Episode 11 - Why Saying No Might Save Your Company - Part 1

Change without trust feels like chaos; change with trust becomes a flywheel. We sit down with John Monroe to unpack how leaders can reinvent continuously without burning out people, customers, or momentum. From turnarounds where everything stalled at 80 percent to the transparency that rallied teams with only two months of runway, John shares battle-tested ways to reduce fear, build alignment, and ship real outcomes.

We start with the self. John walks us through his daily cadence—prayer and meditation to anchor purpose, honest self-audits to separate truths from lies, and a tough workout to practice progress and resilience. That inner work earns credibility when asking others to change. Then we zoom out to the organization: avoiding whiplash with a visible ideas backlog, cool-down periods before broadcasting new directions, and small cross-functional squads that validate fast without derailing current commitments.

Communication is the lever. Borrowing a board rule—no surprises—we frame reinvention as a series of early signals and questions, not grand reveals. Cascading messaging lets leaders test language, surface blind spots, and pre-align teams so announcements land calmly and execution begins immediately. Along the way, we dig into the power of no: narrowing focus to one or two bets, preventing tech debt and strategy sprawl, and empowering trusted voices to challenge ideas safely. The result is a culture where authorship equals ownership, and reinvention feels intentional, not impulsive.

If you’re leading through growth, turbulence, or both, this conversation gives you practical tools to slow down to go fast, protect culture while you pivot, and finish what you start. Subscribe, share with a leader who needs this, and leave a quick review to help more builders find the show. What will you say no to this quarter?

Transcript

Trust As The Foundation

SPEAKER_02 0:04

I'm here to create trust. I'm here to identify places where trust and uh relationship have broken down. Because if you don't start with those things, anything you go in and say, okay, it's time to actually address this and uh work through this process is gonna fail. One of the most powerful things that I focus on is that we're no. Um and I think as an organization, um, we always think that this is the idea of you know speed up to go faster. You know, we have to sprint and uh and run, and that's what's gonna actually make us have a better outcome, have faster outcomes, get to the course faster.

Welcome And Guest Introduction

SPEAKER_01 0:37

And I actually think it's opposite. 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. Hey everybody, welcome back. You're listening to the Sherpa Leadership Podcast. I'm your host, Reed Moore, here with fellow Sherpa Chase Williams. We're here to help you climb higher in life and leadership. As always, you can find all of our goodies at Sherpa Consulting Group.com. And please, if you love this content, share it with another person who's on a leadership journey and make sure you like and subscribe on all the places that you watch this or listen to this, like YouTube and Apple Podcasts. All right, today we have an incredible opportunity, Chase, to interview another amazing leader.

John’s Journey And Culture Lessons

SPEAKER_00 1:31

Yeah, we do. Yeah. Mr. John Monroe, good friend of ours and an incredible leader in so many different spaces, family, business, and well beyond. We had the good fortune of spending a weekend away together this last weekend in Montana. And, you know, we were doing lots of things refreshing and spending time with Jesus and a lot of other high-caliber men, right, as part of our journeyman group. And I actually had forgotten until today that we were interviewing John today, because we'd scheduled this a while back. Yeah. And so when we chatted briefly this morning on the phone to get the opportunity for John to share part of his story and lessons and leadership around what it is that we do as leaders. And of course, we're going to be covering a portion of the iServe model today. Yes. But you're all in for a real treat, and Reed and I are in for a treat with this guy. So, John, tell us a little bit about yourself, whatever you might share in general.

SPEAKER_02 2:20

Awesome. Well, thank you so much for having me. I'm super excited to be here. What you guys are doing with uh Sherper Consulting as well as some of your other practices is just uh absolutely inspiring to me and so many other folks. So obviously I'm honored to be here today and and hopefully to provide some um some perspective that you know might be unique to me that uh based on my identity and the things I show up with, but uh but maybe uh either obvious or not to other folks. So excited to excited to dig in. So um uh I've been an entrepreneur most of my career, um, have taken a lot of businesses that that uh were already existing and grown those uh either by making them tech enabled or actually moving them to SaaS organizations. Um and in that whole process, I started out uh really as a technical expert. So came out with the information systems degree from college. Uh, thought that was the place to be because of course everybody wants to be there until the.gom uh bust hits.

