My Delegation “Playbook” as a Leader of 75+ Employees | Ep. 24

In this episode of The Sage Investor, Brian Spear explains how business owners, entrepreneurs, and investors can use hiring and delegation to move from owning a demanding job to building a scalable enterprise. The core idea is that growth requires knowing what kind of business you are building, then hiring and delegating according to the stage you are in. Brian distinguishes between a lifestyle business, which typically depends on a small group of highly capable generalists, and a performance business, which requires systems, standard operating procedures, and specialists who can repeatedly execute defined roles.

The episode also connects delegation to capital allocation. Using Warren Buffett and Berkshire Hathaway as an example, Brian argues that investors delegate outcomes every time they allocate capital, whether through a business, a 401(k), a self-directed IRA, a brokerage account, or the S&P 500.

Brian outlines several practical frameworks: hiring early employees like “SEAL Team Six,” choosing missionaries over mercenaries, building a repeatable business playbook, and using Dan Sullivan’s Unique Ability concept to decide what work should stay with the owner. He also explains how to create an activity inventory, identify energy-draining tasks, and delegate responsibilities that do not create the highest enterprise value. The episode is designed for business owners, investors, and leaders who want to scale with more intentional systems, better hiring decisions, and clearer delegation principles.

Key Takeaways

• Decide whether you are building a lifestyle business or a performance business before you hire. Each model requires a different mix of generalists, specialists, systems, and owner involvement.
• Early hires carry outsized importance because each person represents a large percentage of the company. Prioritize culture fit, core values, resourcefulness, and mission alignment before scaling the team.
• Delegation applies to investors as well as business owners. When you allocate capital, you are delegating outcomes to operators, CEOs, fund managers, or businesses that make decisions on your behalf.
• Build a repeatable playbook before trying to scale. Standard operating procedures, clear roles, feedback loops, and consistent execution allow a business to grow without relying on one person’s memory or heroics.
• Use an activity inventory to identify what to delegate first. Keep the work tied to your unique ability and highest enterprise value, then hand off tasks that drain energy or can be done better by someone else.

Key Topics Covered

• Delegation

• Hiring

• Leadership

• Business Systems

• Standard Operating Procedures (SOPs)

• Company Culture

• Predictive Index

• Unique Ability

• Lifestyle Business

• Performance Business

• Scaling a Business

• Entrepreneurship

• Warren Buffett

• Capital Allocation

• Team Building

Episode Chapters

00:00 Intro

Brian opens by challenging entrepreneurs to ask whether they own a real business or simply a demanding job. He frames delegation and hiring as the difference between freedom and becoming trapped by every decision, problem, and operational fire.

00:49 The Two Types of Businesses

This section defines the difference between a lifestyle business and a performance business. Brian explains why lifestyle businesses often depend on a small team of talented generalists, while performance businesses require scalable systems, SOPs, and specialist roles.

04:54 Where Owners Get Stuck

Brian describes the difficult transition between a small lifestyle business and a larger performance business. He calls this stage “the desert,” where the company is too big for everyone to know everything, but not yet mature enough to run on fully developed systems.

06:35 Delegating Your Dollars

Brian connects delegation to investing and capital allocation. Using Warren Buffett and Berkshire Hathaway as the example, he explains that investors delegate outcomes whenever they put capital into a business, fund, retirement account, or market index.

09:23 Your First Hires (Crucial)

This section focuses on early-stage hiring. Brian argues that the first six to twelve hires should be treated like a high-impact special operations team because each person has a major effect on culture, performance, and the future direction of the company.

13:41 Building Your “Playbook”

Brian explains how scaling requires a shift from creative generalists to execution-focused specialists. He emphasizes repeatable processes, standard operating procedures, feedback loops, and a culture of constant improvement so the company can run the play consistently.

17:54 What to Delegate First

Brian introduces his personal delegation framework, beginning with an activity inventory. He explains how owners can list everything they do, identify tasks that drain energy or do not create the highest enterprise value, and compare those tasks against their unique ability.

23:46 How to Delegate

This section breaks down the process of handing off responsibilities effectively. Brian discusses how to assess whether a task should be delegated, how to match work with the right person, and why good delegation requires clarity rather than simply dumping tasks on someone else.

