In my last article, I wrote about the first question I find myself asking in almost every founder workshop: What problem are you solving? It sounds remarkably straightforward until you ask it and discover how difficult it can be to separate the problem from the product that has been created to solve it.
Once we have worked our way through the technology, the features and, increasingly, an enthusiastic explanation of where AI fits into the proposition, we usually arrive at something much clearer. Somewhere underneath everything that has been built is a recognisable problem affecting real people or organisations, and once we can articulate that problem without describing the solution, the conversation begins to change.
There is often a visible sense of relief at this point. We have found the problem, everyone agrees that it exists, and it feels as though the difficult part is behind us. Unfortunately, this is usually when I ask the second question: Who exactly has this problem?
The answers tend to arrive quickly. SMEs, ports, healthcare providers, large enterprises, salmon farmers and manufacturers. These are all perfectly credible markets and they look particularly impressive when supported by industry reports showing thousands of potential organisations and billions in total addressable market.
The difficulty is that none of them is actually a customer.
A market segment can tell you where an opportunity might exist, but it cannot tell you why somebody will buy from you. It cannot explain what happened at work yesterday that made the problem suddenly urgent, who is being held accountable for fixing it, whose budget will pay for the solution or which person inside the organisation has enough influence to get the purchase approved.
Only people can tell you that, and this is where the conversation usually becomes considerably more interesting.
Take something as apparently straightforward as selling a technology solution to a port. Saying that ports are the customer gives us a useful place to begin, but very little guidance about how to sell anything. A port is an ecosystem of people, organisations, responsibilities, incentives and competing priorities. The person experiencing the problem may be completely different from the person responsible for solving it, while the person who recognises the value of the solution may have no authority to purchase it. Somewhere else sits the person controlling the budget, and somewhere else again may be someone with enough influence to prevent the entire thing from happening.
Suddenly, “we sell to ports” isn’t an answer at all, but rather the beginning of a much more useful set of questions.
This distinction matters because businesses don’t buy products in the abstract; people inside businesses make decisions. They make those decisions for different reasons, under different pressures and with different definitions of value. The operational user may care about saving three hours every morning, while their manager is concerned about productivity across an entire team. The CFO may only become interested when those lost hours are translated into money, and the CEO may care because the same inefficiency is preventing the organisation from scaling.
It is the same product, solving the same underlying problem, but there are several different versions of value depending on who is sitting across the table.
This is one of the reasons early customer conversations can be so misleading. A founder speaks to potential customers and receives encouraging feedback. People understand the idea, agree that the problem exists and say the technology sounds impressive. Some may even volunteer to see a demonstration or stay informed as the product develops. Everyone leaves the conversation feeling that the market has validated the proposition, yet several months later nobody has bought anything.
What happened?
Quite often, nothing went wrong. The people they spoke to genuinely liked the idea and the only mistake was assuming that interest and intent were the same thing.
There are countless problems we would happily see solved but would never spend money solving ourselves. We tolerate inefficient processes, irritating software, inconvenient services and imperfect experiences every day because changing them requires more effort than living with them. Organisations behave in much the same way. A problem can be completely real and still not be commercially important enough to trigger action.
This is the point at which the question of who has the problem? needs to become more demanding. How painful is it for them? How frequently does it occur? What are they doing about it today? What does that workaround cost them in money, time, risk or lost opportunity? What happens if they do nothing for another year?
Most importantly, is the cost of continuing with the problem greater than the cost and disruption involved in solving it? That is a very different form of customer research from asking someone whether they like your idea.
The purpose of a good customer conversation isn’t to collect compliments or ask people to predict whether they might buy something in the future. It is to understand behaviour. If a problem matters, people usually leave evidence behind. They develop workarounds, create spreadsheets, employ additional people, tolerate expensive manual processes, complain repeatedly, allocate budgets or cobble together several inadequate solutions because nothing better exists. Those behaviours tell you far more about the commercial value of a problem than enthusiasm ever will.
They may also tell you something you weren’t particularly hoping to hear.
Perhaps the customer you assumed would care most about the problem has learned to live with it, while another group experiences it far more acutely. Perhaps the feature the team spent six months perfecting barely registers in customer conversations, while a capability considered almost incidental turns out to be the reason people would buy.
Perhaps the problem itself has changed since the business first began developing the solution.
This last possibility is particularly easy to overlook because product development takes time, while markets have an inconvenient habit of continuing to move.
Customer priorities change, regulation evolves, budgets tighten, new technologies alter expectations and competitors introduce alternatives. A problem that felt urgent when development began may have become less important by the time the solution reaches the market, while a secondary issue may have grown into something customers are suddenly desperate to address.
The more time, money and emotion founders have invested in a particular version of the business, the harder this can be to recognise objectively. Conviction is essential to entrepreneurship, but it also creates a very human tendency to listen for evidence that confirms what we already believe. Customer conversations then become less about discovery and more about validation, with questions unconsciously framed to produce the answers we were hoping to hear.
Some of the most productive moments I’ve experienced in founder workshops have occurred when the evidence does precisely the opposite.
A founder arrives expecting us to sharpen the messaging or work out how to sell the existing proposition, and the conversation reveals that something further upstream needs attention. The customer isn’t who they thought it was and the pain isn’t sufficiently urgent. The person using the product isn’t the person buying it and the value sits somewhere unexpected, or the market has moved while everyone was busy building.
Those can be uncomfortable discoveries, particularly after significant investment, but they are also extraordinarily valuable. Discovering an assumption is wrong in a workshop or a customer interview is considerably cheaper than discovering it after another year of product development.
The founders who navigate these moments best seem to share a particular quality. They have enough conviction to continue pursuing the vision, but not so much attachment to their assumptions that evidence becomes threatening. They allow what they learn from customers to change the business rather than simply using customer research to confirm the business they have already decided to build.
Over time, that understanding begins to influence far more than the product. It changes which customers the company pursues, how the proposition is positioned, how value is communicated, what the business charges, which markets it enters and which opportunities it deliberately walks away from. At that point, customer obsession stops being a product philosophy and becomes a strategic advantage, because the organisation is making decisions from a depth of customer understanding that competitors may not possess.
Perhaps this is why I have become increasingly wary when founders tell me they know their customer and then describe an industry, a company size or a demographic. Knowing where your customers can be found is useful. Knowing them is something altogether different.
It means understanding the problem through their eyes rather than yours, recognising the difference between the person who experiences it and the person who pays to solve it, and being able to distinguish polite enthusiasm from evidence that someone is sufficiently motivated to change their behaviour.
So, once we have answered the first question and can clearly articulate the problem the business exists to solve, I ask the second: Who exactly has this problem?
The answer I’m looking for isn’t a sector, a segment or a market-sizing statistic. I’m trying to understand the person living with the problem, how much it matters to them, what they are doing about it today and whether solving it is important enough to make them act.
Because identifying a large market can tell you that an opportunity exists somewhere. Understanding the customer tells you where to look for it.
And understanding why that customer will change what they are already doing is where an interesting idea begins to look much more like a business.
written by Shannon Weber
