Reflection: Leading While Still Learning - Inside the Messy Middle of Building Well

Working at a company that eats its own dog food—is it as clean as it looks? Benj Miller sits down with CTO Chris Ames for a rare behind-the-scenes look at leading through frameworks, navigating generational shifts (unlimited PTO, anyone?), and why growth means climbing the same mountain over and over. If you've ever wondered whether leadership coaches actually practice what they preach, this one's for you.

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Chapters

• 0:00 Why this session is different
• 2:43 What it’s like to apply the S2 framework from inside the business
• 6:13 Navigating generational shifts and team expectations
• 9:53 Visionary friction: when to follow the plan vs. break it
• 14:24 Real talk on AI, automation, and business readiness
• 19:04 How leaders actually change (yes, even old dogs)

Transcript

Benj Miller: 0:36

Hey, welcome back to System & Soul, another sessions. And this is a fun one because Mackenzie's on vacation. So while the cat is away, the mice will play. And we are here with my great friend, special guest coworker, Chris Ames. Woo. Yo. Chris is the man. When we started, when we decided we were going into software with system and solve, there was nobody that I wanted to partner with more, nobody that I trusted more. And side perk, nobody that I like hanging out with more chris, welcome to the world, getting you out of the closet. Chris is our CTO, but he gets undersold with that because he is a multifaceted, multi-talented strategic thinker with a D part. So

Chris Ames: 1:20

Chris, thanks man. Appreciate that. I'm just wondering why you stopped with the compliment so soon. There's more adjective. Yeah,

Benj Miller: 1:26

I wanted to save some for, throughout the show and we gotta wrap up and all that so I can't just do 30 minutes. We'll try and slide some more in as we're getting started. Huge shout out to fist bumps for making the show happen, making it possible, making it clean, and dealing with all of our antics along the way. So if you are thinking about putting on a show, getting content for the socials, they're a great partner, both the thinking and execution side of things. So today's episode of Sessions is a reflection, and so since we have Chris. We thought we'd get into some of the inner workings of what is it like to work at a company that is trying to eat its own dog food? We know leadership is like a messy thing, and so it's really easy to get on stage and talk about it or in front of a leadership team and then leave and say, do all the right things, but we're trying to live it. And I wouldn't say we're building an airplane as we're flying. I think we built the airplane and we're flying, but we're always in the messy of figuring things out as well. So maybe I'll just start with that, Chris, like what's it like? Do you ever feel that tension of. Working in an organization that is trying hard to eat its own dog food.

Chris Ames: 2:41

Yeah., Absolutely. It's, it can feel sometimes experimental, but then other times not experimental. And but what I feel about the experiment experimental part is that I don't know that it's unique to us just because we're in the business of coaching leaders and helping leadership teams because the meta around business. Is always changing, right? Like our understand of leadership is still adapting, like all of us who are in leadership, but then also the economic conditions are changing. New technology breakthroughs are happening. Each generation, is entering or leaving the workforce, or they're at some point of progression within their place and the life cycle of their careers generationally and. So all of those changes bring changing expectations. And so it's not like just because we teach leadership, we're either we're static and we have it all figured out or we don't. It's, we can never have it all figured out because the context, the meta around us keeps changing when I feel the most, like we've got it figured out is when we have this past week in our senior leadership team meeting. I think I literally said the words, I love watching this model work because we dipped in, we followed our rhythm, we cleared a bunch of important obstacles and opportunities, and then we left having the right conversations and nothing about that felt experimental. But then if you remember, like a couple weeks ago in, in our senior leadership team meeting, I had an opportunity on the board that was like, I just don't know if this quarterly goal stuff is working. Should, can we try cutting a quarter in half and just setting six week goals? And I was like, I had this itch to experiment and try something new. And so it's I don't know that there's a, one right way or wrong way. I feel like it, it just depends, on, on where we are. So yeah, that's,

