Ask dumb questions. It’s the smartest thing you can do startup investment

Ask dumb questions. It’s the smartest thing you can do

Without a doubt, the single most informative piece of advice in my formative years came from my uncle. Ironically, it came from asking dumb questions. In this blog I’m going to talk about asking dumb questions and why they are critical for your personal development and that of your startup.

How smart… are you?

My uncle was the smartest person I knew growing up. As a 10-year-old, being picked up from boarding school in a convertible BMW with a different Swedish blond bearing exotic candy was also a plus (WTF, is up with salted liquorice though!). I was never terribly interested in what teachers wanted me to learn, I was however intent on getting smarter.

During my first internship, I was invited to a dinner party with another super-nerd friend of my uncle. This gent proceeded to take it upon himself to make every topic of conversation, seem like torture to me, prima facie.

After his friend left, I commented on the fact the night was rather tough on myself and the chap was, in short, a ‘bit of a dick.’ In moderation I was told he was playing an intellectual pitch deckgame with me; he wanted to push me to see how smart I was. He also would disagree with everything I said, despite the fact not believing in his specious line of questioning. Wow.

The notion of playing such games was an epiphany to me; the thought never had crossed my mind. Much to the chagrin of acquaintances I have adopted this habit to amuse myself. Not that it is terribly ingratiating (sorry).

Knowing my uncle was smart and I was clearly missing a beat, I was implored to enquire, “How did you get so smart?”

The secret to not being ignorant

Pausing briefly, my uncle responded momentarily, “Whenever I am in a room and someone says something I don’t understand, I ask a question. I can only not understand something once. So if you keep asking questions, you will eventually know the answers. Also, I found most people in the room didn’t understand what was being discussed either, so were, in fact, happy I asked.”

That is clearly my paraphrase after several bottles of wine and post the commencement of whiskey, more than a decade ago, but the sentiment has persisted into forming an element of my personality.

The job as an investor is to ask questions… all the time

Investors know a little about some things and pretend to know a lot about everything. The difference between the good and great is the ability to ask the right questions to arrive at a cohesive investment thesis, on the basis of available information, at the time a decision is made.

At least once a day I chat with a founder to understand their business model. I do this by dumb questions startup vc investmentasking, what I hope, are the right questions. I know what I don’t know, that I don’t know, and am not ashamed of it. I am not embarrassed by asking ‘dumb questions,’ because if I don’t understand, I know 99% of other people won’t get it either. Founders need to sell their message not to just investors, but customers, journalists, potential and existing staff (continually justifying they don’t go to Google) and all other stakeholders. So my backstop rationalisation, is it’s the founder’s problem, not mine if I come across a bit dim 😉 At least that’s what I tell myself.

So why I am I writing this blog? This morning I received an email from a French entrepreneur I seem to have adopted in some form of a mentor relationship and he asked me:

My turn to be candid what would qualify as an elevator pitch?”

I responded:

lol. glad you asked. Maybe I want to work with you now. 

Explain what you do to a 10-year-old. with the attention span a 10-year-old has.

or better, I am Mark Z. you are in a lift and have 15 seconds to explain what you do to me to MAKE SURE I have a meeting with you. What would you say? That strips away all the BS you want to say. Strip to the absolute core. Why is this cool. who do you focus on. Why you will be big.

You can google too about this.

This is key to pitching people. real clarity on what you are doing and why and how it is done.

Let’s not get into the response quality (please), but two points I will address in this article:

  • Maybe I want to work with you now
  • You can Google about this too

In short:

  • I appreciate the founder asks something that is important to his raise
  • I tell him it is ok to Google (He’s a smart guy and not an intern) because there are some questions you should Google

There are no dumb questions: only dumb people who don’t ask questions

So many people coast through their life on artfully crafting a persona of not being perceived as stupid. A three-hour meeting can go by, which ends with a rhetorical; “does anyone have any questions?” If a meeting ends like that, shoot yourself. The meeting should face a forced end due to too many questions!

