Question Before Answers
The business owners I’ve sat with over the past thirty years are good at solving problems. What I see far less often, and what I think deserves more attention than it usually gets, is a willingness to pause and question whether the problem being solved is actually the right one. Not because owners lack curiosity. Most of the people I work with are genuinely curious. But curiosity about a problem and the habit of examining the question that frames it are not the same thing, and the difference is least visible to people with the most experience.
There’s a story, almost certainly untrue, but attributed to Einstein, that I’ve been thinking about since I came across it. Two workers enter a chimney to clean it. One emerges with a dirty face; the other comes out clean. The question: which one goes to wash? The immediate answer, the one with the dirty face, feels sound, until you see that it’s wrong. The clean-faced worker, seeing a dirty colleague, assumes he must be dirty too and goes to wash instead. But the more revealing observation isn’t about which answer is correct. It’s that the scenario is logically impossible. You cannot enter the same chimney under the same conditions and emerge with different outcomes. There is no valid answer to the question. The flaw is in the question itself.
For anyone who takes their decision-making seriously, and most leaders who’ve been running businesses for ten or fifteen years or more do, for good reason, that’s a genuinely uncomfortable idea. Because it describes something that can happen to capable thinkers: arriving at a question that invites real intelligence, that rewards careful reasoning, while the question itself was never quite right to begin with.
The reason I think this happens so consistently among experienced owners and founders is connected to what experience actually does to the way we think. Over time, leaders build an internal shorthand. A situation presents itself, and before it has been properly articulated as a question, the mind has already begun mapping it to something familiar, a challenge navigated before, a pattern recognised, a similar difficulty that was eventually resolved. This process is efficient, often appropriate, and genuinely useful in many contexts. But it quietly compresses the gap between “what is actually happening here?” and “what should we do about it?” in ways that are almost invisible from inside the business. The question gets assumed rather than examined. Assumptions embedded at the level of the question tend not to surface in the answer; they simply shape it, often without anyone noticing.
What makes this particularly hard to address is that experience also confers real credibility, both to the person who has it and to those around them. When you’ve navigated a hiring crisis, a difficult client relationship, a cash flow problem, or a restructuring, the template you’ve built from those experiences carries an implicit authority. You reached for it before, and it worked, or at least it resolved the situation. What’s harder to notice is that the current situation might not actually fit the template. That the question drawn from experience is quietly leading everyone toward a familiar answer when the real problem is something different entirely.
I had this illustrated for me in a way, during my years working in the hospitality industry. As an area manager, I arrived at one of my restaurants early one day and was greeted by a young team member named Sophie. Rather than the standard welcome in the training manual, she asked me something else entirely: “What brings you to the restaurant today?” It stopped me. That wasn’t what she’d been trained to say. But as I sat eating lunch and watched Sophie greet every subsequent guest with the same question, what she was doing became clear. She wasn’t deviating from her training carelessly. She was trying to understand what each person actually needed before deciding how to help them.
The results were visible. A family celebrating a birthday had dessert recommended before they’d ordered their mains. An elderly couple visiting the area for the first time left with a list of Sophie’s recommendations for where to go next. None of this came from the standard script. All of it came from one better question asked at the start of each interaction.
Her manager, Paul, had been telling her to follow the training (and, to be honest, that was my first reaction when I met Sophie!). He wasn’t wrong to value consistency. But he had never examined the assumption underneath it, that the standard question produced the best outcome. The script existed, and its existence felt like evidence of its own rightness. Nobody, including me as the area manager, making regular visits, had ever thought to ask whether it was the right script in the first place.
The psychologist Chris Argyris called this single-loop thinking: correcting behaviour to fit an existing model without ever questioning whether the model is sound. Its alternative, double-loop thinking, doesn’t ask “are we doing things right?” It asks, “Are we doing the right things?” Sophie had arrived there instinctively. Paul and I, between us, had not. Experience can make you better able to answer questions. It can also make your assumptions feel so settled that they stop feeling like assumptions at all.
In my work helping businesses build the operational and strategic foundations they need, the systems, the processes, the conditions that give leaders space to think clearly rather than reactively, I see this most often in three areas, though not in any tidy order. In operational decisions, owners tend to refine existing processes rather than question whether those processes were ever properly constructed. The conversation becomes about how to make something work better, when the more useful question might be: why does it exist in that form at all? In strategic planning, the destination tends to get assumed before the planning begins, meaning the entire conversation becomes about the route, and the destination itself is never quite examined. And in succession, where the personal weight of the question means it’s often framed in ways that protect the owner from its full implications, rather than honestly examining what the business needs when they’re no longer at the centre of it.
In each case, the difficulty isn’t intelligence or commitment. It is proximity. Years inside a business build capability, but they also build filters. You cannot easily see the frame you’re standing in.
This is where independent perspective has genuine value, though I want to be careful about what I mean by that, because the standard advice to seek outside opinion is often far less useful in practice than it sounds. A significant number of experienced owners have sat across the table from an advisor who listened with apparent openness, asked what looked like probing questions, and then reflected their existing thinking back to them in more structured, and considerably more expensive, language. That is not an independent perspective. That is validation. And validation doesn’t challenge the question. It helps you pursue the wrong one with greater confidence and greater cost.
What actually useful independent observation looks like is someone willing to say, before any conversation about solutions or strategy begins, that they’re not certain the right question is on the table. That is an uncomfortable thing to hear when you’ve been running a business successfully for twenty years. It can feel like a challenge to your judgement. But the discomfort is part of what gives it value. An outsider who hasn’t spent years inside your assumptions can see the frame in a way you cannot. Whether they choose to share that observation or soften it to a point of recognition and move on to more comfortable territory is where the real difference lies.
Sophie’s story has stayed with me not only because of what she achieved with a better question. It stays because of what it required: an environment where she felt free enough to look past the script and ask something more useful. That permission doesn’t exist in every business. And the cost of its absence tends to accumulate quietly, in decisions made with real confidence on foundations that were never quite examined.
The question worth sitting with isn’t whether you’re solving your problems well. Most experienced owners are. The question is whether the questions underpinning those problems were the right ones to start with.
Have a brilliant week!
Dave Rogers – The Business Explorer
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