today, I’m excited to welcome back Charlie Gilkey to discuss his new book, Team Habits. He addresses many of the pain points and fears many of us hold when it comes to working in teams with actionable ways to make meaningful change in our team habits.

Charlie Gilkey helps people start finishing the stuff that matters. He's the founder of Productive Flourishing, author of the book Start Finishing and The Small Business Lifecycle, and host of the Productive Flourishing podcast. Before starting Productive Flourishing, Charlie worked as a Joint Force Military Logistics Coordinator while simultaneously pursuing a PhD in Philosophy. He lives with his wife, Angela, in Portland, Oregon.



Listen to the full episode to hear:

  • How attachment to titles and structures makes us feel like we don’t have agency in our teams at work
  • How work is inherently relational and why it matters how we show up for each other
  • Why efforts to democratize corporate structures have to consider the emotional and social components of decision-making
  • How solid team habits protect against one person dragging down the group
  • The difference between the values on the floor and the values on the wall, and why we need to bring them together
  • How small, mundane changes make significant impact to your team culture over time
  • Why we need to be able to show up as our full selves in our teams


Learn more about Charlie Gilkey:


Learn more about Rebecca:



Scroll Down for The Full Episode Transcript:

Charlie Gilkey: You don't change meeting culture. You don't change a collaboration culture. You change these micro habits, and it takes time, but you know what? You're gonna be showing up to work anyways. Might as well try to make it better because if you make it better for your team, those four to eight people, you make it better for yourself.

[Inspirational Intro Music]

Rebecca Ching: Groups are a microcosm of life and the greater systems in which we live and work. We learn so much about ourselves and others in groups. They refine our leadership and communication skills, they highlight our growth edges and capacity for conflict, and being on a team can bring out the best and the worst in us, sometimes at lightning speed. What comes up for you when you think about your group or team experiences, and when preparing to join or lead a group or a team, what fears or concerns go through your mind?

All right, for me, I actually love working or playing on a great team. It’s truly one of my favorite things. I know that may sound weird, but it really brings me a lot of joy. On the other hand, I deeply loathe working or playing on a poorly-led group or team. I do not run lukewarm in this area, and I suspect I’m not alone.

I'm Rebecca Ching, and you're listening to The Unburdened Leader, the show that goes deep with humans who navigate life’s challenges and lead in their own ways. Our goal is to learn how they address the burdens they carry, how they learn from them and become better and more impactful leaders of themselves and others.

When it comes to working on teams, I have no middle ground. I either enjoy them or I deeply dread them. This polarized feeling about working on teams stems back to my experience in school working on group projects and playing on sports teams.


Now, in school, when I saw a group project in the syllabus for the year, I’d cringe. So often these projects felt like just busy work, something to fill the time that did not hold much purpose for learning. They did not make sense to me, and I never felt taught or mentored by my teachers. I never really understood the purpose. Often the directions for these groups felt like a one-size-fits-all for everyone, and there was a lot of space for mediocrity and dialing it in while one or two people did the bulk of the work. I see my kids going through the same thing in their schooling right now too.

Now, as a group often assigned by the teacher, which could be really awkward depending on who you're placed with, we all kind of flailed with our varying agendas and working styles. Now, the process of assigning who does what and when to meet up and figuring out the work that needs to be done usually was rushed. Depending on who was in the group, the meetups were fun and more social, but work rarely got done. You may recall some of these experiences too.

I often felt it would be easier to do things independently, which, for better or for worse, partnered well with my tendency to over-commit and over-function, right? Not a great combo for sure. Or I would fixate on who did their part and who was not and, I don't know, that was just exhausting and not helpful or enjoyable.

Okay, well, on the other hand, I loved playing on sports teams growing up. The way things were set up made more sense to me. I loved how we all had a role to play in our positions. The goal was to back each other up if we made a mistake and when someone hit a homerun or scored a goal, we all felt the victory. Sure, there were stars on the team, but the best teams I played on were ones where we all felt we had a place and contributed top of the lineup or bottom of the lineup, starter or backup, and the best coaches were the ones who guided us individually well so we could collectively play well together while also striving for the win. 


We practiced regularly together doing the drills and putting in the reps on our individual and collective skills. Now, we all had varying abilities, but the habits we developed together in practicing often changed us personally and as a team.

I know sports are rife with many problematic issues, but I’m grateful my experiences were positive for the most part, and they helped grow my sense of love for working on a team with a shared vision and mission, and my time working on group projects during school taught me how to lead a team or be on a team along with the power of positive habits.

Now, as I reflect on these influences on my relationships with working on teams, I see how working in politics, especially political campaigns and international youth work, connected me to that team feeling. But my corporate work felt more -- not always, but mostly like the assigned group projects I experienced in school. Every week, without fail, I hear stories from my clients and they're frustrating and, too often, harmful experiences working in teams. I hear the pain of working with a team member that drags everyone down without support for change and about burdened systems, rules, and bureaucracies stifling creativity and energy. 

This is why I am so excited to welcome back today’s Unburdened Leader guest to the show and dive deep into his latest book on team habits. He addresses the many pain points of teamwork with actionable ways to make meaningful changes through our team habits.


Charlie Gilkey helps people do their best work and work better together. He founded Productive Flourishing, he’s an executive coach, and he’s the author of Team Habits, and also the critically-acclaimed, best-selling Start Finishing. He lives with his wife Angela in Portland, Oregon.

Now, as you listen to this show today, pay attention to Charlie’s reflection on the impact teams can have to improve lives and not just create more work. Listen to Charlie’s approach to changing a system or a team that is not working in ways that can avoid burnout and checking out. Notice Charlie’s insight that every action you take in a team context is a social action and not an individual one. Let that sink in. All right, y’all. Now, please welcome back Charlie Gilkey to The Unburdened Leader podcast.

Charlie, so glad you're here again! Thank you for coming back! 

Charlie Gilkey: Rebecca, thanks so much for having me! I am pumped to be here just to have the conversation with you generally, but also specifically to talk about teamwork and working better together. So thanks for having me!

Rebecca Ching: First, congratulations on your new book, Team Habits: --

Charlie Gilkey: Thank you.

Rebecca Ching: How Small Actions Lead to Extraordinary Results. This whole book is just speaking my system’s love language. I’m probably gonna read it a couple more times because you really have a lot of just very clear and simple nuggets in here.

In your book you talk about that everyone has the power to change team habits, and I want to start off by hearing more. How is your vision to democratize who is a part of an organization's decision-making process different from conventional wisdom, and how the heck is it connected to team habits?


Charlie Gilkey: There are five questions in there.

Rebecca Ching: I know, I know. 

Charlie Gilkey: I love it. It’s great. It’s great. So let me do some unpacking real quick. So, for our conversation, when I say team, I mean the 4 to 8 people that you spend 80% of your time working with day in, day out. That’s important because a lot of times, especially if you're in an organization, you’ll say “my team” and you're referencing 50 people. That’s your group, right? That’s your department. That’s your unit. That's not your team. Your team is those 4 to 8 people that, again, you work with day in and day out. In that rapport -- so, Rebecca, for today’s call, we’re a team. So just for ease of communication. 

