Inability To Delegate As A Lack Of Trust And Self Awareness

The hardest job a startup CEO has is learning how to let go of stuff she used to need to be heavily involved in and trust that the team she hired knows what they’re doing.

— @ericajoy on Twitter, posted on 8:33 PM, 1 Nov 2018

A friend and former coworker texted me a link to Erica’s Tweet above with a comment about how this reminded him of a startup founder we both used to work for. I don’t know if trust and delegation is the hardest job of a startup CEO, but it sure is one of the hardest and most important things that leaders have to learn.

At first glance, the consequences of lack of delegation seem clear. On one hand, a leader that can’t delegate is not making space for her team to grow; this in turn means building a less capable team, where folks who are leveling up need to leave the team to find space to grow. On the other hand, a leader that can’t delegate is overburdening herself with work that could be adequately accomplished by others; as a consequence, she doesn’t have the bandwidth to do a good job of the really important things on her plate. So you end up with an overworked manager doing a mediocre job, with a team with low motivation and possibly high turn-over. Not exactly a recipe for excellence.

I think, though, that the real harm is done by the lack of trust implicit in an inability to delegate. When a leader can’t delegate, they are telegraphing: “I don’t think you can do a good enough job of this. I need to do it myself to make sure it’s done right”. Imagine someone saying this to your face. It’s unpleasant and hurtful. Perhaps it brings up some familiar self-doubt. Perhaps it makes you angry or causes you to shut down. Whatever your reaction, it is unlikely that your immediate response will be to get energized and motivated. And isn’t that what we want? A team where folks are taking ownership, where they are stepping up to solve problems and make things better?

I get it. Delegating can be scary. “What if they don’t do it right? I’ll be responsible for the bad outcome!”

But ask yourself: is this the main reason why I’m having trouble delegating? Might there be also a deeper reason, aside from this obvious one? Maybe it is a desire to feel needed, a fear of becoming less relevant because you’re “doing less”, or an unhealthy perfectionism that prevents you from seeing different ways of accomplishing a task as equality valid. This is where the hard work of increasing your self-awareness comes in. Work with a therapist, or a pastor, or a coach. Talk to others, journal, meditate or pray. Find the tools that work for you, and learn to look deeper inside yourself. Don’t be afraid of what you might find. We all have unflattering traits, things we want to improve or unlearn. What matters is what you do to grow past those areas that are holding you (and your team!) back. This is the true work of leadership.