On Hacker News on 25 April 2026, one commenter wrote: "It's a really bad sign if they keep asking you the same questions." (news.ycombinator.com, item 47898274.) It is a fair worry. It is also only half the picture, because the same behaviour has two very different causes.
Two causes that look the same
- The person did not take the answer in. That is a coaching question, and it is rare when the answer is short and clear.
- The answer was never written down, or it changes, or it lives only in the founder's head. Then every new person has to ask, and every new person will ask again when they forget the details.
A test you can run this week
- Pick one question you have answered more than twice.
- Ask two other teammates the same question. If they ask you too, the problem is the answer, not the person.
- Write the answer in two or three sentences and add the date.
- Check whether the answer is the same as the one you gave last month. If it is not, you have found a rule that was never decided.
What to do about each cause
- If it is the person: give them the written answer and ask them to read it before the next question.
- If it is the process: write the answer once, put your name and the date on it, and send everyone to the same place.
- If the answer keeps changing: decide it, then write it. The repeats are often a sign of an undecided rule.
Make asking cheap and the answer stable
The goal is not fewer questions. New people should ask. The goal is that the second person to ask gets the same answer as the first, without you typing it again. A clone that answers only from answers you approved, and says so when it does not know, is one way to do that. A shared document with dates is another.
Try it
AskMyStartup is in private beta. You can join the waitlist from the buttons on this page, and you can try a made-up example on the home page without signing up.