How a single conversation with my boss changed my view on delegation and failure

One day, I was having my weekly 1:1 meeting with my boss, Andrew Bosworth. We were going through the regular updates about my team, things going on at Facebook more generally, yada yada. Then he asked me a somewhat startling question….

“So, Margaret, what’s going off the rails on your team?”

I was taken aback. Had he heard rumors that my team was “off the rails”? Did he think I was a screw-up, a leader unable to track the progress my team was making and ensure the right outcomes? My team was pretty big, and I thought I had a handle on everything, but maybe I didn’t. Good lord, maybe I’d finally been found out to be the giant imposter fraud I had always secretly feared I was???!!!

But I looked at him, and he seemed really calm, unconcerned.

“What do you mean?” I asked, trying to sound calm and cavalier. “I don’t think anything is off the rails.”

“Well, that’s a problem,” he said, and my confusion doubled. How could my boss think it was BAD news that nothing was off the rails?

“Listen, if there isn’t something going off the rails on your team, then I know you are micro-managing them. You are really good at what you do, and if you stay in the weeds on everything, you’ll keep things going perfectly, for a while. But eventually two things will happen. One, you will burn out. And two, you will eventually start to seriously piss off your team. So I better see some things going sideways, on a fairly regular basis.”

My head exploded. This was so counter to traditional management philosophy: keeping everything going smoothly and hold leadership accountable when things went awry. This philosophy is certainly better than blaming the team itself, but ultimately it makes leaders paranoid about failing, and that has enormous repercussions. It makes us more conservative in our decisions to avoid failure and embarrassment. It teaches us to cover up our mistakes instead of being open about and learning from them. And worst of all, it keeps us from delegating and growing our leadership bench.

As leaders, we must learn to hand off significant portions of our jobs in order to grow and scale our teams. Sometimes these hand-offs are necessarily to people who may not be quite ready for it. They have to learn a bunch of things that we already know how to do, and initially they will do it slower and less effectively. The short term thinker in us may want to stay involved in everything because it’s less risky. But in doing so, we may unintentionally rob high potential members of our teams of leadership opportunities. We have to give them the space to fail in the short term so they can succeed and grow in the long term. And of course, there is that magical moment when we delegate and allow an emerging leader to grow into their new responsibilities, and they end up being way better at it than we ever were. That’s real management success.

That single conversation with my boss has had a big effect on me. His management philosophy has created a safe space for our leadership team to share what’s not going well. As a result, we are less likely to judge each other for the things that go “off the rails” in our teams. It feels good to be in a place where I can talk about areas of concern without fear of being judged, and instead even be praised for it. And because we share our challenges openly with each other, we are much more able to collaborate in productive ways to help each other succeed.