Ask the RIGHT Questions with AI

Most data work starts with the wrong question:

“What can we show?”

But the best data storytellers flip it:

“What must we decide?”

This single shift decisions first, data second is the difference between noise and insight.

And now, thanks to AI, it’s easier than ever to start where it matters most:
Inside the mind of a strategic leader.

Why This Step Changes Everything

When data teams start by pulling data, they often end up guessing what leadership cares about. That leads to cluttered dashboards, vague presentations, and missed opportunities.

But when you start by asking what they need to decide, everything sharpens.

Clarity goes up. Relevance goes up. Action goes up.

AI can help you get there, fast.

Try This One-Liner Prompt

Use this with ChatGPT or your favorite AI tool:

Act as a [ROLE] at [COMPANY]. List the 3 most important, decision-driving data questions we need answered first. Keep them specific and concise.

That’s it.

With this one line, you unlock the top-of-mind priorities of your audience, even if you’ve never been in their seat or unable to connect with them.

Here are three real-world examples:

1. SaaS Sales Leader

Prompt:
Act as a VP of Sales at a B2B SaaS startup. List the 3 most important, decision-driving data questions we need answered first.

AI Response:

1. Are we on track to hit our Q3 pipeline goals by segment?

2. Which reps are consistently underperforming and why?

3. Which lead sources are converting into revenue most efficiently?

What This Does:
It surfaces decisions, where to double down, who to coach, and what to fund, not just performance metrics.

2. Head of Operations

Prompt:
Act as Head of Operations at a national logistics company. List the 3 most important, decision-driving data questions we need answered first.

AI Response:

1. Where are we seeing delivery delays and what’s causing them?

2. Which warehouses have the most throughput variation?

3. How do our labor costs compare to volume trends?

What This Does:
It directs focus to bottlenecks, resource planning, and performance optimization.

3. Marketing Director

Prompt:
Act as a Marketing Director at a consumer tech brand. List the 3 most important, decision-driving data questions we need answered first.

AI Response:

1. Which campaigns are generating the highest ROI this quarter?

2. What content formats are driving the most engagement by audience segment?

3. Where are we losing potential customers in the journey?

What This Does:
It shapes campaign strategy, creative decisions, and messaging priorities.

Take Action

The next time you start a project, don’t lead with “What data do we have?”

Start with:

• What must be decided?

• Who’s deciding it?

• And what questions are keeping them up at night?

Then plug that into AI and let it surface the top 3 questions you should answer with data.

This one prompt is one of the most powerful ways to instantly:
✔ Align with leadership thinking
✔ Clarify your data story
✔ Deliver insights that get used

Want to Master the Rest of the Process?
We teach business professionals how to think, talk, and deliver like data leaders inside Data Story Academy.

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See you next week!