Benj Miller: 4:25

that's one of the things I love about a framework and why we use the word framework. Because there's a piece of it that like, who cares if it's 30 days, 45 days? There is some strategy around 90 days. The thinking is big. You can do big things, but it's not so long that the energy for those things. Like dissipates, but especially for smaller companies you don't have the ability to predict that as far out. And so those shorter cycles make a lot more sense. Like first financial plan I ever built for a company and I went and showed it to somebody who says there's one thing I know about every financial plan I've ever seen. It's wrong. But then he said it, but it doesn't mean it's not. Useful. And so it's like, how do we do it? Do it well, and if there's something we want to try, we're deviating from something, right? It's not like we're just making things up or not doing it. We're deviate, we're strategically deviating from something and I iterating. Yeah, that's the, I think that's the difference between companies that are just like willy-nilly or negligent versus maybe going a little off script. Which can be strategic, so that's good. I'm glad you brought this. This is a little bit of a tangent, but you brought this up about the generational thing. I was with a team this week and something that came up was they have, for years and years had unlimited PTO and what they're bumping into right now is the younger generation. There's two problems they're seeing. They have almost two x the days off that other generations have and the older generations work to get their work done. To be able to take those days off. They like make it up. They're willing to, pick up the phone at night on the weekends, whereas this latest generation is not they're totally willing to disconnect. And I have unlimited PTO, so I'm gonna take it. And I don't really think about the ramifications on the rest of the team or my commitment. To the company. That's a very interesting dynamic that's emerging.

Chris Ames: 6:21

It is. I'm 50 years old and the mental model that I've had since childhood was you can go out and play once your homework's done. Yes. School first, play second, work first, play second. It's like working for the weekend. There's literally songs written about this, but when I look at my kids, they're like, charge my batteries so that I can work. It's different. It's not, and it's a point of view. I don't know that either one's wrong. As long as it's, in balance. Yeah. Yeah. Charge your batteries first and then the phone will work, is their mental model of what I'm experiencing with my kids. Anyway,

Benj Miller: 6:55

there's a just a cool story regarding that is I was raised with the creation story and we were made on the sixth day, and so what did. God do on the seventh day was rested, but we're not God. So what on our first day with God to then go work. It, there is a both and to that and working from rest I love that. But there is that, we share that Gen X, blue collar, middle America, Midwest, like you can get your work done. Yeah, so that was bred pretty hard, so that'll be interesting. Just generationally. What do you see within working within this framework? It doesn't necessarily match your work style. Is that a fair statement?

Chris Ames: 7:40

Oh yeah, absolutely. My, my default wiring is not to just get on the rail and run in and ride the rail, do the system.

Benj Miller: 7:47

Yeah. So tell me about what that feels like to you and maybe how you've. Had to compensate, or, is it, does it end up being freeing or constricting or what does that do within you?

Chris Ames: 7:58

It's actually freeing because even though I might not self create really consistent systems and follow them rhythmically, I value people like, so I'm more subjective, relational. And what the system does is. It actually creates these oasis for me, where it's okay, I got work to do today, but I get to meet people tomorrow and be with my people tomorrow when we have our regular weekly sync, for example. And also, I work great when other people rely on me. I'm more of a supportive personality. It's if I'm doing something to deliver to somebody that creates. Internal sense of like urgency and even a desire to do it. And so the system really just puts a frame around the things that do motivate me and drive me as a person. Yeah. And but I think the key thing is that somehow early on when I got into computer science and started at my career as like a software engineer, I discovered the value of systems. So even though I wasn't naturally good at systems, I still valued what they could produce and the effects, the outcomes that come on the other side of putting a system together and implementing it. So I think that helped. If you're somebody who is super creative and doesn't then understand or appreciate the value of systems, I can imagine a framework could actually be pretty constricting. But when it comes to getting a bunch of people to work together in a direction, yeah, the only way. Is to do systems and, start light is what I would say is like start light and then only layer in, little by little as you go to see what the group can sustain. So

Benj Miller: 9:36

there's a metaphor that my coach used to use. He said, when you have wild horses, you put the fences in the valleys so they can't see 'em. They don't really know that they're there. They feel like they're. Able to run free. And yes, every once in a while they're gonna come up against a boundary, but because it's down in the valley, they can't see the entire perimeter. So they don't really feel stuck.

Chris Ames: 9:56

Right.

Benj Miller: 9:57

And so it, it does create a little bit of a safety, everybody's in the same place. And I just like that metaphor.'cause I do not like to feel constrained.

Chris Ames: 10:07

I've noticed this about you.

Benj Miller: 10:09

You talked about

Chris Ames: 10:11

Go ahead. Go ahead. Oh, I was, oh, I was gonna say, you said you don't like feeling constrained and I think what I've observed about you is as the visionary that you are, you almost see the constraints as a challenge. It's as a problem to solve. It's that shouldn't be there, let me prove it. Yeah. And and so that's delightful and sometimes frustrating to be on the other side of it.

Benj Miller: 10:33

Oh, talk about that. How is that frustrating?

Chris Ames: 10:36

So because you are like, it's your role to be ahead and to be thinking ahead and you do that better than the rest of us hands down. There's, there can be sometimes an under appreciation of what we've already committed to. Because you've already seen enough of what we've committed to, to realize its inefficiencies. And also you're looking at what's next? And saying this could be, should be, is probably going to be better. Let's go, let's, pivot. And meanwhile, sometimes your team is on the other side going, aren't we working on the pivot? Didn't we already pivot? And, you're wanting to pivot again and adapt again. And so that's the that's the healthy tension, or that's the tension which can be healthy. Yeah. With the right people, the right perspectives. Yeah.

