Prompts for strategic question chains
These prompts are based on the Beyond Prompts: How to Avoid “Faster Mediocrity” with AI webinar, published on the AI Lab by ActiveCampaign.
Get the prompt template
How to use these prompts
These prompts are pulled from the workflow Bob Pearson and Sean Blanda walked through in the webinar—four reusable patterns that replace one-shot prompts with strategic chains.
Use with: ChatGPT, Claude, or ActiveCampaign Active Intelligence — applies to every prompt below unless noted. Copy, paste, and swap in details where you see [BRACKETS]. Every AI model behaves a little differently, so review the first output and refine from there. Run them inside a workspace or project so the AI keeps memory between turns.
Prompt 1: Audience definition cascade
Best for: Defining a target audience for a campaign, product launch, or new channel push when you have a vague brief and need a sharper one.
Why this prompt: Bob walked through this exact cascade as his canonical example of a “prompt supply chain.” The point isn’t to ask the model “who’s my audience?” — that returns the average of the open internet. It’s to ask the same kinds of refining questions a market researcher would ask, in sequence, so the answer narrows with each turn.
Primary prompt
I’m defining the audience for [PRODUCT OR CAMPAIGN] in [GEOGRAPHY].
Walk me through this in five turns. After each answer, wait for me to confirm before moving on.
1. Who buys [PRODUCT TYPE] today, and how would a market researcher describe them?
2. What are the five subtypes of those buyers, and how do they differ in needs and triggers?
3. How many languages do those buyers operate in, and what’s the dominant one per subtype?
4. Geographically, where are most of them concentrated, and which regions are growing fastest?
5. Of those subtypes, which two are the highest-value targets for [SPECIFIC OUTCOME], and why?
Variables to fill in:
- [PRODUCT OR CAMPAIGN] — the specific thing you’re targeting (e.g., “our enterprise CDP”)
- [GEOGRAPHY] — region, country, or “global”
- [PRODUCT TYPE] — the category, in the language a customer would use
- [SPECIFIC OUTCOME] — pipeline, expansion, retention, or whatever the campaign is for
What to expect: A five-turn conversation that gets specific by turn three. If turn one is generic, push back (“Be more specific about decision-makers vs. influencers”) before moving on — the chain only works if each step lands.
Follow-up prompt:
Based on the audience we just defined, what do you NOT know yet that would change my campaign brief if I found out? List the five most important unknowns and how I could research each in under an hour.
Prompt 2: “What am I missing?”
Best for: Pressure-testing a brief, plan, or piece of work before you ship it. Use it after you’ve drafted something — never instead of drafting.
Why this prompt: Sean called this the move that changed how he uses AI: treating the model as a colleague with memory and asking it to find the gap you couldn’t see. Bob extended it with the workspace twist — because the model remembers the chain, the answer to “what am I missing?” gets sharper every time you ask it.
Primary prompt
Here is my draft [BRIEF / PLAN / PIECE OF WORK]:
[PASTE THE FULL DRAFT]
Pretend you’re [ROLE — e.g., a senior creative director, a head of demand gen, a growth strategist]. Read this critically.
What am I missing? Specifically:
- What audience detail isn’t here that should be?
- What channel assumption is implicit that I haven’t named?
- What success metric is vague?
- What objection isn’t addressed?
Be direct. Don’t tell me what’s good — tell me what’s missing.
Variables to fill in:
- [BRIEF / PLAN / PIECE OF WORK] — the artifact you’re testing
- [ROLE] — the perspective you want; pick one with a strong opinion
- [PASTE THE FULL DRAFT] — the actual content, not a summary
What to expect: A list of 4–8 gaps. Some will be obvious (“you didn’t define ROI”). The valuable ones are usually the ones you didn’t see — an assumption you made about the audience or channel that doesn’t hold up.
Follow-up prompt
Of the gaps you listed, which two will move the work forward the most before I ship? Walk me through how you’d close each one in 30 minutes or less.
Prompt 3: Personify the expert
Best for: Making the AI’s recommendations more actionable when the default answer feels like a Wikipedia summary.
Why this prompt: Sean flagged this from the webinar chat — assigning the AI a specific role and constraining its standard (“top 5%”) changes the texture of the answers. Bob’s reframe: think of yourself as a chief workflow officer talking to a chief operating officer. Both of you are operating at the strategic level, not the task level.
Primary prompt
You are my [ROLE — e.g., COO, head of brand, channel strategist]. You’ve been doing this for 20 years.
Do not recommend anything to me unless it would be considered a top 5% practice in your field. If something is standard advice, say “this is standard” and skip it.
The decision I’m trying to make is: [DECISION].
Here’s the context: [PASTE CONTEXT FROM YOUR DATA PUDDLE — customer interview notes, segment data, last quarter’s results]
Walk me through what you would do, in order, with the reasoning behind each step.
Variables to fill in:
- [ROLE] — pick a specific expert role, not a generic title
- [DECISION] — the actual question, framed as a decision (not a research request)
- [PASTE CONTEXT FROM YOUR DATA PUDDLE] — your unique inputs; this is what separates a top 5% answer from the open-internet average
What to expect: A short list of 3–5 strong moves with reasoning, not a comprehensive overview. If the answer drifts back into “best practices” mode, repeat the constraint.
Follow-up prompt:
Of those moves, which one would your most cautious peer disagree with — and why are they wrong?
Prompt 4: Coach yourself on your own questions
Best for: Closing the loop after a successful AI session so the next one starts from a stronger baseline.
Why this prompt: Bob’s editorial tip toward the end of the webinar — when a chain produces a great answer, ask the AI which of your questions did the work. Save the strongest 2–3 to a “questions library” doc. The next time you brief a similar campaign, you start three turns ahead.
Primary prompt:
Look back at our entire conversation in this workspace.
Of all the questions I asked, which 2–3 were the most strategically valuable — meaning they produced information or decisions I couldn’t have reached with a single prompt?
For each one:
- Quote the question I asked
- Explain what made it work
- Give me a generalized version I could reuse on a different topic
Variables to fill in: None — this prompt runs against the conversation history in your workspace.
What to expect: A short list of 2–3 questions with a reusable template version of each. Save these to a running doc — they’re worth more than any single answer the AI gave you.
Follow-up prompt:
What’s a question I should have asked but didn’t, and what do you think the answer would have been?
Tips for better results
- Stay in one workspace. A workspace or project keeps memory across turns. Without it, every chain starts from zero and the compounding effect Bob describes never kicks in.
- Confirm before continuing. When you ask for a multi-turn cascade, tell the model to wait for your “yes” between turns. It stops the model from running ahead with assumptions you’d correct.
- Bring your own data. The puddle matters more than the prompt. Bob’s point in the webinar — proprietary plus open-source data is what produces decisions competitors can’t replicate.
- Push back on first answers. If turn one is generic, say so. “Be more specific” or “What does a senior do here that a junior doesn’t?” — these one-line nudges reshape the rest of the chain.
- Save the questions, not just the answers. Answers are perishable. The questions that produced the answer are reusable.
See these prompts in action
Want to see Bob and Sean walk through each of these patterns live? The full webinar shows the back-and-forth that builds the chain, the moment Sean’s “100 examples” prompt led to him not needing the AI anymore, and Bob’s framing of the puddle as the brain you build over time.
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