32:18 What Owners Get Wrong

Brian closes by addressing common mistakes leaders make when hiring and delegating. He reinforces the importance of mission alignment, thoughtful systems, and understanding that strong delegation is not abdication—it is a disciplined way to build a business that can scale.

Full Transcript

[Transcript begins]

Do you own a business or do you own a job? Most entrepreneurs, they say they want freedom. But then they go out and they build a business where every single decision runs through them. Every single problem lands on their desk. Every single fire needs to be put out by them. And before long, they don’t own a business. They own a very demanding job.

They stop working 40 hours a week for somebody else only to work 60, 70, 80 hours a week for themselves and not make the same amount of money along the way. And that’s the number one reason why entrepreneurs struggle to scale. They never learned to hire well and delegate things off their plate.

So in today’s episode, I’m going to show you the exact hiring and delegation strategies I’ve used to scale my business to over 75 folks now and how you can implement the same strategy in your business. Let’s jump in.

Hiring and delegation. When you’re building a business, you must always start with the end in mind. And all entrepreneurs should first ask themselves, what kind of business am I building? Are you building a lifestyle business or are you building a performance business?

Let’s go ahead and define what these two things are here. So a lifestyle business has a relatively modest amount of teammates, right? I call it maybe six to 12 really talented individuals. A small team, highly talented generalists that do things exceptionally well, but they wear many hats.

When you’re starting a business, you’re relatively small. You might not have all the resources in the world. So the types of human beings that you need to come in, they have to be exceedingly resourceful. They have to be able to have extremely high cognitive loads. Really talented individuals, more like Renaissance men or Renaissance women. The ability to move quickly from task to task, not get bogged down.

Because when you’re first getting started and you only got a handful of people, let’s say you got three people on the team right now, you’re about to hire your fourth, that person that you bring on board is going to ultimately equate to 25% of your business. And the truth is you can’t mess up that hire. It has to be a great fit. It has to be an exceedingly talented individual that is going to pull the organization forward. A great culture fit, a great core value fit, exceedingly resourceful. That’s what’s necessary, certainly early in the business.

And many folks choose over the very long term to stay in a lifestyle business. There’s nothing wrong with that per se. You can really max out at maybe around a dozen employees and build a really high-quality lifestyle business, carve out a great lifestyle business for yourself.

But when that happens, usually in almost every scenario, you’re still acting as what I like to consider a player coach. You’re still in the business. You’re still in the game. You’re still doing the work. You’re not necessarily able to completely move exclusively to the owner’s box where you can get away from some of the day-to-day slog that many different folks are trying to do when ultimately building a business, actually acting like an owner.

So that’s the definition of a lifestyle business: six to 12 uber-talented individuals along the way.

So what’s a performance business? A performance business is after you really get to reasonable scale. You’ve got at least 50 employees. You got at least 50 people running around doing various things in the organization. And you have built scalable systems and processes. You have standard operating procedures and process and procedure documentation along the way.

And this allows you to move away from the more exceedingly talented generalists that do everything pretty well to specialist roles where they become, I don’t mean to be off-putting with the terminology, but a little bit more of a cog in a wheel, where they’re specialized skills doing one thing exceptionally well. They go exceedingly deep on their talent. I don’t mean to be off-putting in terms of the talent that you’re bringing out and folks are replaceable on the cog in the wheel. That’s not what I mean.

But what I mean is once you build the performance business that has that systems and processes and structure in place, it allows you to be able to scale significantly further. Because if you want to go build an additional bolt-on acquisition in whatever business model you’re doing, you can add another bolt into that wheel and just duplicate that same role.

If we go out and buy a brand new manufactured housing community, we have the SOPs across the board for every single thing that a community manager needs to do along the way, and that allows you to scale tremendously. If we only had but a couple of people and we bought another property, it’s hard to manually recreate all of the talents and time and energy and effort that oftentimes are locked up inside of one key person, their brain, and bring it over to that new business, that new venture, that new bolt-on acquisition.

And so that’s the difference between a lifestyle business and a performance business. You have to really understand where you’re at in the journey. It’s not only important to understand and make a decision in advance when you’re launching the business of ultimately your objective, where you want to go, then when you’re thinking about hiring you have to understand where you’re at in the journey of the growth of your business.