So in our team, Rebecca, if our meetings suck, I can come to you and say, “Hey, Rebecca, this ain’t working for you, and it ain’t working for me.” Can we do something a little bit different?” And you're probably gonna be like, “Yeah, it’s not working for me too.” I don't need to go to our team leader or manager or CEO to have that conversation because we have this rapport, right? I think so many people give up their relationships with these wonderful people that they work with day in and day out and defer that to management or senior leaders.

Rebecca Ching: Totally.

Charlie Gilkey: Versus just saying, “You know what? We’re in this together. I’m not thinking about --,” well, I might be thinking about quitting, but I’m not gonna tell you that. But “We’re gonna show up to work every day anyways, so how about we work better together?” That is one of the cores of Team Habits that I want people to come back to.

Rebecca, the book came from when I was giving so many talks about Start Finishing. I was on the book tour, that’s my previous book, Start Finishing: How to go From Idea to Done, and to a tee, I know the questions I’m gonna get from these org folks, right? A manager would raise his hand, and he would be like, “You know, these are really great ideas. How can we get senior leadership to buy off on them?” And I’d talk about things like focus blocks, which is a 90-to-120-minute block of time where you can do your deep, significant work.

Rebecca Ching: Mm-hmm.


Charlie Gilkey: And he’s like, “Yeah, we need more of those, but how can we get management to sign off on them?” I’m like, “Hold on. Hold on. So you're telling me, manager, that over the course of a week, you and your teammates can't find three focus blocks to sort of disappear and do some work during the work week? That’s impossible for you to do?” And he’d be like, “It’s-- oh, shit. Yeah, we could do that.”

Rebecca Ching: Mm-hmm.

Charlie Gilkey: And I’m like, “So if you can do it already, why do you need to go talk to senior leadership about it?” He’d be like, “But our calendars know! We have this stupid policy where people can just put meetings on my calendar.” I was like, “Who decided that? Who decided that that was the way? You're saying that you can't change that?” “Well, crap,” right? 

And so, every objection, it came down to that is a team habit that you've changed. So that’s the team side of it. Habit is just the unconscious ways in which we act. The difference between a team habit and an individual habit that people do is that, as a team, we say, “Hey, this is what we do here,” and there’s a cumulative power to people acting in concert in a certain way, right? There’s a cumulative power that happens with that.

So, Rebecca, you might have a weekly planning process that you sort of squirrel away and you do yourself, and I might have a weekly planning process that I squirrel away and do stuff. But what happens when we come together and say, “Hey, we both, it turns out, do our weekly planning on Monday morning. How about instead of us having a meeting Monday morning, we have our weekly team meeting Monday afternoon after we’ve done our planning for the week so that we can come to the meeting prepared?” Just because we as a team have decided to conjoin those habits, it gives us an additional force multiplication, and that’s what’s super, super important.


Okay, so team, team habits. I’m building up to answering your sort of five-part answer. But before I do, you have a question so go ahead -- or an insight or something.

Rebecca Ching: Yeah, I just want to check in though too. What do you think contributes to folks losing or thinking they don't have agency in their organization to make these small and important adjustments and changes, or even to be curious, or even to say, “I disagree,” or “Can we do it better?” Because it’s like, “I have to check with management.” They feel so constrained. They feel afraid of doing anything that’s gonna break the rules. That’s a theme I hear and I see on the regular, and then when you just were talking about that exchange that you had during your last book tour, and people were like, “Oh, yeah,” it’s like they forget, “I can do this.” What do you think contributes to that? 

Charlie Gilkey: The valorization of labels. “You're a manager. You're a leader. You're an executive. Therefore, you make those decisions. I’m not a manager. I’m not a leader. I’m not a senior. I don't get to make decisions.”

Rebecca Ching: Wow.

Charlie Gilkey: That’s part of the very structure that our society sells. We go to get an MBA so we can be a manager, so we can make decisions, so that we can do things. We don't, I think, realize the inverse of that is that we think if we’re not that person, I don't have agency.

Now, what’s important for our listeners, since they don't already know this about me, is I have an army background, and the military, the United States Department of Defense and our sister forces do a fantastic job of breaking that mindset down. Whenever there are two people -- there’s this thing that you know in field leadership: whenever there are two soldiers doing something together, someone’s in charge, right? It might not be the person with the highest rank, but you learn a lot of things about collaboration and teamwork and leadership and that just because you have a certain rank doesn't mean you do certain things if you can do things.


Now, there are certain guidelines that you have to watch out for. So I grew up in that boy scout and army environment, and so, it was a really big shock hitting the civilian world, seeing how many people had checked out on their ability to make change happen just because they're like, “Well, we need to do something, but we don't have a team for that.” I’m like, “You four people are complaining about it! You're the team!” 

Rebecca Ching: Mm-hmm.

Charlie Gilkey: “Go make it happen,” and they're like, “But we need to -- how do we do that?” I’m like, “What do you mean how do you do that?” I’m not trying to say it in a way of condescending. It was a mystery to me that it wasn't common knowledge. I was like, “Oh, well, looks like I have some work to do. I guess more job security for me,” hence the book.

So I think labels and the valorization of labels is one thing. Two, corporate culture in some organization's cultures. I’m just gonna be real about that. Most organizations’ culture, it’s safer to be mediocre and to not do anything --

Rebecca Ching: Yep.

Charlie Gilkey: -- than to actually try. 

Rebecca Ching: It’s dangerous to try.

Charlie Gilkey: It’s dangerous to try. You could lose your job! You could lose your job for making a mistake. You can't lose your job for just sitting in a meeting, right?

The other thing is there’s a disenfranchisement with work. I say disenfranchise and people think I’ve gone Marxist. We can do that, but still, what I’m still trying to say is some people are just like, “You know what? I just get paid to do a job. I’m gonna do my job and go home because that’s what I’m here to do,” and that’s great, and I also want to remind those folks that work is inherently relational. So yes, you're paid to do a job, but you're paid to do a job with people and those people, like you, have their own needs and wants and things like that, and we have an incredible way, as a team, to make each other’s lives better and do the work without it being a bunch of additional work.


What I want people to change their perspective around is to get away from just phoning it in, making work better and working better together because of their feelings about, say, the organization and the stupid top-down policies or whatever that kind of -- one that’s like, “Oh, that’s there. I get it. I understand. I’ve been there.” And at the same time, what about these four to eight souls that you work with day in, day out, that buy you coffee, that share inside jokes with you, that show up to your weddings, that do all those types of things. Why are those people not getting more of your attention, and why are we not taking better care of each other on that front? Because we have an incredible ability to do that.

A lot of times when I’m working with my executive coaching clients, there’s a thing that some of them do, and I have to call it out. I call it out early in the relationship. What they do is create some idyllic, impossible-to-achieve scenario and then say, “Well, I can't do that, so I’m just gonna do the status quo.” Now, they don't say that in their head, but that’s exactly what they're doing.

Rebecca Ching: Our brain’s wired to do that. 

Charlie Gilkey: Our brains are wired to do that, and to answer your question, I think a lot of people do that with work and why they don't make change -- because, “Well, shit, I can't change everything, so I’m just not gonna change anything.” 

