The safe bet fallacy

2 Dec

If ever there was a square peg in a round hole, it was me when I walked into my first corporate role after leaving the military.

My dreams had been shattered by the discovery of an eye condition I never knew I had. The career I'd built and the skills I'd developed suddenly felt next to useless in a corporate banking environment.

I arrived with three qualities: curiosity, values, and a high rate of learning.

I was up against university-qualified people. Experts who knew the industry inside out. People with MBAs and years of experience in finance.

I had none of that.

What I did have felt "nice" but not enough. Not in a world that valued pedigree, credentials, and safe bets.

Then something happened that changed everything.

A leader saw something in me I didn't see in myself.

While I was staying late, asking questions, diving into problems no one else wanted to touch he was watching. Not my resume. Not my credentials. My appetite to prove that I belonged.

He hooked me into teams driving company-wide strategy, transformation, and growth. High consequence projects that required figuring things out. Problems that didn't have playbooks.

And I thrived.

Not because I knew more than anyone else. But because I asked simple questions, adapted when things changed and tried to connect the dots that others missed in the spirit of trying to learn as fast as possible.

That's when I realised something: In the right context, curiosity, values, and learning speed aren't just "nice to have." They're essential.

Fast forward to 2019.

I was CEO at a growing healthcare diagnostics company, and we needed software engineers. These were critical hires who would help build the platform that would power our entire business.

We interviewed several candidates. Impressive resumes. Big company experience. One had worked at a well-known tech unicorn. Another had a decade of domain expertise.

I also asked a young engineer to apply who interned with me at a previous company.

Quiet. A little nervous. No big brands on their resume.

They studied our business. They asked questions that showed understanding of the technical challenges and the mission. And when we gave them a small project to test their thinking, they came back with ideas we hadn't considered.

They were hired.

Within months, they were considered invaluable. Not because they knew everything. But because they learned at an extraordinary rate, were insatiably curious with a clear set of values.

That hire taught me something I wish I'd understood earlier: The most valuable people aren't the ones who know the most. They're the ones who combine values and curiosity to learn the fastest.

These people have what I call adaptive capacity.

Here's the problem most CEOs face.

We overvalue experience and undervalue adaptive capacity.

We're drawn to long resumes, brand names, and domain tenure believing these reduce risk. We hire people who've "done it before" because it feels safe.

But in high-disruption environments, experience often fossilises into rigidity. The business evolves faster than the leader can. The playbook that worked three years ago doesn't work today.

And suddenly, you've staffed your team with people who were great for the business you used to be, not the one it’s becoming.

The consequence? Slow thinking. Slow decisions. Slow adaptation.

Instead of shaping the market, your organisation starts reacting to it.

Leaders protect old playbooks instead of creating new ones.

Innovation cycles degrade.

You fall behind competitors with higher learning velocity.

You get frustrated that "no one moves fast enough".

Unaware that you hired for stability, not speed.

In the AI-driven era, this problem has become existential.

The half-life of skills is shrinking. What someone learned five years ago is increasingly less relevant. What they can learn in the next six months is everything.

If you thought curiosity was a soft skill, it’s now one that drives survival.

Values aren't about culture fit. They're about decision-making under pressure when there's no playbook.

Learning speed isn't a bonus. It's the foundation of scalable leadership.

But here's the challenge: How do you actually hire for this?

How does a hiring manager know what good looks like when it comes to curiosity, values, and learning speed?

How do you justify that decision to your CEO or board when the market rewards "a safe pair of hands" over what might be more valuable but feels like a wildcard?

Indicators help.

Measurable, observable markers that tell you someone has adaptive capacity.

Here's what I look for:

1. Pattern recognition across contexts
Ask: "Tell me about a time you applied something you learned in one domain to solve a problem in a completely different one."

People with adaptive capacity connect dots and see parallels. If someone can only talk about their narrow domain, that's a red flag.

2. Speed of updating their worldview
Ask: "What's something you believed strongly three years ago that you've completely changed your mind on? What caused the shift?"