As my uncle said, there are people in the room that are glad you asked, as they were too fearful to ask themselves. I have found once the first person asks a question everyone else in the room starts asking too like I broke the ice. I half expect ‘the boss’ to pat me on the back and thank me for getting things going.

Furthermore, there are shy people. The extroverts get the ball rolling and the timid, who dumb questions startup vc investmentare arguably more thoughtful, then feel more confident to chime into a debate. This is a great thing; you want everyone to contribute to making better decisions.

Let’s look at the downside when an employee doesn’t ask the right dumb questions. What happens when an individual, due to the fear of looking dumb, does not ask questions? He will use his partial (probably flawed) knowledge to continue doing his work, which will result in even greater dumb mistakes. In the end, he ends up looking even dumber and the boss ends up having to clean up the mess. Perhaps the boss is dumb himself for not asking the question “do you understand how to complete this task?”

As I address later, there is such thing as dumb questions (how and when you ask), but not asking them is generally stupider. Asking a question makes you a little naked, clearly revealing something you don’t know or understand. If that’s something you are eager to know, asking indeed might make you look dumb (if asked wrong). But if you ask the question, you now know that thing and have eliminated some of your ignorance. If you don’t ask it, sure, you don’t reveal your ignorance, but now you still don’t know. On one hand, you look dumb, but become smarter, on the other hand, you stay dumb, but keep it hidden.  The question is whether you care more about being smart or looking smart.

So, what is better, show a little dumbness today or be a super dumbo tomorrow?

Dallas Cowboys owner Jerry Jones recently confessed that he was most effective early in his tenure “when I didn’t mind sounding stupid” asking questions. Clearly, he learned a lot. Also, not he said he asked a lot early in his tenure, not a year later.

The benefit of asking

You can only be dumb once if you learn

Treat every conversation as a learning opportunity. There is so much to learn in life that you need to keep learning and getting smarter. I love the quote “get busy living or get busy dying.” Apply the same to learning.

Tomorrow you will have something new to learn. You aren’t going to have the same opportunity to ask your question. In fact, you may be talking to an expert and that doesn’t happen every day. How great is it to learn something you can’t Google. Trust me, there is a lot you can’t Google.

Asking shows you are paying attention

People love attention. They want to feel they are being listened to. A lot of relationships arguably end, as one does not feel listened to.

Summarizing what someone said and asking if you understood his or her point is a great way to show this. Asking a pointed question, leveraging the content shared shows you listened, thought about it and is eager to know more. You want to listen even more.

Asking questions is indicative of a precocious mind

Smart people ask questions. They ask a lot of questions. It shows you are always thinking and paying attention to what people say. If you are dealing with smart people it is expected that you ask questions. You can start with dumb questions but work your way up to smart questions.

Reveal hidden ambiguity and question your assumptions

You climb a mountain from the bottom. You can’t comprehend the more complicated questions till you understand the fundamentals. Is a tomato a fruit or a vegetable? If you are discussing fruit, if you don’t ask the dumb question of categorization you may come to an erroneous conclusion.dumb questions investment startup vc pitch

You can learn a lot from dumb questions- how do you know if you are talking about the same thing? I often learn more by answering such questions than more seemingly “smart” questions. The “stupid” ones force me to really dig into my prejudices and assumptions.

Most questions deepen when you progressively examine each word and phrase in them and consider their underlying assumptions. This process tends to reveal hidden ambiguity. What formerly seemed obvious may now be more complex and nuanced than first thought.

Relate on a plane of your current understanding

You may be on a totally different plane of comprehension with other persons. Dumb questions help you relate on a level that you understand. I don’t understand adtech, but I can ask simple questions that help me to frame a startup in a framework I do understand.

My questions may be dumb to the other person, but hopefully, they understand why I am asking. We are not able to have an intelligible conversation if we can’t get on the same page. I had a chat with a chap in AI. I am upfront that I don’t understand, in fact, I say it. ‘You’re the expert not me, but to help you figure out how much to raise I need to understand the dynamics of your industry.’ The founder doesn’t mind that I don’t know and possibly appreciates my effort to get up to speed.

