This post was originally featured in the Inbox Insights newsletter found here: INBOX INSIGHTS, November 12, 2025: Good Prompting is Delegation, Trust Insights Workshop Review
Good Prompting is Good Delegation
I spent twenty minutes crafting the perfect prompt for an AI tool last week. I included context, specified the format, gave examples of what I wanted, outlined the tone—the whole nine yards.
Got exactly what I needed on the first try. Felt pretty smart about it.
Then I opened my email to delegate a project and started typing: “Hey, can you handle this client report? Need it by Friday.”
I stopped mid-sentence.
Because I realized I was about to make the exact same mistake I made as a brand new manager—the one that taught me one of my hardest lessons about leadership.
Here’s the thing—I know better. Setting clear expectations feels intuitive when you slow down and think about it. But when I’m in a rush or feeling lazy, I can still fall back into bad habits. And I was about to do exactly that.
The Lesson From Early in My Career
Way back when I was a brand new manager, nobody had taught me how to properly delegate. I thought delegation meant “assign it and walk away.”
So when a project came up, I’d confidently tell someone, “Hey, just handle this. It needs to be done by Friday.”
And then I’d watch it completely fall apart.
The deliverable was nothing like what I expected. The approach was all wrong. We missed deadlines. And my team members were frustrated because they felt like they’d failed—even though I had set them up to fail by giving them approximately zero useful information.
Yikes.
I should have known better, even as a new manager. The signs were all there. But I thought delegation was supposed to be quick and easy, not detailed and thoughtful.
Spoiler: I was wrong.
Eventually I figured out that setting clear expectations is the key to successful delegation.
And I don’t just mean saying “do a good job” or “make it professional.” I mean actually spelling out:
- How it should be done – What’s the approach? What’s the process?
- SOPs and resources – If documented processes exist, share them. If they don’t, explain the steps.
- Clear timelines – Not just the final deadline, but check-in points along the way.
- Examples of the output – Show what “good” looks like. Share past examples or similar work.
Was this more work for me upfront? Absolutely.
Did it feel inefficient at first? You bet.
But here’s the thing—it’s exactly like requirements gathering in a project. You can either spend the time upfront getting clarity, or you can spend triple that time later fixing everything that went wrong because of ambiguity.
I learned this lesson years ago. And yet, when I’m in a rush or feeling lazy, I still have to catch myself before falling back into “just handle it” mode.
Why We Get Lazy
Sometimes we skip the clear expectations because:
- We’re busy and it feels faster to just say “you know what I mean”
- We assume the other person has context they don’t actually have
- We’ve explained something before and don’t want to repeat ourselves
- Writing out detailed instructions feels like overkill for a “simple” task
- We’re just…tired
But every single time I give in to that laziness, I end up spending more time fixing the results than I would have spent being clear upfront.
The math never works in favor of vague delegation. Never.
The Real Win
When you give someone clear expectations, resources, and examples, you’re actually giving them a real shot at learning and being successful.
When I just said “handle this,” I was setting my team members up to either fail or spend hours spinning their wheels trying to read my mind. Neither option felt good for them.
But when I took the time to say, “Here’s what we need, here’s how we’ve done similar projects before, here’s what success looks like, and here are the key milestones along the way”—suddenly they could actually learn something. They could be successful. And that success motivated them to take on more.
Turns out, people like being set up to win. Who knew?
The AI Connection
Which brings me back to that prompt I wrote last week—and that email I almost sent.
Good prompting is good delegation.
The same skills I had to learn as a manager—being specific, providing context, sharing examples, setting clear expectations—are exactly the skills you need to get good results from AI.
Compare these two prompts:
Bad prompt (my rushed, lazy energy): “Write a blog post about marketing.”
Good prompt (when I actually try): “Write a 750-word blog post about email marketing best practices for small business owners. Use a conversational tone, include 3-5 specific actionable tips, and format with clear headers. The audience is entrepreneurs who are doing their own marketing with limited time and budget. Include a brief example for each tip.”
See the difference? The second version includes:
- Specific scope and length
- Clear audience
- Tone guidance
- Format expectations
- Examples of what to include
It’s the same framework I eventually learned for delegating to my team. And when I use it for AI prompts, I get great results. When I skip it because I’m in a hurry? I get garbage and have to start over.
The AI won’t be frustrated or demotivated by my vague prompt—it’ll just give me mediocre results. But my team members? They deserve better than my lazy shortcuts.
Why This Matters for Everyone
If you’re struggling with AI tools and thinking “these just don’t work well,” I’d ask you to look at your prompts.
Because here’s the uncomfortable truth: if your prompts are vague, your delegation to your human team is probably vague too.
The quality of your prompts is a pretty good mirror for the quality of your delegation. And just like with my management mistakes, vague direction leads to:
- Wasted time
- Frustrating do-overs
- Deliverables that miss the mark
- People (or AI) that can’t learn what you actually need
We know better. It feels intuitive when we slow down. But when we’re rushed or lazy, we skip the work—and then we deal with the consequences.
The Upfront Work Pays Off
Yes, writing detailed prompts takes more time initially. Just like proper delegation takes more time upfront.
But just like I learned with requirements gathering—do the work on the front end, and you save massive amounts of time on execution and revisions.
When you give clear direction to your team, they can:
- Work more independently
- Make better decisions
- Deliver what you actually need
- Learn and grow in the process
- Feel motivated by success instead of deflated by confusion
The same is true when you give clear prompts to AI tools.
The Bottom Line
Good prompting is good delegation. They require the same skills: clarity, context, examples, and realistic expectations.
Every time you craft a better prompt, you’re practicing the skills that make you a better manager. And every time you improve your delegation, you’ll get better results from AI tools.
I learned this lesson the hard way as a new manager. And apparently I still need reminders not to fall back into lazy habits when I’m busy or rushed.
The results will always reflect the effort we put in upfront—whether we’re delegating to a person or prompting an AI.
So next time you’re about to delegate something—or write a prompt—ask yourself: “Am I being clear and thorough, or am I being rushed and lazy?”
Catch yourself before you hit send on that vague email.
Your team (and your AI tools) will thank you.
Are you effectively delegating? Reply to this email or join the conversation in our free Slack community, Analytics for Marketers!
– Katie Robbert, CEO
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