The trap of hiring early employees to be future leaders

Tell me if this sounds familiar: You start your own business, and at first, you (and possibly a co-founder) are doing everything yourself. You build the product, find customers, provide support, etc.

Eventually you’re making enough money to hire someone. But you don’t just want to hire any random employee, you want to hire someone who can own their entire area of the business so you can focus on other things. You’re the CEO, and it’s your job to delegate, right?

So you scour your network looking for the right person. You’re in luck! It just so happens that you used to work with someone who is the best of the best in that field. You liked working with them, they liked working with you, it seems like the perfect fit, so you hire them. That’s when you run into one of two problems:


  1. Despite their pedigree, they’re just not that productive. They talk a big game, but work isn’t getting done as quickly as you expected. As a matter of fact, it kind of seems like more was getting done when you were the one doing it.
  2. They get tons of work done, but for some reason, you’re still spending a bunch of your time working with them. The whole point was to delegate, but you just can’t seem to hand off ownership to them.

This happened to me and I’ve seen it happen to so many other founders. It’s an easy trap to fall into, but it’s one that can be easily avoided once you learn this lesson: Being a good individual contributor and being able to own an area of the business are two different skill sets.

The two skill sets

Think about the most talented, successful people you know. They probably mostly fall into two categories:

  • Practitioners: People who are masters of their craft. If you give them a project in their wheelhouse, they can get it done.
  • Leaders: People who are excellent at helping other people succeed. They can hire, manage, communicate, and organize.

These are two completely different skill sets. This is one of the reason why so many people hate their managers (the managers were good practitioners who got promoted into a job they’re not actually good at).

Not many people have both of these skill sets. Even if they do, leaders don’t normally have time to keep their skills as a practitioner sharp (I’m experiencing this right now as I become a worse programmer since I’ve delegated that work to others). It's best to assume you can only hire for one or the other.

Are you hiring to move faster, or to take work off your plate?

This is the question you should be asking yourself when you hire. Are you hiring the person because you want to be able to focus on other things, or are you hiring because you want the company to move faster? If it’s the former, hire a leader. If it’s the latter, hire a practitioner.

The reality is, in the early days, you almost have to hire practitioners. Unless you raised a bunch of money and can afford to hire an entire team all at once, it doesn’t make much sense to have a leader who doesn’t have anyone to lead. Progress will grind to a halt. Trust me, I’ve been there.

You might be thinking, “but that means I can’t truly delegate anything at first!” Yup! You can’t. The idea that the CEO of a 3-person company should fully delegated a major part of the business to someone else is unrealistic. As I wrote in my post Entrepreneur vs. CEO, you don’t really start doing the work of CEO until later. While you’re small, you need to be leading all areas. The rest of the team should be practitioners who can grow the business to the point where it actually makes sense for you to delegate responsibility to another leader.

This doesn't mean you can't trust your employees, or that they won't be able to show leadership. It just means that the business isn't ready for you to take your eye off the ball.

Anecdote: My first job after graduating college was at a startup that had just raised a Series A. I was employee number 8, and I believe there was only one other person who didn't have a "chief ____ officer" or "VP of ____" title. The company was full of leaders, and had almost no practitioners. I'll let you guess how that ended.

So early hires don’t get to be future leaders?

That’s not what I’m saying. What I’m saying is that at the time you hire them they need to be practitioners. They won’t have a team to manage yet, so it’s imperative that they can get the work done on their own. As your team grows over time, some of your practitioners will grow into leaders.

But I have learned a few tricks to help with this:

  • It’s easier for a practitioner to become a leader than the other way around. There are exceptions of course, but once someone is used to delegating things, it’s common for their individual contributor skills to atrophy. As tempting as it might be to hire some hot shot executive from a different tech company as your first engineering, marketing, or sales hire, they probably won't be effective without a team and significant budget to work with.
  • Don’t make promises about future leadership opportunities. This is a super common mistake. You want to attract a really talented first hire, so you give the person a Chief Whatever Officer title. But you’re not hiring them to be a leader yet, and you don’t even know if they’ll want to stop being a practitioner when the time comes. Maybe your second or third hires are better suited for leadership. It sure would be uncomfortable having to demote the Chief Whatever Officer so someone else can take that leadership role, so it's best to just avoid titles like that as long as you can.

Again, their are exceptions, but I think a smart default is to plan on hiring practitioners in the early stages, expect some of them to grow into leadership roles, but don’t assume that the first person you hire on a team is obviously more suited to becoming the eventual leader than the second or third person.

Have thoughts on this post? I'd love to hear from you! I'm @TylerMKing on Twitter.