SPEAKER_03 3:08

Yeah.

Reinventing Continuously Defined

SPEAKER_02 3:08

Second that hits, it's over. And all of a sudden, you know, there are no jobs, there's no opportunities. And so that really reset my targets in the way that I was kind of moving through what I thought was my initial trajectory. Of course, best laid plans as you're in college thinking about those things. But um, have had a wonderful journey over the last 25 years growing a lot of organizations, uh, focusing on customer experience and all those things. And kind of as I've I've operated, if you go from cradle to grave from mergers and acquisitions, acquiring, uh, divesting companies, um, uh growing and expanding, adding value in organizations. Um, I think one of the things that I've always really kind of uh, as I step back and I actually reflect on what's most important, um, I see that culture and the way that you interact with humans and and the way that those humans are within your organization are really all that matters, right? As you're thinking about strategy, the best strategy is gonna be wildly outpaced by culture. So the people, the way that they're engaged, the way that they actually engage with that culture, with that strategy, um, I think creates the right environment for them to be successful in the org to be successful.

SPEAKER_01 4:12

I love that. So one of the hardest things that we've experienced with culture is kind of what we're talking about today, and that is as we're going through the iceurf model, uh, you get the uh the task of helping us walk through how a leader uh addresses or engages with reinventing continuously. And it's one of those things as leaders that we have to do, especially in today's high-paced, you know, fast-paced world. You wake up and every day sometimes you find yourself in just a brand new arena. And change has has been one of those things that I've always seen as something that is very hard to navigate people through uh in a healthy way, especially when it's a lot of people. So how have you engaged or what are your insights into this idea of uh the mandate as a leader of you have to be able to reinvent continuously and being able to do that in a way that really uh uh stabilizes culture or or or protects it?

Trust As The Antidote To Fear

SPEAKER_02 5:04

Yeah, I just love the fact that you guys have really called out that piece, and and many people in their core values call those pieces out, right? What does it look like to um uh uh win and learn? How do you move the organization forward? How do you continue to uh drive that success uh with longevity? And oftentimes it means a lot of change, especially in kind of high growth startups, which I've spent a lot of my career in. And so um, as you think about that, um, one of the things that I always just kind of, you know, as you as you back up and you look at the 30,000-foot view, um, in my opinion, all of that is based on trust, right? How do you create trust with individuals? Because that's really what you're talking about. When you think about culture, when you think about uh continuous change, it's really how can people be in a place where they're not operating in fear of what's gonna change today? Um, how is my job gonna be protected or not? How do they go into kind of self-preservation mode? And so if you can get them out of those modes and actually get yourself into a place where and the organization into a place where there is trust created, right? Between individuals, between leadership and individuals, between you know, uh all assets in the in the organization. By assets I mean people, not thinking about them as numbers, but thinking about them as humans. That's when you can create the right environment as you actually navigate through those journeys of reinventing and actually doing that on a continuous basis. So without trust, everything else falls apart.

Reinventing The Self: Daily Disciplines

SPEAKER_00 6:20

Love it, love it. Yeah, I was just thinking as you were saying that, that's so important, right? We we know that in general, generally speaking, people are uncomfortable with change. And here we are talking about continuous reinvention as a necessity of leadership, and those two things are like holy smokes, are they in conflict, but you know, potentially. And so I love that you shared that, right? Because like the the conduit is trust, right? If if if change is already hard enough for most people, and your job in part as a leader is to continuously reinvent, but they trust that it's for the good of the organization, it's for uh the good of the mission, it's for their good, then it doesn't, it's not a magic button, I'm assuming, but it makes it uh possible. It makes it easier to move people towards something new, which they can be resistant to, right? So one of the questions I have, John, I'd love to understand your experience around this, is part of reinventing continuously is actually reinventing yourself as a leader, right? And how you show up in the world and show up for others and show up in the organization as an example or your family, et cetera. What does that look like for you? When you think about like reinventing personally, what are some maybe examples, or how do you think about that or have experienced that over the years? Yeah.

