Herding Wild Cats: How to Manage Self-Starters

Herding Wild Cats: How to Manage Self-Starters

Hiring entrepreneurs sounds like a great idea.  Sometimes... until they start working for you.

Or rather, until you realise they'll only begrudgingly work for you — if at all.

I know. I've been this person.

I told Lyft I'm not a great employee. It was one of the main reasons I left. I'll work like a dog to help people, but any company that's big enough for formal performance and compensation reviews is one that's too big for me.

I even told this to other companies as they tried to hire me. "We don't want employees," they said. "We want entrepreneurs."

Why? Let's explore.

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The allure of hiring entrepreneurs (and how it can go wrong)

Hiring people who have entrepreneurial spirit has a lot of attractions.

In sales and business development, entrepreneurs are naturals and can make you tons of cash. They have hustle, grit and a competitive streak that will help you out. They'll think of creative ways to land big customers, the tenacity to withstand many rejections for a few successes, and they'll work hard to be the best salespeople in your company (provided you pay them well enough for their efforts to not go somewhere else).

In operations, they have a lot of what it takes to make your business work like a machine, without being micromanaged. Entrepreneurs teach themselves things they don't know about management and analytics. They'll excitedly share information and new techniques around a company, hoping others will share with them as well. And they'll be logical, thinking of the company's money and time as their own and using those resources the same way.

These are great things. But how can it go wrong?

There are three main ways to kill an entrepreneur: suffocate them in process, incentivise them poorly, and try to control them.

(By the way, if you actually do need your workers to do these things... it might mean that you don't need entrepreneurs.)

Suffocating entrepreneurs in process: this means asking them too many regular, procedural things that don't require creativity.

You might need daily reports done, or emails sent out at certain times, or for some spreadsheet to be filled out in a certain way every day. These tasks might take hours. They're critical for the business and "someone has to do them".

That's fine, but the entrepreneur is poorly suited for this. They are impatient, and often lack attention to detail (speaking for myself; I try constantly, but I see other superstars that are much better at detail naturally no matter how hard I try).

The entrepreneur is good at a job like that if you give them certain parameters to improve it and get them to make themselves redundant: "I want you to do this, but I really want you to figure out how to do it better. Find products out there, hire offshore people, whatever." If they don't have that latitude or the resources to achieve this, they'll be unhappy.

Incentivising entrepreneurs poorly: this can happen two main ways.

Firstly, you might not be giving them enough bonuses or equity as part of their compensation, tied to actual goals.

The challenge is that it's hard to set quantifiable goals for every job. But again, if you can't, then maybe you shouldn't hire entrepreneurs.

Set sales targets, operational targets (like efficiency) or something else. Give the person the resources to get there. And watch them go. You can be lenient in them, like prescribe a range. But they have to be clearly measurable.

The second way it can go wrong is comparative compensation might be bad.

If an entrepreneur knows they're working like a dog to make the company millions, but some other jamoke is making more money and doing less, they'll hate the situation. Even if you can't control it, it'll cause a downward spiral that will have them quitting in rage eventually. And their next pay-check will be 50-100% higher than the one they got previously. (This has happened to me. Most recently, I quadrupled my pay-check leaving Lyft.)

Trying to control entrepreneurs: This is a death knell to any managerial relationship with any entrepreneurial self-starter.

Try to tell an entrepreneur directly what to do (without asking them for their opinion) and you'll just watch them squirm as they try to get out of it, or explain why that's a bad idea.

A few things I've seen this kind of employee struggle with

  • Monthly performance reports (me, and many others)
  • Making presentations (when they're asked to, anyway... surprisingly they might do it when they have no obligation to at all)
  • Filing expenses in a certain way (never! I'll just give you an abominable amount on my last day)
  • Implementing something that someone else came up with (watch as they try to re-invent it themselves)

Oh man, I was a bad employee. I feel bad. All of the above are things I've done (I'm sorry!)

