An ex-boss of mine and I were catching up a couple of weeks ago. We were meeting after years, and in the years that have passed us by, he had a mega-exit in his last startup, and after a brief gap he took to figure out what’s next, he is back in the driver’s seat. The startup is already making some waves and coupled with his previous success and trust investors have in him, they have raised decent capital in no time. As a result, hiring the right talent is not an issue. The problem, as he himself described, is coming with delegating the work.
The last team we built, it took everyone a while to understand my expectations, and while I was fortunate enough to find a bunch of great guys, the initial couple of years needed me to be on top of everything, figuring out what needs to be done, keeping track of those items, pushing everyone to get results. Unfortunately, I have to do it all again. We will get there again where people can work independently, without me having to drive everything, but it is going to take some time to get in the groove.
And this is the biggest challenge entrepreneurs face when delegating work to their teams. Entrepreneurs inherently love getting stuff done (and getting it done NOW), and they don’t mind getting their hands dirty to ensure it gets done right, and at the right time. The result? The idea of delegating work to others is often an uncomfortable thought, and they would always rather prefer to do it themselves.
Also, I believe I must note that this is not just a problem with new entrepreneurs who haven’t had much experience managing people. As we just saw in case of my ex-boss, no matter how seasoned an entrepreneur, the minute you put him in a new setup, in a new environment, with a new team and a blank slate, it is back to day 1. And with day 1 comes up all the challenges of day 1.