What CEOs Get Wrong About Their Own Story

After fifteen years of extracting stories from high-performing execs and elite athletes, I’ve found that the most valuable insights are the ones that they almost never mentioned, because they’d stopped registering them as interesting a long time ago.

The Questions No One Asks

Every leader has a prepared, rehearsed version of their story. It’s the one they reach for whenever they’re asked the standard questions, which is almost every time. The problem is that the rehearsed answer is the version the market has already heard, so it carries no real signal, and what should be a demonstration of expertise ends up as repeated noise dressed in the language of substance.

The real material surfaces when a leader is forced to think in real time. That's where the genuine insight lives. But asking the unexpected question is only half the discipline. The other half is knowing where to dig once you’re in. A good extraction is a constant calibration of which thread to pursue and which to leave alone, of recognising the throwaway line that warrants more questions and the impressive-sounding answer that leads nowhere.

I’ve sat across from World Cup winners and people at the absolute peak of their profession, and the difference between a forgettable conversation and a genuinely revealing one is almost always whether I was prepared to make them think rather than feeding them the questions they were expecting. Deference to status produces the rehearsed answer every time, whereas challenge, paired with the judgement to know where to dig, is what produces the real one.

For most CEOs, this dynamic plays out constantly. Executive profiles, podcasts, and panel appearances ask the expected questions, receive the expected answers, and the leader walks away sounding indistinguishable from every other leader in their category. That's Signal Loss, the misalignment between a leader's institutional expertise and their external market perception, happening in plain sight, and the leader rarely even recognises it's occurred.

Why Are CEOs Bad at Telling Their Own Story?

When you’re deep inside your own story, two distortions take hold of your judgement. The moments that feel significant to you often carry very little weight externally, and the moments that feel mundane, the small and obvious things you’ve done a thousand times, are frequently the ones the market actually needs to hear.

This matters because entertainment storytelling and business storytelling operate on completely different principles. In entertainment, you manufacture interest to hold an audience’s attention, because anyone could be watching and the entire job is retention. Business storytelling works on a different basis entirely. People don’t engage with a leader’s story to be entertained, they engage to learn something, to understand how this person actually operates, and to take something applicable away from it. The learning lives in the small, non-obvious, seemingly mundane detail that the leader doesn't even register as interesting, not in the grand outcomes that occupy headlines.

The Detail That Gets Buried

I spoke with a CEO at an event last year who’d turned around a company that had been close to failing. He walked me through the restructure, the strategy, and the numbers that eventually recovered, because to him those were the story. The detail he dismissed as barely worth mentioning was that in his first week he’d moved his desk out of the corner office and onto the operations floor, right next to the team handling customer complaints, because he wanted to hear the actual problem before making a single strategic decision. He treated that as a footnote when it was the entire story.

The same dynamic is visible in leaders the whole market already knows. Indra Nooyi ran PepsiCo for twelve years, and there’s no shortage of material on her strategy, the acquisitions, and the financial performance. But the detail that has always stayed with me is a much smaller one: she used to write personal letters to the parents of her senior executives, thanking them for the gift of their child. She wrote over 400 of these letters a year. This is the kind of detail that never surfaces in the headline version of a CEO’s story, and it tells you more about how she built loyalty at the top of a global organisation than any earnings call ever could.

Why It’s So Hard for a CEO To Do This Alone

It’s genuinely difficult for anyone to surface their own buried detail because they aren’t objective about their own experience, and objectivity is the entire requirement.

Think about yourself. Every moment in your story carries emotional weight, and that emotion has already sorted what counts as important and what doesn’t, usually incorrectly. The detail that feels routine gets classified as routine precisely because you’ve lived it so many times that it’s lost its significance, and proximity isn’t something you can simply decide to override.

What Surfacing It Actually Changes

Two things shift when the buried detail finally comes to the surface, and it’s the combination of the two that matters.

First, authority rises. When an audience encounters the real detail, they finally understand the mechanics of how you reached the level you’re operating at. The actual decisions and instincts that produced the result, rather than the headline version of it, are what build genuine authority. That understanding is different from the hollow recognition that comes from reciting a list of achievements.

Second, and this is the more subtle shift, you become human without becoming vulnerable. The audience recognises that you aren’t superhuman, that you’re someone who made specific decisions in a specific way to arrive where you are, and that recognition creates a real connection without costing you anything in credibility.

The conventional storytelling advice tells you to be vulnerable, to open up and show weakness. That approach quietly trades authority away in exchange for relatability. Surfacing the buried detail achieves something different, because it builds connection and authority simultaneously, through specificity rather than confession. You humanise yourself through how you operate, and that distinction is what protects your standing while still allowing people to connect with you.

The Story Is Already There

The most valuable part of your story is almost always the part you consider unremarkable, and you will continue burying it for as long as you are the only person examining it. Telling your own story well isn’t a matter of effort or openness, it requires a perspective that isn’t emotionally invested in your version of events, one whose entire purpose is to locate the thing you’ve stopped being able to see.

The detail that makes you genuinely worth listening to almost always already exists, buried under the version you believe you're supposed to tell.

About the author

Karan Kashyap is a former psychometric interviewer for Gartner and filmmaker for the Premier League. He has spent 15 years of his career extracting and codifying trapped expertise, from elite athletes to high-performing executives. Both disciplines trained the same capability: identifying what makes a leader credible and building it into a format the right audience trusts. He is the founder of Blackwood Row, where he works with high-stakes leaders to install their authority as permanent market infrastructure.