Scaling Leadership with Jeff Chastain

Jeff Chastain is a business transformation coach, he’s the founder and CEO of Admentus Inc and the podcast host of Building to Scale. In this show you can learn about:

  • The differences between leadership in a Start-up vs. a growth-oriented business
  • Leading with a visionary mindset, how is that different from the well versed Growth vs. Fixed
  • The key components of an effective business vision and how does the business leader make that vision actionable
  • The reasons some leaders are unable to break through the glass ceiling that could be holding their team or business back

The Leadership Hacker News

Steve Rush: Now we’re already a hop skip in a jump into 2022, and there are lots of emerging things that leaders need to consider. So, I’m going to give you my top six predictions based on what I’m hearing and what I’m seeing in the world of leadership and people transformation. 

Number one, leaders need to give people a reason to stay beyond money and beyond extrinsic motivators. The great resignation is absolute for sure. There are so many people across the globe quitting their jobs because they’re focusing on what really means for their life. Therefore, as the problem continues to grow, leaders need to continue to adapt and change and think about their proposition. So, people feel connected to the organization. They have a purpose and most importantly feel that they have something to add value to their lives and their work beyond their compensation. I believe the most productive companies this year will be those that give people a reason to stay beyond money. 

Spear no expense when it comes to real time gatherings. Whenever the COVID 19 pandemic moves to an endemic and companies move back to a normality in ways of working, whatever that may be in the future. When the hybrid world has cemented itself in our workplace, we will need as leaders to spear no expense in bringing people together, whether it’s once a year, twice a year or infrequently, but leverage the opportunity in bringing people into a real time place together, create experiences for those two, spend time together and experiential team building activities, nice dinners, real quality time together just as if they were long lost family and expect people to be spending more money on hiring the best people.

There’ll be a point where organizations wherever they’re from in the world facing into this war of talent and therefore we’ll need to compensate people better and compensate search firms in helping them find that talent too. I think accountability will come back to the forth. Since remote workers cemented itself in our future and our culture. We’re able to see very clearly people’s productivity. And it’s evident if team members are doing the job that we expect or not even in a hybrid and remote world. And managers have noticed that making people accountable must be a priority in their leadership approach for this year. And I define accountability is the obligation of an individual or organization to be accountable for its activities and accept responsibility for them. And to be transparent, accountable leaders provide a path of person improvement, team performance and life performance.

I can see organizations focusing on their underperforming leaders in a far more rigorous way. In a recent study. Gartner predicted 30% of teams won’t have bosses by 2024. And I don’t see it this way because leader’s teams don’t work. However, collaborative, broad, bigger teams may be part of the case, but poor leadership cannot be tolerated. Organizations will invest more time in assessments and surveys and understanding the human experience. Great leaders will notice this and unlock it in their teams. Poor leaders will fall by the wayside. 

And the final one to wrap it up is probably the most controversial of all. Multiple income streams will be accepted by most organizations in the future. In the hybrid will world. There’s no reason why we couldn’t do two or three roles, two or three jobs. But if this is really about life and human experiences, suppose if we had the opportunity to negotiate with our employer, that I wanted to work three or four days a week for them, and maybe another day a week for some philanthropic activities and giving back to the community, but also maybe a subtle pivot to how I go about earning my total compensation, who knows.

But if we do want to retain our best talent, we might need those leaders to be thoughtful and encourage multiple ways of them making money for their family and their lives, whatever the future holds for us as leaders. It requires flexible thinking, rapid action and elevating others into leadership, thinking and behaviors. The leadership environment we’re already in, in 2022 has already changed from 2021 and will continue to rapidly change. And if you don’t change with it, you’ll be one of those victims too. That’s been The Leadership Hacker News. I’m looking forward to more news and more stories that keep coming on a regular basis. So please keep sending them in. Let’s get onto the show. 

Start of Podcast

Steve Rush: Our special guest on today’s show is Jeff Chastain. He’s a business transformation coach and the founder and CEO Admentus Incorporated. He’s also the podcast host of Building to Scale. Jeff. Welcome to the show.

Jeff Chastain: Hey, thank you. And thank you for having me. 

Steve Rush: It’s my pleasure. So, tell us a little bit about Jeff, where did it all begin for you and how did you end up here?

