Vance Sterling

Archives
Log in
Subscribe
May 12, 2026

A Prompt Framework for Executive Decision-Making

Most executives use AI wrong.

They use it to write emails. To summarize documents. To draft slide decks. Those are fine. They're also a waste of the most powerful decision-support tool ever created.

Today I'm giving you a framework for using AI where it matters most: strategic decisions.

The DECIDE Prompt Framework

I've developed a six-part prompt framework that turns any AI assistant into an executive decision advisor. Each letter is a prompt component:

D — Define the Decision

"The decision I'm facing is: [describe the decision clearly]. The timeline for this decision is [deadline]. The stakeholders affected include [list them]. The constraints I'm operating under are [budget, politics, regulation, etc.]."

Don't skimp here. The more context you provide, the better the analysis.

E — Explore the Options

"Generate 5 distinct options for this decision, including at least one unconventional or contrarian option. For each, describe the approach, the likely outcome, the risks, and the resource requirements. Don't limit yourself to the options I've already considered."

That last line is key. You're using AI to expand your option space beyond your own biases.

C — Challenge the Assumptions

"What assumptions am I making about this decision that might be wrong? What would a skeptic say about each option? What information am I missing that could change the analysis? Be contrarian."

This is where AI earns its keep. It will challenge assumptions you didn't know you had.

I — Identify Second-Order Effects

"For my top two options, map the second and third-order effects. What happens after the initial impact? What downstream consequences might emerge in 6, 12, and 24 months? What might break that isn't obvious?"

Most leaders optimize for first-order effects. Second-order effects are where strategies fail.

D — Design the Decision Criteria

"Help me build a weighted scorecard for this decision. The criteria should include [strategic alignment, financial impact, execution risk, organizational readiness, speed to value]. Weight them based on what matters most in this context."

Now you have a framework, not a gut feeling.

E — Evaluate and Recommend

"Using the scorecard, evaluate each option. Score them honestly. Then give me your recommendation — and tell me what would have to be true for a DIFFERENT option to be the better choice."

That last clause is crucial. It tells you the conditions under which you should change your mind.

Try This Monday

Take the hardest decision on your plate right now. Run all six prompts in sequence. It takes about fifteen minutes. The clarity it produces would normally take weeks of meetings and consultant interviews.

The leaders who will thrive with AI aren't the ones who use it for admin tasks. They're the ones who use it for the decisions that shape organizations.

— Vance Sterling

Don't miss what's next. Subscribe to Vance Sterling:
← Newer The Weekly AI Leadership Toolkit: What to Ask Your Team Every Monday Older → The Strategic Alignment Test Most Leaders Fail
Powered by Buttondown, the easiest way to start and grow your newsletter.