Rebecca Ching: I also know a lot of people that tried to change things and then just got shut down and they just kind of said, “Heck with it. I’ll just dial it in.” They got beat down too, and so, they tried.

Charlie Gilkey: Yeah, but what did they try to change is my thing -- I’m sorry to interrupt -- right?

Rebecca Ching: No, I think you're right. I think it’s more of like, “Okay, how did you go about it and how did you work with your team?” I like the differentiation of team and organization too. Again, some systems are super rigid and closed, and change is hard, but I appreciate that.


Charlie Gilkey: Yeah, and I understand that. I’m not trying to present in team habits that you can change everything about your organization. That’s not in there because you can't. Organizations change slowly over time. Even CEOs learn the hard way. New CEOs, “I’m gonna come in and change everything,” and then three years later they bounce out. Why? Because of corporate culture and the team habits that have so much inertia that the system wins. The system wins most of the time when you let the enormity of the system continue to do what it does. But when you start chipping away at what makes the system work, people win, right?

And so, that’s what I’m trying to do in Team Habits is say, “Look, there’s this massive system that you work in. If you try to change the whole system at once, you're gonna be exactly --,” as you said, “Well, I tried to change it, and it didn't work.” But really? Really? Let’s say I’m gonna poke on meeting cultures, right? Because meetings, we love them, right? [Laughs] You know, “Well, I tried to change our meeting culture, and it didn't work, and we just had these stupid meetings.” Well, we don't change meeting culture. We change a collection of habits that we do in meetings.

So I’ll start with one. Let’s just leave five minutes at the end of every meeting so that we can capture next actions from the meeting. In the moment while we’re talking about it, we assign who’s doing something and by when and very simple things that I talk about in Team Habits. This isn't rocket science. This isn't hard to understand. It’s rocket practice. It’s hard to practice and to do it consistently.

So yeah, throughout the day I might say some things that are completely obvious, like let’s have five minutes a day, and you're like, “Yeah, yeah, yeah, yeah, we get it.” But do you do it though? Let’s get that in place, and maybe we work in a big corporate culture and things are slow. We just spend a quarter practicing that one team habit. Okay, great. Then we spend a quarter practicing getting update blocks out of our meetings because we can read an email about that, right? We spend that quarter -- so we got next actions to end the meeting. Great. Next quarter we’re just gonna get the stupid update section out of the meetings. Cool.


The next meeting the next quarter, we might put in some bonding and belonging stuff that we all like to do. We show up with the favorite song we heard last week. Something fun and cool. What we’re doing is stealing time. So if that meeting was 80 minutes plus or minus 20 minutes, even though it was supposed to be 60 minutes, we steal five minutes here, we steal ten minutes there, we steal 30 minutes there. We get that meeting down to a time that’s appropriate, but fundamentally, we start looking forward to going to those meetings because we know why we’re there and they're doing work for us and they're not pissing us off to do a bunch of pointless updates and things we don't care about, all the while we’re stressed about the work that we’re not able to get to that we’re gonna get in trouble for not getting to.

Rebecca Ching: For sure. For sure.

Charlie Gilkey: So that’s what we’re trying to unpack here. You don't change meeting culture. You don't change a collaboration culture. You change these micro habits, and it takes time, but you know what? You're gonna be showing up to work anyways. Might as well try to make it better because if you make it better for your team, those four to eight people, you make it better for yourself.

Rebecca Ching: Yeah, and that premise of change really happens in the context of relationships, not blowing things up or having a big policy. It’s really through relationships it makes sense, and it takes time. It’s about putting in the reps. It’s about staying curious. And that’s not always what we’re taught either, to be patient in those practices. 

So I want to bring it back to my question, though. Your vision to democratize who is a part of an organization's decision-making process. How is that different? I think you touched on that a little bit. Anything else you want to add on how that vision is connected to Team Habits?

Charlie Gilkey: Well, so how to democratize decision making. I’m doing it the same way that we’ve gotten from lean manufacturing. The people closest to the work should have the most autonomy over the decisions being made about the work. 

Rebecca Ching: Mm, imagine that.


Charlie Gilkey: Right? The thing about it is I decided intentionally not to push really hard on holacratic, sociocratic, and anti-hierarchical government models, right? Because we need to have a conversation about that, right? I don't know how much time we have today, Rebecca, but this is gonna get me in trouble from all sorts of folks.

Rebecca Ching: Yeah.

Charlie Gilkey: Most individual workers love the idea of more autonomy, of more decision making, of being able to sort of do that until they're presented with the real work of that, until they're presented with, “You have to make this $50,000 decision,” and work through how to do that. It’s your choice. Then they're like, “Wait a second. No, no, no, no, no, no.” Or you have to make this decision that’s going to affect the livelihood of 20, 25 people around you. Like, well, maybe not so much that, right? What I wanted is more decision making about my work and my schedule and what I get to do, but you know what? You work in a team. You work in an organization. This is what’s different about personal productivity or sort of personal effectiveness and team effectiveness. Every action you take in a team context is a social action. It’s not an individual action.

So Rebecca, you, as an individual, you can make all sorts of changes to your schedule. It doesn't matter until we’re in a team context and you change and block off your Tuesday afternoon, but I have work that I need from you on Tuesday afternoon, and I can't get it from you, right? 

Rebecca Ching: Mm-hmm.

Charlie Gilkey: And so, the reason we have to get real about some of these governance models is people want them. Again, I’ve done this coaching for the last decade and change and worked with some organizations to go to some of those models, and it’s actually not the owners, founders, and executives that end up bailing on the project. It’s usually the folks who --

Rebecca Ching: Really?


Charlie Gilkey: -- were claiming that because they're like -- because they won't make the decisions, they won't take the initiative. It really is a reprogramming of what it means to work together.

Rebecca Ching: Huh.

Charlie Gilkey: And so, I’ve seen more of those initiatives fail, not because senior leaders were like screw it, we don't want to do it anymore. So a lot of these models take the functional roles of, say, executives and managers and distribute them to teammates and distribute them across the organization. What we’ve done in a traditional work model is we’ve equated the position with the functional roles. So executives are the strategic decision makers, priority sitters and things like that. In the models that we’re talking about, these new governance models, you take those roles, and you distribute them across different people. That’s great. People want it until they're really complex decisions that involve people’s lives and jobs and livelihood. Like, “Ooh, I’m not prepared for that. That’s a hard decision. I don't want to do it. I just want to show up and do the thing.” You can't really have it both ways on this one, right? 

And so, again, this is gonna get me in trouble from all sorts of things. But we need to get real about that because in this same way that we don't take agency of our lives in our personal relationships, when you introduce some of these models at work, you see those same things happen. And so, Rebecca and I bump into each other. I'm hurt about it, but I decide that it’s uncomfortable for me to talk about it, and Rebecca doesn't know she bumped into me, so I don't take that initiative to do anything, and we let these frustrations creep. I could have reconciled it the whole time with Rebecca. I just didn't. It turns out if you're really interested in democratizing decision making, you're actually gonna have to talk a lot about the emotional components and the emotional and social components of making these decisions, and it’s not as simple and easy.