Jeff Chastain: We probably don’t want an hour long to show just on that, but I’ll give you the quick version. It’s been lots of lots of twists and turns over the lifetime, but that’s been, I don’t know, I’ve find that’s the journey of most entrepreneurs. We jump into the deep end and have it all figured out right off the bat. But now, my background actually started actually in corporate America and in technology so completely different fields there but spent a number of years with corporate America and just honestly was bored as anything. It’s like, okay. Just showing up for a job every day just was not my mentality, not my wiring. At that point and couple that together with a reshuffling, reorganization of the company, and one day, all of a sudden it was surprised. Find myself out with the corporate umbrella without the parachute, et cetera there, and trying to figure out, okay, what do we do now?

So, like most people in business getting started, I said, hey, I’ve got a technology background. Let’s go form a CTO, kind of consulting firm. And that’s really, where Admentus actually got its start, was in the technology world. But over the years in working with different companies, both large and small, from a technology standpoint, I kept having people coming to me, working with people, et cetera, that were looking to technology basically as business solved. I go back to one case I had where the guy, of course, all great decisions are made on the golf was kind of a thing there. The one CEO was talking to his friend on the golf course and saying, hey, our sales numbers, our sales trajectories down this year. And his buddies said, well, we just got this new CRM. We’ve really been using this new CRM. It’s really helped our team. So that was the point of introduction to me was say, hey, can you help us implement this new CRM system in our business and go going through the process effectively. We figured out, hey, you don’t have a sales process. You’ve technically got a sales team in terms of people, but there’s no strategy. There’s no vision. There’s nothing to your sales team here. They’re just kind of fly by the sea of their pants and just putting in a shiny new object, a new CRM system here, not really going to fix things by any means. So just ran into that over and over with business leaders. That for most of us in business, we probably identify pretty well. I know I’m that case of the shiny object syndrome, kind of a thing there, hey, let’s go try this. Let’s go try that. 

And people, these days tend to turn to two technologies quite often for that. To me, technology is just a magnifier of whatever’s underneath. If you’ve got a great system, a great process, yes, technology can make you more efficient, but it’s not going to fix the underlying foundation. So, that was really the transition pivot point to me to say, hey, instead of sitting here trying to sell you a new CRM system or something like that, that honestly, I know is not going to really get at the root of your issue. Let’s go in and fix the business foundation. Let’s fix the underlying systems, the underlying structures, where it’s still kind of my systems, my process nature. But that was really my transition to say, okay, let’s move from consulting into the coaching realm and say, let’s get the foundation fixed. And then we can go put on technology, or then we can go scale the company, whatever we want to do, but we got to get that foundation structured first.

Steve Rush: Yeah. And it’s interesting, even if you remove technology period, the behavioral stuff that is still needed to think about strategy, vision, and structure of an organization and a team. That’s kind of transferable across every sector, every industry, isn’t it?

Jeff Chastain: Oh, it really is. And I’ll see it, even talking like marketing or sales, hey, we’ve been doing Google ads now we’re going to try Facebook ads. This salesperson’s not performing, so we’re going to go hire a new salesperson or we’re going do an outsource sales or something like that. It’s like, we’re always trying new things because what we’ve got may or may not be living up to expectations. It’ the grass is always greener kind of mentality. There’s always got to be something over there that might work a little bit better without ever really getting to the root of the issue at that point. 

Steve Rush: Right. So, what’s the key focus for the work at Admentus right now?

Jeff Chastain: I’m actually narrowed things down recently here within the last year, really focusing on those smaller business, smaller entrepreneurs’ kind of thing. A lot of the times, what I found over the years was the coaching industry, especially out there, when you look at big name systems, like an EOS or like a scaling up or anything, they always focused on more the larger size companies. You got at least 20, 30 kinds of employees. You’ve got a three- or four-person leadership team. And it’s like, wait a minute. We’re leaving out the smaller guys, the guys that, hey, I want to go out and I’ve got a dream, I’ve got a vision. I want to go build my business, but I don’t have $30,000 to go invest in a coach, or I don’t have a big team yet that’s profitable.

We’re still in the early stages. But at the same time, this individual is typically forward thinking enough to say, hey, I want to lay the foundation right in the first place. Let’s figure this out in the first place, rather than creating a huge mess and having to come back and pay to clean it up. So, we’re really focusing more on that. I don’t want to say entry level, but still that early-stage kind of entrepreneur, that early-stage business owner that says, hey, I’m an expert in my field. I know my field, whether that medical, legal, finance, whatever, kind of an area they’re in, but saying, hey, I realize there’s a lot more to business. And to building a profitable and scalable business than just being a good lawyer, or just being a good accountant or whatever, the case may be there. 

