☄️ Prompts That Don’t Suck

Why your AI results suck

Most execs use AI like interns.

They toss in vague requests. Get vague answers. Waste 30 minutes rewriting.

AI should be your co-exec instead.

Better prompts = better outputs. I created the CRISCO Framework to get reliable outputs that are slick, strategic, and ready to ship.

The CRISCO Framework

Context + Role + Intent + Structure + COnstraints = Ready-to-Ship Output

C = Context

What's happening right now?

AI can't read the room. Feed it every variable that would change your decision. Company dynamics, market conditions, personal stakes, etc.

Bad prompt: "Help me write an email to the board."

CRISCO prompt: "We're a $50M SaaS company. Growth slowed from 40% to 15% last quarter. Board meeting Tuesday. CEO credibility on the line."

Give AI:

• Company: Stage, sector, velocity

• Decision: Urgency, politics, financial stakes

• You: Title, authority, what's on the line

R = Role

Who should the AI become?

Skip generic outputs by “casting” AI as the exact expert you'd hire to tackle the problem. You can go deep on their experience level and specialty.

Generic AI sounds like Wikipedia regurgitated.

Tell it who to be: "You're a McKinsey senior partner with 15 years in SaaS turnarounds."

Pick your advisor:

• Strategy Partner

• Devil's Advocate

• Industry Insider

• Communications Chief

I = Intent

Why do you actually want?

State your desired output Vague intent gets you 5 pages of fluff.

Sharp intent: "Give me 3 acquisition targets under $20M that fix our churn problem. Provide the rationale for each and then provide your final recommendation considering all of the reasons."

Be specific:

• Market teardown with entry points

• Board brief with 3 scenarios

• Decision matrix with weighted criteria

• Email draft that preserves relationships

S = Structure

How should it look?

Pre-format for your actual use case. Tell AI exactly how you'll present this (who reads it, how fast, what they decide).

Wall of text = ignored output.

"Format this as a 2-minute boardroom readout. Lead with the decision, then three supporting points, then risks." Better yet, give it an outline to fill in.

Match the moment:

• 3-line exec summary for Slack

• Slide outline for presentations

• Action checklist for Monday morning

• Briefing doc with these 5 sections: [section headers]

CO = Constraints

What matters most?

AI will boil the ocean unless you fence it in. List your non-negotiables.

"Stay under $5M investment. Assume no new hires for 6 months. Work within the current tech stack."

Set boundaries:

• Timeline: 24 hours or 6 months?

• Budget: $300k or $30M?

• Politics: Who needs buy-in?

• Legal: What kills the deal?

Same problems, different prompts

Watch the CRISCO difference with a bad prompt vs a good one. One wastes your time. One saves your quarter.

Acquisition Analysis

Instead of: "Should we buy this company?"

Try: "You're our Corp Dev VP. TechCo is for sale at 4x revenue. We have $40M cash, need AI capabilities yesterday, and our biggest competitor is also bidding. Give me a go/no-go recommendation with three supporting arguments and top integration risks. Format as executive decision memo."

Market Entry

Instead of: "How do we enter Europe?"

Try: "You're an expansion expert who launched Stripe in Europe. Our payment platform does $30M ARR in the US. Analyze Germany as our beachhead. Include regulatory costs, competitive landscape, and 18-month revenue projection. When evaluating, skip markets under $1B. Format as an outline for a board presentation."

Four advanced techniques using CRISCO

1/ Chain-of-Thought

Force AI to show its work to make its work auditable. Use this for complex decisions where you need to verify logic, catch flawed assumptions, or explain your reasoning.

Example Prompt: "Don’t just give me an answer, think step-by-step to walk me through the analysis. Explain each assumption you're making."

2/ Meta-Prompting

Use AI to help speak to AI. Ask AI to help improve your prompt before running it through.

Example Prompt: "You are an AI engineer and prompt engineering expert. Improve the following prompt to help me achieve the goal. [insert prompt]

3/ Scenario Planning

Stress-test decisions against multiple futures (great for board presentations, strategic pivots, or decisions you can't easily reverse.)

Example Prompt: "Run this go-to-market strategy against three scenarios: we hit 2x growth targets, we barely break even, our main competitor undercuts our pricing by 40%."

4/ Red Team Analysis

Deploy AI as your harshest critic. Use before major launches, acquisitions, or strategic shifts.

Example Prompt: "You're the activist investor trying to tank this deal. Attack every weakness. Where would you apply pressure? What would kill this strategy?"

Your Next Prompt

Open your AI chatbot of choice right now.

Take your current challenge. Build a CRISCO prompt.

Watch the intern become an executive.

CRISCO transforms AI from toy to tactical weapon.

Prompt like a CEO.

Until Next Time,

David Lobo

Head of Growth, Workmate

P.S. What recent prompt have you used to gain new insights in your workflow?