Episode 12 – The Next Climb: Stretch, Partner, or Step Aside? - Part 2

Growth doesn’t glide upward; it climbs in stair steps that demand new traits, new systems, and sometimes new leaders. We sit down with John Monroe to unpack why the abilities that got us here rarely carry us there, and how to decide whether to stretch, partner, or step aside so the organization can make its next climb. This is a candid look at reinvention under real pressure, from AI shifts to changing customer expectations, and the identity questions leaders must answer to stay relevant.

We dig into a powerful blind spot: most product validation skips the number that matters. Price turns casual interest into a real commitment and reveals whether your timing matches the market. John explains how to use MVPs to test willingness to pay, avoid idea worship, and pace change so teams don’t burn out. When signals say pivot, trust is the multiplier. If you’ve built it through clear metrics, shared authorship, and open feedback loops, the next turn gets easier, not harder.

Culture comes alive through discretionary effort. Titles can demand function, but only trust earns the extra 20 percent that fuels creativity and resilience. We explore practical ways to connect personal purpose to company mission, give people a visible path to grow, and communicate change without triggering alarm. From naming the bear-in-the-bushes fear to shrinking the power gap by letting ground-level leaders carry the message, we show how micro moments add up to a durable culture that can adapt fast.

If this conversation sparked ideas, subscribe, share it with a leader who needs it, and leave a review so others can find it. For the action guide and more tools, visit Sherpa Consulting Group.com.

Transcript

Cold Open: Why Reinvent Now

SPEAKER_00 0:04

Why would we think that the traits and the talents that got us to today are going to be the same things that are going to be required to get us to five years from now? We are wildly created in order to be able to fear change, right? Sure. To be able to fear differences, things that are new, net new. When you don't know if it's a bear or, you know, or a bunny coming out of the bushes, we are built to think it's a bear.

The Stair-Step Model Of Growth

SPEAKER_01 0:29

You're listening to the Sherpa Leadership Podcast, your guide to climbing higher in life and leadership. I'm Reed Moore, and alongside Chase Williams, we're here to help you break through obstacles, scale your potential, and lead with greater clarity and purpose. And we are excited to bring you part two of our incredible interview with John Monroe. As always, go to Sherpa Consulting Group.com. You'll be able to get the action guide for both part one and part two, as well as all kinds of other goodies. And if you do us a solid like, subscribe, and share this with a friend and a leader that you know needs encouragement. Here we go with part two of John Monroe. There's a group of leaders out there that have built incredibly stable businesses. I mean, they just, you know, they're like clockwork, they work, but now they're running into, whether they see it or not, right, they're running into some some headwinds or some serious disruption, and they don't understand how to reinvent continuously. Their issue is they have a good stable culture, but it's built off of this, like we've just been, we do what we do and we'll die doing it. Uh how do you address a leader who's who's phenomenal in so many ways and and this one thing could take them out?

From Identity Vs To Identity

SPEAKER_00 1:53

Yeah, I I think um just as you're saying that, it really made me reflect on one of the things that I think is most baseline is why would we think that the traits and the talents that got us to today are gonna be the same things that that are gonna be required to get us to five years from now, right? So this idea of continuous reinvention, if you really step into it, we're actually looking at a scenario where the things that work today cannot work into the future, right? And so you have that stability, somebody's hitting a um, you know, I always like to look at it as a stair step, right? So many organizations, even when you see the the hockey puck growth, you know, especially in startups that I've I've been a part of, venture capital growth, even PE, they they see this hockey puck, but it's actually not that. It's stair steps, right? It's a stair step, bang, we hit a wall. Okay, we actually can't go above this. Now we did some uh uh reinvention, right, internally of the person, of the process, of the people that are on board, and then we moved up. And not every leader is positioned to actually make that stair step, right? They actually might be, and oftentimes I think when we do those leadership assessments on what are you good at, there are leaders that are phenomenal at that process. I'm terrible at it, right? When you're talking about managing something continuously over time that's not growing or not expanding or doesn't have the opportunity to be creative, I'm not great at that, right? What I am great at is identifying some of those opportunities to bring the people in to get them on board so then we can have that, we can have that growth and move that direction. So, but I think at every organization there are times for absolute stability and then there's times for growth, and then there's times for stability. So I think it's much more of a stair-step model than it is that hockey puck growth. So, so in those scenarios, I think that the leader needs to decide am I willing to do the things that are necessary, necessary to grow with the organization, right? To actually put the organization in a position to win. And am I the right leader to do that? It might mean that they say, no, it's time for me to actually step aside as the integrator, and I'm gonna bring in a creative to actually ideate, do skunk works, to test out the markets, to test out the places we could go without disrupt disrupting or um you know breaking the model that's worked so successfully for us while allowing us to uh be creative and and uh uh innovate uh that's gonna take us in the future. Love it.