Benj Miller: 11:18

Yeah. Yeah. You should have seen that, experienced that before the framework. Good Lord. I'm so sorry. Apologize. People I love a decade ago. That's that's the renegade story in the book though is how literal it. Bad that is you talked about systems and one of my favorite things with you is I feel like we're on the similar, same wavelength when it comes to what AI is and isn't, and passing tools and trying things. And I think in the marketplace there's a promise of what AI is, that it is not actually. And at the same time, it is more than most people are leveraging. Yeah. So it's it's not the promise of everything that they're saying. It is. But it is a lot more than people are taking advantage of in, in businesses that we experience. What's your kind of current take and what are you seeing right now? Yeah,

Chris Ames: 12:10

man, there's so many con ways this conversation could go honestly. But there the, what it rolls back up in my brain too is if there's something I would want all business leaders to know and understand that they maybe not, might not have thought about in this way is that this isn't the first digital disruption that we've seen of the magnitude of this magnitude. We've seen the internet revolution. We've seen the digital revolution with the internet. We've seen mobile phone, the admin and mobile phones. Et cetera, et cetera. And if there's a lesson we can learn from all those things, it's that we overvalue how it's gonna change and improve our lives in the short term. And so we can be restless and be like, ah, I thought it would be, thought it was gonna change everything right away. But then we undervalue how the new technology or the disruption changes things in the long term. And so for the people who jump on the bandwagon too early, they're not gonna get as much value as they think. For the people that wait too long, their competition already has a competitive. Marketing advantage, right? And so where is the strike point, and what should we be doing in the present is really a hard question to answer and it's gonna be unique to each business leader industry. And so it can be really tough to navigate. And but if you can keep that in mind, it's what I would say to everybody is you're going to have to do something at some point, and the best thing you can do is have one person on your team. Who is responsible to figure that out like what we should be doing right now, because if everybody's just experimenting and we're just sharing notes. Along the way, it's one of those things where if if everybody's watching the baby, no one's watching the baby. And and you're not gonna make a smart strategic decision for your business with regard. So that's, my broad analysis, like where would I start? It's put someone in charge. Of making sure that you are able to adapt to the changing landscape because it is as big as they say it will be as, disruptive as they say, but we don't, but the, when it'll be as disruptive for each business is gonna be different. It's not there's not like a one size fits all solution for that. So that's my overall thing as far as technology is concerned, which is where, where we've been. You and I have been doing a lot of this legwork. We started pretty early, honestly, in trying to like unlock value with AI and and I think that is paying off in really big ways, but also as like it's brought some frustrations. There are some things that we thought, oh, surely in six months at this pace, we're going to be able to unlock more value. Yeah. And we haven't seen that yet. Yeah. And so yeah it's a challenge.

Benj Miller: 14:40

I feel like the thing that it's doing right now is helping people maybe work smarter than they could have and create more capacity than they could have. And maybe that's through, there's a lot of these automations that have an AI layer to them, but they're really more automation. Than they are AI and like process flows, workflows. All those things. I think it's making us, it's creating capacity. It should, I think that's the universal, it should be making us smarter as individual contributors to the business smarter. And growing our capacity for what we can produce at an organizational layer. There's some promises that I don't think it's delivered on yet, or it has for very few, and it takes a lot of resources to, to pull that off at this point. But we're not to a plug and play, we're not to, to AI replacing people. I think it's, I think it's coming quickly. I love the convergence of that and some of the robotics, some of that's gonna be really cool. I'm not looking forward to I read a paper recently that said we're within 10 years of an AI chip in our brain to directly interact with ai, and that's the first time that I feel like an old man that's like, why would you. Send an email when you have a fax machine, because I'm like, I do not wanna live in that world. I, there's no part of that I think who cares how productive we are as a society if we stop being a society? Yeah, that's the first thing I've seen that's it, scary is not the right word. It's just, actually it's really cool. It'd be fun to play with, but I just don't wanna live in that world.

