235: Minimizing the Social Overhead of Managing Teams with Charlie Gilkey

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Teamwork can be challenging. When it is challenging, I hope you lean in on the beautiful humanity of the people that you work with and what would happen if you take it from the place of they're doing their best, they're overloaded just like you are, and they actually want to win in the same way that you want to win and they're just some damn broken printers that you all need to work on.

This is your time. How can we earn twice as much in half the time with joy and ease while serving the highest good? That is our guiding question here at the Freetime Cafe, your home for heart based business. I'm your host Jenny Blake. Join me for conversations with authors, friends and fellow business owners as we explore ways to free your mind, time and team to do your best work. Now onto today's show.

Welcome back Free Timers. We have a long time recurring guest of the pod. One could even say sort of the godfather of life after college. Pivot Free Time. Charlie Gilkey has been a longtime friend to her and inspiration. He has advised hundreds of teams from Fortune 100 companies to tiny nonprofits through Productive Flourishing, his coaching and training company. He's a former army logistics Officer and near PhD in Philosophy living in Portland, Oregon. He's the author of Start how to Go From Idea to Done, a book we talked about on the Pivot podcast. I'll put that in the show notes. And today we're talking about his beautiful new book team How Small Actions Lead to Extraordinary Results. Charlie Cakes, welcome back to the podcast.

Oh Danny Cakes, I didn't know we get to do the cakes today. Thanks for having me on the show. I'm pumped as always to talk to you but also to share this with the Free Timers.

It's just so exciting. We were kind of working on books at the same time and you said so sweetly on your podcast. Thank you for writing free time because now I don't have to and that it kind of freed up this bigger conversation about work ways. And before we hit record, I was saying free time for me is about the fact that I don't like running teams. And then for you, team habits is about. This is really a zone of genius for you. So the place I want to start was that I really appreciated one of your chapter subheads because it was the first time I had heard it put in precisely this way. You said, accept the unwanted gifts of Vuca and Covid. That Covid shredded almost all of our existing habits and we all got a crash course in change management. And so Vuca, you can say what that means, but I love just finally acknowledging, like all of us who are running businesses, we do need to, we still need to reconcile what the heck has happened the last few years and even accept those unwanted gifts. I'm curious what you see as a high level. Some of those, quote unquote, unwanted gifts have been.

Yeah, and so I love that I was talking to some folks yesterday and just reminding them that as of when we're recording, which is September 2023, we are like three and a half years into at least a five year pandemic cycle. And so in 2020, I'm usually tone deaf in all sorts of different ways. Right? Because I'm not saying the thing that people want to hear and that makes me sound extreme. But what I was saying in 2020 was, look, we're going to be all right. It's scary right now, but we're going to be all right. And this is going to be a long haul. This is not going to be a, like flatten the curve. And then three months we're back. It's like the upset that this is causing to our society and culture and economy is going to play out over this time because study history. And so we're three and a half years into this cycle. As of today, there are two new variants that are out and like, that's just part of the deal and the opportunity. The unwanted gifts of Vuca, while Vuca, it's a term that started in the military and sort of went into corporate speak, but it stands for volatile, uncertainty, complex and ambiguous. And operating in a Vuca environment is completely different than operating in stable environments in a lot of different ways. And I'll talk about this for free timers because of the complexity and ambiguity and most.

Free timers who are entrepreneurs have a control freak bent right to them. And so not knowing if you press this button, what happens on the other side? And you press the button one day and this one thing happens, and you press that same button another day and another thing happens. It's frustrating, right? But part of the unwanted gifts of Vuca for all of us is that all of those sort of status quo, what I call broken printers that were just living there, they got thrown out too. And it forced us to reimagine how we might work. And in a lot of ways nothing was sacred. So it's like why do we have these stupid meetings? Or why don't we meet at all? Right. It can go either way. Or why do we show up and talk about what we're going to do and we all write down what we're going to do on our pieces of paper and then disperse and then wonder why we don't feel like we're aligned and coordinated. Like that's crazy. One of the unwanted gifts is that it showed us that change not only was possible, but that we were the agents of change. It didn't happen to us. It can happen with and for us and we can lead that. 2 Is it illuminated all of those broken ass printers that had just been laying around and I might have to set that up here in a second. Denny, I realize it's common shared language between you and I, so it illuminated them and created that wedge where we can probably talk about them. And third thing is it was not possible for us to opt out of creating a new normal. So for many folks, and this is what I was coaching during the time again, still being tome, death was okay, why don't we create a better new normal? We're going to be creating a new normal anyways. Let's make it better than the one we had before. And I know we're three and a half years into it, meaning folks are tired of recreating and renormalizing and refiguring things out. But that's part of the gig, right? And for free timers who also probably have a Kaizen bent, like a little bit better every day. I think the main change from COVID is you had to get a lot better faster. But at core you're all about a little bit better every day. So you're already changing. How about we embrace that? So those are a few of the gifts of Vuca and Covid.

