Questions you should be asking more often

The best answers founders gave when asked: what’s one question you wish was asked more often?

Can you teach me something that you’re passionate about?

As VC’s, we spend much of our time asking questions — tons of them. We’re constantly refining our questions and looking for the right ones, to help us more deeply understand specific startups and make better decisions. We believe that insightful questions can be powerful.

So at the end of each of the 20+ founder interviews we conducted, we asked founders: what’s one question you wish was asked more often? A few interviewees were a little stumped. Others gave surprising answers on topics including purpose, passion, and failure. Here are some of the best answers — and food for thought. (Feel free to scroll to the bottom for the full list!)

Questions to dig deeper

Dr. Pamela Contag, CEO of BioEclipse Therapeutics

I’m from Minnesota in the Midwest. We have a reputation for being direct. One of the questions I like to ask is: Why do you think that? What makes you think that? I’m trying to understand someone’s point of view and the source of their thought. Where did you hear that? Where’s the data? I think if more people could frankly discuss their answers and their positions, we would find that we have a lot more common ground than we think.

Ed King, CEO of Openprise

Investors don’t ask this question often, which I find very strange. They don’t ask: why did you start a company? Or for people who are looking to start a company, they don’t ask: why do you want to start a company? I think you should try to really understand why — not the media version.

Dr. Joe Choi, COO of Hypercare

I think people should be asking themselves more often: Why am I doing this? The answer could be as superficial or as deep as you want it to be. But a lot of people just do things, without thinking about the value or implications of what they’re doing.

I work in healthcare administration and I know how complicated a hospital is. So I’m always one to simplify. My approach to life and work is always to ask: why am I doing this? What is the value of doing this?

As an extension, I also try to think of why someone else is doing something. That builds sensitivity and empathy to understand the other person and where they’re coming from. Then, if you have conflicts or interaction with them, you can better understand them.

At the end of the day, if you don’t have empathy, and you have to work with people in the manner that I do, it makes your life a million times harder. So if I get frustrated or caught in conflicts, I have to stop and ask myself: Why am I having this reaction? Why am I doing these actions that may be counterproductive? Having that conscious check on yourself is really beneficial.

Jonathan Tan, CEO of Coreshell Technologies

What is your personal journey? Often, it’s really easy to talk about the company. As founders, we get asked a lot of questions about our startups and spend a lot of time talking about our companies. But really thinking about the personal entrepreneur’s journey is also important because it fuels the direction of the company. As founders, we have a lot of influence on the culture. The way we run the company really affects how our employees act and how the company continues to grow. So I think understanding personal journeys is really important.

Questions on failure

Dr. Pamela Contag, CEO of BioEclipse Therapeutics

One question that people ask and then don’t really listen to the answer to is: what are some of your important failures? It’s a hard question to ask and answer, but sometimes it’s good to vocalize the failures.

Dr. Lisha Li, CEO of Rosebud AI

What did you fail at? It’s easy to fixate on the success stories. I would love to have more podcasts where it’s like: tell me about all the things you failed at. Just so people have a really good distribution and there’s not confirmation bias for success stories or confusion about which features actually matter.

Questions on purpose and passion

Dr. Gabriel Sanchez, CEO of EnSpectra Health

No one ever really asked: Are you proud of what you do? That’s a good question. There are a lot of places you can go and you can turn a crank and make some money. But there are a lot of those cranks out there that don’t really excite me. I want to make something impactful and different. I am immensely proud of what we’re doing here and what our team has been able to accomplish.

As a leader, you should not want to be anywhere else. That’s a good sign that you’re probably working on something worthy. I’m proud because I think it’s the right thing to do.

Albert Tai, CEO of Hypercare

Can you teach me something that you’re passionate about? It’s a really cool question, so you can learn something out of every conversation.

Dr. Igor Ivanov, COO of Axbio

Questions are usually for specific situations. But if I talk to someone, I like to ask: What do you want to do as a person? And you can tell. Some people want to work in a nice place, some people want to have fun, some people want to work on cancer.

Other specific questions

Dr. Kiana Aran, CSO of Cardea Bio

Instead of asking questions about challenges women face in male-dominated fields, I hope that people ask: How can we motivate more women to join this field and to become leaders? This provides a more positive angle. If we really want to see change in society, we must support each other and lift each other up.

Akilesh Bapu, CEO of DeepScribe

As a startup founder, you run into new challenges every day. You always have to answer questions and work through problems. Employees and customers are coming up with problems that they want you to solve. One question I think everyone should ask more to themselves is: What would it take to fix this myself? Instead of running into problems and automatically asking for a meeting, they can ask, what can I do to fix it myself? Probably 60 to 70 percent of the time, they’ll find that they can probably answer it themselves.

List of all questions:

• Why do you think that? What makes you think that? Where did you hear that? Where’s the data?
• Why did you start a company? Why do you want to start a company?
• Why am I doing this? What is the value of doing this? Why am I having this reaction? Why am I doing these actions that may be counterproductive?
• What is your personal journey?
• What are some of your important failures?
• What did you fail at?
• Are you proud of what you do?
• Can you teach me something that you’re passionate about?
• What do you want to do as a person?
• How can you motivate more women to join this field and to become leaders?
• What would it take to fix this myself?

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Tsingyuan Ventures is a $100M seed-stage technology firm. We back technical founders across software, life sciences, and frontier technologies. Learn more about our origin story and our approach here.

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