SPEAKER_02 4:04

Yeah. Yeah, we have there's this idea of reinventing right uh from identity versus to identity, right? And so there's a there's all these um you know well-known examples of of companies that decided not to reinvent. You know, you've got the blockbusters and Kodaks and Nokia, right, with smartphones. And they said, no, like our we're moving toward our identity, which is you know, renting videos out of a retail store.

SPEAKER_01 4:31

Yeah.

Product Market Fit And Price

SPEAKER_02 4:31

And it causes them to be irrelevant versus like from identity, which is like, hey, what do we actually do for the consumer? And might there be a new strategy like streaming that they're interested in as an example, right? I think that's the risk of not reinventing. One of the most common uh topics of the day right now is AI, sure, right? And how that's causing reinvention or forcing reinvention or deserves reinvention because of the benefit it can bring, right? John, you were in the tech industry, right, with kind of like a uh tech experience. I can I can only imagine that the pace of reinvention in a tech space is potentially even faster than in other industries, right? How do you manage the pace of reinvention, right? How do you determine uh when is the right time and how much is too much? And like how do you think through that when it's something that is just a a constant?

MVPs, Timing, And Market Readiness

SPEAKER_00 5:23

Yeah. Uh so I hear two different questions in that, and one really focused on identity, right? Which I think is really the most important question that we all need to ask. Are we operating in a way that gets us a um a promotion, right? Are we operating in a place that that says, well, the successful person that I'm looking at has done X, right? Which may or may not be aligned with your personal identity, right? It may be aligned with their identity. So as we try to step into those identity characteristics that are not ours, that are not of our identity, we find ourselves running into those walls of why is this not working? I saw what the model was, I replicated the model, but it's not part of your identity. That's not the way that you actually show up. So as you talk about from versus to identity, I think that's really an important thing for us to look at as organizations. And I think to the second part of your question is as we're looking at organizations and thinking about how you actually work through continuous change and constant change, especially in an ever-evolving environment. Um, as you look back, I think this this idea, it's fascinating. They talk a lot about product market fit, especially in startups, right? Venture capital-based startups, et cetera. And they say, well, what are we looking at from product market fit? Well, one of the things that they oftentimes miss in that process is product market fit price, right? And the reason price is so important that it truly gets down to the soul of it, right? It truly gets down to I'm not just asking you if you like this, if this is the way that we should, uh, if this is the widget we should uh create, um, if you're willing to buy it. But actually, we're going down to the point of sign on the data line that says you are willing to pay for this if I create it, right? And actually getting getting that. So that last little small question that actually gets to somebody's soul and actually creates fear in the buyer of, well, I guess I'm not necessarily sure. I was, but you were confident two minutes ago. Yeah. I just told you all you have to do is now say, okay, here's what you're gonna pay for it. Will you sign up for it? If I build it, I'll build it, you know, a year from now and bring it to you. Will you pay for it? Oh, well, that's a different conversation, right? So it really gets down to those baselines of their identity and their fear in the process. Um, and there's a lot of different things that can do that, but that's just one of the ones that I've seen most be most consistent in that process. So you're reinventing, you're testing, you're creating MVPs. MVP has been a buzzword in in tech for so long, right? How do you create the minimum viable product in order to be able to test it? Will people actually consume it? Um, is the best idea ever. Because I have uh met some incredibly brilliant people that are 10x as as intelligent as I am. And some of the ideas they come up with and some of the theories that they're actually based on, it is, it's it will be the wave of the future. Sure. And I guarantee, just like the Palm Pilot, right now, the the world is not ready to accept us. They're not ready to buy in. They're not, you know, they can't actually get themselves to a place. I could hardly get myself to a place of understanding how it's gonna impact how you would actually create that from a sustainability model.