I appreciate you sharing that. I'm wondering, I feel like another theme. There has been so much change so fast and there is still so much VUCA in the environment that for me personally, I feel a little fatigued at this point in now. I'm curious if you feel that at all or if you felt that at any point in the last few years and how you deal with that, knowing that you're a systems guy. And this is really one of your zone of genius. You did logistics in the army. So adapting in this way is down your strike zone. And at the same time, what do you do when you're just tired of it? Okay, I get it. Me too. I wrote a book on how to be more agile and write and adapt to change, and yet I still hit these dips where I get tired.

Yeah. So that's the uncertainty bit. I think of that because how long is this going to last? What's it going to look like? And so what many people are tired of is not the actual work of change, but having their expectations shattered so frequently and having to do all the little micro negotiations because they don't have enough defaults. Part of what I hoped to do in team habits was to help the team recreate defaults so that they didn't have to figure out how to do 80% of their work every damn day. The reality is, whether you're in a small business or a larger business, about every 18 months, you're going to go through two pretty significant shifts in your team or your organization. One is likely to come from outside and one is likely to come from inside. That time cycle is probably shorter if you're in a small business. I think the other gift is, well, in our community, especially in our academy, one of the things our people are put on the bingo card, which I say a lot of things because I have go to's, is, you know, I ask them, what are the gifts of not knowing? Not what's the down part? Right. Because we're so afraid of uncertainty. But when we accept the gift of not going, then I think we can be more experimental and be less hard on ourselves about what the outcomes are. And I want to give people permission to where it makes sense to not change things. If you have team habits that are working really, really well for you, don't mess with them, acknowledge them, celebrate them, and really go to those things that are pissing you off and just work on those. I may or may not be answering your question, Jenny, but I think what we need to do is shrink the scope of our world enough.

Such that we don't feel like we have to fix everything everywhere, all the time and just say, you know what? This month we're working on meetings. That's the one thing we're going to do. And there's a specific habit we're going to work on, like leaving five minutes at the end of the conversation so we can capture next actions together. That's the one thing we're doing this month. And it brings down that sense that you got to change everything all the time right now.

I love that. The shrink the scope of our world so we don't have to fix everything everywhere all the time. It's like that movie title, Everything everywhere all at once.

Yeah.

You've done a great job of putting language both to the team habits. I mean, the phrase itself, team habits, is like, aha. It's not just all of us on individual islands trying to be more productive and efficient every day. There are team habits. And you've done a great job of naming some of the things that could go wrong. So I want to ask you, because ever since I read it, I can't get the phrase out of my head. Crisco watermelons, what are they and what is it indicative of in terms of the systems issue?

Yeah, thanks for that. Cause one of the things that I try to do in my work, but especially in this work, was not make it so corporate speak and not make it so unrelatable because I needed to sound smarter than everybody. That's not my game here. So Crisco watermelon comes from the Boy Scout camp that I used to work at when I was a teenager. And every Friday we would do watermelon relays. And so the basic point was it's like a swim relay with a few twists. So it was usually 50 or 75 meters, depending upon the water conditions. And you had four people. So think of a relay. But we added a watermelon that was slathered in Crisco. If you're not from the south, don't know where Crisco is. It's Greece, right? And they had to swim this relay, but hand off the watermelon to the next swimmer. If you've ever seen this or tried it, it's hilarious because a watermelon is one hard to swim with by itself, but when it's slippery, like, it's terrible. And if you dropped a watermelon, you had to go back to the beginning. You take a simple thing, just a relay of work, right? Handing off a thing and make it slippery and mayhem breaks out. It's hilarious when it's a fun, playful thing. It sucks when it's everyday at work. And the sort of Crisco watermelon work is like, you start like, okay, we're gonna do this thing and here's the plan. Boom, boom, boom, boom. And everybody's like, cool. And then Charlie takes his piece and then hands it off to Jenny. And in that handoff Somewhere it gets slippery. I don't know if she's got it or if I've got it. It went a different way. We gotta start over. I gotta swim backwards and figure out what happened and just things become slippery and hard and sometimes it's hard to tell why. So that's a Crisco watermelon, right? And so it's another way of saying cluster, fork, but in a corporate environment, think about who gets to say the real word and who doesn't. And so I was like, let's get out of that and have a different term that describes the same thing, that doesn't put people in awkward conversations. So that's all it is. And what I wanted to normalize with that is that it's normal. It is a common thing of working with people, especially when your readiness is low and you haven't really articulated your team habits and you haven't been working together. It just gets slippery and it's nobody's fault, but it's fixable.

