Start With A Win - Overwhelmed? Listen To This / Jan Rutherford

Starting point is 00:00:00 And we both kind of concluded it was, you know, people are overwhelmed. That's the symptom. You know, what's the root cause of that? We can't be command and control and be successful leaders in business. It just doesn't work. Welcome to Start With A Win, where we unpack leadership, personal growth and development, and how to build a better business. Let's go. You feel overworked, overwhelmed, and underperforming?

Starting point is 00:00:24 Today, we talk about that on Start With A Win. Coming to you from Area 15 Ventures and Start With A Win headquarters, it's Adam Kantos with Start With A Win. We're sitting down with Jan Rutherford, a man who's faced challenges on the battlefield and in the boardroom. As a former Green Beret-turned-executive coach and entrepreneur, Jan has spent over 25 years helping leaders cultivate grit and self-reliance.

Starting point is 00:00:48 He's the mastermind behind the Crucible, Wilderness Expeditions, and a co-host of the Leadership Podcast. If you're curious about how to build indomitable teams and push through your own limits, this is the episode for you. Jan, welcome to Start With a Win. Yeah, thanks, Adam. Thanks for having me on. It's my pleasure. You've been in the leadership space for a long time, and I really am excited

Starting point is 00:01:10 about digging deep into this because leadership, personal improvement, business improvement, they all really go hand in hand because we have to lead ourselves in order to lead our businesses. So please give us a little bit of a brief history about yourself and how did you get into the leadership space? Oh, gosh. I'd have to go back to being a teenager in the Army. Wow. You know, I joined at 17 and I remember one of the first things as I was going through Green Beret training was I was on a patrol, a training patrol. And, you know, there's different people that are assigned leadership roles at different times and all of a sudden at three in the morning we're walking like zombies and they go okay the the leader's dead you know you you're in charge and um that was really when it hit me you know

Starting point is 00:01:57 um what what's involved and i remember i got um a really good review by the you know the the sergeant that was in charge. And he said, I really liked your decisiveness. You took charge. And, and, and, and, and in my military career, I was surrounded by some really, you know, great, great leaders, medal of honor recipients, former prisoners of war. And I started to think, you know, gosh, not everybody that has the highest rank is really the leader. You know, there's people that don't have the highest rank that are really influential

Starting point is 00:02:31 around here. What is it about them that, you know, the way they carry themselves? So I've been fascinated with what makes a leader ever since then. And after my military career, got into the business world, started teaching at University of Colorado, Denver part-time. And one thing led to another, but the favorite parts of any job I've ever had is the leadership development piece. I love it. I love it. And you've taken, obviously, that little stint in the wilderness that I'm sure was quite extensive over time and turn it into, you know, wilderness experience. You have a program right now. Um, it's, it seems like you've led in many of the world's most challenging environments. How do you carry this transition

Starting point is 00:03:19 across leading in the wilderness to leading in the boardroom? What are the similarities that occur there that you've been able to, to tie together? Yeah. So I lead these crucible expeditions with executives and we pair them up with military veterans that are transitioning into the business world. And the things that always come up are communication, decision-making, and how one deals with adversity. And back to my military days, I always thought, you know, this is just a tremendous laboratory because when you're cold, wet, tired and hungry, it really reveals character. And then, and you know, the corporate industries I was in, we'd get a lot of leadership training, but it was in windowless rooms at hotels and corporate training centers. And it was great, but it wasn't the same as being out there. So I

Starting point is 00:04:11 wanted to replicate that. And it's not a military experience, but what we do is we get out there and we always have a different leader in charge each day. And we debrief and really talk about what happened and all those things, you know, going too fast, not paying attention to the team, not communicating how decisions were made about how we're going to cross this stream or whatever it is. All those things relate to what happens in the business world. And the big takeaway to cut to the chase is everyone comes out of that and says, I've got to slow down to speed up. You know, I've got to, I've got to slow down. And just yesterday I was talking to the best boss I ever had, who's a dear friend. And we were talking about, you know, what's the biggest problem out there these days. And, um, we both kind of concluded it was, you know, people are overwhelmed.