SPEAKER_02 8:08

So that's really, really good. I think that's so smart, right? Adding in that price, right? You say, like, hey Chase, would you like to fly to Mars and back safely? I'm like, yeah, that sounds awesome. Great, no problem. It's only gonna cost you 30 million for one trip. I'm like, whoa, not ready for that yet. Totally, right? So, like, that is really, really good. I I don't want anyone listening to miss that piece because it it plays to timing. It doesn't mean that people will not actually regularly pay to fly to Mars one day, but the price has to fit in there too, right? Yeah, and that could go along with any service or any product. It's like this vision that's so far out. If we start moving to it too quickly and the marketplace isn't ready to accept it from a price standpoint, it causes us to ask those questions around when, how quickly, right? So I love that.

Emotion, Fear, And Buyer Commitments

SPEAKER_00 8:52

That's so, so and it really goes, you know, if you if you break that down, I hope this came across, but as you break that down, that's actually an emotive scenario, right? Oh, sorry, my most you know valued resource, I have to now promise it for this. A it goes to their heart to see where their heart is actually positioned, but then it truly creates emotion where some of the other things of excitement and opportunity and creativity and wow, that would be rad. Um those really drive the initial decision. This really takes it back to a core soul question, right? What are you fearful of? What how are you willing to um you know put yourself out there to engage in this?

SPEAKER_01 9:27

It makes me think just kind of tying that conversation back into the identity conversation that we had a little bit earlier. Um, it seems like one of the one of the leaders' uh worst enemies is a motive that's aligned with the love of their idea or the love of reinvention, because it really misaligns the motives of the company and the people all the way to the consumer from the next decision that you're going to make. Right? It was just one of those things where, like, man, if if I get really excited about my idea and I get some level of identity out of that, boy, I'm running blind. And that could be really bad for me, for the people, and for the consumer if I can't um shift out of that.

Discretionary Effort And Culture

SPEAKER_00 10:08

Yeah. I think um is this idea of uh discretionary effort that I've talked about for years, and it comes based on a thesis of, you know, as we're talking about what is culture, it's actually identifying what creates discretionary effort. It's a it's a really easy leading and legging indicator. Are you getting discretionary effort from this employee? And what that really means is are you getting that top 20%, right? They're gonna show up with somewhere between 50 and 80% just because they don't want to get fired, because they want to be identified as doing a good job. But that's wildly different than when they're truly engaged, right? When they're thinking about the problems when they're at home, when they have, you know, they're they're off time, they're excited to actually engage in this. And there's a uh uh a bunch of matrixes that have been um matrices, I guess it would be matrixes, some one of those things that have been created around this idea. What actually creates that safety in a culture, right? What creates the safety in an individual? So there's things like uh do they understand the mission and vision of the organization? Does that mission and vision align with their personal mission and vision, which again goes back to identity? Do they actually know their personal mission and vision, right? Is the organization um uh investing in them? Do they have opportunities to grow? Do they see a clear path to move forward? Do they understand how their unique impact every day impacts that? A bunch of different things that actually go into this kind of full matrix that allow for that person to be so wildly excited that they're going to give that discretionary effort, right? So as you think about as a leader, how do we actually get in a position where we can measure discretionary effort of our people? Because that really tells you the true story of how engaged they are, um, how much uh they're ready to dig in and kind of go that extra mile. And that doesn't mean you know, tons of extra hours. It doesn't, a lot of those things are are, I think, misidentified as those leading indicators. If somebody's really engaged, they're putting in 80 hours. No, they just know that's the expectation. They don't want to get fired. That's way different than you actually getting their heart and soul and creativity. And that's where that true magic comes for every organization. The more folks that you have on fire for the organization, the the higher likelihood that you're gonna have success and you're gonna be able to build that.

