7 sharp questions and prompts to help leaders close the gap between AI potential and performance.
By Graham Rowe
1. Are you using AI at all?
If not today, when last? If it’s not in your rhythm, it’s not in your stack.
Self-check: When did AI last touch your work rhythm—today, this week, or longer ago?
Prompt: Help me audit where AI is already showing up in my workweek—and where the missed opportunities or blind spots might be.
2. Are you querying, conversing, or delegating?
The depth of interaction defines the leverage.
Self-check: Are you just asking questions? Or are you using AI to think through strategy, run repeatable processes or even build tools?
Prompt: Ask me 5 uncomfortable questions about why I still hesitate to delegate real work to AI.
3. Is AI making you faster—or enabling new things entirely?
Speed is obvious. Scope is the shift.
Self-check: What are you doing now that felt out of reach before AI?
Prompt: What’s something I could prototype or test in 1 hour using AI that I would’ve avoided last year?
4. Are you making money with or from AI?
Where it touches the P&L, it’s real.
Self-check: Is AI directly or indirectly improving revenue, margin, or conversion?
Prompt: Where am I overlooking clear opportunities to increase profit with AI—whether in sales, delivery, retention, or internal efficiency?
5. Are you spending money on AI?
Strategic tools usually cost something.
Self-check: What’s your monthly or annual AI budget? Is it a line item or a leftover?
Prompt: Where could I be getting a 10x return on AI spend—in time, talent, or decision velocity?
6. Has it changed your day, your team, your rhythm?
You can feel this in your calendar.
Self-check: What meetings, drafts, or habits have changed because AI now plays a role?
Prompt: Audit how my emails, calls, and meetings could be reinvented to achieve better results with less time and energy—using AI for prep, synthesis, and follow-through.
7. Has it changed how you lead?
Not just output—but orientation.
Self-check: Where has AI nudged your risk appetite, strategy cadence, or leadership identity?
Prompt: What are 3 mental habits or blind spots that routinely distort my judgment as a leader—and how could AI help expose or interrupt them in real time?
