One thing I see leaders struggle with time and again is the idea of delegating. And to be honest, it’s hard. It most often breaks down in two ways:

  1. Trusting the person will get it done + the accountability and follow through from the person who said they’d do it.
  2. Right sizing the project for the skills of the person.

Trust and accountability

There’s two ends of the spectrum here: micromanaging <–> no accountability.

Micromanaging is you jumping into the situation and removing their agency to do great work. It becomes your project instead of theirs. When I was an people manager at a startup, I would never touch a team members work – I saw time and again with more junior managers that did this the other team members would stop referring to the project as “their’s”, and more as “ours” – meaning it belonged to the team member AND manager. It was awful to watch – and the same thing happens in the working world. Let people struggle, and check in on them, but don’t create dependence.

On the lack of accountability, I think this always goes back to the idea of consistency with folks you work with. If you’re consistent in your follow through and ask the right questions about blockers/timing/deadlines, then they’ll understand what’s expected of them from a “hey I trust you’ll do this” perspective. At most companies that I have worked for, we have skew heavily to this side of the spectrum, and this is usually why delegation fails – because we don’t put real structure in place to hold people accountable for deliverables. If you’re checking in and asking questions, you’re able to get in front of problems. People dragging on timelines? Diagnose why they’re dragging their feet. Work is sloppy? Figure out why they’re rushing.

Right sizing skills

Tasks are pretty easy to figure out who can handle it and can’t. It’s a discrete piece of work that has basic inputs and a single output: task completed. The problem with delegation is we’re not looking at a single one off task, but complex problem spaces and project work. So, when we treat these like tasks we make an unconscious assumption that the person can handle the complexity, which is when we set them up for failure.

Getting in front of it

So here’s how to delegate complex work to someone and keep the accountability in a sweet spot between no support and micromanaging: break apart projects into their discrete tasks.

The sum of the tasks can be overwhelming, so getting the right altitude is important, but by analyzing a person’s ability across all the different disciplines needed for project work, you can then flex to their development in any given moment. That’s it. It’s the magic sauce… the delegating vodka sauce to the penne of work if you will. And because you’re awesome, I’ve whipped up a little sheet to help you with this.

The delegation sheet

Sit down with the person you want to delegate work with.

Brainstorm the things someone needs to do for the broader work – just list out as much as you can. If something feels ambiguous, at least put it on paper so you can discuss with the person

Next to each task, talk through with the person if it’s the first time they’ve done it and their confidence level with it (sounding like a situational leadership convo yet?)

Assign a level of commitment you’ll take on with each of the tasks – directive support, coaching, checking in, and what that looks like on a regular basis.


An engineer is going to lead some project work – they are new to the role and looking to lead more across this team and a few cross functional partners. I’d sit down with her to brainstorm all the pieces out:

Project Puppies and Rainbows (working title)

Tasks areas:

  • Assigning code work
  • Diff review
  • Leading meetings
  • Working with cross functional partners
  • Regular communications – what’s the cadence to teams
  • Spec doc writing

Looking at this list, we can then have a conversation and I could see she’s super strong on the technical side, but hasn’t done much work with partners and communicating to broader team groups – in fact, that stuff gives her anxiety.

So, I’d coach/support on things like review and assigning work, whereas I’d get more directive and spend more time with her on the comms and partner support. With our weekly checkins, we can then go through the list to understand where things are blocked and celebrate where she’s feeling great. This’ll help her feel heard, help you spot growth areas, and also track the project in a non-process heavy way.

Have tips on delegating and supporting leaders in your team? Holler in the comments.