Again, I learned this in the army because I was an officer, and then I had people like, “It must be great to have your job, sir.” It’s a joke. They said it in joke. I was like, “I'll tell you what, though. You're gonna go with me tomorrow. You're gonna do everything that I do on my schedule, and I’m gonna consult you on every decision that I make that’s not confidential, and you're gonna be in the driver seat of doing my job.” Usually after about half the day, the troops will be like, “You know what? I kind of like my job. Can I go back and do that now? Peace out,” right?

Rebecca Ching: [Laughs] Yeah.

Charlie Gilkey: I’m not trying to say my job was better. It was different. It’s fundamentally different.

Rebecca Ching: Well, the stakes are higher.

Charlie Gilkey: The stakes are higher. 

Rebecca Ching: And so, what’s coming up for me -- I don't know, have you read Cedar Barstow’s book Right Use of Power?

Charlie Gilkey: Yeah.

Rebecca Ching: Because if not, I’d definitely check it out. She’s coming on this show soon too, and she talks about these different types of power, personal power, and so many people kind of forget that we’re born with our own personal power, and there are so many systemic things, let alone things in our personal lives that cloud that, and then there’s role power, status power, and institutional power, and then up power, down power, and those different things to stay curious about. But I think there’s something about power that’s woven into this individual and systemic power that’s part of this. I kept thinking about it as I was reading your book.

Charlie Gilkey: Yeah, I’m glad you mentioned that. Earlier in the drafts of Team Habits I was really clear that so much of the book is about power, and much like what I was talking about in the greenroom, I decided to trojan horse that. The funny thing about it is as much as I’ve been reeling against some of the challenges with converting into an anti-hierarchical or sociocratic governance model, if you practice team habits, you’re doing that. 

Rebecca Ching: Yeah, it’s egalitarian.


Charlie Gilkey: It’s egalitarian. You are effectively doing that, and while you're having conversations, conversations about power will come up. We don't have very good communication structures and facility with talking about power directly. And so, to make the book about talking about power up front sets a whole meta conversation of the executives are like, “We’re in the middle of COVID, man. Are we really having this conversation about power right now?” And then on the flipside, to have some of the real conversations with line workers around what the emotional, social, and mental components of power and the relation on all the things you're talking about that’s like --

Rebecca Ching: They're like, “I'm trying to just breathe.” 

Charlie Gilkey: “I’m just trying to breathe, man. We are just trying to breathe.” And so, for better or worse, I decided in this one I was like we’re all just trying to breathe and do better together. What is the simplest way to talk about that?

[Inspirational Music]

Rebecca Ching: Leading is hard. Leading is also often controversial as you navigate staying aligned with your values, your mission, your teams, and your boundaries. Navigating the inevitable controversy can challenge your confidence, clarity, and calm. Now, I know you don’t mind making the hard decisions, but sometimes the stakes seem higher and can bring up echoes of old doubts and insecurities during times when you need to feel rock solid on your plan and action. Finding a coach who gets the nuances of your business and leading yourself and teams in our complex and polarized world can help you identify the blocks that keep you playing at safe and small.

Now, leading today is not a fancy title or fluffy bragging rights. It truly is brave and bold work to stay the course when the future is unknown and the doubts and pains from the past keep showing up to shake things up. Internal emotional practices and systemic strategies are needed to keep the protector of cynicism at bay and foster a hope that is both actionable and aligned.


When the stakes are high and you don't want to lose focus, when you want to navigate inevitable conflict with the teams you lead and in between your ears, when time is of the essence and you want to make hard decisions with confidence and clarity, then Unburdened Leader Coaching is for you and where you want to deepen the capacity to tolerate the vulnerability of change, innovation, and doing things differently than you were taught.

To start your Unburdened Leader Coaching process with me go to www.rebeccaching.com and book a free connection call. I can’t wait to hear from you!

[Inspirational Music] 

I’d love to pull some quotes from your book because there’s so much I wanted to talk to you about. So I think I’m gonna just pull some quotes and have you riff on it. We’ll see how many we can get through. [Laughs] There are so many. I couldn't pick a favorite, so they're not in any particular order, more than just the flow of the book.

So you said in your book: “If teams are working well or poorly, it’s really not about the people on the team. It’s about how they're working together.” Before you respond, because a lot of people are like, “Well, we would be doing so much better if so-and-so wasn't on the team or if so-and-so showed up on time or if so-and-so’s attitude --.” So tell me more about how it’s not about the people on the team (whether they're working well or poorly), it’s about how they're working.

Charlie Gilkey: I want to acknowledge that there are absolutely folks on the team that can drag a whole team down.

Rebecca Ching: For sure.

Charlie Gilkey: That’s absolutely true, and what I would say is what is it about the team and org structures that allows that to persist long enough that it becomes a drag?


Are you actually having the conversations that you need to or is everyone phoning it in and hoping someone else tells them, “No, honestly, you really do need to show up to meetings on time. That’s not cool,” right? Who’s having that conversation or are you just deferring that to your manager and differing that to HR? Again, deferring it to someone else, right? It turns out that humans are incredibly malleable creatures, right?

Rebecca Ching: Yes, we are.

Charlie Gilkey: And we are very susceptible to peer pressure. We know that, right?

Rebecca Ching: [Laughs]

Charlie Gilkey: And so, if everyone on your team is like, “Dude! The meeting! We love you. We respect you as a person, but this is not working. This is uncool,” you need to fix that. In whatever ways they talk about it, one of two things is going to happen. They're going to fix it or it’s gonna be so awkward that they quit.

Rebecca Ching: And that’s not a bad thing either. They can self-select out.

Charlie Gilkey: That’s not a bad thing, right?

Rebecca Ching: Yeah, yeah.

Charlie Gilkey: But if no one says anything, and we put all the burden on the manager and HR, that stuff can go on for two years before they finally have enough of the paper trail to make the decision, right? And so, even in these conversations, that’s how the team works with each other, right?

And so, here’s the funny thing. I’ll try to be brief on this which, Rebecca, let’s acknowledge that me being brief is a practice.

Rebecca Ching: [Laughs] Well, keep rolling. I appreciate it all.

Charlie Gilkey: A lot of times people are like this person came in and then this team thing started, and they put it on the person. But when you really pay attention, that thing, that behavior, that team habit was in place before the person and it’s thereafter. This is why I get so much in my professional feels about books like It’s The Manager and the power of a great manager and things like that because it puts so much pressure on one person to change the system, right?


It does the very thing that I don't want us to do, which is say, “If we had a great manager, the team would be better.” You can be a great teammate and make the team better. That’s how you all can work together. You can self-correct, you can self-praise, you can do a lot of those types of things on the team. So it’s not about that one person on the team or not about the individuals on the team. It’s about how those individuals come together and play well. This is why when you see really powerful, enduring teams, people come and go all the time. If it were about the people, one of those players would leave and the team all of a sudden is like, “Oh, it’s different,” well, I mean, it’s gonna be different because there’s performing, there are all of those types of things. But when you look at really good teams that have solid ratedness, people can come and go and the team retains a relative level of performance because it’s not about the individuals on the team, it’s about how that team as a unit works together. Teams, especially in larger organizations but I’ll say in almost any unit, are the atomic unit of value of organizations. Individuals, not so much, right? Teams are what create value. The interactions of members of teams is what creates value. That’s why I want to keep us focused on team dynamics, team habits, team interactions, not necessarily Charlie’s interaction with Rebecca. 

