The Specific Question: Unlocking Business Stories

Most people insist their own work is too ordinary to be a story. The truth is almost never the work; it’s that nobody has asked a question specific enough to make them go looking for it.

I run a version of the same exercise in a lot of the workshops I facilitate, and it never fails to surprise the room. I’ll talk for a while about finding stories in everyday business moments, like customer calls, team decisions, the small wins that turn out to reveal something bigger, and I watch people nodding along, agreeing with the idea in principle.

Then, reliably, someone raises a hand and says some version of: “But what if my work isn’t interesting?”

The room usually goes quiet when it happens. A few people nod. You can tell the rest are thinking it too; they just hadn’t said it out loud yet. That’s the actual barrier, and it isn’t technique or talent; it’s the belief that your own work isn’t “story-worthy,” and it’s remarkably common even among people doing genuinely interesting things every day.

The story is almost never actually missing. What’s missing is a question specific enough to make someone go looking for it.

What finding actually means

A woman in one of these workshops told me she worked in procurement. She said her work involved nothing dramatic; it was all spreadsheets and vendor calls. I asked her one thing: had a vendor ever let her down at the worst possible time?

She laughed. Last Diwali, she said, their packaging supplier had ghosted them two weeks before a product launch. She spent an entire weekend calling seventeen suppliers across three states, trying to find someone who could deliver in time. At 11 p.m. on a Sunday, she found a small vendor in Tirunelveli. They delivered in four days. They’re still her company’s supplier today.

That’s not a spreadsheet story, I told her. That’s a story about resourcefulness, pressure, and relationships.

She smiled, the kind of smile that comes from noticing something about your own life you hadn’t realized was there. I hadn’t invented anything. The seventeen phone calls, the specific city, the specific hour, all of it had already happened, exactly as she described it, long before either of us was in that room.

The only thing that changed was a question specific enough to send her looking for it instead of reaching for the flat description of her job that came to mind first.

That’s the pattern I’ve come to trust more than almost anything else in this work: the story is very rarely missing. What’s missing is a question specific enough to make someone stop summarizing their life and start remembering it.

The pattern, tested question by question

Over time, I’ve settled on a small handful of questions that work this way across almost any team or organization, and I lead with the same one most often: if you had to explain your organization’s culture to a new joinee, what three stories would you tell?

Not values. Not “we’re a fast-paced, collaborative team.” Actual stories, like things that happened. People almost never answer right away. They go quiet for a second, thinking, and honestly, that pause is the answer. The real culture is sitting in memory, not in whatever’s written on the careers page.

A second question does similar work: if the newest person on your team sat through your last presentation, would they walk out understanding why their work matters? Can you point to the exact moment that would have landed for them, or the moment it wouldn’t have? Most people say “yes” fast, then quietly take it back a few seconds later, once they try to name the actual moment.

A third: what’s a mistake or a screw-up that people around here still bring up months later? Not what happened, but what happened after. How a place handles its own failures tells you more than anything printed on a wall ever will.

A fourth, and the one that tends to land hardest: whose name keeps coming up when people say “this is just how we do things here”? And what’s the story about them? Culture usually isn’t a policy. It’s a person everyone keeps quoting, whether that person realizes it or not.

None of these four take longer than a few seconds to ask, but together they usually surface more of an organization’s real culture than a values workshop manages in a full day.

How to ask it yourself

Every one of these questions shares the same structural trick, and it’s worth naming directly: they ask for an event, not an opinion.

“What are our values” invites a summary—a compressed, pre-approved answer that was probably written by someone else, for a different purpose, at a different time. “What three stories would you tell” invites a memory, and a memory has details in it that a summary never keeps: a city, an hour, a supplier’s name, a wall between two houses. Those details are exactly the raw material a story needs, and they show up only when the question is specific enough to push someone past the summary they’d otherwise default to. This works the same way whether you’re asking about a company’s culture or a single vendor relationship; the mechanism doesn’t care how big the subject is, only how specific the question is.

This is also why the pause matters so much. When someone hesitates before answering, it isn’t because they don’t have an answer. It’s because they’re searching actual memory instead of retrieving a rehearsed line, and that search takes a beat longer. I’ve started treating the pause itself as useful information: the longer it runs, the more likely what comes out afterward will be something real, something that hasn’t been said in quite that shape before.

None of this is a writing skill, though it’s easy to mistake it for one. The seventeen phone calls happened. The Tirunelveli vendor happened. The mistake everyone still brings up happened; all of it existed, in full, before I ever asked a single question about it. The discipline reduces to two things:

• Get better at asking questions that request a memory instead of a description.
• Get comfortable sitting in the pause that follows while someone goes looking for one.

Most workplace conversations run on the flat version by design, with questions like “how’s it going,” “anything interesting happen this week,” questions built for a quick, low-effort answer, not a real one. Nobody’s being dishonest when they say “fine, same as usual” to a question like that; they’re just answering accurately, given how little the question actually asked for.

So, when someone tells me their work or their team is nothing special, I’ve stopped trusting my own first instinct to agree. It’s rarely true, and it’s rarely a judgment worth taking at face value; it’s usually just the answer to a question nobody has bothered making specific yet. The procurement story sat quietly behind the word spreadsheets for months, waiting for someone to ask about a vendor letting her down instead of asking how her job was going.

Once you notice how often that gap exists between what someone will say about their work in general and what they’ll say about one specific day in October, you start to see it everywhere, in almost every team, in almost every organization, including your own.