Starting point is 00:05:02 That's the symptom, you know, what's the root cause of that? And it goes to what you said, you know, if, if you're not leading yourself, it's really hard to lead the organization. And so when people are out there in the wilderness, they realize, um, Hey, you know, when they come in on Sunday and we were done with our trip, they realize half the problems that occurred, you know, took care of themselves. I love that. It's, it's funny. You mentioned a few of those things. I mean, I was in the Marine Corps and you mentioned cold, wet, tired, and hungry. If you want to put somebody under stress, you make them cold, wet, tired, and hungry. And then you throw a problem into their brain that

Starting point is 00:05:38 they have to solve. It's so fascinating how the, uh, the physiological aspects tie into the business and problem-solving aspects there. So as a former Green Beret, you've obviously faced situations where failure wasn't an option. We're talking life or death situations here. How do you cultivate a mindset of resilience in leaders when they're faced with high stakes decisions in business? I mean, it's kind of crazy, but obviously we have these do or die situations in business that obviously are not life and death, but they're do or die for the business. They're life and death for the business. How can we cultivate the resilience mindset into business leaders around some of these principles?

Starting point is 00:06:25 Yeah. I tend to think of resilience as a decision in and of itself. Like that. I mean, you're faced with something and you have to decide, do I have control over the situation? Am I going to own it? Does it reach into every fiber of my being, can I endure? So, you know, is it temporary or is it permanent? So we get to decide. And part of that decision making, what I see is people tend to look at decisions, whatever they are, as pros, cons, good, bad. And I think the big disconnect is in how we make decisions.

Starting point is 00:07:04 They should be based on certain criteria, based on our values, the values of the organization that are prioritized. So as an example, when we're leading an expedition, we get to a stream. You know, the criteria by which we decide how we're going to cross the stream is first and foremost safety. We don't want anybody to get hurt or lose anybody or anything. So that's always the criteria at the top of the list. The other part is, you know, we want to push people without breaking them, stretch them without breaking them. And we want to see, you know, what happens with the team. And we like when there's, you know, indecision and conundrum and somebody's in the back going, I don't know what's going on.

Starting point is 00:07:46 And then we literally will stop them and say, well, how does this relate to the business world? You know, because we, you know, even out in the wilderness, we can't communicate enough. If the leader basically every hour stops for five minutes and lets people know, here's where we're at, here's where we're going, here's how long we're going to get there. It's not enough. There's always somebody who goes, I don't know what's going on. And then I'll say to leaders, so you have a 15-minute stand-up once a week, and you think that's adequate. And with remote and hybrid teams, you don't even have eyes on them. It's crazy. So anyway, I really think it's a mindset. And I think it's about being deliberate and really saying, okay, this is a decision to make.

Starting point is 00:08:28 What's the criteria by which we're going to make it? What's the process? Who has the authority? You alluded to communication and clarity amongst the subordinates or really the team overall when it comes to that. It seems like when we have challenges in business and people, you also mentioned the word overwhelm. What's the number one reason why business deals don't get done? Overwhelm. So you've got all these functions. Overwhelm is solved by communication and clarity generally and having purpose and going after that. But why do we always end up with that person that

Starting point is 00:09:03 you brought up here that says, well, I don't know what we're doing. I don't know why we're doing this. It seems like they're kind of washing their hands of the responsibility of the mission of the team. Or are they truly without communication or is it a combination of both? And how do we kind of deal with that as a leader? Because it seems like it happens. People want to push that responsibility away from themselves by going, nobody told me, you know, on our podcast, we've had a lot of guests and, and a lot of guests, primarily more so from the academic area that say corporations should, should, should, should.

Starting point is 00:09:35 Right. And to me, oftentimes that sounds like a lot of entitlement, a lot of shooting on people. Yeah. And I'm always asking about personal response. Well, where's personal responsibility fall into this? So my firm is called Self Reliant Leadership. A lot of people think that's a dichotomy, but it really is about the interplay between being squared away and taking care of yourself and having some ownership and then a duty, a disciplined sense of duty to the team and the organization. So when we're out there, we'll say, hey, the leader should have communicated more effectively. Hey, you should have been proactive. You should have been paying attention. You know, to go back to a military thing, you should know where you're at on the map. So, you know, again, that ultimate responsibility rests with the leader to paint that as an expectation. You know, that, hey, you need to be squared away because you have a duty to one another. And if you're not squared away, somebody is taking care of you instead of you taking care of the team.

Starting point is 00:10:39 Right. I love this proactive mindset piece. I always talk about there's three things a leader should never say. I didn't know. Nobody told me. And it wasn't my fault. And I mean, it's OK to not know. But it's not OK to continue not knowing if the situation is there. Like you said, proactive in finding solutions and understanding opportunities there.