SPEAKER_02 7:36

Um, I I love that question. And I think uh, you know, if I think about it, uh theorize on how you actually create that opportunity to reinvent uh continuously, it has to start with self, right? You start with the self, then you actually move towards uh how do I serve others with that, right? So if you're not, if your cup isn't full, filled, if you're not challenging yourself to grow and continually adjust, people are gonna say, What do you what do you think you're doing? Telling me to change and you're not changing. I can see that that's not happening. And so there's a culture of curiosity, and there's all those things that are baselines. But I really go back to individual daily disciplines, right? So as I think about what does that look like on a daily, weekly, monthly uh cadence, what are the things that I'm doing to self-assess, right? Go through and identify the truth that I'm telling myself and the lies that I'm telling myself, uh, the truth and the lies that the world is telling me about uh my value, what value I bring, the way that I contribute most beneficially to an organization or to those relationships within the organization. And so constantly kind of looking at those. So it starts for me, you know, at the beginning of the day of reset, right? How do I actually reset myself to show up that day, both knowing the truths, knowing the lies, as well as then navigating through and you know, finding an environment where I can actually challenge myself. So that starts with me, with uh a workout. It starts uh with my prayer and meditation, it starts with, you know, really resetting kind of those core attributes or core values that I live by every day, you know, resetting every single day I write down what my why is, right, and how I'm actually going to approach that for the day. Um, I write down some baseline uh attitudes and attributes that I need to remember to step into every day. And then it goes to beat myself up with an gnarly workout because that's one of the ways that I find that it resets both physically and mentally my ability to say, you're challenging yourself, you failed in this area, you succeeded in this area, here's an opportunity for growth, here's an opportunity for uh celebration of, oh man, I made progress on I can, you know, do 10 pull-ups for the first time ever, or whatever it might be. Or for a lot of people, it's one pull-up, right? They work months and months to be able to do one pull-up. Um, I think those things are perfect examples of how you're actually putting in the work to ensure that you have those right attitudes to uh continuously improve.

SPEAKER_01 9:45

So just thinking about the um the thin ice that reinventing continuously is, uh maybe what is one story where it went really, really well for you in business? And maybe one that uh results may vary.