Steve Rush: Of course, most big businesses started out with some more businesses and smaller ideas that then just grew, and that’s been a force of your work. Isn’t it? It’s helping businesses scale up.

Jeff Chastain: It really is. And even still, I take a lot of this, even from my personal journey that when I first got into I.T. consulting. The company was me, myself, and I kind of a thing there. While yes, I was having fun with the work I was doing, and I had ideas for what I wanted to become. We actually talked about it just briefly before we got on kind of a thing. It’s like all of a sudden, I’m looking at, okay, kids got soccer games or an awards ceremony at school or for that matter, even a vacation with my wife, kind of a thing there. And I started putting that into the mentality or I had what came to mind every time started looking at those as well.

That’s two hours at a soccer game and equating that back to a billable, right? Wait a minute. That’s a $300,400 soccer game there. Do I really want to do that? Or the vacation, the worst case, actually the vacation turns into three and four times the cost, because not only am I paying to go rent the hotel or do the travel. Now I’m looking at the effectively lost time, lost wages to go do that. And it’s like, okay, this is not a good place mentally to be. But at the same time, it’s like, okay, what’s the solution when it’s just you? Because most people jump in and say, well, I’m going to go create a new business. I’m going to start a new business. But effectively what they’ve created is a job for themselves where, it’s they’re the CEO, they’re the frontline worker and the janitor all in one.

And unless you can figure out how to scale that, how to grow that, then you’re effectively locked into that job. And if that’s okay with you great. But when it was turning into my direct time was the service to be delivered. It just wasn’t scalable at that point. So that’s really where it’s like, okay, got to figure out a better way to do this. I know other people are doing this, we got to figure this out. So that kind of led journey and now turn around and handing that back to other people that way.

Steve Rush: Yeah, great stuff. So, when it comes to leadership of businesses that you’ve helped scale up from startups to some of the larger organizations, what do you see as being the differences between leadership and a startup versus leadership in a traditional growth orientated, established business?

Jeff Chastain: I don’t think they are necessarily different leaderships. I think what it is, is a case of many times people having to learn how to lead or learning what it means to lead because you take the lawyer that’s used to, okay, this is my law practice at best. I’ve got a virtual assistant or a paralegal, somebody kind of working with me, but it’s a different mentality for them to say, okay, now I want to go manage two or three other lawyers in my firm and actually build out a firm model with a support staff, et cetera, kind of a thing there. So, they really have to make that mental shift to say, okay, this is not just me doing whatever it takes today to move the business forward. And now I’ve actually got to have a plan, have a strategy in place for everybody. Otherwise, we’re effectively kind of that rudderless ship of saying, okay, I’m going to walk into the office today and figure out, okay, which way is the boss leaning today? Because that’s the direction we’re going today. And that’s to me is not leadership. 

Steve Rush: Right. 

Jeff Chastain: That’s somebody that’s still struggling saying, okay. I don’t know how to move out of the solo practitioner into an actual leader in a firm leading a team, driving a business forward.

Steve Rush: And what is it you think when you think about those folk who scale quicker versus those who may be more laggards in that space? Is there a, maybe some secret sauce that goes on there? 

Jeff Chastain: There’s always a little bit of, I’d say any business, there’s always a little bit of luck involved, but to me it’s more the planning side. It’s the system, it’s the strategy because okay. I refer to it kind of as the cornerstone of any significant business or any business there is really what I refer to as a strategic vision and execution plan. Anytime, again, going back to my corporate days, we always talked about strategy planning and stuff like that. And it’d be multiple days of just boring meetings and marketing mumbo jumbo kind of talk. You ended up with all these plans that would go into some drawer or some cabinet that never got seen for another year or two. So, when we look at that from a small business standpoint, we say, I can’t do that.

I can’t afford to put that together and there’s no use for it. Why am I investing in that? And while yes, I completely agree with that. I also say, okay, you can’t go the other end of the stream and say no plan at all. We’ve got to have an entrepreneurial focus middle ground that says, I literally document your entire strategy, your entire execution plan on a single page, caveat, asterisk it’s double-sided so you could call it two pages, but still it’s that small, that tight that you can sit there and identify who we are as an organization, where we’re going, how we’re planning on getting there, such that even if you are still the solo premier entrepreneur, you’ve got that plan to say, okay, I know the direction we’re going. I know what we’re trying to hit. So that when that shiny object does come in, I’ve got a measuring stick that I can say, okay, is this a good fit?