People with adaptive capacity aren't attached to being right. They update when new information arrives. If someone can't name a significant shift in belief, they're not learning fast enough.

3. Comfort with ambiguity
Ask: "Describe a situation where you had to make progress without clear direction. How did you decide what to do?"

High learners don't freeze when there's no playbook. They experiment, gather feedback, and iterate. If they need perfect clarity to move, they'll struggle in a growth environment.

4. Curiosity as a default mode
Listen for questions during the interview. Do they ask thoughtful, clarifying questions? Or do they just answer what you ask?

High learners are naturally curious. They want to understand context, constraints, and why things are the way they are.

5. Values under pressure
Ask: "Tell me about a time you had to choose between delivering a result and doing what you believed was right. What did you do?"

People with adaptive capacity don't compromise integrity for speed. They find ways to do both or they make the hard call and own it.

When I’m hiring today, these questions live in every expression of interest and job advertisement.

What actually changes

While pedigree matters, when you start hiring for learning speed, curiosity and values your team transforms.

You stop chasing "perfect resumes" and start seeking "high-velocity learners."

You build a team that evolves as quickly as your strategy does.

You create an organisation where people quickly digest information, update their thinking and thrive in ambiguity.

And you (as the CEO) stop being frustrated that no one moves fast enough, because you've hired people who were built for speed.

The bottom line

Your business can't scale faster than your team can learn.

So here's my question for you: Are you hiring for the business you used to be, or the one you're becoming?

What if your next hire wasn't the "safest" candidate, but the fastest learner?

What would that unlock?

Reply and tell me.

I read every email.

I’ll see you next Wednesday.

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The Partnership Playbook Podcast

Here are this week’s podcast episodes.

PARTNERSHIPS MOMENT

EP 143 - 12 min: How Go-To-Market leaders can reverse slowing growth. This episode breaks down the four symptoms slowing your revenue momentum and gives you simple, practical ways to regain clarity, control, and confidence. Learn how to build a pipeline based on truth (not hope), remove buyer risk faster than you add value and use partners to restore momentum and accelerate growth. Listen on Apple Podcasts | Spotify

LEADERSHIP MOMENT

EP 141 - 8 min: How to match energy with workload to drive growth and become a more effective CEO. When energy drops, CEOs don’t just feel tired — they lose clarity, emotional steadiness, strategic judgment, and the ability to lead partnership-driven growth with intention. In this episode learn how to make sharper, calmer decisions by aligning your physiology with the outcomes you expect. Listen on Apple Podcasts | Spotify

CEO INTERVIEW

EP 142 - 46 min: David Homan. In this episode, David Homan shares how relationship orchestration, not transactions, is the core ingredient to partnership growth. You’ll learn how to turn relationships into non-linear growth engines, his 5-principle framework that outperforms traditional networking and the biggest mistake people make after saying thank you (and how to fix it). Listen on Apple Podcasts | Spotify

When you're ready, there are four ways I can help you:

1. CEO Coaching: For CEO’s who want to lead with clarity and grow their business without sacrificing what matters most. A tailored 12-week experience with three interconnected elements: scaling you as a leader, elevating how you lead others, and creating conditions for sustainable business growth.

2. The Partnership Lab: A 6-week experience for founders, CEOs, and GTM leaders who are done with slow growth and stalled conversations. Learn to rapidly qualify and prioritise high-value partners, Install a system that turns conversations into contracts and capture outsized returns from partnerships that scale. Apply to join the first 2026 cohort today!

3. Join a free masterclass: Each week I pull back the curtain on frameworks, tactics, and real-world partnership strategies you can put into play immediate. Invite your team and bring your questions. This is your time.

4. Leadership Events: From Cochlear and Lifeblood to military leaders, I have shared inspiring stories and practical frameworks and insights that shift how leaders leverage partnerships for growth. Book me to speak at your next conference, offsite, or leadership event.

Looking for something different? Send me an email.