Rebecca Ching: Okay, so here’s the segue to another kind of snippet that you wrote a little bit more extensively about the difference between a venting session versus problem-solving session. So let’s build on kind of what you just said with talking more about how we as teams can start to identify are we just falling into -- because I’m like if we’re gonna vent, is this to vent to really move things forward, or is this just to offload pain and then keep the status quo, right? Tell me more.

Charlie Gilkey: So I talk a lot at the very beginning of the book about broken printers because every organization I’ve worked at or consulted with has a broken printer that everyone knows about, right?


It’s some annoying thing that inevitably will trip people up five to seven times a week and create a bunch of downstream effects. It’s this stupid printer. It’s a $500 or less decision that no one makes to fix that’s actually having fairly outsized morale, performance, and belonging effects on the team. It doesn't have to be a real printer, although most of us -- you know, the CC thread from hell is a broken printer, right? Why do we do that to each other?

Rebecca Ching: Why! Stop! Stop!

Charlie Gilkey: We all hate it, but we continue to do it. 

Rebecca Ching: Yes. [Laughs]

Charlie Gilkey: So that’s an example of a broken printer. And so, you and I, Rebecca, as teammates might be like, “Oh, stupid broken printer.” “Yeah, man! It sucks. Every time!” We just go on and we get the emotion out, and then we go back to work. That’s a venting session.

Rebecca Ching: With the broken printer still in --

Charlie Gilkey: With the broken printer still there! Knowing damn well next week we’re gonna be venting about the same thing, right?

Rebecca Ching: It gets old.

Charlie Gilkey: It gets old. It’s changing that from saying, “You know what? What would it actually take to get rid of this damn thing? What is the process for getting a new printer and getting rid of that one?” 

Rebecca Ching: There is that dopamine hit that you think you’ve done something by venting. But the problem solving involves vulnerability. It involves putting some investment in it, something on the line. It opens you up to exposure. But it’s also your responsibility and using your power, your individual power and also maybe collective power. That’s scary.

Charlie Gilkey: The other thing about this book that came up is I would be giving talks about Start Finishing. This is a classic sort of thing where I would have senior executives and leaders be like, “We just wish people would take more initiative and own their own work and just stop bringing a bunch of small problems to us,” right? “We just wish that we can do our jobs and they would do theirs.” And then we’d have managers and line workers be like we just wish that the executives would let us make decisions and give us autonomy over our work and just not have to take everything to it. I’m like you're both complaining about the same thing, right? What is really going on here? This is the team habits and the culture at play.


And so, the difference between the venting session and the problem-solving session is you're right, it requires owning that that thing that you just complained about is something that you're willing to invest in changing and you're willing to risk having a conversation or you're willing to risk some time. We’re short-term thinkers as humans by default. We just are, right? We’re like, “Oh, well, I don't have time for it,” right? “I gotta get back to work.” And then next week, you and I spend 20 minutes venting about the printer again. 

Rebecca Ching: We’ve got time.

Charlie Gilkey: And we’ve got time. Every week, 20 minutes complaining about the broken printer. Put it in your calendar, right? What if we spent an hour or two to actually solve it, not have to vent, and then maybe we can spend those 20 minutes -- if we’re stealing time to vent, we can steal time to mess around with each other and have fun, right?

Rebecca Ching: Yeah. Wouldn't you say, though, there’s maybe a little bit of a culture or at least from higher ups to empower folks with permission or to remind folks about that, too. I mean, wouldn’t that help?

Charlie Gilkey: It would absolutely help.

Rebecca Ching: Okay. [Laughs]

Charlie Gilkey: So I’m not trying to -- as much as I’ve been -- everybody please hear me. As much as I’ve been saying the patterns that we line workers do and where we get ourselves in trouble, I am fundamentally for us all, especially the folks down in that chain that don't have that, it’s fundamentally for that, right? I have to say because I do a lot of the org change work and executive coaching work, how we show up in those conversations as line workers is a huge predictor of the partnership we’re gonna create with everyone else.


So we’re a part of it. And yes, absolutely. The next book has already started to work on me. I hate that, but that’s just where it is. It’s really from the leader’s side, like here’s what you have to do, right? The exact opposite of what most people think, right? For that one, it’s like saying, “Look, your time is valuable actually. I get that. I pay for that. It’s in the budget. We see that. If you are seeing things you can change within this amount of spend, with this amount of money, with this amount of time, please make a plan. I talk about a decision recommendation, intention, or plan. Please suggest a solution and work it through and let us know what you want to do. We’ll do the best we can to make that happen.

Rebecca Ching: Okay, tell me what you mean when you wrote about: “Put your team values on the floor, not the wall.”

Charlie Gilkey: Yeah, so this is about walking your values. That’s what I’m trying to do in that one. A lot of times we create team values or corporate values, and they’re just these aspirational posters on the wall like integrity and excellence and whatever, value, right? Really broad words that we -- 

Rebecca Ching: #reallycool.

Charlie Gilkey: #reallycool. They're aspirational values. But when you look at the values on the floor, what people are walking and talking every day, they're not those, right? 

Rebecca Ching: Yeah.  

Charlie Gilkey: And so, you might have “innovation” on the wall but then have so many team habits and corporate workways that prevent people from innovating. Well, guess what your real values are? As I’m working with folks, especially executive coaches and things like that and founders, I’m like, “Here’s the thing. Your values -- here’s how to know what your real values are. What you promote people by and what you fire people by,” right? If those aren’t actually in your stated values, your stated values are BS because people are going to do what gets them promoted and not do what gets them fired, regardless of what’s on the damn wall.


So your choices here are to either put the values that you have on the wall on the floor or put the values that you have on the floor on the wall, but this two-values system has got to go. It creates too much gaslighting and social overhead that’s in the way of people actually showing up and getting good work done. 

Rebecca Ching: Amen. This one really stood out to me too. “We have a bias in our society, especially in the business world, towards making sweeping changes, like if something’s not working well, let’s clear it out and start fresh. Burn it down, and then we’ll just clear out what we built up in two years, and we’ll invest in something again,” instead of staying the course or tweaking. I really appreciate you bringing this up and would love for you to speak a little bit more about this bias, especially for leadership when they hear about complaints and just want to get rid of it versus rumble with it. 

Charlie Gilkey: We are, as a people, grandiose thinkers. We think in terms of monuments, and we think in terms of big, big, big, right? And so, to come in and be like -- again, some of the listeners might have heard me talking about five minutes at the end of a meeting like, “Really? Really bro? That’s what you're telling us to do?” I’m like, “Actually, that is what I’m telling you to do, because that’s not going to show up in your performance review. That’s not gonna show up like you're not gonna be high fiving your friends about that,” right? It’s gonna be this really mundane thing that over time will have a huge difference. But we are social creatures. We tell stories that make ourselves bigger. We love a tall tale. We love fishing stories. And so, that’s unfortunately what primes us on how to think about things. And also, we’re usually not good at decompartmentalizing problems. That takes a certain way of thinking and a certain patience and a certain diligence that we don't have the time for because by the time you're six minutes into it, you get the next text message and it’s the next problem to solve and you jump to the next thing.


