The Best Explainer in the Building

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I’ve started asking a question early in first conversations with founders.

“Who in your company explains what you do as well as you do?”

Most pause. Some laugh. A few name someone (usually a head of sales or a co-founder), then immediately qualify it. “Well, she’s close, but she doesn’t quite…”

The majority just say: nobody.

And they say it like it’s a compliment.

That’s the tell.

Not because they’re wrong. They probably are the best explainer in the building. The explanation probably never transferred either. “I’m the only one who can explain this” isn’t a sign the company is doing something genuinely complex or special.

What Happens When the Story Never Transfers?

I was talking to someone recently who’d spent years inside mid-market software companies, usually brought in to close exactly this gap: between what leadership believed and what the market was actually hearing.

He told me about one company. Language translation business trying to expand into customer experience. Real product. Real capability. CEO who couldn’t hold the story together in a room.

They ran decent campaigns. Booked conference slots. Put together the decks.

But at every industry event, they sounded like everyone else. The CRM company, the web content management company, the translation company: all saying the same things, in the same order, about the same customer outcomes. Nobody could tell them apart. And the CEO couldn’t cut through it either.

The story had diluted (not good) to the point it couldn’t transfer.

I was the fractional CMO for a startup building technology to connect people. I spent more than a year shaping its narrative. But every meeting with the founder brought another flood of direction: what the product should do, what it could become, what else we needed to explain.

The team would work to make one version clear, then leave the next meeting with more to absorb and reconcile. Whatever we clarified was still subject to the next thing in his head.

This spilled into investor meetings. Members of the team would disagree, in front of potential investors, about what the company was.

I raised the overwhelm in a one-to-one. We agreed that the company’s purpose was connecting people. Then I asked why he wasn’t addressing the team’s concerns.

“If you can’t handle it, Matthew, maybe this isn’t the right environment for you.”

That was the moment I understood why the narrative work couldn’t stick. We could edit the words, but we couldn’t hold him to the decisions those words represented. When the team pushed back, he questioned their capacity. His own role in creating the confusion stayed outside the conversation.

What Does Being the Sole Explainer Cost?

Here’s what that costs.

When you’re the only one who can explain the company, every room you’re not in is a liability. Your VP of Sales walks into a meeting. Does their best. Gets the category right, maybe. Loses the thread on why it matters. Comes back with a qualified lead that’s actually the wrong ICP, or a deal that’ll churn in eight months because the buyer’s expectations were set on the wrong premise.

You won’t find out until later. Much later.

Inside the building, it’s slower and harder to see. The same decision comes back three times. Product wants to go one direction, sales another, marketing a third. None of them are exactly wrong, because nobody has zeroed in on and stated specifically why the company exists now, not at its founding. They briefed from the founder’s explanation. They didn’t absorb it.

That accumulation, the gap between what you mean and what your organization can act on without you translating it again, is what I call narrative debt. Not the dramatic kind. Just the quiet drift that happens one meeting at a time, until the story your company is telling is a faint copy of the story you started with.

Why Does Being the Only Explainer Feel Like Leadership?

I’ve watched founders find this flattering.

The keeper of the vision. The one who holds it together. Indispensable in a way that feels like leadership.

I get why it’s appealing. It looks like leadership from the outside, for a while. Then they scale.

The team doubles, then triples. New markets. New hires who weren’t in the early rooms, didn’t hear the original conviction, working from copies of copies. Each remove, the story softens. The specificity leaks. What started as “we exist because X is broken and nobody has fixed it this way” becomes “we help companies with their Y process.” Which sounds exactly like every other company helping companies with their Y process.

Here’s a sobering number. Roughly one in three companies that raise a Series A never make it to a Series B. After Series B, the failure rate drops to about 1%. That stretch of growth is where narrative debt compounds, whether or not a round sits at either end of it. Not in the financials. In the explanation and whether it tells or shows. Telling is about the how and what. Showing is about the why and who. Don’t get me wrong, you need the how and what. But if that is all you have, you are telling and not showing. When you give people a reason to care by including other people (who) and their problems (why) they will sit up and listen. Better yet, they will remember. Better yet, they will tell others.

But if the founder or CEO doesn’t show people why to care? Well, one day they look around and realize their company has become the kind of company they set out to disrupt.

What Does a Story Built From the Outside In Look Like?

The counter-example is worth naming.

An example founder I’ve heard described like this (not a client), Tomer London, co-founder of Gusto, had an unusual habit. He would deeply engage in customer conversations and try to understand what the customer was working through, in their language, not his.

A laundromat. A convenience store. A veterinary clinic. Didn’t matter. He adjusted. He listened for the need underneath the question. He asked owners to explain things he didn’t understand. One opening was: “I’m not from here, can you explain to me what this means?”

Those conversations changed their direction. They thought enterprise platforms would love their payroll API. The response was lukewarm. Small-business owners, meanwhile, had an urgent problem they wanted solved. First Round’s interview

That’s not a communication skill. That’s a belief that the customer’s problem is data: that the explanation will never be complete if it is never factored in.

His story transferred because he built it from the outside in. He reflected their reality back at them, with his solution in the middle.

I think about this often. Most founders I meet are still on the inside looking out, explaining their vision outward, waiting for the market to catch up. What London did was the opposite: he let the market explain itself to him first, then built the story around what he heard. That’s rarer than it should be.

What’s Happening in Rooms You’re Not In?

So here’s the question I’d put to any founder who thinks they’re the best explainer in the building.

What’s happening in rooms you’re not in?

Not hypothetically. Actually, go find out. Ask your VP of Sales to explain the company to you like you’re a prospect they’ve never met. Listen for what falls out. The edges that soften. The specificity that disappears. The moment they go from crisp to approximate.

That gap, between your version and their version, is the exact size of your exposure.

It’s not a reflection of their ability.

It’s a reflection of what you never actually transferred.

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Want to know what actually transferred? Book a 20-minute narrative diagnostic. I’ll show you where the story leaks.

Not ready for a conversation? Take the narrative assessment first.

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