How to Write Prompts That Actually Work: A Business Leader’s Guide

You’ve heard the buzz. You’ve maybe even opened ChatGPT, typed something in, and gotten back a response that felt… underwhelming. Generic. Like asking a brilliant new hire to do something important and getting back a book report from a tenth grader.

You’re not alone. Most business leaders we talk to at Squishy AI have the same experience. They know AI is powerful — they’ve seen the headlines, the competitor announcements, the breathless LinkedIn posts — but when they sit down to actually use it, the results fall flat. And that gap between expectation and reality creates a quiet fear: “Maybe I’m just not technical enough for this.”

Here’s the truth: the problem isn’t you. It’s the prompt. And learning to write better prompts isn’t a technical skill — it’s a communication skill. One you already have.

Why Prompts Matter More Than You Think

Think of AI like the most eager, capable intern you’ve ever hired. This intern has read the entire internet, works at lightning speed, and never sleeps. But they have one critical flaw: they only do exactly what you ask them to do.

If you walk up to that intern and say, “Write me a marketing email,” you’ll get something. But it probably won’t sound like your brand, speak to your audience, or accomplish your goal. Not because the intern is bad — but because you didn’t give them enough to work with.

A prompt is simply your instructions to the AI. The quality of your output is directly tied to the quality of your input. In the AI world, this is often called prompt engineering, but don’t let the fancy name intimidate you. It’s really just learning how to ask clearly.

The 5 Elements of a Prompt That Actually Works

After coaching hundreds of business leaders through their first AI implementations, we’ve identified five elements that consistently turn mediocre prompts into powerful ones. We call it the R.O.L.E.S. framework.

1. Role — Tell AI Who It Is

Start by assigning the AI a role. This immediately focuses its vast knowledge into a relevant lane.

  • Weak: “Write me a product description.”
  • Strong: “You are an experienced e-commerce copywriter who specializes in luxury skincare brands.”

Just like you’d brief a freelancer or agency, tell the AI what kind of expert it should “be.” This single addition can dramatically improve your results.

2. Objective — State Exactly What You Want

Be specific about the task and the desired outcome. Vague requests produce vague results.

  • Weak: “Help me with my sales process.”
  • Strong: “Write a follow-up email for prospects who attended our webinar but didn’t book a demo. The goal is to get them to schedule a 15-minute call.”

Notice the difference? The second prompt defines the audience, the context, and the desired action. The AI doesn’t have to guess.

3. Limits — Set Boundaries and Constraints

AI will ramble if you let it. Give it guardrails — word counts, formats, things to avoid.

  • “Keep it under 200 words.”
  • “Use bullet points, not paragraphs.”
  • “Don’t use jargon — this is for a non-technical audience.”
  • “Do not make up statistics. If you’re unsure, say so.”

Constraints aren’t limiting — they’re liberating. They force the AI to give you something focused and usable.

4. Examples — Show, Don’t Just Tell

One of the most underused prompt techniques is simply giving the AI an example of what “good” looks like. Paste in a previous email you loved, a competitor’s landing page you admire, or a tone of voice sample from your brand guide.

You might say: “Here’s an example of the tone and style I’m looking for: [paste example]. Write something similar for our new product launch.”

This is the equivalent of showing your intern a finished project and saying, “Like this, but for our new campaign.” It removes ambiguity fast.

5. Sequence — Break Complex Tasks Into Steps

If you’re asking AI to do something complex — like building a full content strategy or analyzing a financial report — don’t cram it into one giant prompt. Break it down.

  • Step 1: “Summarize the key findings from this quarterly report.”
  • Step 2: “Based on those findings, identify the top 3 risks to our growth target.”
  • Step 3: “Draft talking points I can use to present these risks to my board.”

Think of it like a conversation, not a single command. Each step builds on the last, and you can course-correct along the way. This is how business leaders get truly executive-level output from AI.

Common Mistakes That Kill Your Results

Even with a good framework, there are a few traps we see business leaders fall into repeatedly:

  • Being too polite and too vague. “Could you maybe help me think about some ideas for possibly improving our marketing?” Give direct instructions. AI doesn’t need pleasantries (though there’s nothing wrong with being polite — just don’t sacrifice clarity for courtesy).
  • Accepting the first output. Your first result is a draft, not a final product. Follow up with, “Make it more concise,” “Adjust the tone to be more authoritative,” or “Give me three alternative versions.” Iteration is where the magic happens.
  • Not providing context about your business. AI doesn’t know your industry, your customers, or your competitive landscape unless you tell it. A sentence or two of context goes a remarkably long way.
  • Using AI for the wrong tasks. AI is extraordinary at drafting, summarizing, brainstorming, reformatting, and analyzing. It’s not great at making strategic judgment calls for you. Use it as a thinking partner, not a replacement for leadership.

A Real Example: Before and After

Let’s put this all together. Imagine you’re a CEO who needs to draft a company-wide announcement about a new AI policy.

Before (Weak Prompt)

“Write an announcement about our new AI policy.”

After (Strong Prompt Using R.O.L.E.S.)

“You are an internal communications specialist for a mid-size professional services firm (Role). Write a company-wide email announcing our new AI acceptable use policy (Objective). Keep it under 300 words, use a warm but professional tone, and avoid fearmongering — we want employees to feel excited and supported, not policed (Limits). Here’s an example of our typical internal email tone: [paste example] (Examples). Start with the ‘why’ behind the policy, then summarize the three key guidelines, then close with where employees can go for questions (Sequence).”

The difference in output quality between these two prompts is staggering — and it takes less than two minutes to write the better version.

The Bigger Picture: Prompt Skills Are Leadership Skills

Here’s what we tell every executive we work with: getting good at prompts is really about getting good at clear communication and clear thinking. Defining roles, setting objectives, establishing constraints, providing examples, and sequencing tasks — these are things great leaders already do when they delegate to humans. AI just requires you to be more explicit about it.

The leaders who thrive in the AI era won’t necessarily be the most technical. They’ll be the ones who learn to ask the right questions, in the right way, at the right time.

Ready to Put AI to Work in Your Business?

Learning to write great prompts is just the beginning. The real transformation happens when you connect prompt skills to your actual business workflows — sales, operations, marketing, strategy, and beyond.

At Squishy AI, we help business leaders move from AI-curious to AI-confident. No jargon. No hype. Just practical, personalized guidance that meets you where you are.

Book a free AI strategy call with our team today. We’ll help you identify the highest-impact opportunities for AI in your business and show you how to get started — even if you’ve never written a prompt before. Let’s make AI work for you, not the other way around.