Are you early on, more in that lifestyle section? Are you already at the performance section? Or are you kind of in that messy middle? We like to call this the desert, where you’re moving from a dozen employees up to 50. And that is a really, really tough time during a business because you’re scaling and you’re transitioning away from these extremely qualified generalists up to those more specialist roles.

And the reason it’s so difficult is that when you only have 12 people inside of the team, you can get everybody inside of one room at one time, sit around a boardroom table, and everybody knows what’s going on in everybody’s lives. They understand what all associates are doing at all times. The lines of communication are significantly smaller.

But the minute you get to 15, 20, 25, 30 employees, you are too large to understand what’s going on inside of every individual role in the organization, what they’re doing every single day, but you’re also too small to have full-throttle scalable SOPs across the entirety of the organization. It’s a really difficult time. And so when you’re going through that, we like to call it the desert. You want to try to get across the desert as fast as humanly possible.

I think it’s important for you to determine what you’re seeking to achieve. Do you want to build a lifestyle business or performance business? You don’t really want to get stuck in the messy middle here. And then when you’re going through it, understand where you’re at in that journey so that you’re bringing on the type of human beings that are appropriate at that respective stage of the growth of your business.

Thus far, we’ve gotten pretty granular and folks might be thinking, hey man, this is interesting information, but I’m not a business owner per se. I’m just an investor. Let me try to share a little bit of color in terms of how this is still practical and impactful for you as just an investor. I’ll quote unquote “just an investor.”

I’ll use an example of Warren Buffett. What does he do? He is the chairman over at Berkshire Hathaway. And if you looked at that massive international conglomerate, Berkshire Hathaway has 400,000 employees globally, roughly. That’s a huge number of human beings. But when you look at Berkshire Hathaway and their corporate office in Omaha, how many people do they have? A mere 25.

How is it that Warren Buffett can manage hundreds of thousands of employees and ultimately allocate capital as an investor exceptionally well, better than anybody else in our entire generation, and only have 25 individuals inside of his corporate office? Because he understands how to delegate. He understands how to appropriately delegate.

If you do not believe that you’re actually delegating when you are investing capital, I think that that’s a myopic perspective. Even if you are simply allocating capital in a 401k or a self-directed IRA or a brokerage account, all you’re doing is buying the S&P 500, you are still, as a capital allocator, in the same exact vein as Warren Buffett. You’re allocating capital. And in this example, you’re delegating the results of your investment to the 500 different CEOs that are inside of the S&P 500.

You’re making a decision, whether it is conscious or unconscious. You’re delegating the investment results to those CEOs and those 500 organizations if you’re investing in the S&P 500. So it’s important for you to understand the delegation framework, how to not only survive in this but thrive in it, do it effectively for the betterment of you and your family’s progress.

Because I don’t think that anybody’s done it better than Warren Buffett. When he goes and buys a brand new business, he uses sports analogies all the time, specifically baseball. At one point he wrote in one of the annual letters, when I bring on Mark McGwire, I’m not going to go teach him how to swing the bat. He knows that better than me. If we’re going to bring on Tom Brady onto our team, I’m not going to teach that guy how to throw the football. But your role as the owner is to ultimately ensure that you put that individual in place to thrive and do that job exceptionally well so they’re thriving in their individual unique ability along the way.

So that philosophy and the logic remains true. Folks are delegating the results of their investments whether they’re doing it cognitively or not. That’s really truly dependent upon each individual out there. But most assuredly, it is relevant to understand delegation when you’re allocating capital out there in the marketplace. There’s a huge, huge correlation there.

Let’s talk about hiring early on in the business. When you’re hiring at the early stage, I view this from the framework of when you’re bringing on brand new employees, the first six, 10, 12 people, you got to view it like SEAL Team Six. When you’re starting a business, you should treat your first hires like SEAL Team Six.

And here’s what I mean by that. Every single hire has extremely high impact in the organization. When you have a really small team, there is zero room for mediocrity. Every single one of them has to be an exceptional culture fit, a great core value fit, exceptionally talented, more like a Renaissance man or Renaissance woman.

So early on in the growth of the business, what I look for when I’m bringing on those associates are exceptional core value fits and culture fits. And again, how do you even know that they’re good core value or culture fits? You actually have to decide upon that before you can scale.

