Don't delegate the most important thing
A while ago I was discussing hiring plans with a co-founder of a recently-funded startup. Their story was something like this:
"The company is growing very fast and we now have about a dozen people. We have tight deadlines, and none of the founders has much experience in project management or people management. So, we're trying to hire an experienced project manager and an experienced engineering lead / people manager."
This course of action is pretty common. It also always makes me nervous, but I haven't thought much about it until now. This discussion finally forced me to clarify my thoughts on the subject.
First of all, I asked the co-founder what their role is. The answer was a good one, albeit vague, as startup roles always are: "I don't really know. It's frustrating that I never know. But I do know my job is whatever it takes to make the company successful."
Well, what are the most important problems that the other co-founders aren't solving? The answer came quickly: "We don't have a clear idea of our project schedule. And nobody is managing interpersonal, cultural, social issues. There are lots of other problems, but people are handling those." So those were the top two. Nobody was managing those, and it was getting serious.
This reminded me of some advice I must have heard somewhere, but no longer remember where: Don't delegate the most important thing. Or maybe it was a 1980's management book: Don't outsource your core competency.1
This advice is counterintuitive. At first glance it sounds like it should be intuitive, but once you think about it, it's not. The most important thing - whatever it is! - needs to be done well. Shouldn't we hire the best person possible to handle it? And isn't it vanishingly unlikely that the person already works here?
You're right! In an ideal world, you would get the best, most motivated, most passionate project manager in the world to manage your project. And the best, most motivated, most empathetic, most wise people manager to manage your people. But the real world is rarely ideal. You are unlikely to find the best person in the world on short notice. You probably can't afford to pay them what they deserve. In a wide world where they have their choice of exciting projects, they (statistically) probably don't care enough about your project anyway. And because they're so good, they're probably accustomed to leading huge teams with huge problems that need huge solutions.
In short, you aren't likely to hire the ideal person. You can probably hire a pretty good person. Or you might get unlucky and hire a terribly mismatched person.
That variability is a huge problem. Even if the average person you could hire might be better than you, the standard deviation is very high. It's essentially a random chance, a lottery ticket. Do you want to buy a lottery ticket for the (self-selected) most important thing in your entire domain, whatever it is?
The alternative is to find a person with less specific expertise, but who can understand the company vision, connect with everyone on the team personally, be highly invested in the shared outcome (not just personal gain), and be so passionate about the project that they'd be willing to step aside if they can someday find someone who is a better fit. As a bonus, this person already works at your company: it's you.
Relatively speaking, it's actually pretty easy to learn project management and scheduling or people management. It takes time and effort, but not much more, to become passably decent at either one. Whereas you can't buy shared vision, personal knowledge, shared motivation, or humility, for any amount of money.
Once the schedule or the management of small teams is no longer your most critical problem, then delegate those. Better still, by then you will know how to do the jobs, so you will be very good at interviewing your replacement.
1 "Core competencies" is one of those once-useful terms that has been badly diluted through overuse. It mostly just means "things that uniquely make you special compared to your competitors." If you're a software company, that's probably your software.2 So buy some commodity package (or service) to do your accounting, which doesn't differentiate you, and hire people to write your software, which does.
2 Even at a software company, sometimes your software is crappy and your customer service or sales organizations are your real advantage. Confusion about this has led to horrible strategic blunders. IBM's core competency, for example, clearly is not software.