The other thing about it that I’ll say here is because of the grand sweeping things, we also -- in Leidy Klotz’s book Subtract -- everybody should read this, right? But Leidy pointed out so well that we have a bias towards addition and problem solving, and we neglect subtraction as a vector for problem solving. And so, usually the sweeping changes are we’re gonna get rid of it and then we’re gonna add something, we’re gonna build something, not we’re just gonna delete those three things from it, and once we delete those three things from it, it’s basically there.

Rebecca Ching: Lastly, you said, “Many organizations implicitly or explicitly discourage people from bringing their whole selves into the workplace. It’s almost impossible to feel a strong sense of belonging in a team where you can express only a fraction of yourself.” Tell me more about that quote.

Charlie Gilkey: Yeah, I think what happens here is that some policies about professionality and how you show up and how you posture at work get supersized across all contexts. We understand intuitively that if we’re at a full team or organization meeting, there’s a certain way we show up. Ain’t nobody got time for all the different quirks and things like that, but we forget (again, it’s about your team) with your team, right, like Rebecca might put her hair up in the management meeting. 

Rebecca Ching: Top knots for the win, yes!

Charlie Gilkey: But when we’re just chilling back in our team -- and there’s a reason I keep using doing this, and one, because I’m fond of Rebecca, but I keep using teammate’s names because you have to remember it’s not a teammate.


It’s not this concrete, abstract thing. It’s this person that you know well, and you know Rebecca has your back and you have hers. It’s personal in that way. Rebecca might be 100% polished in that management meeting and then come and curse like a sailor to me.

Rebecca Ching: [Laughs] 

Charlie Gilkey: Right? Because it’s cool. She’s a teammate, right? We understand that there are different roles, but I know who Rebecca is, and she can switch in that way, right? And so, she can be her full self in the team if we build that with each other. If we build that with each other.

So yeah, we can do that. I currently see Rebecca’s background. We might say in corporate, “No backgrounds,” right? “Because you might see something inappropriate,” and then there’s a conversation and HR and all those sorts of things that happen, right? But when it’s me and Rebecca talking or my team talking, it’s like, “You know what? We’re just gonna show up,” because we want to be together in a way that has the least social and emotional overhead, so we can actually have fun with each other and be ourselves and get to work, right? We have to be, at any moment, ready to snap into that. But that’s the team focus.

From the corporate sort of side, it’s like, “Really?” If your policies get supersized in that way, even if you don't mean for them to be, what you're essentially doing is making interchangeable cogs out of people, and it turns out people don't like that. You don't like that, right? So I just want you to take on the full cost of that because if you're in the executive seat making some of those decisions, seeing this happen, and not doing something guess what? It’s your broken printer, and if you allow things to happen that make people feel like they are cogs in the machine, you should not be surprised that they work like they're cogs in the machine and only as much as a cog in a machine will work until they can find a better machine to work it. That’s on you.


Rebecca Ching: I think the belonging piece, I mean, people feel like they have to lose themselves just to get a paycheck. 

Charlie Gilkey: Yeah.

Rebecca Ching: And that we really need to move away from that and, with your team, that sense of connection and camaraderie, if that even expanded, right? That actually really does help with retention. It helps with profit. It helps with all the things that a business wants and needs, but there’s just still so much fear and scarcity around it.

Charlie Gilkey: Yeah, it’s so much fear and scarcity, and I’m glad you mentioned that because from a leader’s perspective, the main things that they all talk about retention, you got it, (talent, cultivation, and improvement), working on team habits helps with that, right? Innovation helps with that. Efficiency helps with that, right? All the things you actually care about are solved by working on better team habits and especially belonging. Again, if you treat everyone as irreplaceable numbers on a line, you should expect them to treat your organization like a replaceable number on the line. So if you want them to be with you, you need to be with them. 

Rebecca Ching: Period. That’s relationship right there. We don't have to be the same, but to really create a culture of belonging means being comfortable with difference. Imagine that. Imagine that. 

I’m curious, I keep coming back to these conversations we’ve been having right now with folks who -- a lot of businesses that were traditionally all in the office and then with COVID a lot of folks worked from home.


Some companies were already a little bit of a hybrid mixture, and now there’s like you're coming back or at least a few days a week, and this is connected to your performance review or you’re gonna lose your job if you don't relocate. I’m wondering where team habits come into play with some of these -- I think there are some other things that are in play too, but kind of like, “You're not getting work done if we don't see you,” or “We need to fill office space.” I’ve heard that from many of my clients. The boss will say, “I see too many empty desks here. Get people back in here,” you know? But why, you know what I mean, if the work’s getting done? I’m wondering how, if leaders who are really looking at your philosophy on team habits, what would be different in some of their policies around work, whether it’s all in the office, hybrid, or all remote? 

Charlie Gilkey: I wish I were the person that came up with this, but I’m not, and it’s been around for decades. It’s written by a guy named Peter Drucker, right? It would be management by objectives, which we say nowadays as management by outcomes, right? What are you actually trying to do? What is the outcome you're looking for? Be super clear about that. What are the outcomes you're looking for? What are the parameters that dictate that are useful? Then what are the priorities? That’s really what we need executives to focus on. What are the outcomes we’re looking for? What are the parameters that we have to follow by? And then what’s the priority stack? 

And so, teammates, if they really follow the whole organization and the team, the conversation would be not, “I don't see you sitting at a desk, therefore, you're not working.” It would be, “The outcomes we’ve agreed need to happen or that you know need to happen if we can't come to agreement, are not happening. What the team, what the department is currently doing is not sufficient to meet that.”


Let’s have a conversation like, “Explain to me why the goals and the outcomes that we’ve set are unrealistic or unmeetable and how that works,” right? Because maybe you're seeing something that I don't see. So I talk about the chapter on goal setting and prioritization. There would be that reconciliation that it’s not just that we came up with crazy ass -- oh, don't get me on BX. Please don't get me on BX. Okay, I’m on BX. Big, hairy, audacious goals, right? Great! And we know there’s this weird thing from goal-setting science and studies. We are more likely to achieve a harder goal than a less difficult goal because we’ve fallen into less difficult goals like, “Oh, if we can get it done, then we don't prioritize it,” and then it doesn't happen. We fall down on it. But I think that’s also been supersized is like, “We’re gonna make impossible longshot goals that are gonna get people motivated to do that,” and I was like, “There's a time and place,” right?

But leaders’ and executives’ job in this one is to really set those stretch goals that focus people’s attention, and then remove the BS and bureaucracy and roadblocks that keep people from achieving those goals because it turns out, once most people and teams commit to a goal that is a little bit difficult, but they think they can do it, guess what? They want to achieve that goal. You are, at that moment in time, aligned. Everything that happens after that, in your workways and in your team habits, is what you need to work on as a leader. 

You know, a lot of times when I’m  brought in to do some of this work and we’re talking about alignment and especially from what seems like, “How do you get your teams in line,” I’m like, “Well, first, I just want to ask the simple question: why do we assume we’re not? What if we were aligned already, and there’s something else in the way?” Of course now you know what that something else is.