Chris Ames: 16:19

Yeah. It's like I wanna live in that world when it takes somebody who you know, is. Quadriplegic and it drastically improves their life. My nephew is my nephew's blind and a pair of like meta glasses where it could just read out what he sees. If he could grab a can off of his shelf and pull it up to his face, and put it down and not have to go get the special pair of glasses, that just does that, then another. Tool that does that. If it could just wear glasses and help me navigate the world. He's he went on a walk pushing his child in a stroller and he had his cane, but which is a signal, right? It's you gotta hold your cane. Not because he needed to like tap. He knows he was in a place to, he knew, like the back of his hand. But, but still, there was a near an accident where a car brushed the side of the kid's stroller as it went by because they weren't picking up the signals. He was doing everything right. But the person has decided to turn anyway, and but for him to have warning. Like he just wants to go on a walk with his kid. He should be able to,

Benj Miller: 17:22

yeah. Yeah, absolutely. So that when,

Chris Ames: 17:25

that's when it makes sense, but where it doesn't make sense is when we cease to be human. Yeah. Like when we have completely replaced, human thought, creativity and the thing that makes us, uniquely us, we're so augmented. And where that line is, I'm gonna leave that to philosophers and to figure that out. And religious people, but not. I have speculations, but that's way beyond this conversation. Getting out of

Benj Miller: 17:48

the sci-fi for a minute, what's one like leadership principle that you believe now that you wouldn't have a couple years ago?

Chris Ames: 17:57

Ooh. Okay. So one, it's that you can't teach an old dog new tricks. Several years ago I would've said like even about myself my cake is baked. I can't un bake my cake, like my way, my flow, my rhythms, my practices. All I can do at best is like scrape off the frosting and like rost, but the cake is baked. But something that I've seen is that I have. Changed for the better. And when I look at leaders who feel like they've gotten in a rut and not able to really make meaningful change, especially at an organizational level, they feel I've led this organization, I've got us where I've helped get us where we are. And, but I, but they hit a ceiling and I think they just feel like it's because like I'm the limiting factor. It's because of me. I'm never gonna change, therefore the business is never going to grow. And I would have, five years ago, 10 years ago, said, yeah the problem with that company is the person running it and he ain't never gonna change, or she ain't never gonna change. So that's that. But I have seen too many changes internally. I've seen too many breakthroughs with people I've talked to. I've caught up with people that. I lost track of and then reengaged with, and they were a brand new version of themselves. And so to me the leadership principle is maybe what got us here won't get us there. Maybe you know that, but you can actually be liberated from that feeling like you will never change because you actually can, with the right people and the right system and the right support you can all be a better version of yourselves.

Benj Miller: 19:26

That's such a great message. I think it's. We definitely run into people that we have put into a box of they are never gonna change. Whereas the people that do change you, you usually see a pattern of their willingness and engagement in changing. I'm curious if there, if you look back at some of the people that went through your brain as you were thinking about that, was there an instigating event that took them out of, stuck into change? Because that's, that feels the thing that doesn't happen very much is like if you're stuck. If you're changing. But to go from stuck to changing, growing, it usually takes, unfortunately, it usually takes a painful circumstance.

Chris Ames: 20:06

Yeah. So there was a guy I fired once. It was because he just wasn't a good fit in that moment. He was not a good fit for where the team needed, what they needed for what he needed, and I remember I got a a text message from him like two years later and he said, thank you. And he had. Gone, gone on to a different career. It was related, but it was just a totally different path. And and also he said I had to let somebody go this week for the first time. He was in a leadership position. And I have newfound appreciation. For what I put you through, which really wasn't bad. We have, we had a good relationship back then and but and still do I just texted with him this past week because we play video games together. But but yeah, no, it was just a I think it freed him up. To be to have that shift. And you're right, it was extremely painful on our end. On my end. Obviously I can only imagine how painful it was for him. Yeah.'Cause that's a deeply, it's a shameful thing. It can feel very shameful. And it really was just a fit more than he wasn't capable. He was good at things, just not the role he was in. Yeah. The other person that came through my mind was me. And there have been several painful events. But I think the the most clarifying was I have a leadership coach that I would got paired up with and she was my leadership coach for eight years straight. And there were just several points along the way where she just did not sugarcoat. Anything. And I knew that I had, I, if I told her what I would tell her like a situation, I would say, and here's what I said or did. And every now and then she would just go, Ooh, and I'm like, I did not expect that. I was expecting, attaboy, good job. And she would go, Ooh. And I was like, oh, Fran what do you mean by that? And she would just, put it all out there. Did you consider, what about? And I'm like, no. No didn't think about that at all. So there were a bunch of baby, like oof, along the way that really helped steer me and be a better version. When I think about those coaching things and you being a coach I know you've had a coach for many years. What were some of the big is there something where. Along the way you felt like? I don't think, I don't let me start, lemme start that over. Sorry. Yeah. I know you also, Ben, have had a coach for many years. What are some of the big moments, there where you felt like Uhoh, I've disappointed him? Or I, you didn't, you had that moment where you're like, you thought it was gonna go one way and it went the other way.