Turnaround Story And Transparency

Whiplash: The 80 Percent Graveyard

SPEAKER_02 9:58

Sure. Yeah, yeah, great, great, uh, great question. So um, you know, I've I've had the privilege of doing a couple of turnarounds. Um, and in those turnarounds, you know, uh what's always interesting is you find something at a state that it is uh currently, right? And there's uh various opinions in those scenarios. Some people think it's perfect. Some people think, uh, just get this thing out of the way and it's already perfect. Others, sometimes vestors, think, oh wait, this is not perfect, right? This is not where we want to be at all. In fact, we're stepping out. We're no longer in uh we're no longer engaged, we're no longer excited about what the outcome is. And so I've had the opportunity in a couple of those startups to be put in a position where I needed to walk in and say, what's working, what's not, how do we improve it, et cetera. Now, the knee-jerk is to say, I got this list, and some of the things are net obvious, right? You have enough pattern recognition, you've done it enough times to really look at an organization and say, we need to address this, this, and this, right? So you kind of have your priority list. But that's actually the knee-jerk reaction. What needs to happen is you go into an organization and say, I am not changing anything. I'm here to create trust. I'm here to identify places where trust and uh relationship have broken down. Because if you don't start with those things, anything you go in and say, okay, it's time to actually address this and uh work through this process is gonna fail. So a couple of examples. Um one example I had a wonderful organization that I got brought in by um the uh kind of venture capital team uh that was that was um uh driving the organization's success historically, had got to a point where they really needed to see some change. And it was a wild opportunity, just massive demand, massive opportunity. The the prior CEO to me had done a wonderful job at creating that um buzz and creating the opportunity for people to be excited. But we got in and and as I got into the organization, I noticed there was massive brilliance within the organization. They were executing on some things just incredibly, and you know, we've we've talked before about that concept of whiplash, right? Yeah. The the organization was going through some whiplash, right? Massive whiplash, in fact, if you look at it. Um there were things that were focused on for a couple of weeks, and then wait, that's not the right thing. We need to pivot and we need to go to uh the next strategy or the next idea, or this is really we're gonna win. So what you ended up having is kind of this graveyard of things that were completed to 80%, and not by anybody's fault, just by the fact that, oh, we have new input. How do we actually move forward and move on this input? But what you end up having is everything's done at 80%, nothing's done to 100%, nothing to be delivered. You go back and you have a bunch of tech debt in those scenarios. You have a bunch of customers that are feeling that whiplash and seeing that where are we today, where are we going next week, how do we actually get there? Um, and so in that environment, it it took really stepping back and saying, okay, we have to start with the trust. We have to start with here are some bright spots, here are some weak spots. How do we all get aligned on what that actually looks like? How do we get really to that truth telling across the organization? And for me, that was a lot looked a lot like transparency. None of them knew how we were doing it as an organization. None of them knew that we had two months of runway to keep the business going. And so there were a lot of opportunities for transparency that were scary to a lot of people. The board said, You're gonna share with everybody? You only have two months, everybody's gonna run out the door. But instead, we used it as a a really catalyzer that brought everybody together. And and again, not because of me, just I had the opportunity to experience this and lead them through this. But um, it was a wonderful example of once you bring people together and create a safe space for them to both share their concerns, um, share the opportunities, the barrage of brilliant ideas, the barrage of here's how we can solve these uh challenges that we're actually up against, um, just come over and over and over. And so then it took some no's. And I want to talk a little bit later about no's and how important the word no is in organizations, especially around uh continuous change. But uh yeah, that was one example where um it really was a struggle uh to kind of get to that part and uh that place. And then once we got there, we started to see some of the magic come out of the backside of that.

SPEAKER_01 13:49

Love it. Yeah. What what about a time maybe maybe earlier in your leadership where uh it didn't go so well? Uh maybe maybe it was the learning, uh, the the you know, the the crucible that led to that one going well.

SPEAKER_02 14:00

Or actually opposite. You know, I think I think what's fascinating is that how many times did I have a success and then the very next uh situation I was I was in was a you know I would consider a learning opportunity, i.e. failure, right?

SPEAKER_03 14:11

Yeah.

SPEAKER_02 14:11

Um where it wasn't effective and it wasn't successful. So um I had scenarios um kind of in that middle range of my career where um uh uh I found that my idea of what change looked like did not align with the organizations or the executives that were already there, or you know, the idea that um of where the organization was going was um the right path. We just needed to you know trim off the fat on this side, we needed to you know round off the backs, do a box, do a little sanding on the on the corners of the of this beautiful sculpture they had created. Um and so when you get into those dynamics, it's really difficult then to step in and say, okay, well, how do I create trust to be able to help them identify we need to do more continuous uh reinvention, right? We need to actually go through that process. Um, and so in in uh one particular scenario, I'm gonna keep the name out because it probably uh is more powerful that way. Um you know, there there was that challenge, and there was that um the trust was broken down to such a level where we actually were not able to reset those trust dynamics, right? Um, as soon as we would make progress, then you know, somebody would come in what I call swoop and poop, right? Somebody from senior leadership would come in and, you know, we're on path, we're moving the right direction, we're starting to get alignment, and then boom, you know, something comes in and everybody's day has changed, right? You you change the entire dynamic of how people are showing up because you say, you know, this is what we were doing last week, and now this is what we're doing this week, and not really assessing and aligning on well, what does that change look like? At what point can we deliver this information? What are people working on that they're so passionate about that we told them to be passionate about? And we got alignment on that we're actually moving forward with, and then um, you know, now are re-injecting into that process saying, that's awesome that you spent the last three weeks thinking about that, doing that, executing on that. But now our entire vision mission has changed. Here you go, drop that in, reset. Yeah, and and how that actually impacts um, you know, the people throughout the organization, the employees both top to bottom.