SPEAKER_01 12:11

I heard a mentor of mine say uh a couple weeks ago, he said, uh, your position entitles you to somebody's function, but it doesn't entitle you to their person. And I thought, oh wow, that's that's a big deal. That discretionary effort that comes from their person. Like there's there's you know, the you know, that's not a title thing, right? And even if the even if the hours line up and it's more hours versus more hours, wildly different. Wildly different.

Pivoting With Trust And Metrics

SPEAKER_02 12:38

Yeah. Okay, so I've got one for you. So uh, you know, you're a leader and you've you've got this idea or vision, or you're you're paying attention to the marketplace way out, and it's clear to you that there needs to be some sort of reinvention or change in the organization, and you've done everything right. You've taken the proper time, you have good discipline around the strategy, you've uh let people in the organization help you with their perspective and authoring the reinvention, and and now everything's like in place, and we're starting to move toward this thing that we all believe in. We have their their hearts and minds around this change that needs to be made. And we look up after implementing uh after a few months and we're like, whoops, I I think this was wrong, right? Like, I'm seeing something different now, or we're getting feedback from the marketplace, and like this this change that we actually executed perfectly may not actually be the right change. Yeah. Now what do I do? Yeah, what does a leader do in that position?

SPEAKER_00 13:37

I love that. And you know, I'm I'm gonna, it's gonna be a really easy answer for me on this one because if you did that process the right way, the trust that's built in that environment allows for exactly the same trust for the next pivot, right? And in fact, it makes every pivot easier. You know, as I as I hear about you as a leader and how open uh you are to feedback, criticism, all of those pieces throughout folks in your organization, that's gonna create an environment where when you have that pivot, you say, yikes, oops, we're seeing these indicators that are telling us metrics that are telling us we're not facing the right direction. Do we feel like we are? Do we feel like we're not, et cetera. You wanna be really careful with that because if you start asking those questions, again, too early, too early in the process where you still need people to be executing on that, you got to make sure that you do that at the right time at the right stage. But certainly going back to the top in that process and saying, okay, so now that we actually are executing on this, what do we think? And actually we're seeing things that that suggest that we're not going the right direction. You go through that same framework, and again, a lot of times it's kind of a waterfall, unfortunately, top to bottom. But sometimes there's other, you know, uh uh sears at different levels of the organization that you can get immediate feedback from. Again, not making them question, oh, Reed just came in and said and asked me five or six questions that knowing Reed, that means he's worried that we're going the wrong direction. So, you know, that's where the mastery comes in in that process. How do we actually ask those questions in a curious manner in order to see is what I'm seeing here accurate? Just like you did in that same process. So it's really just replicating that same process up and down. And then people get more and more used to that and say, well, it's okay that we change because I know why we did this. I knew what the measurements were that we were we were moving for. The measurements are not coming out, the metrics are not coming out, telling us that we're aligned, starting back at the top. What you have to be careful of is that that's not happening every week, right? Yeah, every other week, and and you go through the process. So I think that's where your challenges come in, is there's too much of that. And it's literally constant change rather than incremental change or change at the right time for the right reasons, right?

SPEAKER_01 15:34

So, kind of as a follow-up to that, um, how do you navigate it when you're unclear whether you need to wait longer for something to mature versus you need to change uh targets? And I've had that happen more times than I can count where I like, I can't tell if we're going the right direction and you just need to hold fast, or if we actually need to pivot, which unfortunately comes with a level of starting over in that kind of maturation process. So, how do you how do you navigate um the best timing for making that decision?