If you want to grow a real legitimate business and ultimately thrive and scale in a significant manner, you would be much better served to have missionaries in the business as opposed to mercenaries. When you’re hiring, I would much prefer to hire missionaries as opposed to mercenaries.

And what I mean by that is a missionary is somebody who’s driven organically, natively, and intrinsically driven by the mission of the business. They adhere and abide by the core values and the mission that you’re trying to achieve, a big, hairy, audacious goal. You’re making a big, significant impact, and it fills them up. Not only do they receive income deriving from the work that they do, but they also get an emotional paycheck. And that is the style of connection that you want to ultimately build throughout the entirety of the growth of the organization, but absolutely at the very beginning.

And you don’t just want exclusively mercenaries. Mercenaries are defined as individuals who only care about the almighty dollar, individuals who are only there for a paycheck, that could care less about you, your customers, etc., only there to make a couple of bucks. That can be prudent for specialized knowledge in very short periods of time, oftentimes outsourced consultants and the like, but it is not for people that are going to be around over the very long term.

You would much prefer and be much better served to have missionaries: people who understand what we’re seeking to achieve on behalf of all of the stakeholders, believe deeply in the profound mission that you’re ultimately trying to craft, and get an emotional paycheck from the work that they do on a daily basis.

Our president on the operation side of the house, Todd, has mentioned on numerous occasions, if you’ve got guys and gals inside of the organization that it’s the Sunday night test, and on Sunday evening they’re petrified to go to bed because they know on Monday morning they got to wake up and go, “I got to go to work again. Another case of the Mondays,” that is not the type of individual that you want to have in the organization.

You want the guy that goes to bed Sunday night thinking, “All right, rock on. We get to get up in the morning and actually go make a difference.” That’s what you want to have and foster that, nurture it. And so you have to set the vision and the culture prior to bringing on these individuals.

And you as the leader, as the founder, as the visionary, it is incumbent upon you to ultimately set the table stakes, put that post out in place, share the horizon. We’ll never make it to the horizon, but you’re pointing and casting towards that big, hairy, audacious goal. And so you must do that and then paint the picture of the horizon for any new associate coming on board.

And if it resonates with them emotionally, you have to not only check the box academically, background, experience, all the things, but you need to ultimately ensure that it resonates with them emotionally as well. You’ve got to ensure that during that interview process they’re getting an emotional paycheck along the way because it will be hard. Any new venture that you start will be extremely difficult, and you need to have somebody that’s going to be willing to get in the trenches with you and overcome that inevitable adversity that is extremely difficult.

It never goes away, but in the early journey, it is wrought with difficult landmines in every step of the way. So you’ve got to make sure that you’ve got people that are going to be willing to go through the trenches just like SEAL Team Six with you in those early, early, early days.

As you progress and the business starts to scale, let’s say you’re working through the messy middle, it’s very, very difficult. You need to begin transitioning over towards specialists, more towards that performance business. You’re crafting the business, you’re crafting the SOPs, the standardized operating procedures, etc. And in doing so, it allows you and affords you the luxury of going in and beginning to bring on board specialists.

So as you scale the company beyond that first dozen associates, you should shift the hiring base to focus less on generalists and more on specialists. The analogy that I would use is the following. In Sunrise, we’ve been very fortunate to get to the point and size and scale where we have this pretty well locked down. We’ve run the same exact business model now for about 15 years. When we buy a brand new property, we didn’t want to go do any additional verticals, any additional new platforms, i.e., parking, until we had actually knocked out mobile home parks.

We bought a brand new mobile home park. It did not adversely affect anything in the flywheel. It is humming along. So we buy a new deal, we plug it into the machine, it doesn’t adversely affect the machine at all. The only way you could do that is by having really high-quality standard operating procedures and a playbook that you run.

How do you do that? I use the term playbook intentionally. It reminds me of Remember the Titans with Denzel Washington, if you guys are familiar with this, where he basically had seven plays that they ran. And every day that they showed up, it was run the play. Run the play. We’ve already figured this out. We know how to sell a mobile home. We’ve done it a thousand times. Run the play. Do this. It’s a standardized operating procedure. Do it with a smile on your face.