Intentional Reinvention Over Novelty

SPEAKER_00 16:10

Yeah. It strikes me as um, and what you shared there strikes me as even more important than I initially thought around being intentional with reinvention, right? So, like it's this idea of not reinventing for reinventing's sake, right? Because that could lead to things like organizational whiplash, right? But rather like deciding what key areas of the business, key relationships, trust, strategy are most important to be reinventing, right? I could tell you about the time I reinvented um Casual Friday, right? Like it was my idea that canceling Casual Friday was a good idea in reinventing the organization early on in my leadership. Turns out that didn't go very well, right? And all joking aside, uh that's a real story, by the way, but all joking aside, uh it wasn't not gonna move the needle to start with, right? That might be a silly example, but it's like, ooh, how do we reinvent intentionally as it pertains to the mission, right? As it pertains to the need of the organization, which isn't the same in every case, right? One of the one of the questions I had for you, John, is in terms of being strategic with reinvention, it strikes me as maybe easier to reinvent or change something when it's obvious to everyone it's not working, and potentially harder to reinvent when everyone feels like it is working, or actually like we're in times of plenty. Everything seems to be going well. And as a leader, if it's my job to be looking out further and potentially reinventing something, it's kind of one of those if it ain't broke, don't fix it kind of resistance, maybe in the organization. So talk to me about the importance of reinventing when everything seems to be going well in an organization.

No Surprises: Cascading Messaging

SPEAKER_02 17:52

It's so interesting. I uh that makes me think of some experiences I've had with boards, right? As uh I interacted with the boards, as I I really learned that process fairly late in my career of how do you go from uh pretty privately uh tightly held organizations to ones that were venture-backed or private equity backed. And in those processes, that was a massive learning opportunity for me, massive growth, right? What worked for me previously did not work for me now. Um, and one of the key things that a couple of advisors, I think they had to kind of hit me over the head with it, told me two or three or four times, was um nothing should ever be in the board meeting that you haven't haven't already talked about, right? So there should be no surprises ever. Um and initially I said, okay, that makes sense logically, but I think that process actually applies across organizations, right? That same exact framework of nothing should be a surprise, should be the same way that we actually apply these. So, and as you think about, you know, you're seeing a uh shift in in uh way the where the market's going and how the organization needs to respond to that, right? The first thing shouldn't be we see a shift in the market and here's where we're going, right? That should never ever be for anybody in the entire organization, should never be the first time they hear about it. What they should hear about is we're seeing this theme, we're seeing this opportunity, we're seeing this potential risk that's coming up. Is anybody else aware of it, right? So I always think about um, you know, when I think about what Jesus did, right, right? Um, he asked lots of questions. He all answered almost none, right? Actually straight answering. So so as I think about that same process as we apply it to that, how are we asking questions that bring people to those same um outcomes? And maybe beneficially, we they don't. They say, actually, I hear what you're saying, but I have a totally different perspective on this. Here's why. And then then it helps to identify our blind spots, right? Because as soon as we are from the, we'll call it from the Ivor Tower, looking forward, making decisions, we are so far off in organizations away from the customer, we're away from what's actually happening, you know, uh directly with kind of the daily work that we actually don't have the right inputs to be able to make those decisions clearly. So that doesn't mean we just go and and uh you know take all the inputs from everybody, and that's how we all we make our decisions. We still need To be leaders, we still need to be thinking ahead, we still need to be seeing the um uh you know the forest instead of just the trees. Yeah, um, but with that said, I think that uh opportunity to say, hey, does anybody else see a forest out there? Oh, you do. And again, it's not everybody's sweet spot, and we shouldn't try to put them in positions that you know where that's not something that they're great at. And uh with that said, us setting the right expectation by saying, here's what we're seeing, what do you think? Here's where we're going. Okay, now we're actually making a thesis around this. Now we're going forward. You might have done that in a 24-hour period or even a two-hour period of said, aha, I see this, it's all coming together, let's go. But really recognizing that it will never be successful if the organization is not with you, right? Yeah. That power of one that just showing up and saying, Well, I have the right answers, let's go.