Human Nature: Why Change Feels Risky

SPEAKER_00 16:08

Yeah. It's interesting you asked that because that's uh one of the challenges I think I have as a professional is a lot of times I have really strong visibility into where to go, what feels right, uh, a lot more of the gut feel. What people would a lot of times say is I have a gut feel about this. But that really means they're actually putting together data points that might not be that obvious. They might not be able to measure that well, but you're you're able to kind of collectively put those together in a really powerful manner that can um that can uh both in uh inform change and incentivize change. But I'm actually not a master at that. So in that process, I always bring in people in the process who are better at measurement, right? What's a metric that we can actually stick in here? I'll tell you one challenge from history, and it's it's a it's still um, I think a question that is out there is how do you actually measure engineering output, right? Do you measure the number of releases that they do? Um, do you read lines of code written? There are so many different ways that you could actually put an objective measurement on that rather than a subjective one that are gonna move you in the wrong direction. Oh, they all created more code because they were incentivized to create more code. What's crap code, right? It actually isn't isn't moving us forward in the way that we want it to. And so I think that's just a really great example of that. Takes some brilliant minds, way more brilliant than my own, to actually identify a process to measure that, right? To because we know the outcome, we know where we're trying to go. Oftentimes I can feel it actually feels like we're doing really well, but that's not gonna do the in uh you know informing the organization and informing our decision. So having those people in that process that allow for those metrics to be created. Same reason I always have a CFO or somebody in that style is because that's where I fall short, right? I I can absolutely, I'd love to take the information that's created from that report and uh you know create a thesis or strategy beyond that, which sometimes the the the uh matrix people can't. Um with that said, I just fall short in that matrix process. So I always make sure there's somebody running alongside me that can help me with that process that can really dig in there.

SPEAKER_01 18:04

Love it, love it. Yeah. Well, what questions have we not asked that we should talk about today? This has been awesome.

Communicating Change And Power Gaps

SPEAKER_00 18:12

So good. You know, um, I think as we as we talk through this idea of like seeing the future and identifying the things that are gonna make change either uh hyper successful or not, I think you know, there's this natural tendency to say, oh, I'm you know, I'm I'm not doing well, or or I'm not a great strategist, or um, you know, my team doesn't do well on continuous change. I think you said something right out of the gate. There's, you know, we're creating unnatural processes for a lot of people. There are certainly people who cannot stay in an environment for very long at all if there's not constant change, right? Maybe that's their ADHD or my ADHD, or um, you know, some of those things that actually drive that need uh for continuous adjustment or change. But most people in organizations um are fearful of change, especially if they don't have visibility. And so I want to really make sure that everybody realizes that from a human nature standpoint, you know, we are wildly uh created in order to be able to fear change, right? Sure. To be able to fear differences, things that are new, net new. When you don't know if it's a bear or, you know, or a bunny coming out of the bushes, yeah, we are built to think it's a bear because that's actually gonna create the the safest environment for us, right? So that same thing happens throughout organizations. I see change. I don't know if that means I'm gonna get fired, if we're gonna restructure the organization, if there's gonna be a re-org, if we're gonna now fail and I can't um move forward. So that that need for stability, that need for security, um, that automatically switches on in all of us when when we go through change dynamics. Even as leaders who need that change, we oftentimes find ourselves saying, ooh, am I gonna all of a sudden I, you know, this is really going well. We're doing great. And now all of a sudden we're gonna take us down a rabbit hole that that makes us fail. Yeah. Um, so so I guess there's empathy in that process of making sure that everybody realizes human nature drives us that direction, and that's okay. And we have to be aware of it and able to kind of um uh address that as it goes.

SPEAKER_02 20:05

It strikes me as, gosh, what a what a powerful conversation here, right? It strikes me as one of the most uh important pieces of leadership, right? Because here we are talking again about like we know logically that change is the only constant in business, right? If we're playing the infinite game, change is really the only constant. We know that logically. And we're also acknowledging that emotionally, as people, we tend to resist change. And in the gap, right? You mentioned trust earlier in the gap, but also in the gap is leadership, right? This, like if there's gonna be constant conflict around change, which is never gonna stop, then we need great leaders in that space to help people navigate it. And gosh, you just shared so much wisdom around that with us today and and with those listening and watching the podcast, because it's not easy, right? There's nothing easy about leadership in general, but there's certain certainly nothing easy about helping people navigate the one thing they resist the most. That's critical to the future success of them, the organization, the mission, and otherwise. So it's it's definitely one of those obvious gaps that a leader needs to stand in, I think.