Together I realized we jumped right into team habits. But it occurs to me that there are a lot of solo or solo pluspreneurs that I speak with who are either hesitant to build out a team at all, or maybe they've been burned in the past, or they do have a delightfully tiny team, but they're not really letting stuff go. See also your comments about control fetishization of keeping all the control. Just the other day I was chatting with somebody whose team member was very frustrated that they were waiting on the owner for a lot of things and they were piling up on the owner's desk. And I'm sure you see this all the time, every day. So my question is, it's really even a step prior to improving the team habits. I think a lot of business owners get stuck at creating the team in the first place or relinquishing tasks to the team. Like there must be some roadblock that you have discovered because they've been reading the business books. They know that they can't do everything themselves or they don't want to be the bottleneck. And yet there's still sometimes this big psychological chasm of getting to the place you've gotten of this, you know, well oiled, yet not criscoed team set of workways as you call them.

This might take the conversation in a completely different direction. And I love that. I think a lot of solo plus folks haven't really aligned to scaling or not. They want to scale, but they don't want to do the work. That it takes to scale and so they end up stuck. And I'm not saying that you should scale. I'm not a pro scale guy. I'm just saying if you want to double or triple your revenue, you got to make some changes. Because to go back to the scope of your world, it's too big. There is in a solo plus place for many people, there's like a $300,000 speed bump, right? Because that's depending upon your offer ecosystem. But inevitably, whether you sell products or whether you sell service or some combination between, so many people get stuck right there and think it's about them. It's not about you. It's about what the system of value that your business is creating and when that system gets too big for one person to deliver. So you have some options here. One, if you do the math and you're profit centered, $300,000 is a really good income for a lot of people. You can embrace that. Maybe instead of the standard business pathway that gets taught in all the books and on Entrepreneur magazine, where you build a business and then sell it, and then you build another business and then sell it, maybe you just Decide to invest 50, 100k in your 401k over 10 to 15 years doing a business that you love to do. And guess what? Wealth wise, you end in the same frigging spot, right? Ego wise, it's a different spot. But wealth wise, it's about the same. Having advised people that have gone a lot of different pathways to get to that point, many solo plus people don't give themselves the option that that's sufficient because they want to scale and they want to be the big business and they want to be on stage and they want to do all those types of things. Well, if that's what you want to do for most people means having a team and you switch roles from maker maker entrepreneur to manager entrepreneur. And many people don't want to make that jump. And that's okay. But that is the road that you're on. Because again, even if you have products to deliver, unless you're just tapping into the limits of AI, which by the way, you're still managing, you're going to reach that speed bump. What are you going to do about it? The difference between working by yourself, this is what really gets a lot of people. The difference between working by yourself and working with a team is that in a team, every action is a social, collective action. There's social overhead that goes with that. So me as an individual person working by myself in my Own solo business. I want to change my schedule, I want to do all that kind of whatnot. I want to change my email program, I want to do all that. Guess what? It's just me. I don't have to talk to anybody about it. I don't have to worry about their training. I don't have to worry about whether they want it. I just get to do it. Cool. Same situation, add a person. Well, if I want to switch those things around, like that person is impacted by those options. They may not be able to use it, they may pick it up slower, they might not be able to be as agile with it. So that same decision is the decision plus the social overhead. And not only are many entrepreneurs and solo plus folks control freaks, they're also people pleasers. And you put those two combinations together, that means you get a team and you're stuck between.

Controlling something and having it be the way you want it to be and pleasing other people on your team. And it feels upside down and backwards. It's like, why am I worried about pleasing them all the time? And I'm not getting what, like I'm paying them. But that feels weird. That feels old corporate model and I'm sort of anti capitalist, so I don't believe in that model. What's this model over here? Right. And you get all sorts of social overhead and existential crises around some of these things. Right. And I think that's where so much of the stick stuck. Because you're not defining this is the actual role that I'm hiring you to do for them. Here are the key outcomes that we want from this role. Here's how we're going to work together from the beginning. And you're just making it up on the fly without realizing that. I need to speak to this because I don't know that we speak it to enough, especially where we are in the pandemic cycle and the burnout that we're seeing in so many people. Fact owners typically can't quit and they can't be fired. This creates critical asymmetries between them and their team, such that owners need to center their self and their needs differently than they might need to center their team's needs because their teammates can quit, get a better job and be fired and move on. But the owner is stuck with that. And I don't think enough owners, especially owners who are women, really consider that because so much of free time and so much of team habits light is really about people acknowledging what they need for the work to be joyful and sustainable and long term and building and baking that into the business as opposed to expecting that a business on conventional terms is going to defeat those things. P.S. it won't.

We'll be right back just after this.