SPEAKER_03 20:45

Yeah.

Slowing Down To Go Fast

SPEAKER_02 20:46

You're gonna lose every time compared to an organization where there's where they're, you know, you're following much more of that process, bringing everybody on board. Everybody kind of has that understanding. And man, again, that doesn't mean moving slow, right? Which is why I think back to your original statement of creating a culture of innovation and continuous improvement. Um, you know, that's you you have to have that as one of your core strategies in order for people to realize what that means. Yeah. And then show them what it doesn't mean as well. It doesn't mean that we're always going to change things every day. It doesn't mean that we're not gonna stay consistent on something that we um uh go out to do to see if it can actually work, right? In that scenario of if everything's 80% done, they never got to test if it actually worked. Never actually delivered something to market to say, is this the right thing? Is this the wrong thing? What did we learn in the process? How do we actually navigate through that? That answered the question.

SPEAKER_03 21:30

Yeah, I think so.

SPEAKER_00 21:31

Just shout out to Reed. One of the things that he does really, really well, because he has this ability to see far in the future and dynamic things changing before others, but he does a great job of involving the organization and particularly the other leaders and helping author what reinvention may be necessary. A lot of times he has it pretty clear in his head of how he's thinking about it, but he's he's not just um placating the rest of the leaders by asking, he's generally looking for other perspectives and blind spots, and at the same time kind of pointing them in, like, hey, are you guys noticing this? Because I'm noticing it, and then how do we need to think about it? And then what should we do on what timeline? And so it's really does a masterful job of, like you're saying, like involving the organization and helping them author some of the reinvention so that everyone's moving as one when and if it's time to make a change. Yeah.

SPEAKER_02 22:21

And we all know that authorship equals ownership, right? Just across the board. And if you miss that critical piece, I think it's so easy for us as leaders just to say, oh, they'll get on board, they'll get excited, they'll they'll come along. Yeah, absolutely not. What you're gonna get is a lot of people that are giving 70 to 80 percent, right? They're engaged, but kind of because they know that the the dialogue might change, they know that that process, especially if they see it consistently, that that process continues to occur. Well, why am I gonna invest in this when it's gonna change next week? Right? How do I go through that process?

Building Structures To Hear No

SPEAKER_01 22:50

Yeah, we I was just thinking about this where uh Patrick Lincioni calls it cascading messaging. Uh, and it really is he basically says this is this is a positive use of gossip. Um and so the ideal, you know, change the the tactical actions of change and what it's gonna require of people is hard enough already. The the whiplash of change, surprise we're going in a new direction, uh is is a part of change that I would say maybe a lot of times is actually unnecessary. The the hard work is gonna always be necessary. But um ideally in our in our company, if we can talk to a few key people about maybe what we think we're seeing and rely on them to talk to a few other trusted people who then talk to other trusted people, by the time you have the meeting to make the announcement, ideally, everybody already knows. Ideally, it's just a giant yawn uh as far as the shock and awe goes. And now there's a lot of questions about what what are we gonna do now? Um though those changes have been the most successful that we've had, right? As opposed to, you know, as a leader, sometimes you want to, you know, like get up and say, like, we're going this way now, right? But man, that creates a lot of a lot of challenges, especially in trust, especially if you're an entrepreneur and you've done that every week for the last four years. Yeah, 100%.