Is this something that’s still going to further advance my strategy here or do I ignore it? And then once they start growing into multiple employees, bigger team, it gives that visibility to the rest of the team so that, okay, we know as a team. Again, who we are, where we’re going, how we’re planning on getting there. So, you’ve got everybody kind of united the boat, everybody’s rowing together the same direction, rather than just flailing about trying to thing, wasting resources that honestly most small businesses don’t have. So, it’s really having that plan. Having that guide, is what’s going to jumpstart that the most right there, just to say, hey, we know what we’re doing. We’re not out there changing direction every month, kind of a thing. And wasting the time, wasting the limited financial resources that we’ve got. 

Steve Rush: A lot of this is also down to mindset, isn’t it? Of those individuals and the way that they approach it. And I know that from most people listening to this, they might be well versed with things like growth mindset, fixed mindset, but you have a different take on this around visionary mindset. And I wondered if you could just give us a bit of a sense of what that would mean?

Jeff Chastain: In a lot of ways, it kind of encompasses both of them really. I really see most people and it’s not a across the board people, but most people that go out and start a new business have that kind of visionary mindset. They’ve got this big idea of, I want to go bring this problem to solve, or I’ve got a help kind of attitude. I want to go attack this issue I see out in the market or out in the community, kind of a thing there. They’ve got that bigger picture, visionary attitude to them to say, okay, this is where I want to go. Where they struggle with the most is saying, okay, I’m not necessary the tactician. I’m not necessarily the execution to say, okay, how do I get from where I am right now to that big picture vision that honestly may take 15 or 20 years something out there.

And that’s where a lot of times I’ll see them struggle because they’re still, again, they’ve got the big idea and great, okay, here’s this new other idea. And they end up moving all over the place. It’s almost a pairing is what I see the best. Companies in place to say, okay, you’ve got that visionary person, but you’ve also got that second in command, that strategist or that technician kind of thing right there to say, okay, feed off of each other. We’re work off of each other there, but you’ve almost got to have both mindsets. And it’s rare I find that it’s one person has both in place. So, it’s either that visionary to say, okay, we need a plan that can kind of reign you in a little bit. Or we work with the technician types to say, okay, it’s not just about today. We’ve got to figure out a bigger plan. We’ve got to figure out a bigger aim for your business. So, it’s almost kind of creating that dual mindset in the case that we don’t have a partnership working together to figure out, okay, how do you balance long term, big picture vision with execution today to help you reach that longer term vision?

Steve Rush: Yeah. And I don’t know who it was. It was for almost quote wasn’t there? That said, a vision without a strategy and a plan is merely a dream. I think that’s what you’re inferring at there, right?

Jeff Chastain: It really is. 

Steve Rush: And without that kind of core foundations and components, then it’s just a hypothetical dream.

Jeff Chastain: You’ve got to be able to come back in and execute on it. And the same time, the flip side is that, okay. Execution without out a longer-term vision is just busy work at that point. And, yeah, that quote’s been rewritten so many times. I always wonder, like, okay, who’s the original purpose on this one thing? Because I’ve seen it rewritten several different ways and it always means the same thing, but yeah, that’s exactly what it is.

Steve Rush: It was some guy called “anon”. He’s written loads of quotes.

Jeff Chastain: Quite a few, yeah.

Steve Rush: So, talking about then that kind of execution, that business vision, what are the key components that you’d expect to see happen for every team, every business as they kind of grow?

Jeff Chastain: Well, it really starts out with me for that long term picture to say, okay, I put everything in terms of like climbing a mountain or something like that to say, okay, this is our path up the mountain. We’re aiming for that peak, that pinnacle on top of the mountain. So, it’s clearly identifying what that is in the first place to say, okay, where are we even trying to get to in the next 10 to 15 years? And this is not something that’s super detailed. It’s kind of the peak, the mountain up there in the clouds. On a given day it may not necessarily be super clear. And the reality in what I like to coach people with is to say, okay, if there’s not at least some bit of doubt in your mind that you can even reach that, then it’s not big enough kind of a thing.

Steve Rush: Right.