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Well, that phrase social overhead is so apt and I think you've just coined yet another term that's going to help me articulate something I would add to that Venn diagram of the owner who leans to the side of liking control and keeping it people pleasing. I'm also going to add introversion because the thing that holds me back from having a bigger team, I don't want to deal with people all the time or social overhead. I actually can't stand that. That's why I love automation software and I love the team members I do have. Right now I have one part time VA and a podcast production team. That's it. Ironically, when I was launching Freetime the book in March 2022, the team was the biggest it had ever been and I was the most unhappy. As soon as I cut it all down, stopped even having an attorney on retainer. Like every extended person who was meeting with me wanting things from me, I was never happier. I like all of a sudden I got back to my happy place. Less people, less social overhead. And I do think the people pleasing is a big part or just being empathetic and highly sensitive to other people. Because I'm kind of thinking about my clients. I'm thinking about anyone on my team anyway. So here's my therapy Charlie Gilbert therapy request here for it. I've been reading business books for 20 years. Whenever we talk about team size effectiveness, it's always in the lens of productivity and efficiency. Never does it say at what team size is the manager happy? And I think you and I have talked about this before, but at what point can I give myself permission that I don't enjoy anything more than the minimum level of social overhead of managing a team versus trying to improve and get better at it. I love team habits and there's always room for improvement. Otherwise I'll make my own life miserable if I just stay stuck in old habits that don't work. But I also think there's this sense of pressure in the business realm that we all must become like great people, managers and leaders and running teams. And I just so rarely hear people admit, I don't like that, or I'm not good at that, or no matter how much I try, I don't get energy or from doing that.

The business literature culture at large has a pro big bias, which means pro scale bias, because largely they're thinking about the economics of things. And so in that world, if you're not building $100 million or billion dollar business, you're basically over there in the lifestyle business camp. And lifestyle in that world is never meant as a positive sort of thing. It's kind of like, okay, you're playing small, that works for you, but you're not really part of the business conversation. Bullshit. Depending upon how you count, 94 to 96% of businesses are not the pro big businesses. They're not those other stock. Part of it is because there's just not enough market buying power for that to be at play. Now. That's part of the business landscape. This is why I stopped writing for some of those articles or some of those places. This is why I'm not writing for Inc and Entrepreneur in any of those anymore. Because I'm like, I don't know that I want to be a part of that conversation anymore. Right. I don't want to push those values on people indirectly. There are some people who want to build a scalable team, and I love that. I'm here for it, but there are other people who don't. So the real therapy question for you, Jenny, is what's it going to take for you to give yourself permission to be good enough?

Because if you start from the place where you're already good enough and your business could be an expression of your unique contributions and joy in the world, and you build and optimize around that, then you might get to a place to where it's sufficient. So we don't talk about sufficiency in business. About the only other person that I see really push that limit is Paul Jarvis in Company of One, where he had the radical idea in that book of what would happen if you put a limit to your revenue and your growth and your scale and had to Stay underneath that. I'm paraphrasing, but he's another person pushing against that. So no, you don't have to grow, you don't have to scale, you don't have to improve every day, you don't have to do all of that. And it's all about the choices and trade offs. Like, if you want to, like, fight with the broken printer every week, okay, fight with the broken printer every week. But understand that when you talk about the broken printer and when you vent about the broken printer, it's just commiseration, you're just complaining and that's okay. You can have your feelings, you can have that conversation, but don't go into that place of someone should fix that or something like that, because that someone might be you, right? So if you're willing to accept that pain and live with it, let it go. But if you are like most people and don't want to fight with the broken printer and don't want to stub your toe on the chair every damn day and don't want to spend 15 minutes running around the house looking for your keys, then maybe it makes a little sense to take care of yourself in that way.

For sure. And we should say that the broken printer. Just for listeners who maybe didn't catch our earlier convos, you want to say what that is, what that represents?

Yeah. So every organization I've ever worked at or consulted with has had a literal broken printer somewhere that everybody knows about. It has that stupid streak that goes down it, or it's always using the special paper or the freaking printer code is in the office manager's office and their door is always shut. There's something broken with that and it's a pain in the butt, like, and you have those office space moments. So right in the crunch time, like the meeting is about to happen and you need to give the handout and you hit print and then it goes to the wrong printer is like, oh, no. Right. Because you see what the next 15 minutes of your life is going to be and you're going to be scattered. And so it's just a broken printer. We don't fix it. But it's really endemic of a system of work and it's the downstream effects of those broken printers that we don't take seriously enough. So people can't focus during a meeting because they're looking on devices because there's no printout. And so you're fighting emails and social media posts and text messages while you're trying to present something important and wondering why their teammate's not getting it. Or you're presenting to the big boss and you hit print and you're like, oh shit. And then you're running in three minutes late, frazzled because you had to send it to the different printer that works. Well, I can go on. Everyone knows this and has experienced the broken printer. At the retreat that I just hosted, the printer that we took there literally broke. And I was like, okay, it's going to be a week.

The real systems question is, why are printers so effing bad? Like at an industry level, what on earth is going on? Talk about a dearth of innovation. See, it's not even just our team members fault. I love technology and I love troubleshooting. And still the other day I ordered a printer, never could set it up, ended up putting right back to the curb, not even having success. So I just print at Staples now when I need to. They have a really easy scan your barcode, print your shit out and oh God, printer.

Yeah.

What is going on?

