Delegating

Delegation is one of the core tools in every manager’s toolbox. Founders typically need to start practicing it as soon as they’ve hired a handful of employees.

Successful delegation feels like giving someone else an end goal to run toward, as well as bumpers they can bounce off of as they move forward, in the form of constraints and success criteria.

Delegation is a knowledge transfer that includes the following elements:

Defined task with clear scope (if known)

“I’d like to delegate something to you. The task is…”

If your definition of the task is overly detailed and specific, you run the risk of killing the other person’s creativity, ownership, autonomy, and potential to learn through execution. You’ll be unwittingly positioning yourself as the ‘expert’, so your direct report is likely to ask you frequent questions to doublecheck that they’re doing it ‘right’ by your standard.

Instead, provide a ‘detailed enough’ definition of the task and scope - or define it together in conversation with your direct report - to give yourself a clean break from the task so you can focus on your priorities instead.

Owner

“I want you to fully own this task from ideation, planning, and execution.”

Overcommunicate ownership so it’s clear you’re handing the task over fully.

This should empower your direct report to throw their full bodyweight behind the task and will also make performance evaluation clearer because it allows you to hold them accountable. It avoids the future possibility that they failed because they were waiting for you on something, or didn’t fully know to take this and run with it.

Objective // Impact

“What we’re trying to achieve with this is…” or “If you’re successful, we’ll…”

What’s the high-level goal or impact of this task on your company’s main metrics? Why is this task important? What does it achieve?

Sharing the impact of the task should help your direct report appropriately prioritize this task against the rest of their workload. It also helps them understand why their work is important, which drives motivation and a sense of ownership and loyalty to the startup’s mission.

Measurement

“Please track success as you go along by using [metric].”

How will we track success/progress as we go along? How frequently will we measure? If unknown, you can discuss this together with your direct report - but make sure you name and agree to something.

Success criteria // Expectations

“’Success’ looks like…”

Describe what success looks like - in terms of the metric achieved and/or its impact. How will we know when/if we’re successful? What are your expectations in terms of quality or eventual performance?

Timeline

“This needs to be completed by [date]…”

When does this need to be complete? Why? Name any other critical contingencies if known.

Clarify your involvement

When you delegate, you become an indirect object in your direct report’s success. It’s helpful to name how you’d like your direct report to use you and your time. Here are some examples to give you a sense of various levels of involvement:

• Pull me in if you get blocked or stuck and I’ll help you problemsolve.

• Slack me anytime with questions - this is a priority so I’ll be available to help you every step of the way.

• I trust you to be fully autonomous here, so I’d like you to unblock yourself if you get stuck, and to only pull me in if you’ve tried absolutely everything you can think of and still nothing’s working.

• I have to focus on [my priority] so I’ll only be available to talk with you about this in our weekly sync/1:1. I’d prefer you hold all questions about this until we meet.

Context (if any)

Delegation is a knowledge transfer, which indicates that you’ll likely know more than your audience about the broader context surrounding this task. What do you know - about the user and the problem this task solves, about the desired solution and what it should/shouldn’t achieve, or about the company in general - that would be helpful for this person to think about as they take this task on?

The more you teach your employees what you know and how you think, the more their decisionmaking will look like yours. This is one way you scale yourself.

Optional inclusions:

• Prioritizations: Clarify how your direct report should prioritize this task alongside their existing workload.

  This will save you from the common failure mode of handing a task off, then watching your employee not do it in the same timeline that you would, and then going into a doom loop of worrying about when your employee will get to it, fearing they never will, deciding they must not have a “sense of urgency,” and then growing anxious, frustrated, and resentful at their “lack of performance.

  Save yourself the emotional energy - and save your relationship with your direct report - by simply stating how important this task is in relation to their other work, in the first conversation you delegate the task to them.

• Optimizations: How should your direct report evaluate the known tradeoffs? e.g. speed vs. reliability, perfect vs. done, long-term scaleable vs. short-term usable

• Resources your direct can use to get unblocked or unstuck (i.e. 1:1s with you? Other team members/experts who can help? Your users? Mentors or investors?)

• A follow-up: When’s the next time you’d like to check in about how this task is going? Put something (or several things) on the cal, even if it’s just a 5-min sync to check in.