Jeff Chastain: It actually goes back to like Jim Collins, The Big Hair Audacious Goal kind of attitude, right there is, we’ve got this big thing out there on the horizon, but then it’s really working from the execution standpoint to start backing that down to say, okay, great. That thing is out there at 10, 15, 20 years. Something way out there, that’s take some time, some significant effort to get there, but okay, great. What do we need to do now as more of a plateau, a resting spot, a milestone on the mountain to say, okay, our first goal is just to get here? Yeah, we’ve got that in mind. But our first goal is just to get to this first camping spot here. And that’s really in the three to five kind of year range to say, okay, this one’s a little bit closer, a little bit more defined, but I don’t want to go overboard with this. I don’t want to get super detailed roadmap because especially after the last year or two with the COVID pandemic, we all realize now for sure. The world changes pretty quick, kind of a thing. 

Steve Rush: Doesn’t it, yeah. 

Jeff Chastain: So, we’ve got to be able to adapt, but still we’ve got to have those kind of pictures out there. So, it’s a three-to-five-year kind of milestone there. And then bring that back down again to say, okay, with that three-to-five-year milestone, what do we have to accomplish this year? The one-year kind of plan, that’s what I’m working with through everybody right now to say, okay, what is our plan for 2022 here? What are our specific goals, objectives, things that we need to go accomplish? And then working with that back down into what I refer to as more the 90-day world to say, okay, we’re only carrying specific details from a detailed planning standpoint about this quarter.

We need everybody on the team this quarter to understand, okay, what’s our key number. What’s our key metric that we’re working towards, what specific goals, tasks, projects, et cetera, need to be done this quarter again, in order to reach our one-year goals, in order to reach our three-to-five-year milestones, kind of a thing like that. So, it’s bringing that back down step by step. And each step, it gets closer. It gets more detailed, but that way you’ve got this longer-term picture, this longer-term strategy laid out that everybody understands. Because that was one of my biggest issues in corporate America was just like, I was just going in every day. Yeah, I kind of knew what my responsibilities was. Maybe I knew what a project was at that point, but I didn’t have any bigger picture vision to say, okay, what am I doing right here?

How does that really matter? Even in terms of the overall division, much less the company and with a small business, we can’t afford to have our limited resources right there effectively kind of get disillusioned. They need to understand and feel part of the overall mission of the organization. Not just be there for a paycheck, because honestly most of the time we’re not going to pay them top dollars. So, we need them to really feel like being bought into the organization, bought into the company there for something more than just that paycheck and having this kind of a plan to where they can see, hey, this my role. And this is exactly how I fit into our 90-day numbers or our one-year numbers. And I can see what piece of this I’m carrying is really what gives them that buy-in, that incentive right there to say, hey, I really am a part of this. I’m not just here for a paycheck. 

Steve Rush: Yeah, it’s one of the big things, you know, I notice when I coach other business leaders and other leaders of teams is they’re able to articulate the vision really, really well. And it’s well versed amongst a team, but if there’s any gaps in context, people don’t buy in as well as they could do, right?

Jeff Chastain: Exactly, yeah. And they people throw around the terms all over the place, but it’s almost like, okay, treating the business itself as its own entity to say, okay. We talk about, okay, your personal legacy. What do you want people to remember you by? I almost looking at it in terms of the business, what do you want the business to be known by? If your business was to go away in 20 years or something, what would you want people to remember? That, hey, this business accomplishes this, it’s like, we look at a lot of the stuff going on today with like an Elon Musk sitting there putting the new space flight missions up kind of a thing there outside of our NASA program here in the states.

And it’s like, okay, he’s got a bigger picture legacy, a bigger picture vision. And you look at that and say, okay, what’s the business legacy? Then bring it down to say, okay, what’s our mission? Why are we here beyond just out to make a profit? In my case, out to make entrepreneurs’ lives better, give them back the freedom, give them back the enjoyment of their business while still being able to profitably grow and scale. And it’s kind of that articulation that you’re sitting there. I’m assuming you’re referring to, to say, okay, my whole team needs to understand this is really what our end goal is. Yes, we’re a for profit business. Most people are kind of a thing there. And even if you’re not for profit, you’re still got to raise money either way, but got to have a bigger picture mission out there or that people can really understand and buy into. And you’ve got to be able to articulate that and define that both from an employee attraction standpoint and a hiring perspective from an employee retention standpoint, and even from an outside perspective to say, okay, your customers looking at that, do they identify and believe in that? And most likely that’s what attracting them to the company. In addition to the solution that you’re solving at that point. 

Steve Rush: You talked about getting your plan, your strategy down to kind of a quarter in 90 days, but for you, does it ever get more detailed down into the weeks and the days?