They're broken because of the way people who buy printers optimize in the same way. I don't want to step into an Apple versus PC sort of conversation, but there are some people who are just like, I'm going to pay for stuff to work and I'm going to pay more for it to work. And then there are some people where I'm going to pay the cheapest that I can get it and then I'm going to fix it when it breaks. Most of the printers are bought by people who are like, well, we have people who can fix those things. And so we're going to optimize for a lower purchase price that we can get in bulk versus a higher it just works price. Because again, there are these hidden costs in work that are often not dollarized, right. And so a lot of times when I come in as a business consultant, whether it's a big business or a little business, the first place I look is just the value that falls out the door. Just broken stuff, right? That it comes is like, why is this printer there that's costing you this much? Let's get rid of that. And so I find my page this and that, and then I can create a bunch of other value on top of that. But it's just saying like, oh, so you have a team of five people and each one of them spend 20 minutes a week forking around with this printer. We know how much those salaries are. So you pay that times 52 indefinitely. Okay, that's a choice. You're willing to make because that printer cost at most 500 bucks. By the way, why is it that fixing that printer is a whole ordeal? Getting the purchase requisition, all that bullshit. We can all call a meeting that cost way more money without talking to anybody about it. I can just throw a meeting on Denny's calendar and eat up her time for 60 to 75 minutes for a reason she doesn't know. But the printer's an insurmountable problem. Come on.

Right?

And so printers are bad because the macro consuming society allows them to be bad. That broken printer that needs to be replaced is allowed to be broken and bad because the team allows it to be broken and bad and doesn't fix it. Most organizations, again, it's a $500 purchase. It doesn't take a whole lot for someone to be like, that printer sucks. I did some research, I spent 30 minutes. I think this is a better printer for our situation. Here's both the short term and long term cost of that. Can we please fix that? If someone took that to a team leader or manager, probably get fixed pretty quickly. And noticed also that there are very rarely broken printers in executives offices. Right. Because it's prioritized in a certain way. And it's not just about will the executives get a budget and things like that. It's just that they have that mindset to fix it. Right. And it's unacceptable where when you're lower down it's like, well, someone should fix that. And then they walk away only to three days later come back and have the same fricking problem over again.

Well, I love how you described it as the hidden costs at work that aren't dollarized. I don't know if you made that up. That's a good word.

Gokiism, hidden cost or dollarized.

Dollarized.

Dollarized. It comes from a book, I think it's called the Dollarization Principle.

Wow.

Okay.

It's for coaches and consultants and people who do that work sort of dollarize or to quantify what the actual cost of problems and opportunities are as you're proposing change.

And to go back to our conversation of maker versus manager and I'll link to the Paul Graham essay, which is a classic on that topic. I've also learned having kind of experimented a little bit, I've never grown a big company. I've had very interesting PODC people who used to have a hundred employees and then go down to like five part timers and they're also happy. So I'm always curious about people Who've done both. Admittedly, I really haven't, other than working within corporate and then outside of it. But I will say that you are just kind of trading one set of problems for the other.

Precisely.

There is no there there in terms of the problem free business. Because the more I return to maker mode, well, there I'm the bottleneck again. Like inherently and by definition having a maker heavy business focused on my creativity is a bottleneck. But I was losing all the joy from just trying to like pursue sales and marketing for corporate licensing clients. I was like, I'll just go get another job if that becomes the business. As much as I could see what was possible, I couldn't bring myself to do it. And so it's really a case of like, okay, which problems do you want? And then how are you going to solve for them? And not letting the proverbial broken printers exist anywhere. Like the things that are just death by a thousand cuts, annoying, that linger. That's usually what sparks my system's thinking is like what is annoying me. I hate repeating myself. It's usually just coming from my own frustration that something gets fixed or solved. But as you say in the book, it's better not to solve it as a one off. You have a fancier name for it of like, how do you say it?

