Good Questions Versus Bad Questions

A good question can show your depth of preparation and thinking; a bad question might be better off not asked.

A.T. Gimbel
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April 23, 2024

Meeting with entrepreneurs, I get asked a lot of questions (as well as ask a bunch myself). Questions are a great way to learn more about something, but there are good questions and bad questions. A good question can show your depth of preparation and thinking; a bad question might be better off not asked. Here are a few examples based on some recent conversations.

Entrepreneurs Asking Questions to a VC:

Bad question: What stage do you invest in?

The information is on our website, so could imply you did not do any research

Good question: I see from your website you invest in early stage companies with check sizes from $X-YM, what are the most important things you look for to invest at that stage?

Shows they did some research, and could even also mention a portfolio company that seems relevant to understand how that deal played out or a specific topic if the website describes some more detail on their investment thesis

Entrepreneurs Asking Questions to Potential Customers:

Bad question: What do you think of my idea?

Biased question (see Mom Test) that will not get much real feedback as most people will say they like it

Good question: You mentioned that doing manual research on a customer prospect was a major pain point - when was the last time that happened and what did you do about it?

Dive deeper into a problem and what they actually did, not what they say they think on a topic

Venture Capitalists Asking Questions to an Entrepreneur:

Bad question: What traction do you have so far?

Without a pitch deck this could be okay and also interesting to see how the entrepreneur defines traction, but if a pitch deck was sent this could imply the VC did not read the deck

Good question: I see you have 10 paying customers; how did you find and acquire them?

Shows they read the pitch deck and focus the limited time in the meeting on a specific topic they care about

There are just a few simple examples. Asking good questions can be a huge plus; conversely asking bad questions can reflect poorly on your preparation.

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