Starting point is 00:11:03 I want to bring something up you just mentioned here. Self-reliance. Self-reliance leadership, that's the foundation. That's the key pillar of what we're talking about here. It's obviously the key theme in your work product and how you deliver leaders forward. Can you share a time when relying on yourself was the difference between success and failure so that we have a story to put this into context with? Well, there's two things that come to mind. I don't know if

Starting point is 00:11:31 they're as relevant to the business world, but I'll just tell you two quick ones. I remember landing out at Centennial once. I was by myself landing a plane. And every time I went in to land, this wind gust came from this pond and just lifted me up. And as I was about to land, and so you're almost in a stall mode. And instead of being five feet off the ground, all of a sudden you're 20 or 30 feet. So you have to go around. And I remember going, I really wish somebody was in the right seat and I could go, you're playing. And I remember going, you know, it's up to you.

Starting point is 00:12:06 And I had that same feeling as a medic. One time there was a guy in my aid station had a bleeder and I couldn't, I couldn't get the bleeder stopped. I couldn't. And there's no, you know, it's like, it's just me. Nobody's coming. You know, the closest physician is 50 miles away. And I just remember you've got to do it. In the business world, I think, you know, often, you know, when you feel alone is kind of when you're in trouble. Like you've made a mistake, you know, you've screwed up. You've lost trust in somebody. You made a bad decision. And you've got to you've got to you know, you've got to fix it. You've got to apologize. I mean, you've got to do something. And it's like this feeling like, but my intention was so good. And it's and that was the hardest lesson I learned as a CEO was my intention didn't matter at all. All that mattered with the people that were counting on me was my words and deeds. And

Starting point is 00:13:11 sometimes I screwed up with my words and deeds. And I remember feeling really alone, like I got to fix this. I can't just tell them my intentions were good. That's amazing. I mean, that's the reality. Everybody wants to know that somebody had good intention, but if let's just believe that people have good intention to begin with folks, but let's take a look at what Jen said here, words and deeds. What are the actions that they're taking and what direction are they going with those? What kind of clarity communication, things like that. That's really an amazing story. I love the articulation of this around, okay, there's nobody in the right seat of the airplane

Starting point is 00:13:52 to save me. Because I mean, frankly, you look at Green Berets, you look at, I commanded a SWAT team for a long time. The reality is nobody's coming to save you. And as the CEO of a company, as a key leader in a project, something like that, you got to realize nobody's coming to save you. It's up to you to make some decisions to work your way through this. And if we have that paradigm shift in our mind, where we understand, okay, I'm, I'm in charge of this right now. I'm the pilot of this airplane. Nobody's going to save me. I have to realize what my opportunities and actions are here and take those actions in order to work our way through it.

Starting point is 00:14:33 So that's an incredible piece of advice, Jan. So in your experience, what do you think is the most underrated leadership quality and how can we develop it to make a tangible impact as leaders? Yeah, I think, I think the most underrated thing is preparation. Okay. I like that. Is, you know, I mean, most of the leaders that I work with have no white space in their calendar. They go meeting to meeting to meeting. They know that they need to that they leading best is by asking questions. But if you don't have preparation, you can't formulate the questions that you need to ask to help people self-discover. And that goes back to people support what they help create now more than ever. We can't be command and control and be successful leaders in business. It just doesn't work. So, you know, I always go back to the calendar exercise and the word discipline. At the end of the day, I mean, that's what we have absolute control over, even though

Starting point is 00:15:41 the higher up you go, it feels like the less amount of control you have over your day. But this is where the discipline comes in to really say, hey, the only thing I can do as a high level leader is communicate effectively to the people I work with the expectations and the follow up and catching them doing things right. And if I'm not taking time to prepare for those interactions one-on-one or in meetings and then taking time to follow up and sort of debrief myself, you know, how did I come across?

Starting point is 00:16:13 How did I make people feel? Did they get it? Are they committed? Are they loyal? Not just compliant. And I think that's, you know, something that everyone knows, but they lack the discipline to execute that, you know, within their calendar. That's a strong statement. I love that. Two questions I have out of what you just said. You talked about preparation as being kind of this underrated piece, but sometimes we see people who lack the confidence to execute after preparing. So they over-prepare and you, um, you know, there's,

Starting point is 00:16:54 there's this, this balance of done is better than perfect. How do you find a comfort zone around done is better than perfect when, you know, it's, it's time to go sometimes. I mean, it's, you know, the, if the mission's happening, it's time to go. If the, um, you know, there's a, there's a calendar piece where we have a budget or we have a supplier deadline. We, who knows what it is, but how can we, how can we get ourselves over this over-preparation piece so that we're prepared, that key piece, but we're not wasting time because we're overthinking this? Yeah, it's a great question. I often ask how many perfectionists are in front of me right now, and I think that it goes back to the values that they don't understand. Hey, this needs to be an A. This needs to be a B. This needs to be a C.

