Questions to ask a founder about what they would change

Start by understanding why the broad question does not work. When you ask a founder what they would do differently, they have to choose from years of experience on the spot. Most pick something safe and general, such as starting earlier or trusting their instincts. Those answers are not false, but they teach little. A narrower question gives the founder something specific to remember, and it usually brings out a more honest answer.

So ask about a moment. Instead of 'what would you do differently', try 'what was the hardest month in the first two years, and what was happening?' or 'think of one decision you were unsure about. What did you do?' A moment has a shape: something happened, someone was involved, a choice was made. You will hear more detail and, often, more candour.

Then ask about what they knew at the time. People tend to judge their past decisions by how they turned out, which is unfair to their earlier selves. A question like 'what did you know when you decided, and what did you not know?' lets the founder describe the decision as it looked then. It also teaches the listener something real about deciding without full information, which is what most business decisions are.

Take money, people and customers one at a time, because founders often have a different story for each. On money you might ask how long it was before the business paid them anything, what they lived on in the meantime, and what they spent on that turned out not to matter. Do not ask for figures. Many founders will not give them, and they are not needed to understand the experience. If they offer a number, treat it as one person's account at one time and not a rule.

On people, you might ask about the first person they hired or worked with. What did they get right about that choice, and what did they miss? What would they ask a candidate today that they did not ask then? If the founder works with family or a partner, you can ask how they agreed who decided what, and when that was hard. These are sensitive topics, so listen carefully and do not push for names or details about others.

On customers, ask who the first ones really were and how they were found. Ask what customers wanted that was not in the plan. Ask what the founder assumed about customers that turned out to be wrong.

Ask about advice, too. 'Was there advice you were given and did not take?' is one of the more revealing questions, because it shows the founder's reasoning and sometimes their regrets. A follow-up, 'were you right?', is often answered with a pause and an honest reply. You can also ask who they would speak to first if they were starting now, which tells you where they think good help comes from.

Ask what is still hard. Founders are often asked about success and rarely about what remains difficult. 'What is the thing you still have not worked out?' can be the most useful question in the room, because it tells you that experience does not remove difficulty. It also reassures listeners who think they are the only ones still struggling.

Ask what they would say to somebody starting this month, and what they would say not to worry about. The second gives you permission to leave something out, which new founders need as much as a list of tasks.

Now think about how to listen. Notice what is particular to their business: their city, their customers, their time, the stage they were at. A founder who ran a manufacturing unit a decade ago may have lessons that do not apply to an online service started last year. Before you apply an answer to your own plan, ask whether your situation is similar in the ways that matter. If you are not sure, ask the founder: 'would this apply to a business like mine?'

Avoid asking for anything that puts the founder in a difficult position. Do not ask them to name competitors, former employees or partners. Do not ask for their income, their profit or how much they have invested. Do not ask for legal or tax advice. They are not in a position to give it for your case, and it can be misleading to treat their experience as if it were. If a founder declines a question, accept it without comment. A person who feels free to decline usually answers the next question more openly.

Finally, say thank you, and if it is appropriate, follow up. A short message a week later, saying what you took from the conversation and what you did with it, is rare and is remembered. It also makes it more likely that the founder will agree to talk to the next person who asks.

A good conversation with a founder does not give you a plan. It gives you better questions to ask yourself, and a clearer sense of what you are choosing when you decide to start, to stay, or to grow.