The Three Worst Types of Questions
The average child asks about 73 questions a day, while the average adult asks about 20.
Asking questions seems to be one of the few skills that we get progressively worse at as we get older.
Some might disagree and suggest as we know more, we ask fewer questions.
But Children not only ask more, they ask better questions. Unknowingly, they often use the Socratic method in every line of questioning:
Child: Why do I need to go to school?
Parent: To get good grades, Timmy!
Child: Why do I need to get good grades?
Parent: To get into university!
Child: Why do I need to get into university?
Parent: To get a job!
Child: Why do I need a job?
Parent: Stop asking questions, I need to get to work.
In many ways, being a venture capitalist is like being a professional questioner. Every day you ask founders questions, you ask customers questions, and you ask yourself questions.
Unlike most professions, where you are highly skilled at the profession itself, many venture capitalists may be unaware of what makes a good or bad question.
Including myself, most of all. I’ve had to re-learn the entire process.
When I started asking questions, I would fall into a few of these traps:
Trap One
Me: What do you think of this company?
Industry Expert: I think it’s the worst idea I have ever heard.
Me: Okay awesome, thanks, just wanted to check.
Trap Two
Me: [Waffling 350 words about a really complex topic that makes me sound smart] Do you agree?
Founder: Sure mate! Such a great question. That’s exactly what we are building.
Trap Three
Me: What is your big 200-year vision of the company?
Founder: Save the entire human species with my SaaS product.
Me: Wow so much ambition, can we invest?
I have fallen into all of these traps hundreds of times. I didn’t learn that I was asking such poor questions until I read the The Mom Test by Rob Fitzpatrick. Between what Fitzpatrick lays out in the book and my own learnings, I have come up with three cardinal sins of question asking.
Sin One — Opinions Over Facts
Me: What do you think of this company?
Industry Expert: I think it’s the worst idea I have ever heard.
On the surface, the mistake here is not obvious. It’s only obvious in contrast to an example of good questioning.
Me: In your industry, how many hours does it take the average radiologist to do X?
Industry Expert: About 4 hours but [insert some qualification].
The purpose of asking a question is not to gather opinions, it is to gather facts. It is a ruthless data extraction process where you are competing against the subjectivity of a wildly irrational beast — humans.
The purpose of questioning is truth seeking.
The enemy of truth seeking is questions that elicit answers that are generic, opinions or speculations about the future. Questions need to be designed to extract data about actual behaviour, past or present.
Now, let’s say the company did something in diagnostic AI and we are trying to find out whether it is a good idea. The key is to never ask the expert what they think, or at least wait to ask until the very end, once we have extracted every data point we can.
Instead, a great question elicits facts. In this case, the facts we need revolve around whether the company is solving a real problem. We can figure this out by understanding the specifics of how long it takes a radiologist to solve the problem with legacy tools.
The truth is you don’t even need to ask the expert for an opinion on the company. It is your job as a venture capitalist to form an opinion on the company as an investment opportunity.
If you have data on the exact nature of the problem, and you have data on how solutions are evaluated, you can likely deduce whether it’s a good idea.
Every time you ask for an opinion, as opposed to actual qualitative data, you expose yourself to more errors and biases in human thinking. Many hotel experts would have told you that Airbnb would never work.
But all of them would have told you that high fixed costs and variable demand were the hardest part of running their business.
Go figure.
Sin Two — Exposing your Ego
Me: [Waffling 350 words about really complex topic that makes me sound smart] Do you agree?
Everyone has an ego. Everyone likes to feel smart, often at the expense of hearing the truth. A cardinal sin of asking questions is exposing your ego. Now this trap is esoteric, let me explain through example:
Ego: I am going to ask a question, but first let me pretend I am smart by saying smart stuff. Oh by the way, I want your answer to this question to agree with me because I really like what I am saying and think it’s right.
Responder’s Ego: I should say what this person wants to hear. That will make us get on better.
Basically, every time you ask questions, you expose your ego. This can be your motivation for asking the question, your desire for a particular answer or even your fear of being wrong. The respondent is also a social being. Their ego will not want to conflict with yours.
The outcome is a disaster.
They will not give you accurate data. Instead, it will be highly infected data that only confirms your viewpoint. It is the equivalent of asking your mum if your idea is good.
Mum: It’s the best idea ever honey!
But there are gradations of exposing your ego. Some are so subtle you may not even be aware of it.
Me: Would you buy this solution for yourself?
Responders Ego: Just say yes, it’s probably the whole point of this 30-minute call, don’t want to ruin it.
Here it is very subtle, but your ego has exposed that you have an invested interested in someone buying this product. It could be because you built it, you’re selling it, or you’re investing in it.
Either way it taints data extraction.
The better way to figure out whether it is valuable:
Me: How long does X take you to do? How much is your hourly salary?
This formula allows you to quantify exactly how much the problem is worth to a radiologist.
Note: Be weary, when the user is not the buyer, it complicates things…
Sin Three –Piercing the veil
Me: What is your big 200-year vision of the company?
Founder: Save the entire human species with my SaaS product.
Me: Okay.
Big picture questions can be useful, but are terrible if you don’t pierce the veil. Socrates was the undisputed GOAT.
Piercing the veil is Socratic questioning. This involves continually asking questions until you get to the core of the reasoning.
Founder: Save the entire human species with my SaaS product.
Me: Save them from what?
Founder: From a life of boredom and despair.
Me: In which situations would they most commonly experience boredom and despair?
Founder: When using their email.
It is an art to employ Socratic questioning without being confrontational, but it has a very high yield. It allows you to peel through vagueness and fluff to understand the essential properties of something.
Thank you for reading, here is some bonus content from The Mom Test:
Good Questions
● Why do you bother?
● What are the implications of that?
● Talk me through the last time that happened?
● Talk me through your workflow?
● What else have you tried?
● How are you dealing with it now?
● Where does the money come from?
● Who else should I talk to?
Bad Questions
● Do you think it’s a good idea?
● Would you buy a product which did X?
● How much would you pay for Y?
● Would you pay X for product which did Y?