SPEAKER_02 24:02

It's so fascinating when you think about the retrospective that you do as a leader oftentimes of what was successful, what wasn't, and how many times we're biasing towards the wrong things. Was it unsuccessful because I didn't do a good job of what you just described, right? I didn't actually have, we didn't have the cascading messaging. There's two leaders in that in the organization that weren't either bought in or didn't understand where we were going. And so then you get the game of telephone. You go down to the person that's farthest down in the uh company tree or organization, which oftentimes is closest to the the customers, um, and you ask them what the messaging is, et cetera. And it's wildly different than what you delivered, right? Sometimes that that creates a bias effect of, oh, that wasn't the right idea. That wasn't the right strategy, we didn't move the right direction. And actually what failed was the communication piece of that. Somehow something in that in that process failed.

SPEAKER_01 24:47

Yeah. So what do you do? Um, and maybe you didn't have this issue as an entrepreneur, but my experience personally, as well as working with entrepreneurs, is that um ideas are a mile a minute, there's an addiction to new ideas, and the natural state of things is whiplash. Um, how did you build the discipline to not do that? Or if you never had that issue, how do you help other people not do that in their organizations?

Authorship Equals Ownership

SPEAKER_02 25:12

So I have made every uh uh snafu and sin and other things in an organization that probably could exist. So um coming from it from that bias of kind of understanding that one of the most powerful things that I focus on is the word no. Um and I think as an organization, um, we always think that this is the idea of you know speed up to go faster, you know, we have to sprint and and uh and and run, and and that's what's gonna actually make us have better outcomes, have faster outcomes, get to the course faster. And I actually think it's opposite. And I've found pretty consistently that it's opposite. This idea of slowdown to go fast, I think is absolutely brilliant. And oftentimes what that means is why are we addressing five verticals at the same time? Let's focus on two. Maybe we even just need to focus on one and just absolutely knock that out of the park, right? Until we have uh you know 20% of the market, or before there's a bunch of different things that can tell that story of when you've been successful enough to move on. Um, but I think that's that's kind of the idea that typically there's the organizations are just doing wildly too many things, both from a product standpoint, um, from a what are we going to actually focus on as an organization? And so being able to get that alignment, so it's not every part of the org is doing something wildly different, but that they all see how they tie together and oftentimes uh interacting, putting together uh work teams where it's you know somebody from in my world, somebody from engineering, a product person, a salesperson, and as a customer success person, they might not otherwise get to actually uh integrate or navigate that often. You put them together as a subgroup and and give them a Skunkworks project, right? And say, hey, we don't want to spend too much time on this, but go spend time on this, right? Go ideate on this, go go research this, the power that comes out of that process and the visibility. And again, we started this whole thing with trust, right? And the trust that gets created in that environment, seeing how they come with perspectives, seeing the challenges that actually uh bubble to the top, that then sometimes create more uh uh visualization of, oh, we actually have a uh challenge as an organization we need to address around trust or around communication or or some of those other things, or even around strategy, that a lot of those things I think boil to the top as part of that process. Love it.

SPEAKER_00 27:16

Okay, so I want to go a little deeper on this because I love that question. So, like here I am, I'm a wild entrepreneur running naked through the field all the time. And I've come to this realization that I may be creating organizational whiplash because I have a new idea every time I wake up in the morning and I'm ready to go execute it, a new priority. Nope, we're not doing that anymore, we're doing this, right? So learning to say no is really important for me. How do I learn how to hear no from others that I trust inside of the organization? What does that look like? People who are experiencing what I'm clued into now uh and can help me by saying no to the wrong things. What does that look like from a leadership perspective? Is this for me? For us. Okay. Like I think we had this conversation like an hour ago.