And you’re bringing on the individuals that are going to thrive in that individual role, but you’re simply requesting folks to run the play. Run the play. Run it again over and over. Perfect it until you get exceptionally good at that. We already know what works. Now you need people who are going to be willing to execute that repeatedly, optimize one function deeply, continue to drive efficiency, and report if and when any changes need to be made.

Because you’re going to delegate and elevate out of that role. So you need somebody who’s natively curious and willing to continually implement what I call the version of Kaizen, where you’re constantly focused on never-ending improvement because you’re no longer going to be in that seat doing that individual role.

So you need to establish and nurture a culture that provides you with a feedback loop that will continuously strengthen the system. Meaning, when they’re doing that role on a day-to-day basis, things eventually change. New technology occurs. New software, new hardware, all the media things that happen. They need to understand that it is incumbent upon them now to provide you as a manager with feedback when something can be iterated and improved and optimized.

But over the very long term, in the very near term, it’s like when you’re hiring the football team. You’re hiring all the players for the football team and each of them are running the individual portions of that play. Just run the play. Run it over and over and over again, and eventually you become unstoppable.

It reminds me of the triple option. If you run that thing exceptionally well, it’s very difficult to stop. Trust me, because I’m very fortunate. I played a lot of different sports growing up. I ended up going to Mount Carmel High School in Chicago, more state championships in football than any other high school in the state. It’s just unbelievable. Numerous exceptional athletes, tons of different professional sportsmen, congressmen, and the like. Going to that school ultimately changed my life. And they ran the triple option for decades and decades and decades to great effect. It was unstoppable, but they had just a couple of plays. You run it over and over and over and over again.

So early-stage lifestyle takeaway is that you want creative folks, folks that are extremely talented, extremely high cognitive load, that are extremely resourceful. Later stage, you want execution excellence, people that are willing to grind on one thing and do it exceptionally well over and over and over, refining that one individual thing. A subtle difference and takeaway, the types of personalities that you’re going to need to bring on board.

Let’s talk a little bit about how to actually delegate. We’ve covered the hiring part of the episode, but I want to share the exact framework that I use to actually delegate along the way. Because when you’re just getting started, you do everything. You wear every single hat in the business. It’s absolute, utter chaos, as you well know.

So how do you delegate? I literally always have a list on my desk. It’s a piece of paper. It’s just a notepad. It’s got 30, 40 lines on it. I am constantly listing out all of the activities that I do. It’s an activity inventory. What are all the things that I actually do?

And when you find yourself doing one of these activities, especially if it’s an activity you don’t like, write it down. I’m paying the bills. I’m running the meetings. I’m creating the marketing. I just got off of a sales call. I’ve got to collect all of the respective cash or capital from XYZ that I got to do. I’m running operations. I’m doing administrative work.

You literally list every single tactical item that you’re doing, the things that you’re accountable for. And you end up breaking it into categories.

Dan Sullivan has this great framework. He talks about this unique ability, something that you’re uniquely gifted at. A unique ability is the intersection of what you are naturally excellent at, something that you love doing, something that gives you tons of energy, and it’s something that you could just keep improving forever.

That’s your unique ability. It’s got a handful of qualities, right? Something that you have superior skill in. You’re naturally gifted in something. You produce unusually strong results and others rely on you for this one thing, whatever it is. You’re extremely passionate about it. It fills you up. You enjoy doing it. You genuinely like it even before you get paid doing it. It just fills you up.

It also gives you energy rather than drains you. And it’s something that you can find yourself doing over and over and over again. It’s like Play-Doh. You’re playing with it and focusing on never-ending improvement. You’re always looking for different tweaks and refining it for decades without getting bored. If you can find that style of work, then that is what you would consider to be your unique ability.

It’s not just simply something that you’re good at. You might be good at underwriting. You might be good at running team meetings. You might be good at email or good at hiring or solving fires, but those things are activities that often drain you, or if they don’t create your highest enterprise value that you bring to the organization, they are not your unique ability and you should be looking to try to find ways to delegate them off of your plate in time.

So for me, over many, many moons, just by way of example, I like to think of my unique ability as distilling complex investment or business or leadership ideas into very clear frameworks that my team gets aligned around, that aligns the team and that ultimately compounds the enterprise value that we have in the organization.