Jeff Chastain: From a company standpoint, I don’t ever break it down further than that. From an individual standpoint, we don’t typically look at that or our coach kind of a thing into that. There are all kinds of systems out there for managing your week and stuff like that. But to me, the bigger picture issue is to say, okay, you understand from an individual standpoint it’s the, who was it? Steven Covey. The rocks, sand, water kind of model, kind of a thing. 

Steve Rush: Yeah. 

Jeff Chastain: You understand what your big rocks are for this quarter to know that, hey, I know I’ve got to get project X done, or I know I’ve got to get these five steps towards that project done. So having in your mindset and then what we do is, or at least what I coached, I’m losing his name now. Meeting rhythm, meeting, Lencioni’s strategies, kind of a thing there to have an effectively a check in style team meeting on a once-a-week basis, because what they found over time was that this goes back to those that still remember their school days, kind of a thing. Most of us, when you get the paper assigned or the project assigned, we don’t start working on it that day. We would effectively wait till the night before and sit there and do the cram kind of style session to get that paper written. And that carried forward into the working environment where you’d see this almost a kind of an exponential curve of effort. Whereas as time got closer, as it got closer and closer to the deadline, all of a sudden, the amount of effort would exponentially increase in order to meet the deadlines. So, by doing more of a weekly style check in, just almost a standup kind of meeting, whatever to say, hey, where are you on your project? What’s going on? It starts bringing that back. And you start seeing these little weekly spikes of effort at that point that, hey, I’ve got a report on this, on Friday’s meeting. So therefore, I better get a little bit done this week. So, I can actually have a positive report Friday. Starts getting some of that progress moved in, but in terms of actually doing like a daily planner or anything like that, that’s typically smaller scale that we typically work with. 

Steve Rush: And let’s be honest, I guess you are expecting people to be smart enough to work out the roadmap of what week to week is going to get you to achieve your quarterly objectives anyway, aren’t you, right? 

Jeff Chastain: You really are. And to me, that’s again. Good leadership is, one being able to hire the right people from a mentality standpoint that yes, they can self-manage. They can be their own person. You’re hiring the expertise there, but the other side is really getting out their way, because it’s interesting with the business leaders I’ve interviewed on my podcast and say, okay, what’s your biggest struggle? What’s been the hardest thing in growing and scaling your own business? Almost always come is back to the idea of delegation that, especially when you start small, you’re used to having to do everything there yourself and being able to start handing that off and saying, okay, yes. Now I’m going to go trust you to do the marketing, or I’m going to go trust you to handle the finances side without sitting there, reinserting myself back into that role is some of the hardest things that people have to deal with. And to me, that’s the sign of a really good leader, is that okay? I can truly hire the right person. I can give you the systems, the tools, et cetera, you need to be successful, but then I’m getting out of the picture. I’m stepping back and letting you run with this, because honestly, hopefully you do a better job at it than I could do, because finance is not my area expertise or marketing for sure. Kind of a thing there.

Steve Rush: So, when you think about the folk that you’ve interviewed for your podcast, typically, what are the kind of common traits that you see that set those really successful leaders apart? What would they be typically?

Jeff Chastain: It actually goes back to kind of what we were talking about earlier with that visionary mindset, the ones that have the big ideas, the ones that really truly know, hey, we’ve got a mission here. We’re out to go solve this mission here. Honestly, the way I started to say, hey, I know I.T, I’m going to go be an its consultant. Those ones typically struggle more because a lot of times they’re more the technical kind of technician type personalities there, the ones that really have that bigger picture vision. And then again, what we’ve talked about can articulate that vision, can bring that vision, turn that it into a plan and bring a team together to drive that mission forwards. Those are the ones that really seem to have more success from the ones that I’ve talked to.

Just, again, having that bigger picture, this is more than just ourselves, more than what I can accomplish. And therefore, I need my team to come alongside me to come out and execute on this. Those are the ones that grow. If you’re just sitting there looking at it solely as I’m the only one that can do this, I’m the best one at all these tasks. That’s just a self-limiter at that point, more than anything. And that’s where a lot of the technician types kind of struggle.

Steve Rush: So preneurs versus entrepreneur, right? 

Jeff Chastain: It really is, yeah. 

Steve Rush: Yeah. So, we’re going to turn the tables a bit now, Jeff. This is where we typically hack into your leadership thinking, your leadership brain. 

Jeff Chastain: Okay. 

Steve Rush: So, I’m going to ask you to think about all of the experiences you’ve had throughout your career and having coached some fantastic leaders yourself too and distill them down to your top three leadership hacks. What would they be? 