Measuring Success And Blind Spots

SPEAKER_02 28:03

Something like it. So a little different. Um, you know, I think my bias would be, you know, as you think about those people that are those um, you know, uh long-sighted that uh, you know, are strategists by nature, that really are going to be going and looking out into the future. I don't think they're naturally naturally good at putting in the protections in place to protect against themselves, right? So creating a structure where you can have a dynamic that, okay, when I have an idea, it goes into this bucket, right? And you never go around the bucket. You you say, you know, that's where the discipline comes in, right? You say, hey, when I have an idea, it goes on a list. And here's where the list is. And here are the steps that it needs to go through. I need to do validation, I need to do, you know, dumping it off into another teammate, I need to do all of these things before it ever makes it to the point of, you know, um dropping into an executive meeting or dropping into a team meeting or being something that actually gets dropped into like an all-hands meeting for the organization, right? So as you navigate through those steps in that process, it helps to hold yourself accountable. And even more, it gives other people the visibility that you are creating a disciplined process. And usually what happens is there's other people who are a part of each of those, right? Stage one might be, you know, you actually put it on a list and it goes and sits out there for you to say, well, I have to reflect on this for 48 hours before I'm gonna tell anybody about it, right? Stage two might be, okay, now I'm gonna communicate with questions to people. Here's what I'm seeing, here's what I'm thinking, here's what I'm feeling. Give me your feedback. What does that look like? That might be your most uh trusted executives, it might be uh folks in certain parts of the organization who would know things. But what we're really wanting to do is ensure that you go through that whole process. So then it can make it onto the list. And if it makes it onto the list, great, let's go. But that also doesn't mean everything else gets ignored, and this is the new most important thing to focus on. Because again, oftentimes you're moving the right direction and there might be some changes that are required to be able to stay relevant, to be able to, you know, um ensure that the organization is ready for the future. But how often has that killed organizations? The new ideation killed organizations versus being able to allow them to have that success.

SPEAKER_00 30:09

I love, I love that you shared that because part of that learning to hear no and say no is part of just your cadence, your structure, and your discipline. I think part of it goes back to what you've shared all along so far in this interview is trust, right? Like as a leader, I need to trust that there's other people in my organization that I can uh create a safe space for them to question or say no or offer concern or a different perspective so that we can, again, the idea being avoiding whiplash and being strategic about reinvention in the right areas. And that takes a um that takes a special kind of leader, right? Somebody who can uh move their ego out of the way and not need to be right all the time and has done a great job of inviting people into the organization and the conversation that are willing to say, hey, wait, hold on a second, I have a concern around that, right? Like again, Reed does a masterful job of this, even though I was ribbing him a little earlier. But he he really does. He's he when when when someone has a concern, they feel incredibly safe in bringing it up into the conversation. And not only does he allow for that in a safe place, but he encourages it, right? We would call it mining for conflict. Like, hey guys, I have this really great idea. I would like for you to beat it up a little bit, just to make sure it's not stupid, like canceling casual Friday, right? Like should have beat that one up with a few other, you know, uh wise counsel. But um, I think that there's an element of trust that has to exist both ways there, right? The people believe in trust that the leader is bringing these ideas of reinvention forward for the good of everyone, and the leader trusts that the people are gonna ask questions, offer their perspective, and and make sure that it's the right thing or it's the right timing, etc. So I think both of those are really key elements. Yeah.

SPEAKER_02 31:51

I think that that awareness uh for those leaders of of how those conversations are impacting, right? How you measure success. Do I measure success that my idea got through? Do I measure success that it was the right idea and the right answer? Or do I measure success based on, oh, we have some alignment, feels like the right direction to move, and so let's actually, you know, now continue the process, right? And so if your measurement of success is I got you know my idea through, which you know typically is gonna come from most um uh vibrant, uh, what's the word I'm looking for? Charismatic. Charismatic leaders, right? They always they're they're there to serve, but also there to uh naturally sometimes be right, right? They say, I am a leader and I can lead from the front in that process. Um, what do you mean we're on the wrong, uh wrong, wrong hill, right? We're going up this side and we're supposed to be going up that side. We're never gonna make it because other people are seeing our blind spots.

SPEAKER_00 32:42

Thanks for listening to this episode of the Sherpa Leadership Podcast. If it inspired you, please remember to subscribe, like, leave a review, or share it with a fellow leader. We hope you'll stay tuned for part two of John Munro's interview. And as always, you can go to Sherpa Consulting Group dot com for more resources. Remember that leadership is a journey. Every step you take matters, so keep climbing. We'll see you next time.