Starting point is 00:17:51 And, you know, because what happens early in your career, you're really good at what you do and everything is perfect. But as you move up, you have to adapt and realize I can't get everything done. I have to prioritize. And again, it should be based on the values of yourself and that of the firm. And, you know, again, I think that's really difficult for people. Because think about a lot of the people we're hiring, they got straight A's, they, you know, all through school, and then they came in and they were an analyst, everything was perfect, because it had to be perfect. And then we promote them and they still have that mindset that everything has got to be perfect. So again, it's a leadership opportunity to help people understand what's really important and what's not. Do you think that's a function of people being afraid to fail in the operation?

Starting point is 00:18:40 Yeah. And again, not understanding what really is important. I mean, kind of, you know, I often ask people I coach, hey, of all the things you can do, what's the one thing you need to get better at every single day? And most leaders will say, well, my ability to communicate. OK. I mean, because that's your tool. I mean, you're supposed to get work done through other people. You know, you have a thinking list, not a to-do list, you know, at a certain level. And I see that, you know, all the time that leaders are working one or two levels below their position. And then I'll ask them, so you're getting this done. It had to get done. Oh my gosh. It had, you know, this RFP had to, you had to get in there and do the RFP. What is it of your responsibilities did not get done? You know, again, you're not sitting up on the Hill and really making sure, you know,

Starting point is 00:19:38 that the right things are getting done in the organization, not just that things are getting done. Right. Like this. You're focusing in or honing in on this key piece called accountability with leadership. Tell me, how should leaders look at accountability as opposed to it being judgment against them? Yeah. Well, I hear every day somebody comes and says, I've got a non-performer. I've got a difficult conversation. I've got somebody. And I always say, okay, you know what? The three questions I'm going to ask you, does this person absolutely understand the expectations, both in terms of results and behaviors? Because that's what performance is, results and behaviors. Two, do they know exactly where they stand with you, that they're meeting,

Starting point is 00:20:30 not meeting or exceeding expectations? And three, do they understand the downstream effect of their performance? You know, if they perform well, do they understand what that means to the organization? If they don't perform well, do they know how that hurts people? And most of the time I'll hear no, no, no. And I'm like, okay there a document? What do you mean? Is there an email? Did you say to this person, hey, why don't you recap our conversation before five o'clock tonight? Send it over. And if it's not right, you clarify. And if it's right, you say, great. So don't put the work on you to recap the conversation. Put it on your direct report so that they're really committed in processing what you've explained the expectation to be. But most people won't do that.

Starting point is 00:21:31 Again, because we're so busy and moving forward. We're addicted to it instead of what really is going to move the needle. I don't know if you all listeners picked up on that gold that Jan just dropped on you, but the reality is most of us in a leadership role, most people in a leadership role in a business have that spicy conversation, if you will, with the employee where they're talking about performance issues or something of that nature. And then that leader goes and recaps it. And it seems like all you're doing is continuing to belabor the situation and beat the person with it. I love what Jan just said. You let the player set the scoreboard here. And this is part of the, you know, if you look at the disciplines of execution,

Starting point is 00:22:22 allowing the player to set the scoreboard really increases performance because the player is bought into the score that they set on the scoreboard that they're going after. So, I mean, that's, I love that piece. You know, can you recap that conversation and the expectations that came out of that so that we're both on, you know, have clarity around the situation. That right there is, I mean, there you go. You just saved yourself tens of thousands of dollars in coaching from Jan right there. But it's, it's a really, a really interesting component of just flipping a tiny paradigm there in order to accomplish things. I had another question. You talked about discipline. So systems versus

Starting point is 00:23:06 discipline, you know, you are systems versus habits or what have you, you know, we hear this, this, this dichotomy amongst those two items quite a bit. Where do they both fit into business? And how should we look at systems, disciplined habits, things like that in order to find success? Well, I mean, discipline, I think really comes down to, you know, again, how you manage your time, where you spend your time. And the system, here's what I'm hearing. And tell me if I'm going in a different direction. When I think of system, I think of, again, slowing down to speed up is at the highest level. I think leadership is really about design. It's a design element. Right.

