How AI Became My Best Leadership Sparring Partner

The real threat to your leadership isn’t disruption—it’s unchallenged thinking.

When ‘usually right’ starts feeling like ‘always right.’

Successful decision after successful decision builds a protective shell around your thinking. Questions get replaced with assertions. Curiosity gives way to conviction.

The business landscape is littered with companies that fell victim to this exact pattern.

Real-World Examples of Leadership Overconfidence

You know the classics—Kodak invented digital photography only to be killed by it; Blockbuster laughed Netflix out of the room; Nokia focused on hardware while Apple’s software took over everything.

And it’s not just the classics, there’s:

  • Peloton’s post-pandemic collapse when leadership became so certain of their pandemic-driven growth model that they stopped questioning its sustainability.
  • Barnes & Noble where confidence in their established retail model hardened into resistance to digital transformation.
  • WeWork where hyper-growth ambitions blinded leadership to the necessity of profitability, structure, and culture—leading to a failed IPO and leadership collapse.

It’s the same mistake on repeat. When you’re used to being right, you stop questioning your own thinking. And that’s where the danger lies.

The Psychology Behind Leadership Blindspots

This isn’t just a problem for the big players. These traps are wired into how all of us think—especially when success convinces us we’ve “cracked the code.

Here are three cognitive biases that quietly sabotage even the smartest leaders:

  • Confirmation bias: We seek out evidence that proves we’re right and unconsciously dismiss what doesn’t fit our worldview.
  • Overconfidence effect: We overestimate our knowledge and abilities—often assuming we understand more than we do, or that our past wins guarantee future success.
  • Status quo bias: We resist change even when evidence suggests it would be better. Familiarity feels safe, even if it’s not serving us anymore.

Add to this the pressure to appear confident and decisive, and you’ve got the perfect recipe for leadership blindspots that can tank performance, culture, and innovation.

“We’re blind to our blindness. We have very little idea of how little we know.” – Daniel Kahneman, psychologist and author of Thinking Fast and Slow

How I’m Using AI to Challenge My Own Thinking

This is where I think AI is creating an opportunity that goes far beyond efficiency and automation. I’ve been experimenting with using AI as a mental sparring partner, and it’s revolutionised how I approach complex decisions.

Here’s why it’s been so powerful:

  1. It has no ego to protect. Unlike advisors who might hesitate to challenge you directly, AI has no status concerns.
  2. Multiple perspectives at once. It can simulate viewpoints from customers, critics, and future scenarios all at once.
  3. It’s available 24/7 for deep exploration. You can test and refine your thinking iteratively at your own pace, exploring branches of thought that might feel too speculative in a formal meeting.

This isn’t about letting AI make decisions for you. It’s about using it to expand the aperture of your thinking—to see around corners you might otherwise miss.

How to Build Your Own AI Leadership Advisory Board

One approach that’s been a game-changer for me is building my own “Advisory Board” using AI. Think of it like inviting a bunch of diverse thinkers into the room to poke holes in your ideas —without the politics or ego. When I throw a new concept their way, I always get insights I hadn’t considered.

Here’s how to build your own:

5 Steps to Build Your AI Advisory Board

Step 1: Define Your Challenge Start by clearly articulating the decision or challenge you’re facing. Be specific about what you’re trying to solve or achieve.

Step 2: Assemble Your Virtual Advisory Panel

Create a diverse set of perspectives that will challenge your thinking from different angles. Here’s my go-to lineup:

  • The First-Principles Thinker: Questions fundamental assumptions
  • The Innovator: Constantly pushing boundaries and finding creative solutions where others see dead-ends.
  • The Customer Advocate: Considers the end-user experience above all else
  • The Risk Manager: Specialises in identifying potential failures
  • The Industry Outsider: Brings fresh perspective from adjacent fields
  • The Contrarian: Deliberately takes the opposite view

Step 3: Pose Your Challenge

Present your idea or decision to the panel using a prompt like:

I’m considering [your idea or decision]. I’d like to hear how each of these different thinkers would view this approach.

Step 4: Ask Better Questions

Don’t just pitch your idea—get them to poke holes in it. Frame your questions to draw out diverse viewpoints.

  • “What’s the biggest blind spot I might be missing?”
  • “What would you do differently and why?”
  • “What’s one assumption here that needs testing?”

Step 5: Sharpen Your Thinking

Use these insights to evolve your original idea. You’re not looking for consensus—you’re looking for a more robust perspective.

AI for leadership blindspots

What This Is Not

Let’s set some boundaries around what this approach isn’t trying to do:

  • It’s not a substitute for real, human diversity. Lived experience matters. Different perspectives matter. This is a tool to help you prepare for those conversations—not to replace them.
  • It’s not a fit for every decision. This works best for the big, strategic calls—the ones with long-term consequences. When it comes to day-to-day stuff, I find simpler approaches get the job done faster.
  • It’s not about outsourcing your judgment. The AI’s not here to make decisions for you. It’s here to broaden your thinking so your judgment is sharper and better-informed.

What decision are you facing right now that could benefit from this kind of perspective expansion? And what would your AI advisory board say?