Micro Moments And Daily Leadership

SPEAKER_01 21:14

Yeah, absolutely. It makes me think of the times where uh I remember being on a call with like our operation staff, and I'm just excited to share some good news. Yeah, right. Uh, and and because their their core job is stability for the organization. I remember getting about three minutes into this, and everybody was already kind of frozen up. I'm like, is everybody okay? And they're like, are you about ready to change something on it? So I'm like, oh no, no, I'm just gonna share some good news. And so that that pattern, uh, you know, one of the things that uh has been somewhat effective is the pattern of telling everybody what's going to happen in advance. Like, hey, we're gonna talk about change that benefits the company and you know is going to make you be able to do more with less effort, you know, just kind of give them the lay of the land, even if it's gonna be hard, because man, my experience has been if you're going to deliver some news around change, um, if you don't address it right out of the gate, nobody's gonna even hear what you said until the very end where maybe it's just all the fear bunched up at once.

SPEAKER_00 22:15

Right. You know, you just you hit home on something that has um always been a bias of mine, again, and I think it's been pretty effective, and that is as you're delivering that news, the less you can talk and the more other people in your organization can speak, it creates validation, it creates safety. There's something unfortunate about being in the CEO's spot or an executive leadership spot that we we almost forget. We're like, no, everybody trusts me. I'm their friend, I'm et cetera. It's totally not true, right? There is something about he is the ultimate boss, she is the ultimate boss that drives, again, that that fear, that uh respect, those other pieces that are natural emotional instincts that create a bias on everything that is said. And so as much as we you create a safe environment, it's not as safe as you think it is, right? It's not as though as I think it is, and it's not as safe as you know how we go through that. And so um I have found that diffusing that oftentimes can come with who's delivering the news, right? How far down the organization are you getting that? Is that actually somebody that's you know a uh line leader at the bottom that is actually, and and I say bottom respectfully, right? Perfectly, that is actually delivering the news. Hey, you know, and you are gonna spend a lot of time coaching, you're gonna spend a lot of time guiding them through that, but how much more powerful is it when it's feels groundsourced instead of read coming down from on high and dropping this news of our most creative strategy, right? Yeah, super, super smart.

SPEAKER_01 23:37

Yeah, we we were just we're uh doing an event last week and talking about communication, and and one of the things I said as a leader, you have to just come from the assumption you're not approachable. It doesn't matter how personally approachable you are and how much you work on it, the fact that you have a position um it makes you unapproachable. And so you have to actively work on that. And I think that's brilliant to be, especially if somebody else has some DNA in the the you know what's being developed and changed, what a cool opportunity for them, and to diffuse that power gap.

SPEAKER_00 24:09

Yeah. You see so many of these uh CEOs and leaders that try to solve that by even just changing their title. Something as simple as I'm not the CEO, I'm the you know uh Chief People Officer, Chief PE Office, Chief Strategist or whatever it is, right? Yeah, yeah, I'm a I'm a innovator, whatever. Um, and you know, they're you can see what they're doing, you can see why they're doing it. And some of those are effective, but you know, again, it's just one thing out of I I think what makes uh people who are are uh perceived to be successful and people who feel like they have more success in in um uh in life and their organizations across the board, I think we forget that there's tiny decisions that they're making every day, all day, right? Every 30 seconds they get to make an impact on somebody or you know, or steal joy from somebody, right? And so how are you actually making those tiny, tiny decisions throughout the day that all added together? It's not like I dropped this big strategy and it won. It's how did I make somebody feel when they came and asked me a question? How did I respond to that scenario, right? And so, so going back to your point, um, you know, the more we can realize that it's those micro moments that are actually defining all of it, uh, I think we can be a lot more impactful and have better, better outcomes across the board.

SPEAKER_02 25:17

Yeah.

SPEAKER_00 25:18

Thank you so much for joining us.

SPEAKER_01 25:19

This has been amazing. I know. It's great to know smarter people. Oh, way smarter people.

SPEAKER_00 25:24

I'm blessed to be here.

Closing And Listener CTA

SPEAKER_02 25:25

We get to expose some of the knowledge to our listeners. Um, thank you for listening to the Sherpa Leadership Podcast. If this episode inspired you, please remember to subscribe, leave a review, share it with another leader. You can also go to Sherpa Consulting Group.com for more tools and resources. Remember, leadership is a journey. Every step you take matters, so keep climbing. We'll see you next time.