There's the local problem and then there's the global problem. And this is very much systems thinking. The broken printer is actually a local problem. The global problem is the team and culture doesn't know how to solve everyday problems that are not client or value focused. Because that's what I get a lot. It's like, look, we're just trying to serve clients. We're just trying to get our customers taken care of. The printer can, like it's not the most important thing until you look at when it becomes the bottleneck or when it becomes that sort of thing and you hit on it. That and Teresa Amabile from the Progress Principle was the one that actually made the most striking case for this, for me at least, is that the small frustrations and dread points and sort of fork my life moments that we have at work play an outsized role in our morale and joy at work. And so you can have an otherwise great week, but then deal with the broken printer on like a Friday afternoon and that colors your whole week. Now I need to say about broken printers, I've used that, the literal printers as a metaphor, but it can be all sorts of ways that your team works together. For instance, the CC thread from Hell, if you worked in a corporate environment like Jenny has, I mean, I have, you know what I'm talking about. You get like 25 of these shits a day and it's like five or 10 minutes of reading just so you know what's going on and you're not blindsided. Or just in case there's something in there that you need to know or someone called you out, like, why do we do that to each other? That's a broken printer at large that teams can solve. Or it could be permission problems on files. Like if you're talking about tiny teams, you're probably using collab docs and there's probably five times a week someone needs to ask for permissions on a document. There's a fix for that, but it's just what you allow to accept. Or it could be calendaring in tiny teams. Like if you do need to talk to Jenny, how does it not become an 18 way Slack message or email chain to figure that out? Or texting error versus you know, there are other solves for those very small ways to get out of this. Either social overhead of just damn, we got to negotiate everything every damn time, or just why is it hard to do something that we do frequently? Even Jenny and I were actually talking about this in the green room today because I was pondering as someone who's on an interview sort of round, I was like, at what frequency of interviews do I set my mic up permanently to be on my desk versus put it in its cubby and pull it out once and twice a day? I don't know the answer to that. But for me, Jenny knows is underneath that it's like there's an annoyance and time cost to me setting this up every time. But there's also countervailing. I don't like it being on my desk and the visual clutter. And so there's a balance that happens to where it's more annoying to have it in my way all day and looking at it all day than it is to set it up. And I'm probably at that threshold if I'm asking the question. Usually my rule is if you're asking the question about whether it's frequent enough, you're probably on the threshold of it being frequent enough. Otherwise, like, I don't try to fix something that I do once a quarter, I make a checklist for it. I have to look at the checklist every damn time because I don't remember how to do it. I follow the checklist, I do it and then that's it, that's the fix for that. But I don't automate it any more than that.

Yeah, that's such a great point if you're asking the question. And again, it goes back to this. I love what you said about hidden costs because we were discussing the podcast sitting at the desk as a metaphor. And there is a hidden cost to that clutter, having it around. And then there may also be hidden costs of having to set it up and take it down. So I mean both sides, but the point is to uncover the hidden costs. And then even at the level of the business model, there are hidden costs to the business model that you choose. What are they? And I think that's something that's one of those unwanted gifts that I've been getting smacked over the head with the last few years is just to try to understand really what different business models, revenue streams, what are the implications, what are the hidden costs that where it looks really shiny, but until you've been in it or you've really examined it, they're hiding. They're in hiding. And there's still going to be attacks, there's still going to be a drain on time, energy, money, whether or not you identify what those are and then let alone try to solve for them.

Yeah, I mean another way of saying that is what constraint are you willing to accept? We know that constraints actually fuel creativity, but on the other side of it, constraints also enable self compassion and peace of mind. I've seen at the business model level, seen plenty of coaches and consultants that follow the scalable dream and productize and do all that kind of whatnot, to realize that even at the same profit levels, they're miserable, they don't like their business, they don't want to do the things all day because why they got into the business is they were people, people. They loved real time conversations and seeing people's transformation and all that kind of whatnot. And they follow the standard bias that service based business are second class businesses. What you really want is an IP and scalable business. They followed that bias and ended up in a business that from the metrics perspective should have been better. But in their real world they didn't want that business anymore. They didn't accept either the constraint or their actual needs and say I actually need to show up and talk to people all day. That is my jam. And I'm saying that because I know we've been focused on introversion and I wanted to give some extroverts to shine. Like sometimes you end up in A place where you're like, oh, well, what I'm supposed to do now is write the book and create the course and do all the kind of whatnot and they fight it for three to six months, think they're broken, do all that kind of whatnot, and then hopefully they'll hear me and say, like, maybe that's not what you really want to do.

Right. Or they've been told time is money, don't trade your time for money, and therefore they stop doing the one on one work that, like you said, got them into it in the first place.

Yeah. And again, what if, when you take the long view, like, what if you build a business and team that's sustainable for you for a couple decades? Most people don't think in terms of decades, but if you think about that, all right, so yeah, maybe you don't build that business that you can grow and scale and flip for 2 million. But how much would you need to invest at 10% over that amount of time to get to the same place building a business that you wake up elated to doing it because you're not looking at screens all day, because you're not trying to figure out how LinkedIn changed the algorithm today, or your email marketing system added a new feature that made your life hell. Like whatever those things are that are all part of the platform place that people don't talk about enough. So either what constraint are you willing to accept or what permission do you need to give yourself to allow your needs to show up and how you build at work.

We'll be right back just after this.

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As you've thought about your business model over the years and the size of your team, how do you Find that sweet spot for yourself. The size of business, that helps you, Charlie Gilkey, and I know you run the business with your wife Angela. That helps you thrive because someone might look at your business or you might even and say, we could really scale this. We could have global impact. This could be huge. And I, Charlie, love managing complexity and logistics at that level. I'm curious if you have also gone through the Goldilocks question of how big is too big and how small is too small. So I'm just curious your personal take on this for the business that you're building and have been building for many decades.