Benj Miller: 22:38

Yeah. What comes to mind for me, and there's a beautiful metaphor for this. If you're taking sheep up a mountain as a shepherd, sheep are not very good at going straight up a mountain. So you walk them around and up and around and up and around and up. And there were, year after year, I would feel like I'm hitting my wall against the same issue. And I felt like I was disappointing him because I hadn't grown past it. I hadn't learned, I hadn't figured it out. I was definitely frustrated at myself. And then somewhere in there I think he, he taught it to me. People use different languages for this, but circular paths of righteousness. So as we are going and growing, it feels like we're in the same place again, but we're not. We went around the mountain one time and were. Back and we're not the same person and the circumstances aren't the same, but we have a deja vu moment.'cause it, I'm looking around when I've been here before, right? But I have it, I'm different and I've gone up the mountain a little bit. And so that, that metaphor to me is so helpful because think about your marriage, if we dove into it, it would be way too vulnerable for this podcast. And there's probably one or two issues that show up. Over and over, and you're like, why can't we get past this? But if you start to shift that mindset into, no, every time we get here, we're getting a little better. And it's not that we're here again. We're here again plus. So I think that, that mindset has really freed me up to not have the guilt and shame that I haven't conquered this thing. And, I'm reminded, there's this guy Paul, that wrote the whole most of the New Testament of the Bible, right? And it always talks about the thorn that he had in his side, that, that. God would never take from him. And I'm reminded that, here's Paul that we put on a peal 'cause he wrote the New Testament. And I feel like whatever that thing is, that's, I'm here again, feels like the thorn in my side. And maybe it's not getting. Pulled out, but maybe it's actually there for a reason to grow me again and grow me again. And grow me again. And so maybe we learn to appreciate that piece of the journey. I also think those things, those issues are the things that keep us humble. I'm a leadership coach, so I walk into a session room and. It's really easy for me to give all the right answers of what you should do, regardless of if I ever did them as a leader or if I do them or not as a leader. So I think if I knew I was perfect, my arrogance would go through the roof. So those crutches that we carry, I think can serve us if we can shift our mindset around the right way.

Chris Ames: 25:28

Yeah. There's child raising is fraught with peril. Obviously for most of us, definitely for me. But I remember many years ago as our kids were getting, through the teen, the tween years into teens where they could actually like rebut any argument I would make. And they, quite handily they could disarm me like intellectually. And it was always unexpected because they're growing rapidly, so I'm not able to really keep pace. I'm on cognitive decline while they're on cognitive incline and,

Benj Miller: 26:01

not true, but keep going.

Chris Ames: 26:03

But I think. My wife and I realized at some point like, we're gonna keep making mistakes and they're gonna keep calling us on our crap. And so what step of improvement can we do? How could be a little bit more up that mountain? It's like we could at least apologize. Afterwards to them directly, because that's something that not a lot of parents from our parents' generation did. Like they didn't apologize to children. It's like I gave you life, shut up. It was more of the mentality and so that was just like, okay, we can at least take a baby step. A baby step, and then maybe over time I can apologize easier, quicker. And then before you know it, hopefully as granny would say, good lord willing in the creek don't rise. Hopefully we, they learn, at least to apologize and take some ownership when they say the wrong thing or, make someone's life unnecessarily difficult like we've done again and again with our kids.

Benj Miller: 26:56

Yeah. My, my takeaway from this conversation, which you and I could talk forever, is that we are all on a journey. Most of us hanging out today, listening, talking, or on a leadership journey, and none of those journeys should go alone. We need, peers like us. We need the coach like we've talked about. We believe that a framework can really help in that leadership journey. So just the gap and gain conversation because we have grown, since the last time that we looked in the mirror. And we do have ambition for where we want to go and grow in the future. And so we're all on a journey and and most of the time on this podcast, I wrap and I'm like, Hey, check out System and Soul's website, or, we have a webinar. I'm gonna do something a little different today. I'm gonna invite you to go to my website. Binge miller.com. And here's why. One, it's fun, but two, from there you can get to System In Soul. If you are interested in a framework or a coach, you can get to the 2 6 1, which is a daily leadership tip reminder that I use for myself. Like it's a reminder for myself that I just tap to let other people in on my reminders. And you can sign up for that. And you can also click over and connect with me on LinkedIn, which I would love to do. I'd love to know who you are and what you're trying to do with your journey. Just so I can, know you and support you. Say I pray for you along the way, thanks to fist bumps, and we'll see you next week for another episode of Sessions.