The false fear that entrepreneurs just want to "start their own thing"

Most recruiters/managers have one main fear: that an entrepreneurial type might just leave and start their own business. This often becomes a common interview question: "I just feel like you want to go start your own thing."

This fear is based in reality, but it's just the symptom of not managing entrepreneurial types well. They don't leave to do this because they always were going to do so; circumstances lead them to it.

Entrepreneurs join companies for a few reasons. Business ideas and opportunities ebb and flow, and we all have lull periods. Some of us want to be entrepreneurs some of the time, and have colleagues and stability in other periods, maybe in periods of relative instability in other aspects of our lives.

And being an entrepreneur is hard work, as any will tell you. You have a constant struggle to balance your time and priorities. You get lonely. You have self-doubt that can be crippling, the more vulnerable positions you put yourself in.

It's a little like people in the gym. There are, loosely speaking, three kinds of people who go to gyms: 1. the competitors, 2. the athletes and 3. the everyday fitness buffs.

Firstly, there are competitors.  train for hours a day, grinding, never letting up, working for years until they succeed or their bodies give way. They hone their diets. They try different regimes and philosophies aiming not just to be in the top 1%, but the top 0.001% that means they'll get podiums in competitions. These are like big-name founders who stop at nothing: Jack Ma, Steve Jobs, Bill Gates or many others like them, like John D. Rockefeller, Larry Ellison, Henry Ford and so on. Good luck trying to employ them!

At the other end there are the everyday fitness buffs. They are involved and hard working, and they manifest this by showing up to classes regularly and spending time on treadmills and rowers. These guys are are the regular workers, like the employees in your accounting firm (not the owners, who might be as entrepreneurial as anyone else). You need them, and you might want to employ them, but there's nothing particularly challenging in doing so: just treat them well with money, rewards and environment.

Those in the middle in the gym are the athletes. They'll come to a gym, having read a book or series of websites on weightlifting theory and getting absorbed in YouTube videos on how to do the perfect deadlift, and think "I'm gonna hit a 500lb lift" or "I'm going to get to 15% body fat" and work away until they get there. They experiment, revise their plans and keep working. Then they get there, and move on to their next goal: climbing a cliff wall, running an ultramarathon or whatever. They might have a coach for a while, but doesn't need them forever. They learn what they can and then mostly take care of themselves.

As you may have guessed, your athletes are the entrepreneurs you're trying to hire.

The athlete is different to the competitor, because the athlete's goals are more varied, and less extreme. The athlete might seek a personal challenge to hit a 5 minute mile (one of my own goals as part of "Discover Discomfort"), but not to qualify for the Olympics. And that goal goes alongside many other goals, like learning Swahili or to rebuild an adventure motorcycle.

Similarly, the entrepreneur is different to the stop-at-nothing founders. The entrepreneur will have goals, but won't pursue each one at the exclusion of everything else in their lives. They enjoy process and people. They also know when to quit, or to re-adjust their goals. They don't seek the podium; just to be excellent. (They might hit the podium, but that wasn't the goal.)

Goals for entrepreneurs are things like:

  • Hitting an $X MRR target, with continuous growth of 5%
  • Launching X independent businesses
  • Employing and providing for X people
  • Providing for their family, achieving financial "independence"

They might achieve this and think... now what? And the answer isn't necessarily to do it again.

Or they may fail at the above (which happens most of the time), and decide... damn it, I need a break.

Entrepreneurship can be exhausting. It hurts your friendships and always puts stress on your personal relationships. So taking a job might be something welcome, as long as it's not suffocating.

What entrepreneurs actually want (and how to give it to them)

Entrepreneurs don't actually want to start their own businesses. They might think they do and say they do, but their drive They do so because it's the only way to get the things they want.

With regards to any particular work project, entrepreneurs want:

  • Autonomy. Within an assignment, an entrepreneur wants to work without guidance (or micromanagement), getting results without being told how.
  • Constant change. The assignment can't be forever, or indefinite. An entrepreneur likes new projects, crises and difficult problems.
  • Freedom. Besides the assignment, an entrepreneur always has ideas about other things in the company, and wants to be able to do them unhindered.