PF is wobbly. So over the last 16 years, my company has been wobbly because there are some times where I'm like, oh crap, that's taken off and I need some help to take it off or to really push it and then it goes that way or there are natural declines and things like that. I'm like, wait a second, I got too many people for that. And so the thing you got to know about me, Jenny, to help me answer this question, is that prior to starting pf, I had commanded companies. Like I had done the big leadership thing and been involved in larger organizations. I didn't have that bug going in. And so it's like I've done that. There's a way in which I can and would do that. I excel when I'm either the manager or the maker. I struggle when I'm both. Sure, I can take an executive position where I'm basically leading and orchestrating people, maybe doing a few doer level things, but like being in a position of doing both is very, very hard. Or I can be in one where I'm a maker, but I'm also, I'm a teams guy. I love doing stuff with people. The question I thought about asking you about 20 minutes ago, Jenny, but I'll resurface this because it's relevant here. Is it that you don't like working with people or that you don't like managing people?

It's probably a combination of both. I'm the happiest tinkering in software and doing things on my own. But I just know, and I begrudgingly admit that everything's better when I work with other people. You know, when I work with a branding agency, when I work with a podcast production team, when I work with my amazing right hand person, Faye, like everything is better, but my natural energy and zone of joy is when I'm alone, working alone. Probably the same goes in my marriage. It's Like, I'm a better person and it's hard for me.

Most of us are hybrid in that way, though. Like, you're unique for all sorts of reasons, but that is not one of the reasons that you're unique. For many people in Solo plus and tiny businesses is not working with people, it's managing people. And they come to you and being the chief question answer and just steal that from you.

Yeah, that's a great point.

Or to do all those types of things. Because, like, I imagine that if I worked for you and I said, hey, Jenny, so here's the thing. Last week we talked about this thing, thought about it for a week, and here's what I recommend we do on this. Here's the plan, here's the budget I'm going to need. Here's the least I need from you to make this happen. All I need for you to just press go on this. Is that something you would like to do? You would probably be like, can we please do more of that? Because it doesn't feel like you're having to do all of that work.

That's true. And I forget who said it, but you should only hire experts, like people who are better than you at that thing because then you're not managing them, they're the ones managing you, telling you what's possible and how things can be done.

Or you build team habits. Right. So that, like, I have a guide for asking better questions for my team because basically the people who ask the best questions get their questions answered first. Because the more labor I have to do to figure out what you're actually asking me and what you need, just because of everything else I'm doing, you fall to the bottom. And that came from people who, when I had a much larger team than I currently have now, it's like, you know, I ask you something and, like, it'll take you like six days to get back to me. What can I do to get answers faster? And my response was, ask better. The reason it takes me six days to answer your question is because it takes me six days to figure out what your question and needs actually are. And the reason I can answer other people faster is because they ask a very precise, specific question. And I know what they'll do after that. So, you know, a few things I would do if I were like king of work for the day. One is I would ban.

The thoughts, question mark thing that you see. That one bugs the crap out of me because it usually goes like this, statement, statement, statement, statement, thoughts, question mark. But none of those statements actually tell you what the thoughts were about. They're just like thoughts, which to me pisses me off because I'm like, you're making me figure out what question you're trying to ask from that collection of random ass facts. Thanks. No, thanks. So in my ask Better guide, it's like, if you ask a thoughts question to me, it goes to the bottom. Figure out what your question is. And I know that makes me sound like a butthole.

No, I love knowing your pet peeves. This is like. And now I'm regretting we didn't spend.

A whole episode Charlie's pet peeves. And why.

Yeah, I know. You did write a book about it, so.

Well, I didn't talk about that because I sound like a butthole. But it's really one of those things where. But it was on me to tell them what better questions look like. Right, right. Versus being like, just ask better in that sense. And so I was like, well, what does that mean? Okay, here's what it means. Boom, boom, boom, boom, boom. If you show me a spreadsheet and say, hey, I need you to look at this and review this. Bottom of the list. If you show me a spreadsheet and say, hey, I'm not sure that my estimate is right in column C3. Does that track for you? I'm going to answer that one super quickly, but just review the document. Review it for what? I don't know. I gotta, like, sit down and dedicate a focus block, which I don't have a lot of to do that. If you show me a doc that has copy on it, say, hey, Charlie, review this. Take a look at it. Bottom of the list. If you say, hey, Charlie, I'm not sure about these headlines. I've got three options for you. Which would you vote for? I'll answer that one super quickly. And though it sounds harsh on the front side, what it hopefully helps my team do is actually think through what they actually need and where they're stuck and owning that versus having someone else pushing that social labor, that social and emotional labor on someone else who in my business, I'm the person that's got the least amount of time. So you're taking the person who's already the bottleneck and stressing that point even more. Nah, I'm out. The other constraint here, or the other thing is I have to tell my teammates this may be going too much into the weeds. It's like part of our significant. Part of our revenue is coaching and consulting, which means I have people who Pay me to be able to ask questions that are ill formed or that takes them a while to get to it or kind of whatnot. Like that's part of the value of the relationship is that I can help them get crisper and clearer about what's actually going for them. If you make me do that and I'm paying you, we have a reverse value flow here because the hours that it takes me to figure out your question that I'm paying myself and you for, I could be getting paid by someone else to help them figure out their questions. It's a constraint. It's the business model here. So if you want to work, we got to shore that up. Otherwise it's going to create a situation to where it's like the system of the business where we look at different people's competencies and capacity gets overstressed in that one spot and there's no way out of that as long as we continue that team habit and pattern.