Jeff Chastain: To me the first one more than anything is kind of knowing your identity. Either personally or having an identity for the business, because especially when you’re the solo entrepreneur or the early-stage entrepreneur, you and the business are both pretty well tied together. So it’s like, okay, how do you define out that identity? Your who and your why kind of a thing of your business at that point to build, get other people on board, and then really the second step or of the second hack there as you were calling it kind of a thing for, okay, we know who we are. Building out a roadmap, building out a strategy. Actually, had it written down. Morris Chan is, one of the quotes that was along those lines, saying. Without strategy, execution is aimless. Without execution, strategy is useless.

So, it’s that same kind of quote that we’ve talked about. There are so many different versions of it out there. And then the third option, like, or third piece of it is really being intentional about the delegation. Plan to delegate, even if you’re still that solo entrepreneur, or you’re still the two- or three-person team, right there. Actually, work with those people to say, okay, we’re going to draw out effectively the org chart, draw out the functional kind of chart there of all the different functions in your business. Even though it may have your name on 90% of these boxes, we need to help you understand what that bigger picture plan is for your business. So, we can start identifying, hey, this box over here, I’m not being very good at accomplishing the goals here. Maybe this is the first one we need to go work at delegating or find somebody to hire in for. So really developing that kind of plan for delegation, that kind of plan for hiring, even if you can’t financially do it right now, but just start thinking in that bigger picture, because the ones that have that bigger picture, vision, that bigger picture strategy to say, okay, next year, I am going to hire these two new people. At that point, you’ve got a goal. You’ve got something to work towards rather than just being solely focused in today. So, to me, that’s almost really the three things in my mindset is, the identity, the roadmap, and then just planning to delegate, planning to grow. 

Steve Rush: I love that last one. And it also relevant for people that work in organizations, where if you theoretically map out an ideal org chart or an ideal team structure, it’s how you then go about either recruiting, hiring, or giving away some of that responsibility in hiring in to fill your gaps playing to your strength, right? 

Jeff Chastain: Exactly, yeah. 

Steve Rush: Yeah. 

Jeff Chastain: As an entrepreneur, we tend to try to take on way too much stuff. And I was like, we were talking about it beforehand, kind of a thing. The ones that can truly sit there and say, okay, yes, I’m not the greatest at everything. And the ones that can delegate are the ones that are going to grow and succeed faster.

Steve Rush: Next part of the show Jeff, we call it Hack to Attack. So, this is typically where something screwed up, hasn’t worked out well, it’s not been a particularly great experience, but as a result of it, we’ve learned from it. And it’s now serving us well in our life or work. So, what would be your Hack to Attack?

Jeff Chastain: Well, I’d say I haven’t necessarily completely dealt with this one yet, but to me, it’s perfectionism and it’s anytime, even previous ventures, everything like that, anytime it was building a product, building a service, anything like it. It had to be completely perfect before it could ever go out the door. And that just leads to paralysis honestly, more than anything.

Steve Rush: Yeah, it does. 

Jeff Chastain: It’s really this idea of saying, hey, just get started. It doesn’t have to be perfect. It’s version 1.0, its version 0.1 kind of a thing here. It doesn’t have to be perfect. And your team, your customers, whatever will provide the feedback, honestly, probably to build a better system or a better product than you would’ve dreamed up in the first place. But that’s still to this day something I have to keep in mind that, okay, this doesn’t have to be perfect. This doesn’t have to have every single bell and whistle right out the door. We just need to get started. We just need to get something out there and move forward and iterate on it. So that’s been my biggest challenge since day one and still tends to be. 

Steve Rush: No thank you for sharing. I think many people listening to this will resonate with that, right. Because we’ve been taught from an early age that you don’t ship a product, you don’t buy something, you don’t finish your homework, you know, whatever it was at high school, all of those things have to be done completely. And to the end degree. And we have to unlearn that in leading teams and leading businesses, don’t we?

Jeff Chastain: We really do. To me that even goes back to the strategy level, that okay, if all you’ve got in mind is that big 20-year goal out there, you end up paralysis at that point saying, okay, I don’t even know how to start reaching that. It’s the adage of the little quote about how you eat an elephant is, one bite at a time. You got to figure out how to break that down to individual bites and just say, okay, I’m going to take the first step. Even if it’s not perfect, I’m going to take the first step, get it done. And then we can move on and start building that momentum at that point in is really the key to it. 

