Why Delegation Fails (And It’s Usually Your Fault)

I had a product we were building — a data solution for a big internal customer. The goal was to replace legacy systems causing problems across the company. We had multiple bespoke data sources being used for the same attributes across different use cases. They all needed to be the same common source so all our models and tools were using the same data elements.

The vision was shared broadly. But I didn't realize the associate managing the effort directly had only partially understood it. And she wasn't speaking up about it. So I'd talk about the vision, about where we were going. But local decisions were happening within the team that weren't aligned with that vision.

I was stretched thin managing multiple products, so I wasn't paying close attention to her choices. They were logical on their face. But thought through more deeply, they would have led to better outcomes. Instead, we ended up with a fair amount of technical debt that would take a couple of planning increments to clean up.

It could have been avoided if I'd done more upfront work to make sure we were aligned on vision versus the tactical solution she was building toward.

The Gap Between Capable and Set Up for Success

There's a difference between delegating to someone who isn't capable and delegating to someone who is capable but you've set up wrong.

He was fully capable. But I didn't set clear expectations about what leading actually meant. I assumed because he was great at individual delivery that he'd know how to lead differently. That was on me.

The One Thing I'd Do Differently

If I could go back, I'd delegate faster. The fear that keeps managers from delegating faster is the same fear that keeps them from developing their people. It's the belief that if you don't know everything about something, you shouldn't be leading it. That's a failure mode. That's where you end up stuck.

This is part of the Delegation Isn’t About Assigning Tasks series.