Brilliantly said in free time. I call it save someone the next steps. Like the example that was the flag for me around this. A team member pinged me saying we just hit our account limit for Zapier and essentially they didn't write thoughts question mark, but they might as well have. I'm like, okay, what does that mean? How much is our current plan? How much is the upgraded plan? What kind of zaps? Do we have any zaps we can turn off? Yeah, gotta give me more information. I don't want to log into Zapier and understand the pricing tier like we're hitting a price wall or a limit in the account. You gotta tell me not only what are the next price buckets, but what do you recommend? And it's like that moment drove me so baddy, even though I didn't have these beautiful words to put around it that you just shared of why. I couldn't articulate exactly why, but I just knew that I was annoyed that that is not rocket science to kind of save me, Jenny, the business owner, the next steps of having to go look at Zapier's website in order to help you make this decision so that you know you can unblock your work as well, because this person was trying to do something good. It's never usually anybody's bad intentions. It's just those signs of frustration are so ripe for some systems thinking as you and I both bond over.

Well, and in that situation, that's part of the team habits conversation of how do we make decisions? Who owns that question? And there's A difference between being the person who owns the answer versus who owns the question.

Or even just thinking through, like, in order for the other person to answer that question, what else might they need to know? To make an informed either advisory comment or decision, you gotta think through the.

Next steps in team habits. I do talk about calling it the Drip. So that's a decision, recommendation, intention, or plan. Like, pick one. When I get those types of things in Slack or whatever the message is, we'll type drip with a question mark and walk away. Because I'm like, I'm not doing, like, what's your decision? What's your recommendation, what's your intention and what's your plan? Like, that's your work. Or another way of saying, that's a level two, which means make a decision, let me know what it is. It is a problem. It's not my problem. It is your problem. And I don't even know why we're in a conversation yet. And I'm not going to do the labor to do it. Why? And so a lot of folks want more autonomy in their work, about their decisions and things like that, and are not in a place where either they feel empowered or realize what autonomy means. Because if you really want that autonomy, that means, hey, Jenny, for this project, we're going to need this many zaps. We hit our limit, it's going to cost us 20 bucks extra a month. I think it makes sense to do it. Unless I hear otherwise, I'm going to go ahead and upgrade by Friday. Jenny actually in that case, doesn't have to respond unless I hear otherwise. Now, if you make the decision and Jenny comes back and be like, why'd you do that? That was a terrible decision. I was like, I was trying to move on this. I gave you what you needed. I gave you a reasonable time frame. If we need to work on that process, that's another matter. But, like, you wanted me to make decisions and run with things. I think I gave you the information that you needed to. What's the bump here? This is especially good for control freaks because if you focus it on either the process or what was really there, it at least minimizes the interpersonal friction.

And it's almost like, which problem would you rather have? I'd rather be overbilled 20 bucks than even deal with the small problems. But like you said, we should decide that in advance what size risks to take. Charlie, you've given us so much today. The last question. You've also given us many a permission slip in the past, but based on everything we talked about today, what permission slip would you want to give fellow business owners of something they could do differently or stop doing altogether?

The permission slip that I would want to get business owners is for them to center their needs and wants and how they build their business and how they build their teams and build it such that they want to show up and do the work versus feeling like they have to show up and do someone else's work.

Thank you so much, Charlie. I'm going to put all these links in the show notes Free Timers get your copy of Team Habits. How small actions lead to extraordinary results. If you don't already have it. Charlie Cakes, you're also on Substack. I'm going to put the link there in addition to your main newsletter and podcast. Is there anywhere else any other book bonuses? I know you were working on all kinds of supplementary material to the book that you want to point people.

If you go to Substack, you're going to get those. Actually, I think we're going to post either today or tomorrow that we've got ample resources and worksheets and tools to actually make some of these ideas tangible for you and your team, like concrete for you and your team. So don't sleep on those resources. And if you go there, you'll get a lot of stuff that's at no cost. I don't want to say it's free because somebody paid for it, but at no cost to you. And if anything, teamwork can be challenging. When it is challenging. I hope you lean in on the beautiful humanity of the people that you work with and what would happen if you take it from the place of they're doing their best, they're overloaded just like you are, and they actually want to win in the same way that you want to win and they're just some damn broken printers that you all need to work on.

I love that. What a perfect reminder to end on. Thank you so much Charlie. Thank you for being you, doing the incredible work that you do and for sharing your wisdom with all of us today.

Thanks for having me.

Thanks everybody for listening.

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