Over the past week or so I have been running mentorship sessions with female entrepreneurs across 17 countries of Eastern Europe and Central Asia, as part of the She’s Next Hackathon 2025.
Different markets, different industries, different stages of growth. Yet in every session, I noticed the same pattern: the real shifts didn’t come when I offered an answer. They came when I asked a question.
It’s easy to assume mentorship is about expertise—the mentor dispensing wisdom, the founder scribbling down solutions. But the truth is more subtle. The most valuable role of a mentor is not to provide a ready-made answer—at the end of the day, as a mentor you only see a small fraction of the idea, the struggle, the process. It’s to ask the question that reframes the challenge, that shifts the ground just enough for someone to see what they’ve been missing.
Creating new space
In one conversation, a founder asked me how to position her product against a competitor. I could have given her a handful of tactical suggestions—tweak the messaging, sharpen the pricing, double down on features.
Instead, I asked: What game could you play that your competitor isn’t even in? That question changed the entire discussion. It shifted the focus from defending territory to creating new space.
In another session, a founder wanted advice on scaling a service model. She was knee-deep in operational detail—optimising systems, balancing costs, running scenarios. My question was simpler: If you were starting from scratch tomorrow, would you build this the same way? The silence that followed was telling. The answer, eventually, was no. Which meant the real problem wasn’t scaling—it was letting go of a structure that no longer fit.
These aren’t tricks. They are reminders. Reminders that the hardest part of reinvention is rarely what you don’t know. It’s what you’re certain you already do. When a mentor—or anyone, for that matter—asks the right question, it cuts through that certainty. It forces you to examine your assumptions.
Stretching perspectives
And it’s not only founders who need this. Businesses of every size are guilty of asking the wrong questions. How do we keep up? How do we protect market share? How do we improve this process by five per cent? These are questions of maintenance, not transformation. They keep you in orbit around the same problems.
The best questions are those that stretch perspective: What do our customers no longer expect from us—because no one has delivered it yet? What are we still doing simply because it once worked? What would we design if we weren’t weighed down by legacy systems, sunk costs, or pride?
Reinvention doesn’t start with a plan. It starts with curiosity. With the willingness to replace easy answers with harder questions. It’s in those moments—when silence follows, when the familiar script breaks—that growth begins.
As I watched the founders this week wrestle with those shifts, I realised the value wasn’t in me providing clarity. It was in them finding it for themselves. The mirror mattered more than the map.
So if you want to future-proof your business—or yourself—don’t start with solutions. Start with the questions you’re avoiding. Because the quality of your reinvention will always depend on the quality of your questions.
And sometimes, the question that makes you pause is the one that moves you forward.
Photo: Dreamstime.
