Who's Really Driving the Car?

By this time, you know how much I value community. As our boys become more involved in activities inside and outside of school, we've discovered entirely new circles of people. There are the communities that naturally form around sport, music, and extracurricular activities, and then there are the parent communities that accompany them. It's been one of the unexpected joys of this season of life. New friendships, familiar faces on the sidelines, and plenty of opportunities to laugh together.

On Friday evening, AJ’s school hosted its annual quiz night. Twenty-five teams, fiercely competitive regulars, long-standing rivalries, and questions that ranged from delightfully obscure to downright cruel. Our team was a newly assembled collection of parents and friends who had never played together before. Untested chemistry, but some exceptionally bright people around the table. We ended up finishing eighth out of twenty-five, which was a respectable result. We weren't going to win, but with two or three different decisions we probably could have found ourselves on the podium.

The interesting part wasn't our score. It was what our wrong answers revealed about the way we think. For example, they asked which country has the most Michelin-starred restaurants. My instinct immediately said France. It simply felt like the obvious answer. Others around the table had recently travelled through Japan and had experienced just how extraordinary its food culture is. Their recent experience made Japan feel overwhelmingly likely. Their confidence became contagious. We changed our answer.

Er, no. France was correct. And you know what? Sometimes the obvious answer really is the right answer. We often assume the best answer must be more complicated than it is, when in reality we have simply talked ourselves away from common sense. Kicked ourselves.

Another question asked who was South Africa's head of state when the country became a republic in 1961. The options being discussed centred around South African political leaders I'd barely heard of. Yet something didn't sit right with me. There was a small voice saying, "You're missing something." The answer, of course, was Queen Elizabeth II. OF COURSE. But hindsight is an exact science, and this one was clever. South Africa became a republic by leaving the Commonwealth. Until that moment, the monarch remained our head of state.

I knew something was off, but I never trusted that little voice.

The final lesson came from a question that should have been in my wheelhouse. Which television series holds the highest IMDb rating? I immediately thought of Breaking Bad, as I LOVED it. Plus, I've read enough articles over the years that constantly reference it as the benchmark. Someone else suggested it was The Sopranos. They spoke with great certainty, and I abandoned my own answer. Mine was a guess... but an educated one. So was theirs, only expressed with more certainty. As it turns out, Breaking Bad is no 1, Sopranos no 3.

Walking away afterwards, I realised that the evening had been less about trivia and more about psychology.

• We overcomplicate obvious truths.

• We ignore the quiet internal signal that tells us something doesn't fit.

• And perhaps most often, we allow someone else's confidence to outweigh our own evidence.

The fascinating thing is that these aren't isolated moments. Nope, they are neural pathways, patterns, and behaviours. Stephen Covey spoke about our paradigms: the mental maps through which we interpret reality. Daniel Kahneman described the cognitive shortcuts and biases that shape our decisions. The Enneagram takes the idea even deeper. It suggests that each of us develops an internal operating system from childhood, a set of unconscious filters that determine what we notice, what we ignore, what we fear and what we instinctively believe.

Those filters are incredibly useful. They help us process an impossibly complex world. AND they blind us.

A Type One may instinctively look for what needs correcting before noticing what is already working. A Type Three may filter every situation through the lens of achievement and success. A Type Six naturally scans for risks before opportunities. As a Type Seven, I naturally chase possibilities, often assuming the next exciting idea deserves attention before fully interrogating whether it's actually the right one.

None of these perspectives is wrong; they’re just us. They are also just one part of the picture. Therefore, the challenge is not changing your personality. The challenge is recognising when your personality is driving the car without your permission. Bruce Springsteen had a great quote on this in an interview once: “I let that guy in my head drive the car sometimes... but not all the time.”

So, this is where self-awareness becomes one of the highest-leverage leadership skills you can develop, and why I am so stoked about our new enhanced Enneagram AI toolkit.

Over the past few months, I've been building a Claude-powered Enneagram coaching system that combines personality insights with Stephen Covey's Seven Habits. Rather than producing a static personality report, it creates an ongoing coaching conversation. Private Victory first, Public Victory next. Self-awareness precedes team leadership and understanding. It’s great stuff, all with Claude/ChatGPT at your side to help create the mental muscle to elevate your own game and that of your peeps. The kit helps identify where your natural strengths are serving you, where your internal biases may be limiting you, and how those same patterns show up inside your team.

The goal isn't to label people. It's to help leaders recognise the invisible assumptions that influence decisions every single day. And whether you're leading a family, a business or an executive team, your greatest competitive advantage might turn out to be seeing your own blind spots before they become expensive mistakes.

I'm excited to be launching this publicly at Workshop17 on 25 August.

For many organisations, professionally facilitated Enneagram work has traditionally been expensive and difficult to scale. This new AI-enabled approach makes it far more accessible while still preserving the quality of the coaching conversation. Existing coaching clients will receive it as part of their ongoing development work, and we're opening a limited number of places for non-clients who would like to experience the workshop. As part of the attendance, you will receive the Starter Kit with 5 Enneagram profiles baked in.

If you or one of your executives would like to join us, click on this link to check out our Enneagram toolkit to get you started. Registration for our workshop series opens next week.

PG's Pro Tip:

Before making an important decision this week, ask AI to challenge not your strategy, but your thinking.

AI Prompt:

Act as an executive coach specialising in the Enneagram, Stephen Covey's Seven Habits, and cognitive bias. My Enneagram type is [insert type, or ask me questions to determine it]. I am currently facing this situation: [describe the situation]. Help me identify the unconscious biases my personality type is most likely bringing into this decision. Challenge my assumptions, identify what I may not be seeing, explain what my "little inner voice" may be trying to tell me, and give me three questions that would help me make a more balanced, principle-centred decision.

After all, the biggest obstacle to better decisions is rarely a lack of intelligence.

More often, it's the story we've already decided is true.

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