20 AI Prompts Every Leader Should Try
- Kristen Ann
- Aug 21
- 2 min read
Leaders today are under more pressure than ever—balancing vision, execution, and the human side of leadership in fast-changing environments. AI can be a powerful thought partner, but the questions you ask matter just as much as the answers you receive.
Here are 20 AI prompts that help leaders think differently, uncover blind spots, and sharpen their leadership impact. Use them in journaling, strategy sessions, or when you need fresh perspective.
Rethinking & Reframing
“Let’s think about this differently: what’s a completely new way to approach [challenge]?”
“What am I not seeing here about my strategy or leadership style?”
“Break this down for me as if I were brand new to the situation.”
“What would my competitors (or critics) say about this decision?”
“What assumptions am I making that could limit my options?”
Strategic Growth & Vision
“If I were designing this company for the first time today, what would I do differently?”
“Fast-forward 5 years: what story will people tell about my leadership?”
“What are three scenarios where this plan could fail—and how can I prepare for them?”
“What would a bold, disruptive version of this strategy look like?”
“If money and resources weren’t a factor, what’s the most visionary path forward?”
Leadership Presence & Influence
“How can I communicate this decision with clarity, confidence, and empathy?”
“What leadership gaps might my team notice that I don’t?”
“What words or stories will build trust fastest in this situation?”
“What would an inspiring leader I admire do in my shoes?”
“What else should I know about how this message might land with different audiences?”
Self-Awareness & Growth
“What patterns show up in how I lead under stress?”
“If I asked my future self for advice, what would they say?”
“What leadership habits bring out my best—and which ones hold me back?”
“What would my team thank me for changing in the next 90 days?”
“How can I bring more presence, curiosity, and impact into my daily leadership?”
The real power of these prompts isn’t in the AI generated answers——they open space for reflection and growth. As a coach, I see myself as a thought partner who helps leaders pause, challenge assumptions and reimagine what’s possible. Think of AI the same way: not as a machine that simply gives you information, but as a partner that surfaces new perspectives, asks sharper questions and pushes your thinking further. When combined, coaching and AI can accelerate clarity, creativity and impact in your leadership journey.
Book your complimentary strategy session here.
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