Steve Rush: Yeah. I think it was Steve Jobs that infamously said that you can’t connect the dots forward, but you can connect them back, but just make dots.

Jeff Chastain: Yep. 

Steve Rush: Yeah. 

Jeff Chastain: Exactly.

Steve Rush: Great. Last part of the show we want to give you some opportunity to bump into Jeff at 21. So, you’re going to do some time travel now.

Jeff Chastain: Yeah. 

Steve Rush: So, you have an opportunity to now visit yourself in the past and give yourself some words of wisdom. What would your advice to Jeff at 21 be?

Jeff Chastain: Oh, and part of it, I would say is just get out there and try things. Again, not worrying so much about okay, what’s it going to look like? Is it going to work? Is it not going to work kind of a thing? Because again, I was always the perfectionist, it goes back to that standpoint of saying, and I would really get stuck on things saying, okay, if I can’t do this perfectly, the first time out, then I’m not going to do it all. I think, honestly, I missed a lot of opportunities by that kind of mindset. 

Steve Rush: Yeah. 

Jeff Chastain: To say that, hey, just try something. If it doesn’t work out, it’s not the end of the world. People are most likely not going to remember it anyways, but just try something and who knows, something will stick. Something will work here. 

Steve Rush: That’s it, great advice. And I often ask this question every week, as most of our listeners listening to this will know already. And it’s interesting, you know, that if we could turn the clock back, how wiser we would’ve been, you know, a relatively short space of time.

Jeff Chastain: It really is, an actually had somebody ask me a slightly different version to say, hey, what do you regret doing? Or what do you regret having made decisions before? And I kind of got to think about, it’s like, you know, I wouldn’t call it regrets on most anything, because hopefully we’ve learned from all of it. 

Steve Rush: Right. 

Jeff Chastain: So that’s kind of the idea of wisdom is that you’ve got to go through the experience to hopefully learn from it and do it better the second in time. And if you didn’t have that experience the first time, then there wouldn’t have been any learning at that point. So, to me, that’s the story of the journey that, hey, very rarely do you see an overnight success, an overnight business or anything. And if you, do it probably crash just as fast. 

Steve Rush: That’s right.

Jeff Chastain: So, most of these, you look at the HP or the Microsoft or anything like that. It’s like HP came out a garage somewhere. It didn’t pop onto the scenes as this massive corporation. You got to start, you got to build. And it’s just one step at a time and plan for it. Just not happening overnight. It’s going to take some time; it’s going to take some effort. And that’s why I always look at it as the mountain climbing journey. We’re not going to just parachute into the top of the mountain here. We’ve got to actually make the climb and it’s going to take some effort there to get there. 

Steve Rush: Yeah, sure. Is. So I’ve really enjoyed chatting, Jeff, we’re coming to the end of the show now, but I want to make sure it’s not the end of our listeners connecting with you. Where’s place for us to send them?

Jeff Chastain: All of our programs right now are wrapped around the idea of Building to Scale. So, it’s is our podcast. It’s the coaching programs, everything like that for small business entrepreneurs. So, if it’s an entrepreneur just simply saying, hey, I know what my dream is. I want to get there, and I don’t have a plan or don’t have a system, don’t have a strategy. Then always just happen to have a conversation at that point, but it’s just

Steve Rush: Awesome. And of course, we’ll make sure all of your social media links are in our show notes. So, folks can listen and connect with you beyond today as well.

Jeff Chastain: I appreciate it.

Steve Rush: Jeff, it’s been great having you on the show. Good luck with the future of what you’re doing and good luck with your or show too. And I appreciate you being part of our community on The Leadership Hacker Podcast. 

Jeff Chastain: Thank you very much. I’ve enjoyed the conversation. 

Steve Rush: Thanks, Jeff.


Steve Rush: I genuinely want to say heartfelt thanks for taking time out of your day to listen in too. We do this in the service of helping others and spreading the word of leadership. Without you listening in, there would be no show. So please subscribe now if you have not done so already. Share this podcast with your communities, network, and help us develop a community and a tribe of leadership hackers. 

Finally, if you would like me to work with your senior team, your leadership community, keynote an event, or you would like to sponsor an episode. Please connect with us, by our social media. And you can do that by following and liking our pages on Twitter and Facebook our handler there: @leadershiphacker. Instagram you can find us there @the_leadership_hacker and at YouTube, we are just Leadership Hacker, so that is me signing off. I am Steve Rush and I have been the leadership hacker.

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