Learning how to ask questions is an essential skill for startup founders

For many of us, learning to ask questions was a matter of the five W’s: who, what, where, when, why (and how).

As I interviewed founders about the most valuable learning resources that allowed them to grow into the leaders they are today, I realized that many of them leaned heavily on carefully crafted approaches to asking questions. In all the interviews, inquiry was by far the most cited learning process. I found these founders to be incredibly methodical, brave, curious, disciplined and efficient in their pursuit of learning.  

Founders showed incredible discipline by approaching information gathering as a structured process. Some founders have a highly systematic approach in how they target their outreach:

I learned by being systematic about talking to people smarter than myself. I needed to know hundreds of people and know what they know. I made a table matrix of who I talk to and for what topic. For example, Eric Schmidt is one of six experts I turn to on establishing management OKRs.

— Reid Hoffman, co-founder of LinkedIn

And in how they catalog/store information about who is an expert …

I kind of “catalog” these people and tap them for their area of expertise rather than constantly “reinventing the wheel.” I email a lot of people about a lot of small things, and in return I’m always responsive when founders ask me questions, no matter how small. The catalog is both in my head but I also have a Google spreadsheet of important contacts — an industry tab, an investor/advisor tab. I send some of them monthly emails. Then I also have a team tab — people who are already part of the team or people who I want to be part of my team. It’s not really that organized — if you look at the spreadsheet it’s not impressive, there’s no formatting, but it’s one of the highest ROI documents I’ve made.

— Sarah Hoffman, co-founder of MakerWine

The systematic nature with which founders approached information acquisition transformed an everyday activity — asking a question — into a skill set that could be honed:

I have learned the most by asking for things. You have to ask everyone and everything for as much help as you can. You have to push a boulder up a hill so you have to ask everyone to help push. It’s a super uncomfortable skill to craft and I’ve had to get good at it for my company.

— Aditi Shekar, co-founder of Zeta

Founders who had honed inquiry as a skill set prepared by making mental shifts to be in a structured “learning mode” and ask simple questions:

When I meet with someone, I approach it like I’m a child. For example, recently, I was trying to get up to speed on yield management. I asked questions like why is it called yield management. I tried to ask as many basic questions as I could. Before I dive into questions I aim to give a lot of context — who I am, why I’m interested, what challenges and opportunities I see. It usually takes 20-30 minutes.

— Chris Bennett, founder of Wonderschool

Some founders preferred to do their own online research before speaking with an expert in a field while others preferred to speak to the experts first, and target their research on expert-suggested resources:

I often do little research before first intro calls where I’m learning about a subject because all the best information is in people’s heads. If I sit down with someone who is an expert and they advise that I read something or speak with someone, I often take that advice. I don’t want to waste time before that though.

— Chris Bennett, founder of Wonderschool

Like many other skill sets, founders optimize the efficiency of asking questions by focusing on speed of decision-making after receiving feedback from trusted sources:

I guess I do have a go-to process but I’ve never thought of it like that. I try to lessen the time it takes to get acquainted with a new idea. Who in my network knows this. I normally start with an email. For example, I needed to get smart on a type of software — I emailed my network and got the same answer that these three companies are the best — so great, I’m going to go with one of them — I don’t need to fact check. If no one in my network knows, then I’ll still delegate/outsource to someone else because I don’t want to spend my time Googling.

— Kristen Jones, founder of Mented Cosmetics 

Founders also thought about inquiry as a skill set whose outcome could be measured:

I know I have reached competency when I can ask three questions about someone’s expertise and these are questions only they can answer, and they say something like, “No one has asked me these questions before.”

— Alan Chiu, co-founder and CEO, Enya

VCs also seemed to view inquiry as an asset in founders:

The best founders ask a ton of questions, they rely a lot on a peer group of founders that are a little bit ahead of them. Great founders ask their network for introductions on specific topics — they’ll say, “Do you know who has gone through this specific issue and can you connect us?”

— Sergio Monsalve, Venture Partner at Norwest 

In learning academia, we call learning through asking questions inquiry-based learning. It’s also a teaching style (the Socratic method). There have been whole books written about how to ask thoughtful questions, such as “Leading with Questions” and “The Art of Asking.” Great founders have developed not just the craft of asking the question itself, but the processes and network for ensuring their questions are worthwhile. 

As a venture capitalist, I love meeting founders whose curiosity shines through. That insatiable drive to learn makes them unstoppable. Founders, I’d love to hear any more insights you’ve gained about asking questions as a skillset or other things that have helped you become the leader you are today. Reach out anytime at mbent@lsvp.com.