How to Delegate Effectively

If you're looking to delegate tasks effectively as a leader, you'll want to read this.



Delegation just might be one of the trickiest skills for a leader to master – especially if you consider yourself a “doer.” That is, a person who enjoys doing the work, fine-tuning the details, meddling in the weeds of how it’ll all work.

I know I enjoy being a “doer.” So I find delegation incredibly hard.

For so many managers and leaders — particularly those of us who are used to be the person doing the work and are now handing off the work to others — learning to delegate is, well, tricky, if not painful.

The good news is that we are by no means alone. I recently happened upon some helpful advice from leaders who similarly have a tough time delegating in a few conversations on The Watercooler. And they were incredibly generous with their advice.

Charlie Elliott, Director of Product at Shopify and Watercooler member, chose to be very honest with his struggle to delegate to others:

My tendency can be to either take on work myself, or dive into the details and hand over a to do list 🤦‍. Both don’t scale, and both behaviours underutilize the incredible people on our team.

However, Charlie then shared this bit of gold that his coach had offered on delegating well:

Invite your team into both the thinking and the doing.

That is, involve your team in co-creating what success looks like — instead of purely asking them to execute and get you there.

Many of us, like Charlie, have a habit of inviting the team into the doing after we’ve done the thinking. We want to know what we’re asking people to step up to, before asking them to do so. Or we’re so worried about the outcome, we don’t trust others on our team enough to take part in the thinking.

Sean Conner, another Watercooler member and VP of Creative at Guerrero Howe, related to this struggle. He admitted how he’d recently experienced the power of Charlie’s advice to “invite your team into both the thinking and the doing” when a coach he was working with said:

Delegate outcomes, not activities.

This means to clear a path for a team member to achieve that outcome however she’d like — because it’s the outcome you truly care about after all.

Now, this is much harder to do in practice. It’s hard to give up control and allow someone to approach an outcome, particularly when we see pitfalls in the approach. We think, “Oh boy, that’s going to take a long time…” or “Ah, they really shouldn’t be doing it that way…” But what Sean pointed out is:

“Delegation is about letting your report learn, and if you believe their approach has a fair chance to get to the outcome, then you must get out of the way.”

Keep that in mind. Not only is delegation a means to getting something done in the here and now — it’s a means for helping your team get something even harder done the next time around. You’re giving your team the opportunity to take in what works and what doesn’t, observe, stumble, fall… and then figure it out themselves. How else will they figure it out if you don’t even give them the chance to try?

When you delegate the outcomes and not the activities, you help employees not just execute for the task at hand, but equip them for every future task after that. You’re giving true ownership to your team.

Thank you, Charlie and Sean. As I divvy up work here at Know Your Company today, I’ll be keeping your advice in mind.

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