And if I’m doing any other tasks than thinking high level about how we can ultimately organize all these complicated ideas, business strategy ranging from competitive advantage or Blue Ocean Strategy or the 7 Powers and finding out how we can implement those frameworks to benefit our business strategy, or how we can ultimately take all the leadership learnings that we’ve had over time and integrate them into the culture of the business, if I’m not doing those things, I’m not adding the most enterprise value for the organization.

And the thing that’s amazing to me is, I’ll give you an example of something. I remember back in the day I used to open every single piece of letter or every single piece of mail that ever came into our organization. Every single piece of mail. Junk mail, actual bills, actual checks that came in—I like those—but the rest of this stuff, absolutely insane. It would drive you crazy. I can’t even look at another piece of mail. My wife knows it absolutely drives me bonkers.

But the amazing thing is that there is somebody out there who absolutely loves to do the things that you dread doing. That is the beautiful aspect of human nature and the differences between personality types, and skill sets, and unique abilities. There is somebody out there that loves it. So your job as the owner or leader is to identify the things that should no longer be on your plate, create clarity around the role, and delegate those responsibilities to somebody whose skill set and energy match the work.

There needs to be an emotional pull to ensure that it gets done for the betterment of the organization and all the stakeholders involved: the customers, the residents, whatever the case may be. It’s why it’s so important, again, back to the culture, to have an extremely high-quality culture and get emotional buy-in on the project that you’re delegating along the way for the betterment of everybody involved.

And if you do this over a long enough period of time, it makes your life so much better. So much better.

Let’s spend a couple of minutes just digging into some of the tactical tools that we use and have used along the way to great effect for the betterment of all. We actually use a tool called Predictive Index. Not sponsored. They’re not paying me to say any of that stuff, but it’s been a great tool for us as we progress.

It’s a behavioral tool. You guys have seen a lot of these things before, but we choose Predictive Index. It gives us two different individual tests that we run everybody through prior to coming into the organization. One is a behavioral index and two is a cognitive index.

The behavioral index is very important because ultimately, when you’re bringing somebody on board, you want them to be naturally wired in such a way that they would thrive by doing the work that you’re looking to delegate. I’m going to use two extremes to exemplify the point.

One is an accountant or a bookkeeper inside of a spreadsheet, dotting i’s, crossing t’s, analytical, got to be extremely precise. One side of the spectrum. The other side of the spectrum is a salesperson: extremely persuasive, great personality, extroverted. Completely opposite of the introverted analytical bookkeeper, right? Completely different perspective.

And so when you’re running the behavioral index, there’s no right or wrong. There’s no win or loss there. It’s just giving you the results of who they are, how they’re naturally wired. Are they more introverted? Are they more extroverted? Are they more precise, or are they more comfortable playing in the vagaries?

And so it’s important to understand that because when you’re hiring somebody during the interview process, they might be more than willing and might actually believe themselves to be able to and willing to perform XYZ role for you.

Let’s say, by way of example, that they’re like, “I’ll do anything. I just want to join the team. I’m so excited about this role. I’m happy to go do the bookkeeping.” But they’re actually more of a salesperson: persuasive, outgoing, extroverted. But you’ve got them in a box sitting behind a spreadsheet all day, 24/7/365.

They might absolutely put their hand on the Bible and say, “Yes, I’m extremely excited. Can’t wait to go do this.” And they’re telling you the truth. But you know how they’re naturally wired. And if they’re wired differently, then putting a square peg into a round hole will inevitably lead to burnout. Not good for you, not good for them. Massive turnover costs, just training. It’s just so much churn. It’s absolutely brutal for the entirety of the organization.

So you have to try to, especially in the specialized roles, find the individuals that are going to thrive inside of the individual specialized roles native to who they are as human beings. Very, very important.

The second test is the cognitive index. And so the cognitive index, it is not necessarily an IQ test. It doesn’t measure the intelligence quotient of the individual taking the test. Rather, it measures the elasticity. It measures how quickly you’re able to process information, the cognitive load you’re able to process.

Why do we find this so important and so valuable? Let me give you an example to exemplify the point. Let’s say you and I are both going to go take a test. The same exact test. There are 100 questions on it. We’ve got an hour to go knock out the test. Let’s say we go in and we both end up scoring 90. Both of us get the exact same score, 90 along the way. We’re both pretty smart. Congratulations. We’ve done a great job.

