Before you delegate, ask yourself these 6 questions

These questions will help your coworkers get set up for success. They're helpful if you are delegating to AI, too.

👋 Hey, it’s Wes. Welcome to my bi-weekly newsletter on managing up, leading teams, and standing out as a high performer. Check out my intensive course on Executive Communication & Influence. You’ll learn alongside mid-career operators from Netflix, Google, Stripe, Anthropic, etc. → Save your spot in the September cohort

Read time: 6 minutes

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“It will take too long to explain how to do to this.”

For years, I resisted delegating because it was faster to do the task myself. Intellectually, I understood the benefits of delegating, including the ability to scale myself, work through others, increase my impact, etc etc etc…

But carving out the time to explain all the nuances of a task felt like a lot of work. I was afraid I wouldn’t explain well and the person wouldn’t do a good job, which would lead to me redoing the work anyway.

One day, I realized that having a checklist might help me quickly identify what to tell someone outside my own head. I’ve since used checklists like the below on hundreds of requests for others. It works in a variety of situations where you need to establish shared context:

• If you used to do the task, and are training someone else to do it going forward

• If you’re not sure how to do a task, but you’re looping in a cross-functional partner to do their part in a project

• If you want to use AI as a thought partner and you want it to give you advice that’s more relevant to your situation

Here are questions I ask myself so I can confidently share context when making a request:

1. What does this person know? What’s new for them?

Considering your colleague’s existing knowledge will help take yourself out of your own head and into theirs. From this question alone, you’ll remind yourself of what they already know (that you can explain more quickly or build on) and what’s new for them (that you probably wouldn’t remember was new for them until you consciously thought about it). This has the positive effect of making you more empathetic and patient.

Every situation, project, etc will be different, so use your judgment. For example, you’d share different context if your colleague is already working on a part of a project and you’re now bringing them into a different part of that project, vs if that same person were hearing about a project for the first time.

2. Why are we doing this?

If the task requires judgment, which almost all beyond the very basic tasks do, you want to help them make the right call when you’re not looking over their shoulder. Sharing the “why” behind the task means they won’t be overly reliant on following mechanical directions or step-by-step instructions.

Also, knowing how your part fits into a broader project makes any task feel more rewarding. You can see how your work is part of something bigger.

🚫: [Silence]

✅: “This matters because…”

✅: “Our goal is to vet which micro-influencers to reach out to for our upcoming campaign. We want to make sure they’re a good fit for the brand and this specific launch.”

✅: “Once you finish this, we’ll share it with X team and they’ll take it and…”

3. What do they need in order to do this task?

This includes access to tools, platforms, spreadsheets, docs, assets, budget, people, etc. Have this ready beforehand, or be ready to list this out verbally so the person can get these assets on their own. This is like mise en place in cooking. You want to gather everything the person might need.

4. What does great look like?

Try to “show, not tell” what great looks like. For example, share mock ups, examples, screenshots, docs, analogies, etc. You want to help them pattern match and viscerally understand what you’re saying. This is where an example can be worth a thousand words.

Even if you don’t have a one-for-one example because the thing you’re asking for is new, you can show examples and say “It’s like this, except…”

🚫: [Silence]

✅: “The final document should look similar to this.”

✅: “Here are a few examples of strategy docs. Yours doesn’t need to have the exact same sections, but notice how these docs cover the ‘why now?’ of a problem and [insert other things you want to point out].”

5. What’s the timeline and priority level?

You’ll want to note if this is a “do this in the next few hours” or a “sometime this week” or “sometime in the next two weeks” type of task. Avoid phrases like “ASAP,” “urgent,” and “priority” because they are too vague and can increase stress levels unnecessarily.

Re: how much time to spend on a task, it’s not always obvious what’s considered “good enough.” I’ve delegated tasks, but when the person delivered their work, I realized they were more detailed than I needed them to be. I didn’t properly set expectations.

I like asking my colleagues to give me a heads up if they’re partway through the project and realize my estimate is off. There’s no shame in this, so don’t blame them or assume they’re “working too slowly.” If you are delegating to junior team members, getting visibility into their process will allow you to help them be more efficient. In my experience, though, what seems like a speed issue is often actually a scope issue, so it’s not something that can be solved by simply trying to work faster.

6. What’s most likely to go wrong? What can I do to prevent this from happening?

These two questions pretty much cover 99% of derisking. If the stakes are low, spend less time on this. If the stakes are high, come up with a more comprehensive set of risks so you can assess the likelihood and impact of each issue. What do you not want the person to do?

🚫: [Silence]

✅: “I don’t need paragraphs of explanation or background about each customer. I only need the name of the customer and a few bullet points about why you picked them. From there, I’ll look up each customer you recommended and review their profile myself.”

To recap, here are the questions:

1. What does this person know? What’s new for them?

2. Why are we doing this?

3. What do they need in order to do this task?

4. What does great look like?

5. What’s the timeline and priority level?

6. What’s most likely to go wrong? What can I do to prevent this from happening?

These questions are a starting point, so there may be questions you want to swap out or add that are more specific to your situation. I encourage you to create your own go-to questions.

The next time you delegate or make a request for help on a project, give these questions a try. I’d love to hear how it goes.

Thanks for being here, and I’ll see you in two weeks on Wednesday at 8am ET.

Wes

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Further reading

How I give the right amount of context (in any situation)

CEDAF framework: Delegating gets easier when you get better at explaining your ideas

How I give high-quality feedback quickly

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