Starting point is 00:23:48 I'll give you an example. Picture a broken intersection with lots of car accidents. You know, a low level leader would say, you know what? Everybody needs driver's education training. Let's send them to training. Somebody at the middle level might say, you know what? We'll put a traffic cop in that intersection during rush hour. And I think a high level leader would say, you know what,

Starting point is 00:24:10 that intersection is broken. Let's put in a roundabout. Wow. And I think in organizations, oftentimes we look at all the problems we see. We have an identified root cause and we exhibit, you know, we exercise brute force on trying to fix it. You know, this person's broken this and you see lots of turnover and firing and we're going to kick their butt instead of saying, you know, this is a systemic problem. Let's look at the big levers, people, how they're incentivized, not just money, but at a at a boy's at a girl and kudos. The processes and the structure. Those are the four levers we have to work with to design an environment where people are going to behave in a way that produces results. And hopefully, it's a really great culture.

Starting point is 00:24:58 And I say, if you do that, you're creating a culture by design, not allowing one to happen by default, which is what I saw happen a lot during the pandemic and it still exists today. So-and-so doesn't ever get on camera. Well, your culture becomes the worst behavior you tolerate, period. So, you know, whose fault is that? Wow. I love that. Was I on the right thread? Absolutely. I mean, the analogy to the intersection is spot on. I'm going to use that. It's definitely key to explaining that point. I love that. Becoming a Self-Reliant Leader, How Grit and Discipline Duty Forge Indomitable Teams.

Starting point is 00:25:46 I love the concept. I love the key points in this book. Give us a quick flyover and where can we find your book? Yeah, it's anywhere you buy a book, you can get it. The foreword is by General Stan McChrystal, who's been a guest on our podcast a bunch of times, and he was kind enough to do that. What we decided to do after 10 years of crucibles, 25 crucibles from Patagonia to Alaska was really outline, Hey, here's what happens on every expedition. You know, so there's 12 chapters, each chapter goes, okay, here's what happens predictably. And we start to tell a story about, you know, what happened. and then we relate that to the

Starting point is 00:26:26 business world. And then we tell the rest of the story, and then we have some takeaways. And it might be on, hey, the first obstacle you encounter, the preparation, the first encounter that we've had, how we wrap up, what happens during a fireside chat or a debrief, all the things that predictably happen that exactly relate to the business world. So we've also interviewed probably half the people that were on the crucibles over the years and brought their stories in. So it's not just mine and my co-author basically telling the story. We're really bringing the stories and what the crucible expedition experience meant to other people. And we're hoping and feel pretty good that it can be a framework by which people can look at their own organizations, their own leadership acumen and continue to grow and develop.

Starting point is 00:27:26 I love it. I love the lessons learned on adventures. It's amazing. I mean, you go all the way back to, you know, Shackleton and his adventures, but all of these, especially current, um, leadership and how it, it relates to business and personal growth is fascinating to me. Folks, make sure you check out Jan at self-reliant leadership.com as well as the leadership podcast. He's been doing a podcast a lot longer than most people. So, um, I mean, it's, and it's a good podcast, a great leadership podcast. Uh, Jan, I have a question. I ask all of our amazing guests and leaders on Start With A Win. How do you start your day with a win? I, as soon as I get up, I take the dog for a long walk, no matter what the weather is. And we're here up in the hills, west of Denver.

Starting point is 00:28:15 So a little walk here is still a little bit of a workout. And then I'll get my workout in, whatever that might be. And, you know, I'm always, um, I'm always catching the sunrise and, um, and I'll tell you, it's the best part of the day. I feel like the whole, this whole Valley I live in is, is all, it's just mine and my dog. We, you know, just us because most people are asleep. I love it. I, for those that have not hiked where Jan is in the, the mountains just West of Colorado,

Starting point is 00:28:48 you got to go do it. It's an incredible place. So Jan, thank you so much for being on start with a win. Everybody make sure you check out Jan's books. Also, you know, check out Jan online.

Starting point is 00:28:58 He's got a lot of great materials. They're done a lot of wonderful coaching, incredible leadership oversight, and some really, really good nuggets. You've heard quite a few of wonderful coaching, incredible leadership oversight, and some really, really good nuggets. You've heard quite a few on this podcast, but there are many, many more. Jan, again, thank you for your service in the U.S. military. And you as well. Thank you.

Starting point is 00:29:17 And thank you for being on Start With a Win. Thanks, Adam. Some great questions. Thank you.

Start With A Win - Overwhelmed? Listen To This / Jan Rutherford

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