How do you you give these things to the budding entrepreneur? It's not that hard. But it takes self-discipline, if you're the kind of manager who can't do this easily.

Again, if this is challenging, perhaps this person is best suited to another job (or company). Not every role demands someone with these characteristics. (I know. It makes for an unhappy partnership.)

Autonomy: Give them broad goals, and complete autonomy to do something the way they want.

Great things to say to an entrepreneurial self-starter are things like:

  • "Get to 10,000 rides a day by the end of the month. You can do whatever you like within your budget to get there. I'm fine with you continuing your other projects, but make sure you're aiming to exceed this or we might not get there. Is there some reason you think we can't?"
  • "A lot of customers are complaining that at rush hour, the rides are far away and they're too expensive. Can you fix the problem and make the complaints go to zero?"
  • "I've gotten a lot of emails about the account owners fighting over who gets to manage what merchants on the platform. I don't have time to deal with it; can you figure out the problem and make sure I never hear about it?"

These goals basically say "This is really annoying me, and I want you to make it go away." The entrepreneur

Bad things to say to an entrepreneurial self-starter are things like

  • "I need you to fix this problem, but please send me a detailed proposal, and then schedule some time with me to go over it so I can review it with you and discuss what you'll do daily." This shows you don't necessarily trust the way the person is going to work. Note: it might not be your fault — I've been in situations where this is structural (people higher up create a micro-managing culture).
  • "Can you please create a process to get rid of account duplicates? Just take this process we used in another division and copy it, I think that worked so you can do it that way." This approach doesn't give the entrepreneurial type any creativity or latitude to do it their own way.

Change: Give a project parameters for ending. This can be time, but better yet, it should be tied to performance or getting to an objective.

Hell for an entrepreneurial self-starter is a never-ending project with no finite parameter. No matter how much money they're making (within reason), they'll feel trapped, and try to fill it with other things — other projects or even side hustles — to the point where it will drive most managers crazy.

Good objectives and parameters for a project for an entrepreneurial self-starter:

  • "I want to see us get 1,000 vehicles on the road at 8am. I think you can get there by the end of the month, but let me know if it'll take less or more time." This sets the primary parameter and an indication of roughly when it should happen, without arbitrary pressure attached to a date.
  • "We need you to do this for no more than a month. Make sure you spend the first two weeks improving things, and then the last two weeks handing over knowledge." The time-binding of the project gives entrepreneurial types both an ambitious timeline and boundaries (and a sense of freedom).

Freedom: Allow the entrepreneur to do whatever the hell they want. Provided, of course, they're doing their job!

Self-starters always look for more projects.

They might think fo a way of cutting costs. Of improving marketing spend. Whatever it is, it's unlikely it's tied to their job, and definitely a distraction.

The wrong thing to do is say "don't do this. I need you to do your thing."

The right thing to do is: "Absolutely, I see the value in that. But I need you to focus on your thing. Ideally, systematise your thing so you can hand it off and have more time for that project you want to do."

This is two challenges in one!

For example, I had a project to help recruiting with something in one job at Lyft. It had nothing to do with my main role, which was in operations. My manager said I could do it, with the obvious proviso that my main attention be on hitting certain numbers.

In the end, hitting those numbers took up so much of my time that I realised myself that I had over-committed and couldn't help recruiting like I wanted (news that they didn't take lightly).

Entrepreneurs do have a sense of value, and understand that language, but they don't want to be bottled down. Give them that freedom, and they'll thrive. More often that not, they won't actually pursue the side project; they'll be happy just knowing they could have.

Final words

Before you decide you want to hire an entrepreneur, spend a while thinking: do you really want to herd wild cats?

Hiring self-starting entrepreneurs is great in the early stages of a growing company. But you have to think really carefully if they're a good fit for the later stages. If you put someone like me into the middle of HP or GE I'd probably suffocate under bureaucracy, where many other more patient types would thrive.

Find the right fit, and the right person, and follow the guidelines above and things will go well.