Sample Prompts to Engage AI as Your Strategic Thought Partner

Unlocking AI as a Thought Partner for Strategic Clarity:

I want to use you as my Strategic Thought Partner, but I’m not sure where to begin. To help me uncover high-value use cases, I’d like you to interview me one question at a time. Start by identifying areas where AI can best support my leadership, decision-making, or strategic planning this week. Then, continue guiding me through follow-up questions to refine my thinking and maximize value."

Generating Breakthrough Insights for a Key Business Challenge:

I need you to act as my Strategic Thought Partner by engaging me in a structured problem-solving process. Here’s the situation: [provide necessary context]. My goal is to [state objective]. Please challenge my current assumptions, ask clarifying questions, and help me think through alternative solutions. I’d like you to surface blind spots and uncover insights I may have overlooked.

Stress-Testing Our Strategic Plan for Long-Term Success:

Attached is our strategic plan. I want you to critically evaluate it by asking me one targeted question at a time to challenge my biases and assumptions. Do we have a truly differentiated approach? Are we accounting for future uncertainties? Is our execution strategy realistic? Once you have enough information, provide a summary of our plan’s strengths, key vulnerabilities, and your recommendations for strengthening it.

Pressure-Testing Our Strategy Against Market Realities:

Help me assess my current strategic plan in the context of emerging trends and our internal capabilities. Where does our strategy align well with macroeconomic forces, industry shifts, and competitive pressures? Where are we most vulnerable? Identify gaps, overlooked opportunities, and areas where we may be overestimating our strengths or underestimating risks.

Executive-Level Challenge: Strengthening Strategic Resilience:

Review our strategic plan for the upcoming fiscal year as if you were an executive coach. Your role is to challenge our thinking and assumptions. Are we being ambitious enough, or are we playing it safe? Is our plan resilient enough to withstand unforeseen challenges? Are we too reliant on ideal conditions? After this exercise, provide your evaluation of our plan’s robustness, identify improvement areas, and offer actionable insights to ensure we’re positioned for long-term success.

Designing a Strategic Review Rhythm for Sustainable Growth:

I’m the leader of [describe your business]. We’ve just completed a strategic off-site where we developed our plan for the year. Now, I need to establish a structured review rhythm to ensure we stay accountable, track progress, and make necessary course corrections. As a growth-minded operations expert, help me design this review process. Start by identifying up to three key questions I should answer during each review cycle to gain deeper insight into execution. Then, ask me these questions one at a time. Once we’ve refined the key focus areas, generate a draft of the review rhythm, and I’ll provide feedback.

Quarterly Strategic Review: A CEO’s Deep Dive:

Act as my Strategic Thought Partner to conduct a structured quarterly strategic review of my business. Interview me one question at a time, focusing on these four key areas:

1. Strategy: Are the actions we are taking today setting us up for sustainable competitive advantage in the long term?

2. Execution: What measurable progress have we made toward our strategic plan this year? Where are we falling short?

3. People: Do we have the right people in the right roles, and are they empowered to succeed? How can we enhance talent alignment?

4. Technology: Are we leveraging technology to improve efficiency, drive innovation, and create more value for customers?

After walking through these areas, summarize your observations, identify blind spots, and highlight the top three priorities I should focus on over the next 90 days.

Unlocking Non-Obvious Growth Levers to Double Revenue:

Our goal is to double revenue within the next 24 months to position ourselves as an attractive acquisition target. Attached is our strategic plan. I want you to act as a strategic growth expert to challenge our thinking and surface non-obvious levers we might be overlooking. Start by asking me up to five targeted questions to understand our business model, current growth drivers, and constraints. Once you have enough context, provide a prioritized list of actionable recommendations—each with a clear rationale on why it matters and how it contributes to our growth objective.

Structuring a High-Impact Business Case for Productivity Gains:

I need your help crafting a compelling business case for an initiative to improve employee productivity across our organization. For context, we are [insert company details]. Please structure the business case around these key sections: (1) What We Are Trying to Achieve & Why It Matters – Define the problem, the opportunity, and why solving it is critical to our success; and (2) How It Will Impact the Organization – Quantify the expected benefits, such as efficiency gains, cost savings, and employee engagement improvements. As we go through this, challenge my assumptions, suggest additional insights I may have missed, and help refine the case to make it as persuasive as possible for internal stakeholders.

Structuring a High-Impact Business Case for Productivity Gains:

I need your help crafting a compelling business case for an initiative to improve employee productivity across our organization. For context, we are [insert company details]. Please structure the business case around these key sections: (1) What We Are Trying to Achieve & Why It Matters – Define the problem, the opportunity, and why solving it is critical to our success; and (2) How It Will Impact the Organization – Quantify the expected benefits, such as efficiency gains, cost savings, and employee engagement improvements. As we go through this, challenge my assumptions, suggest additional insights I may have missed, and help refine the case to make it as persuasive as possible for internal stakeholders.

Inspiration for these prompts came from The AI-Driven Leader by Geoff Woods