How it would look different is you wouldn't see what’s been called The Boomer Power Play of work happens in the office, and so, you all need to come back to the office just because that’s how work happens. 


Well, guess what? It’s 2023. Work hasn't happened that way for the last 23 years. COVID gave us an opportunity, right? It was a forcing function to break that mold. The real power play, while it’s been generational, has been people who think in terms of outcome-focused work and people who think in terms of time and presence-focused work, and that is the fundamental paradigm shift that, if you can get away from that longer head so you can have much more fruitful conversations about in office/out of office, because it turns out, with 13, the way we’re talking about team, I have to keep saying that.

Me and Rebecca, we actually like talking to each other in a useful, constructive conversation two or three times a week. We might actually choose to come into the office together and grab some coffee, work on the whiteboard, hang out. We might choose that because I like Rebecca. I don't need you to tell me to do that. But telling me to do a bunch of stuff that doesn't drive my work forward and then a month later having a conversation with me about my work not being driven forward is fundamentally frustrating. You created the very scenario that I’m now in trouble for. That would be the conversational shift. And so, again, as we do more of this work, as I do more of this work and share more of what’s coming in this next one is it’s like, leaders, what are you injecting into the system that’s creating the very outcomes you don't want?


Rebecca Ching: In your book you talk about the importance -- and you touched on that in this interview today in this conversation about moving stones instead of mountains, right? You talked about the big, grandiose things, and it’s really better to focus on moving these little stones and putting in the reps. What’re the stones that you and your team are working on moving right now?

Charlie Gilkey: Yeah, it’s funny how we do this work much to my team’s chagrin because they're like, “Can we just let things be for a while?” And I’m like, “It’s a slightly broken printer. It’s not a broken, broken, but we can do better.”

Rebecca Ching: [Laughs]

Charlie Gilkey: So this is a problem when you have a [Indiscernible] leader, right? Because I’m like, “One percent better, guys. We can do it,” right? They're like, “Not today, Charlie. Not today. Can I just do the work today?”

We are working a lot on our collaboration team habits. I’ll get a little bit granular here. We’re using a few tools (Slack, Confluence, Asana) and we’ve recognized that there are two tools (Roam and Notion) that might eat all of them.

Rebecca Ching: Ooh!

Charlie Gilkey: And so, rather than having it split across three or four different apps and spaces and where does the information live and it doesn't quite work right, it’s playing with, like do we consolidate in that way, and those are just straight up collaboration. Like where do we put task? How do we talk about task, right? Are we okay as a team with the tasks tasking each other in Slack because it’s the default that so many of us do, right? It’s like, “Hey, will you do a thing, Rebecca?” And you're like, “That’s a task!” Technically that should be in Asana, right? What are we doing about that? So working on those types of things.

The other thing we’re working on, and we have been working on over the last two quarters is our meeting cadences. We got into a place in quarter four where there were just way too many meetings for everybody. And so, we did a meeting audit, and it was just like why are we doing that? Because it wasn't me that said do all these meetings. It was the team having a lot of team meetings.


Now, in our language, a one-on-one conversation like Rebecca if you and I just sort of pull each other aside for ten minutes, that’s a conversation. That’s not a meeting. But they were having full on two/three team meetings a day across different teams, and I’m like, “No wonder you all can't get anything done,” right? I didn't say you can't get anything done. “We’re falling behind.” I’m like, “Why?” Right? So it’s funny.

Rebecca Ching: You're in meetings all the time!

Charlie Gilkey: I’m like, “You're in meetings all the time!” And I’m like, “But why,” right? And so, it’s funny being me in that way because I’m like, “I’m not the one telling you to be in meetings.”

Rebecca Ching: Not good. [Laughs]

Charlie Gilkey: This is not good. Like what is going on here? And so, that is one of those instances to where I actually -- as a leader, you have to adopt different postures. And so, if you're curious about this, Coactive Leadership is a great guide. And so, you've got leaver on top, leader in front, leader behind, leader beside. You have different ways. And so, that one was like, “Okay, I need to be leader in front this one,” right? Because this is something that’s so endemic across the team that as much as top-down decision making doesn't work in so many scenarios, this is one where I need to have a forcing function for us to say, “You know what? Nope. We’re not doing all these meetings.”

Rebecca Ching: Well, you used your up power in a way to help create relief. 

Charlie Gilkey: Yeah, to help create relief because it’s like this is not working for any of us, and you're suffering and continuing to do so. We have to fix this. I’m not gonna say that I’m gonna come up with a solution, but I’m at least gonna stop this team pattern, right, and subtract. So notice it was a subtraction thing, right? So I’m like, “We’re gonna subtract.”

Rebecca Ching: That’s a really good point too is if we’re making sweeping changes, to lean towards the subtracting. That’s a big takeaway for sure.

Charlie Gilkey: So we switched so that now we only have a team meeting every other week. Turns out a lot of people are happy. Our stuff’s happening. We’re starting to reach our performance zone again and things like that.


Rebecca Ching: Oh, I think it’s a great habit for all of us to get into to audit our systems and our meetings on a quarterly or some sort of regular basis. Just how’s it working, how it’s not. I mean, I think sometimes in the past I would be afraid of that because I’m like, “I can't do anymore work.” People are overburdened or seasons of life or whatever, but that fear that change or curiosity’s gonna lead to more work versus it’s actually gonna free us up really is the end game. So I appreciate that.

One thing you noted too, you didn't spend a lot of time on it, but it stood out to me that when teams are working through big commitments and the stones that inevitably there are some individual losses as you move towards the collective wins.

Charlie Gilkey: Yeah. 

Rebecca Ching: How do you help your team move through those individual losses while you're working through the bigger wins with heart and compassion?

Charlie Gilkey: Thanks for pulling that up because I think that’s what’s not acknowledged when we start changing things. Even if you're subtracting things, right?

Rebecca Ching: Yes, good grief. Yeah.

Charlie Gilkey: Someone put that there. It’s grief, and it can be mistaken especially in overly optically-focused organizations. It can be taken as a status loss. Like you removed my thing.

Rebecca Ching: Totally, right? [Laughs]

Charlie Gilkey: It was my idea, and you removed it, right?

Rebecca Ching: Yeah. 

Charlie Gilkey: And so, there’s all that sort of thing that’s in play. So, first, acknowledging, “Hey, Rebecca, I know six months ago you had this idea that we would do the funny joke block of the meeting, and it was super fun and it got us bonded right now, but it’s kind of feeling a little stale now. I’d kind of like to change it to something else, but I know it was your thing, and I appreciate it. It did its job, and I really, really loved it. But how are you feeling with it? What’s going on? Are you open to changing that? Where are you with it?” Even if Rebecca still loves the funny joke block, she might be like, “You know what though? Maybe it’s time for something new too,” right?


Like I can see that we’re in this relationship with each other and there’s some give, but I wasn't just like, “Rebecca, that’s stupid! We’re not doing it anymore! It’s a waste of time” No, it served its purpose. It served us well at that time, and it took really, really good care of us at that time. And we have evolved, right? That’s the thing that we forget about. As you work through your team’s performance and as you get better about working, the training wheels and the things that you needed in that earlier stage you might not need anymore, right?

