Twelve questions to ask a founder who visits college
The first question put to a visiting entrepreneur is rarely the useful one. Twelve better questions, why each is worth asking, and what to listen for.
Share on WhatsApp
Conceptual image · created with AI
A visiting entrepreneur is one of the few chances a student gets to ask someone who has actually done it. Too often the time is spent on questions that produce polite, general answers: how did you get the idea, what is your advice for students, what is the secret of success.
The questions below are written to get a specific answer. They are not trick questions, and a good founder will be glad to be asked them. Pick the three or four that matter to you, write them down before you go, and be ready to follow up.
What you should come away with
- Ask about specific moments, not general advice
- Questions about the first year are more useful than questions about success
- It is fine to ask about money and fear; a good speaker will answer or decline plainly
- Listen for what the speaker says they do not know
- Write your question on paper if you do not want to ask aloud
- Treat one founder's answer as one example, not a rule
Start with the reason most first questions fall flat. 'What is your advice for students?' invites a general answer, and a general answer can be given to any room. 'What would you do if you started again tomorrow with no money?' invites a specific one. The best questions are about something that happened, something the speaker decided or something they would change. Here are twelve, in rough order from the beginning of a business to the end of a hard year.
1. What were you doing in the year before you started? This tells you what circumstances led to it. Listen for whether they planned the start or fell into it.
2. Who did you talk to before you spent anything? A good answer names kinds of people: potential customers, someone who had done something similar, a family member. If they say they talked to nobody, ask what they would do now. The point is to learn how they tested the idea cheaply, if they did.
3. What did the first version look like? Most first versions are smaller and rougher than students expect.
4. How did you find your first customer? This is the most useful question for most students, because it replaces the idea of marketing with an actual story. Listen for who they were, how the founder knew them, and how long it took.
5. How did you decide what to charge? Pricing is where many first businesses go wrong. Ask what they did, whether they changed it, and what they would say to someone about to name a price for the first time. If they say they got it wrong, ask how they found out.
6. How did you manage money in the first year? You are not asking how much they earn. You are asking how they covered their living costs, what they spent on and what they refused to spend on. Ask whether they kept an income from somewhere else. A speaker may choose not to give numbers, and that is fair. The shape of the answer is still useful.
7. What does a normal day look like now, and what did it look like in the first year? This is a direct way to see what the work is. The answer often shows the work that fills the time, such as following up on payments and fixing small problems.
8. What did you give up? Every choice costs something. It may be income, time with family, holidays or a safer career path. Asking this plainly, and listening to the answer, helps you judge whether you would be willing to pay the same price. A thoughtful speaker will not pretend there was no cost.
9. What did you get wrong, and what did it cost? A good speaker will have a real answer and will not turn it into a boast. Listen for how they noticed, how long it took, and what they changed. Be wary of an answer that is really a strength in disguise, such as 'I worked too hard'.
10. What did people tell you that turned out to be wrong? Everybody gives advice to someone starting a business, and much of it conflicts. This question shows which advice the speaker ignored and why, and it reminds you to be careful with advice, including theirs.
11. What would make you stop? This reveals how they think about risk. Founders who have thought about it will name a limit, such as a time, a sum of money or a sign. Those who have not may say they would never stop, which is worth noticing. It may help you set your own limit if you ever try something.
12. What should I find out before I decide anything? This question hands the speaker the job of pointing you to the next step, and it usually produces a practical answer: talk to five customers, learn to read a basic account, find out what your college allows. Write it down.
If you do not want to ask in front of a room, write your question on a slip of paper or send it in advance through your faculty adviser, if the college allows. Ask one question at a time and leave room for the answer. Do not ask for a job, a loan or an investment from a speaker at a campus talk. That is not what the occasion is for, and it can leave a poor impression. Remember that the speaker is describing one business; another founder may say the opposite.
Finally, listen for the phrases 'I do not know' and 'it depends'. They are signs of an honest speaker. If someone has a confident rule for everything, treat it carefully. The most useful thing you can take from a founder's visit is not their advice, but a sharper question of your own to try out in the week afterwards.