INBOX INSIGHTS, November 12, 2025: Good Prompting is Delegation, Trust Insights Workshop Review - Trust Insights Marketing Analytics Consulting

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INBOX INSIGHTS: Good Prompting is Delegation, Trust Insights Workshop Review (2025-11-12)

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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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In this episode of In-Ear Insights, the Trust Insights podcast, Katie and Chris discuss essential selling frameworks and why they often fail today.

You will understand why traditional sales methods like Challenger and SPIN selling struggle with modern complex purchases. You will learn how to shift your sales focus from rigid, linear frameworks to the actual non-linear journey of the customer. You will discover how to use ideal customer profiles and strong documentation to build crucial trust and qualify better prospects. You will explore methods for leveraging artificial intelligence to objectively evaluate sales opportunities and improve your go/no-go decisions. Watch this episode to revolutionize your approach to high-stakes complex sales.

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In this week’s Data Diaries, let’s recap the events of our very first Trust Insights event, the Generative AI for B2B Marketers Workshop in London. What did people learn? What did we learn? And what does the road ahead look like?

We built the London Workshop to be a small event just to test out the process of setting up an event. We’ve all had plenty of experience setting up events in the past, from co-founding PodCamp back in 2006 through helping friends and colleagues build and deploy their events, like Brooke Sellas’ HELLO Conference and many others.

Workshops are inherently different from conferences. They’re more like educational intensives, bootcamps to pack as much learning into a period of time as possible. Conferences are better suited for giving a shallow, diverse set of perspectives on a subject or issue. An excellent event like MarketingProfs B2B Forum brings two days of lots of different points of view about B2B marketing, but each session is a tasting of the topic.

A workshop is the equivalent of a full-course meal. Rather than individual perspectives and a broad survey, it’s a deep dive – in our case, on B2B marketing and generative AI. We taught the most current version of our prompt engineering basics, dove into the 7 major use case categories of AI with examples and exercises for each, and then finished off with agentic AI and the foundation principles for building effective AI agents.

What we learned was that in our own event, when we go at our own pace… we needed more time. Without an externally imposed schedule, we dug deeper into each topic, each use case, answered more questions and questions in greater depth and detail from the attendees. While that provided a ton of value for questions specific to each attendee’s needs, we also didn’t get to as much of the content as we wanted.

We also learned that people are hungry, desperately hungry, for the basics in a format that’s compact and highly effective. All the advanced tools and techniques like Gems/GPTs etc. are predicated on having strong foundational basics, and with frameworks like RACE, CASINO, the 5 Ps, and others, they could make or upgrade more advanced AI applications to perform better. That gap, of missing solid basics, remains significant.

Other things we learned? Keeping it small – 25 people in a highly focused environment – is the way to go. It allows people to ask questions, it allows us time to walk around and help people individually during exercises, and it lets people network and get to know each other. 25 people to 1 instructor felt like a good ratio; in future events, when we have the entire Trust Insights team available to help, we’ll be able to accommodate more attendees, but I still don’t ever see a Trust Insights workshop exceeding the 25:1 ratio, and 20:1 would be even better.

For the road ahead? Stay tuned, but we will absolutely be bringing this event back in 2026. We’ll likely be running a survey at some point in this newsletter to determine which locations in 2026 we’ll be holding workshops; for sure, one (likely in the first quarter) will be in Boston.

Almost every AI course is the same, conceptually. They show you how to prompt, how to set things up – the cooking equivalents of how to use a blender or how to cook a dish. These are foundation skills, and while they’re good and important, you know what’s missing from all of them? How to run a restaurant successfully. That’s the big miss. We’re so focused on the how that we completely lose sight of the why and the what.

This is why our new course, the AI-Ready Strategist, is different. It’s not a collection of prompting techniques or a set of recipes; it’s about why we do things with AI. AI strategy has nothing to do with prompting or the shiny object of the day — it has everything to do with extracting value from AI and avoiding preventable disasters. This course is for everyone in a decision-making capacity because it answers the questions almost every AI hype artist ignores: Why are you even considering AI in the first place? What will you do with it? If your AI strategy is the equivalent of obsessing over blenders while your steakhouse goes out of business, this is the course to get you back on course.

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Where can you find Trust Insights face-to-face?

MarketingProfs B2B Forum, Boston, November 2025
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