And so, that block that I was talking about, that financial review block, those might be training wheels now to get us all used to revenue stream ownership and so we can align and prioritize work around that and some other things we were going through as a company. Six months from now we may not need those training wheels. This small team that we have may just be at a level of readiness and context and know-how and team habits that it’s just sort of embedded knowledge, and we can roll the hell on and get our 25 minutes back. We don't need to keep talking about it. We did it. Or we might go through a cycle where things get crazy again and it’s like, “Hey, remember when we used to do that? Well, we’re not doing our habits. We need to do that again.”

So, my point is, just because something’s not working for you now doesn't mean that it didn't work for you in the past and doesn't mean that the person’s good intentions and good ideas and good heart can and should be dismissed. If Rebecca put the funny joke block into the meeting, I want to go back to Rebecca and say, “That seemed like a great idea, and it did some good work for us. What do we really need to work on now?” and pull Rebecca into that process to help me cocreate the next great thing versus just shutting her down and excluding her and saying, “You know what? That’s old and busted. I got some new hotness. Deal with it. Cool, cool, cool.”

Rebecca Ching: [Laughs] Totally. Oh, my gosh. Yeah, those are all really, really good points. I feel like that’s most often what I talk about even with when we’re trying to change our own individual habits or practices. and things that we’ve done that maybe were comforting us but comforting us in ways that were doing harm. But they served a purpose. So I just really appreciate that external compassion shown too.


As we wind down, what is your relationship with your team today and how has it evolved over the years?

Charlie Gilkey: That’s a broad question. What is my relationship? You know, I always feel sort of awkward about these conversations because it’s like you should ask them.

Rebecca Ching: Fair enough. Fair enough. 

Charlie Gilkey: They're not here on the podcast, right, so they can't speak for themselves. 

Rebecca Ching: No, I appreciate that.

Charlie Gilkey: Well, as big-hearted as I can be and as much of the coach and friend and guide as I can be, I also pay their checks, and there’s an inherent power dynamic there, right? I just want to acknowledge that even if -- and I do believe that they would tell me the truth because they’ve told me plenty of truths, right? We’ve opened the door for that, right? You know, there’s still that place to where their relationship with me is a part of their livelihood, and so, I take that very, very seriously.

So, as best as possible, I try to treat my employees much more like they're my clients (I’m an executive coach and things like that) than the folks who work for me, right? And fundamentally they do. So my relationship with them I think it’s deeply and frustrating collaborative for them, right? 

Rebecca Ching: Sounds pretty human.

Charlie Gilkey: Yeah, in the sense where I try not to make a lot of decisions on their part, so they have to make a lot of decisions. I try to give them -- I don't even like saying try to give them autonomy. I try to set it up so that there is autonomy as much as possible in their work. Right now because I’m in the middle of a book launch, they need more from me in terms of feedback and guidance than the time that I have available with everything else that I’m doing. And so, that’s probably the deeply frustrating part of the collaboration.


My default is not to be a leader in front, to be honest, right? It’s really not. In the best ways, as being a leader and being a teammate, I’m not around and that’s a good thing because the things that I’ve set up allow us to work without me being around. 

Rebecca Ching: And has it been evolution over the years, or has it always been pretty constant for you to not want to lead from the front?

Charlie Gilkey: It’s been fairly constant when I know it’s my role. So, for instance, in the army, there were plenty of times where I had a leader-in-front job. That was the job. I was the face. Okay, that’s my job when it was my time to be that, but when it was in the small team with my leaders, I fundamentally don't know your troops the way you know your troops right? I don't know what they're working on to the degree that you know they're working on, so I had a few rules. One, don't make me chase you down to figure out what’s going on with your projects and assignments, right? Because then I’m doing two jobs. I’m doing your job of communicating with me, and I’m also doing my job of managing you. I only want to do one job. So you do your job, I’ll do mine, right? Simple things like that, and “Hey, if you need me, I’m here, but my job, as much as I don't like it, is to sit in this office and be the switchboard for priorities and tough issues.”

So that was the job then, and there were times that I needed to be up front and needed to do the saluting and the parade and all that sort of stuff, and I did it, and I did it well, but that wasn't the fun part for me, right? My fun part was actually seeing my leaders and teams excel with as little interaction from me as possible, so I could focus on the things they couldn't do.


So that was easier to do there when I’m commanding 219 troops than when I have a smaller team because it actually is my job to make sure they get paid. So it’s just different. I try to evoke as much as that because here’s my theory of human nature that drives so much about this, and I write about it in Team Habits.

One, people are inherently goal motivated. Two, they want to be in good relationships with other people. Three feels like the same as the first but it’s not, they enjoy getting stuff done. How do I as a leader, as a founder, as an owner, as a teacher set up the conditions where people get to do what they already want to do and be who they already want to be. What’s in the way of that and what do I need to add so that that happens?

Rebecca Ching: I appreciate that. Thank you so much for sharing that. Where can people find you and connect with your work, get your new book, and get access to anything else that your body of work that you've put together?

Charlie Gilkey: I appreciate that. Thanks so much for having me, first. So all roads lead back to Productive Flourishing. You’ll be able to see prior bodies of work but also Team Habits. But if you're really, really interested in Team Habits and the conversation we’re having today, go to www.betterteamhabits.com, and you’ll learn more about the book but also learn more about the writing that we’re doing around this as well.

Rebecca Ching: Really, thank you so much for this conversation. My brain is going a mile a minute. I’ve been taking notes and other things too, so you really are a wealth of knowledge, and I just appreciate your presence in so many businesses, organizations, lives, and also just speaking truth to BS in so many of the business and entrepreneurial spaces. So just grateful for you and your heart and the impact that you have.

I really wish you all the best with this book, and I cannot wait to have you come back again to talk about the next one, if you're willing! [Laughs]


Charlie Gilkey: I am definitely willing. I appreciate your time. Listeners, I appreciate you. I know we’ve gone a little bit long on the day, but hopefully it’s been worthwhile. Thanks for being with us.

Rebecca Ching: Absolutely.

[Inspirational Music] 

Before you go, I want to ensure you take away some of the incredible wisdom Charlie shared with us today. Charlie challenged us to put our values on the floor and get them off the wall. He also encouraged us to focus on changing micro habits over time instead of trying to make big, sweeping changes which can often lead to burnout and us tapping out. Lastly, and I really valued this, Charlie shared how the things we care about can be solved by working on better team habits, imagine that! 

Now, after listening to today’s conversation, did anything shift in how you see the way teams can impact change? What is a micro habit you and a team you're on can focus on changing and measuring over the next few months? If you lead a team, what can you do to help your team have the space to do the work that they can do with the least amount of bureaucracy and burdens? Oh, gosh, we breathe in the messages like a firehose about how much we need to change our personal habits to see the results we want in our life. We learned today when we focus on our collective habits, we not only change individually but we change as a team. This is the ongoing work of an Unburdened Leader.

Thank you so much for joining this episode of The Unburdened Leader. You can find this episode, show notes, and the free Unburdened Leader resources, along with ways to work with me www.rebeccaching.com!


And if this episode meant something to you and was impactful, I’d be honored if you left a rating, a review and shared it with someone who you think would benefit from it. Thank you so much for listening!


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