But you finished the test in 30 minutes and I finished the test in 60 minutes. Which one of us is smarter? Well, we both got the same exact score, but one of us was able to process the information at 2x the speed. Much, much quicker.

Why is this important? It is unbelievably important, specifically early on in the growth of an organization, because you want individuals that are exceedingly dynamic. Especially in small businesses, you have to have folks that are very resourceful, quick, and willing and able to think on their feet.

So what is the cognitive load that they can process? What is their RAM? How quickly can they process information to get to the same exact end goal? Very, very important, especially when you’re in that early phase of the journey of ultimately hiring the SEAL Team Six associates.

I would convey that when I’m in that portion of the growth of a business, I want individuals with an exceedingly high cognitive load, that are extremely sharp, extremely capable, can bounce around from task to task, department to department, because they will need to. Because they’re going to be wearing five or six different hats, and they’ve got to be able to bounce around very quickly and be sharp and on the ball there.

We’ve found a lot of success using these two tests over time. The truth is different roles that you end up hiring for are definitely going to have different behavioral needs, and they’re also going to have different cognitive loads that are likely necessary for that respective role over time. You might not need the most massive cognitive scores for individuals doing more mundane tasks, whatever that might be.

But it’s important for you to understand who that human being is, how they’re naturally wired, and then you could ultimately put them in a place so that they can be successful, so it fills them up, and they thoroughly enjoy the ride along the way.

So when does this go wrong? Here are some of the biggest reasons why entrepreneurs fail when they’re delegating.

I would say that oftentimes it’s because they don’t actually provide clarity. They have no systems, no processes, no clarity along the way. And even if they don’t have that SOP fully in place at the very beginning, they at least have to provide the clarity to those SEAL Team Six associates of what are the non-negotiables, what are the things that actually must be accomplished.

The clarity, the vision, even if they don’t have the full-throttle SOPs lined out, the value engine mapping, and all the explicit KPIs that are necessary, you still have to provide clarity outside of what you want that guy to do and what you want them to do.

If they don’t have that, they’re going to ultimately fail at some point, because if you don’t provide them with clarity, they’re just going to make it up. They’re going to try their best to solve the problem. And if you haven’t given them that end game, that end state of what you’re seeking, then ultimately you will end up frustrated and they will not even know why you’re mad because you didn’t provide them with that level of clarity in advance.

So sometimes folks fail because they don’t have systems. Sometimes folks fail because they don’t have clarity. They didn’t give the outcome and the expectations. Sometimes folks fail because they hired the wrong people. Oftentimes, it’s the square peg in the round hole, wrong behavioral wiring for a particular role, even if they’re willing to do it for the near term.

Let’s say somebody says they want to be a salesperson. They’re willing to do outbound cold calls, and they do it for 100, 200 cold calls a day. Eventually, they will quit if they’re more of an accountant behaviorally, if they’re more introverted.

The correct approach when delegating is to ultimately document the process. The sooner you can ultimately get to having a simple, repeatable process and actual playbook, the better it will be for everybody involved. Document the value engine map. Document the system and SOP, the process along the way. Get that knocked out. Very simple playbooks. Set clear expectations along the way and make sure that you’re bringing on the right people for the right roles.

I’d further convey that I’ve got no problem with individuals coming back to me and telling me that I’m an idiot and we have done something inside of the organization that is not optimal. Perfect. How could I possibly know that there was a better way if you didn’t ultimately tell me?

So I’m more than happy to hear you out. Is that always going to be the case where we implement it? No. But I am yearning for the feedback. I’m yearning for the feedback from every associate in the entirety of the organization. How could I possibly know to improve a task, a role, an SOP, if we don’t get the feedback from you?

We have that run-the-play philosophy once we’ve ironed it out. Run the play over and over and over again.

So where does this go wrong? Here are some of the biggest reasons why entrepreneurs ultimately fail when delegating, in my humble opinion. They don’t have systems. They don’t have value engines mapped. They don’t have standard operating procedures. That’s one reason.

