There is a question I find myself asking in almost every mentoring session. It doesn’t matter whether the founder is building an AI platform, a biotechnology company, a climate-tech solution or the next disruptive software product. Nor does it seem to matter whether they’ve been working on the business for six months or six years. The conversation almost always reaches the same point, and when it does, I ask a question that appears deceptively simple.
“What problem are you solving?”
You would imagine that founders, having devoted so much of their lives to an idea, would answer without hesitation. Yet the responses are rarely as immediate as you’d expect. More often than not, the explanation begins with the product itself. I hear about sophisticated algorithms, proprietary technology, innovative features, dashboards, integrations and carefully considered product roadmaps. The passion is undeniable, and so is the ingenuity behind what they’ve built.
What I don’t hear, at least not immediately, is the human story.
Somewhere beneath the architecture and functionality is usually a customer who is frustrated, overwhelmed, losing time, wasting money or trying to solve a problem that genuinely matters. Yet that person has quietly disappeared beneath layers of technical explanation. It’s a pattern I’ve seen often enough to recognise that it isn’t really a communication problem, it’s a founder problem.
When you’ve spent months, or even years, building something from the ground up, it’s almost impossible not to see the world through the lens of your solution. Every feature represents a decision, every enhancement reflects another late night, another difficult trade-off, another obstacle overcome. Naturally, you begin to believe that if other people could simply appreciate the brilliance of what you’ve built, they would immediately understand its value.
Customers don’t think that way, neither do investors and if we’re honest, neither do most people. They don’t wake up wondering whether your platform has a better dashboard or whether you’ve integrated the latest AI model. They wake up thinking about the problems waiting for them that day and they’re looking for something that saves them time, reduces risk, makes their lives easier or helps them achieve an outcome they couldn’t achieve before. Don’t get me wrong, the technology matters enormously, it just isn’t where the story begins.
One of the privileges of mentoring founders is that, over time, you begin to notice recurring behaviours that have very little to do with the businesses themselves. They are, instead, observations about people.
One of the most fascinating is the relationship between conviction and certainty. Every entrepreneur needs conviction, as building a company requires an extraordinary belief that something which doesn’t yet exist should exist, despite the market offering very little reassurance in the early days. Without that resilience, very few businesses would survive the inevitable setbacks that accompany innovation.
The difficulty is that conviction has a habit of quietly evolving into certainty. It rarely happens overnight. Instead, it arrives gradually, disguised as confidence. Customer feedback begins to feel like criticism rather than insight and investor questions are interpreted as misunderstanding instead of curiosity. Suggestions to simplify the product become frustrating because they overlook all the complexity the founder worked so hard to create.
Ironically, the market isn’t asking founders to build more, it’s usually asking them to explain less. The founders who consistently impress me are not always the ones with the most advanced technology or the largest funding rounds. More often, they are the ones who remain curious long after everyone else believes they’ve found the answer. They are comfortable changing their minds when the evidence demands it. They test assumptions instead of defending them, and they listen with the understanding that every difficult question is an opportunity to learn something they didn’t know yesterday.
That willingness to learn extends beyond product development and it shapes how they spend money, how they engage with customers and how they define progress. I’ve watched startups invest heavily in looking established before they’ve proven they’re valuable. Beautiful branding, polished launch events, professionally produced videos and offices designed to project success can all create the appearance of momentum.
Yet appearances have an unfortunate habit of convincing founders before they’ve convinced customers. The market is remarkably indifferent to appearances, it responds to value.
Every successful company I’ve encountered eventually arrives at the same place. It develops an almost obsessive understanding of the customer, conversations become more important than assumptions and outcomes matter more than features. The business becomes less interested in talking about itself and more interested in understanding the people it exists to serve.
Perhaps that’s why the question I ask at the beginning of every mentoring session remains the most important one by the end.
“What problem are you solving?”
It isn’t really a question about products, it’s a question about perspective. Because the most successful founders I’ve worked with haven’t simply built remarkable technology. They’ve remained humble enough to remember that their business was never the hero of the story, their customer was.
And once you understand that, almost every strategic decision becomes a little clearer.
written by Shannon Weber
