On Building a Leadership Team

Photo courtesy Susanica
Photo courtesy Susanica

Here’s how lots of tech companies start: two guys with an idea or a client, coding in a spare bedroom. One day there’s too much work, so they hire a cousin who knows HTML. Then a friend’s younger sister graduates with a degree in graphic design, so they hire her to design a login process and beyond.

Suddenly the founders (who didn’t really realize what they were founding, by the way), look up and they’ve got a 15-person company. Suddenly they have employees who depend on their income for mortgages and child care and health benefits. Suddenly the whole operation is a train moving so fast that it’s impossible to pause and take stock. A company that never had growth strategy to begin with now lacks the time for growth strategy. Yikes.

I’ve been reading a lot lately, mostly books and articles about entrepreneurship and teams and leadership. And I have to say, there is an obscene amount of pressure on the CEOs and founders of these small companies. “Ignore this advice at your PERIL!” the headlines scream. Apparently there are several hundred ways you can screw your company up, all of them balls you’re juggling in the air, each one of them powerful enough to sink the ship. These balls have names like “business development,” “hourly rates,” “hiring and recruiting,” and “ping-pong tables.”

How the hell did we get from coding in a spare bedroom to ping-pong tables? If you’re asking yourself this question, I have one thing to say to you:

Quite simply, you are not alone.

I know a number of founders whose stories are similar to these. I meet up with them for drinks or coffee or lunch and I see that the passion in their eyes has been boarded up behind responsibility. They’re doing a bang-up job on 32% of what their company needs. The remaining 68% flails in the wind.

Are leaders superheroes? Nope. Should CEOs and founders be forgiven for the flailing 68%? Gently, I’m sad to say, they can’t be. Because the impossibility of the task is actually the task at hand.

So what’s the answer, other than gray hair, stress-induced medical issues and the constant feeling of drowning?

Trust. TRUST! Not trust in the gods of the universe, but in other people. When you get to the point that running your company is ruining your life, it is time to hire wingmen and wingwomen to man the ship. There’s no magical algorithm to figure out how many years into the company this must happen, but you will know when it’s time. You’ll know because you will not see a way forward without help.

Who are these magical people you’re supposed to trust? You probably already know them. Some of them have been working for you, others you’ve met over drinks at a meet-up. Your popular project manager, who navigates clients effortlessly, could transition to Business Development. The COO of a startup whose funding recently dried up is looking for the chance to board a more stable ship. The designer who has accurate instincts on who’s feeling burned out is a perfect candidate for Chief of Staff.

You won’t hire or promote them all at once. You’ll start with the the one  you trust the most. Then, like a balancing act, you’ll build a leadership team, piece by piece.

Does the responsibility disappear? It doesn’t. But two things happen:
1. Some of the boards that were covering your passion are safely removed by your leadership team, and
2. Now you have people to laugh with.

When a client goes ballistic or when your most prized developer quits or when there’s barely enough cash to make payroll, you have colleagues to share the load. You’ll cry about it alone, but you’ll laugh about it with people you trust. The release of that laughter, the acknowledgement that you came from a spare bedroom and now you’re debating ping-pong tables, will release the pressure valve just enough to let some steam through.

And that will give you just enough energy to get up tomorrow, to show up at this bizarre job you’ve made for yourself and to tackle the impossible again.