Also, they don’t provide clarity. They didn’t give explicit clarity. They didn’t set the table stakes. They don’t provide an emotional connection to why the work matters. They didn’t provide that explicit clarity of what is a non-negotiable that must be done during this project as you’re handing it off that needs to be done.

No systems, no clarity, or they’re just the wrong people, where you’ve tried to hire people, you put a square peg into a round hole, and you thought it was a great fit. Either you come to realize it’s not a good core value fit, or even if it’s a great culture fit, you realize, “Golly, this individual told me they were going to be willing to jump on and have 100 calls a day, but now you realize that they are more wired to be an introverted accountant on the back end.”

Wrong people. And it might not be the wrong people. It just might be the wrong seat. But you have to kind of understand that in advance, and you do so by understanding how that human being is wired before they ever get inside of your organization.

From my perspective, how can you get out in front of that? You document everything, right? As soon as you possibly can, you get to standard operating procedures. You get simple playbooks in place. You set clear expectations along the way. And then again, you run some of that behavioral test. You run the cognitive test to understand how they’re wired, to ensure that when they come in, they can actually hit the ground running.

And then you can just run the play over and over and over and over again. We know what works. Been there, done that, got the T-shirt. Run the play. Run the play. Run the play. And if you see something out there on the field that I can’t see from the owner’s box, please tell me. That’s okay too. Completely fine.

There’s a great example provided by Gregg Popovich and the Little General, if you’re familiar with him, Avery Johnson. Avery Johnson—I had the pleasure of watching him speak at a YPO event over the course of the last year, and he has many, many amazing stories about him. He’s about five foot ten, played in the NBA for many years, ultimately became a coach in the NBA, was a great coach also in college.

So how did Avery Johnson, a mere five foot ten, end up bossing around David Robinson, otherwise known as the Admiral? He was in the Navy. Literally seven foot tall, an absolute monster of a man. Chiseled, seven foot tall, ridiculous, 280 pounds of raw muscle. And he got Avery Johnson, the Little General, five foot ten, bossing around the Admiral as well as Hall of Fame coach Pop.

How does he do that? Because he sees things out on the court that other folks don’t see. He sees things on the field that you cannot see from the sideline, that you cannot see from the owner’s box.

Gregg Popovich, internationally renowned Hall of Fame coach, one of the best of all time in the NBA, at one point was telling the players that when they were setting screens, we needed to go under the screens. Needed to go under the screens. Needed to go under the screens.

And the Little General piped up to the boss man and told Pop, screamed at him in the middle of the timeout, “You don’t see what we’re seeing out there,” after telling him, “No, we got to go over. We got to go over. We got to go over.”

And the truth is Avery Johnson was right. Because sometimes when the players are on the field, they see things that you cannot see from the sideline or from the owner’s box.

So while you have the best plays in the history of mankind, at the end of the day you have to trust the people that are on the field playing the game. And if they continue to tell you over and over that there is a better way to do something, you’d be well served to learn from them and actually iterate and improve the processes and procedures that you’ve had along the way.

And that ties into the leadership side of the house. It’s not complete autonomy, and it’s not an autocratic environment where you’re a Führer pushing down the individuals to tell them exactly what needs to be done the way that you demand it must be done. Rather, it is you stewarding the organization in such a way that you’re providing them with a playbook, a simple playbook, a repeatable playbook that you know works.

But when they tell you that there is a better way, you’d be well served to listen.

If you want to build a bigger business, you’re signing up for bigger problems. Got more people, more moving pieces, more complexity. And that is not necessarily a bad thing. That is the game. That is the game.

The entrepreneurs that win, they’re not the ones who avoid problems. They’re the ones who build teams that can solve the problems better than they could ever do on their own. Because at a certain point, your business is only going to grow to the extent that you’re willing to let go.

That’s how you get freedom. You got to let go of control. Let go of doing everything yourself. Let go of being the bottleneck and step into the role of a true owner, where your job is no longer getting out there and actually doing the work, but rather building the machine that does the work.

If you take anything away from this episode, it should be this: hire like it matters, because it does. Delegate with clarity, because confusion kills momentum. And build systems that allow great people to execute without you, because that is how you scale. That is how you create real freedom. That’s how you build something that lasts.

And for me, why is it so important to delegate? Because I’m not chasing Ferraris. I’m chasing freedom.

Until next time, be great.

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