We Must Unlearn Having All the Answers

“Dad, how do I figure out which companies I should work for?”

My 21-year-old’s question caught me off guard. For a moment, I felt that familiar urge – the one that makes parents everywhere launch into a PowerPoint-worthy presentation of life advice. After all, I had decades of experience, an MBA, and strong opinions about every industry from tech to toothpaste.

But then I remembered the expensive lesson I learned about having all the answers.

See, I built my career on being the smartest person in the room. From fourth-grade spelling bees to corporate boardrooms, my superpower was always having the right answer. Every gold star, every promotion reinforced what became my life’s operating system: knowing equals success.

Until it spectacularly didn’t.

I remember it like yesterday. Standing in the empty conference room at 9 PM, staring at the wreckage of our failed project on the whiteboard. Two million dollars and six months, gone.

All because I couldn’t say three simple words: “I don’t know.”

The journey to that moment likely started thirty years before, in Ms. Menezes’ fifth-grade class. I was that kid – hand always up, answer always ready. My identity became wrapped around being the smartest person in the room. Every gold star, every “Good job, Adi!” reinforced what would become my life’s operating system: knowing answers equals success.

The programming served me well, or so I thought. Top grades, great colleges, fast-track career. By 40, I was the guy everyone came to for answers. My opinions were treated with respect. Certainty was my superpower.

Until it wasn’t.

The project seemed straightforward – modernize our global capabilities for the Data age. As the lead executive and strategist, I had all the answers (don’t I always?). When Sarah, a new to our team, product manager, asked about our fundamental assumptions during an early design meeting, I dismissed her concerns with well-practiced authority. “Trust me,” I said, “I’ve done these types of programs a dozen times.”

Six months later, watching our entire effort crash and burn in front of the Board, those words tasted like ashes. Sarah’s “basic” question had identified a critical flaw in our approach. My reflexive need to have the answer had blinded me to the right questions.

That night, staring at the whiteboard, I had my wake-up call.

Naval Ravikant’s words echoed in my head: “The closer you think you are to knowing everything, the further you are from learning anything.”

I’d become so invested in being right that I’d forgotten how to learn.

The next morning, I did something that was radical for me at the time: I went and met my CEO and admitted I was wrong (his generosity and support surprised me – that is another story). Next, I called a team meeting and admitted I was wrong. The silence was deafening. Then Sarah spoke up: “So what questions should we be asking?” Just like that, everything shifted.

Over the next three months, we rebuilt the program from scratch – this time leading with curiosity instead of certainty. Every meeting started not with answers, but with questions. “What if?” became our mantra. “I don’t know – let’s find out” became our battle cry.

The result? We delivered a product that exceeded every target. But the real transformation wasn’t in the project – it was in us – me and the team.

Five Practices that have changed everything for me.

1. The Three-Second Pause: Before answering any question, I force myself to wait three seconds. This tiny gap breaks the autopilot of instant answers.
2. The Wrongness Journal: Every evening, I write down one thing I was wrong about. It’s uncomfortable, but it’s rewarding to see how each mistake leads to growth.
3. The Question Wall: My office now has a wall dedicated to questions. Team members add their “dumb” questions anonymously. Often, these questions spark our biggest breakthroughs.
4. The 70/30 Protocol: In meetings, I aim to listen 70% (or preferably 90%+) of the time and speak 30% (or less). When I speak, I prioritize questions over statements.
5. The Learning Circle: Monthly meetings with three colleagues where we share our uncertainties and learnings. No answers allowed – only questions and discoveries.

Today, when people ask me the secret to success, I tell them this story.

As Adam Grant says, “The hallmark of an intelligent mind is not having all the answers. It’s knowing what questions to ask.”

The world doesn’t need more answering machines – AI has that covered. What we need are question-askers, uncertainty-embracers, curiosity-cultivators. The future belongs not to those who know, but to those who learn.

Start your day with these power questions:

• What am I curious about today?
• What assumptions need challenging?
• Where might I be wrong?
• What questions haven’t I asked yet?

That project failure? It turned out to be a great personal success. It taught me that leadership isn’t about having all the answers – it’s about creating spaces where questions can flourish.

So next time you’re tempted to be the smartest person in the room, try being the most curious instead. Trust me – or better yet, don’t trust me. Question everything, starting with this essay.

We’re all just doing our best to figure it out.

Assume Positive Intent!

Adi