To be a manager is to make yourself irrelevant.
Mark Suster agrees.
Finding the talent that ensures you’re protected in case someone gets hit by a “beer truck” (or in my case, a “soda truck”) makes life really easy. But let’s be honest, the folks that are attracted to a small company that has potential are not necessarily the folks who have “been there and done that”. They won’t immediately be at the level in their career necessary to take on your top levels of executive management. So what needs to happen? You spend more money hiring top talent that accepts positions below their capability in the off chance something happens above them so they can fill the shoes? That seems a bit too altruistic for someone who’s in it for the money and the potential upside of a hot startup making the big time.
Instead, you need to invest in your people. Make them capable to fill your shoes. Mentor them, guide them, teach them to do your job. Increasingly give them more and more responsibility. Don’t just thrust it on them, but nurture them so that when the time comes, they can do the job you need them to do.
By the way, this is not to say you should expect them to do the job you need them to do before you formalize that role for them. You have to do right by your employee. If you expect them to be your CTO, give them the job roles and responsibilities of your CTO formally. Or set their expectations by placing them on a performance plan that in some period of time enables them to take that job. Don’t just expect it of them without any communication.