Isolation is a dangerous place

It is a scary place when you don’t ask basic questions and people tear off in different directions without a fundamental agreement. You need to ask to ensure you are on track together. Asking dumb questions about how to solve a basic problem can save you an incredible amount of time.

Check out what Philip Greenspun had to say on this topic:

“I once encountered a group of 6 people who called themselves “engineers.” To solve what they thought was a new problem, they were going to build their own little database management system with their own query language that was SQL-like without being SQL. I pointed them to some published research by a gang of PhD computer scientists from IBM Almaden, the same lab that developed the RDBMS and SQL to begin with in the 1970s. The research had been done over a five-year period and yet they hadn’t become aware of it during several months of planning. I pointed them to the SQL-99 standard wherein this IBM research approach of augmenting a standard RDBMS to solve the problem they were attacking was becoming an ISO standard. They ignored it and spent another few months trying to build their enormously complex architecture. Exasperated, I got a kid fresh out of school to code up some Java stored procedures to run inside Oracle. After a week he had his system working and ready for open-source release, something that the team of 6 “engineers” hadn’t been able to accomplish in 6 months of full-time work. Yet they never accepted that they were going about things in the wrong way though eventually they did give up on the project.”

Smart people like to be asked (smart) questions

Research has proven that “individuals perceive those who seek advice as more competent than those who do not seek advice.” Asking questions is good. There are caveats of course, but I’ll let someone smarter than me explain:


This is a great video on the topic based off Harvard research.

“Although individuals can derive substantial benefits from exchanging information and ideas, many individuals are reluctant to seek advice from others. We find that people are reticent to seek advice for fear of appearing incompetent. This fear, however, is misplaced. We demonstrate that individuals perceive those who seek advice as more competent than those who do not seek advice. This effect is moderated by task difficulty, advisor egocentrism, and advisor expertise. Individuals perceive those who seek advice as more competent when the task is difficult than when it is easy, when people seek advice from them personally than when they seek advice from others, and when people seek advice from experts than from non-experts or not at all.”

Questions are not all born equal, there are dumb ways of asking

A dumb question is a matter of perspective. What may be an unreasonable question to one may arise at the highest curiosity level of someone else, might not be out of the box for another, and be a serious question.

Clearly, a person’s state of mind and their age and experience are important factors to level. The expectation from a child and an adult make this difference in expectation most evident.

These question types all seem quite reasonable: asking what a term means, how to fulfill a request, and trying to understand another’s position in order to relate to them and give dumb questions startup vc investmentfeedback? But if you ask what accounting is, how to open Excel so you can do the accounting, or ask your boss why you are the one who has to do the accounting, these are all dumb questions.

Why? You can Google accounting later if you don’t need to understand the concept during the conversation, it is expected if you are going to do accounting you would know how to open Excel and if you are an accountant that’s your job.

Dumb questions largely are perceived as dumb for the following reasons:

  • Lazy: You want someone else to do the work so you ask dumb questions because you are lazy and myopic (E.g. who was the 5th president)
  • Competence: Your level of knowledge is expected to be higher and raises questions about your competence
  • Thoughtfulness: The question is not deemed thoughtful, that you don’t think before you open your mouth
  • Timing: You ask at an inappropriate time (E.g. In front of a client)
  • Better alternatives: There are better questions to be asking
  • Task difficulty: The more difficult a topic, the more questions are expected and vice versa
  • Egocentrism: The more capable a recipient of a question is, the more they appreciate tough questions to show off. Alternatively, simple questions are irksome to them

So the content and timing of a question can make you look dumb and whilst your question may be sincere, there are dumb ways of asking questions.

How to ask better questions

  • Use Google for questions you can Google: Write the easy ones for later if you don’t know. Better yet Google whilst you are talking to people (if you can). If you are asked to do a complete task like set up a CRM, use the time to Google the basics and then be more informed to ask more meaningful questions at a later point.dumb questions startup vc investment
  • Ask specific not broad questions: It’s better to ask how do you want the schema to work rather than what is Salesforce. Don’t ask what is Salesforce or “what should I do?” Better to say this is what my plan is; can you give me some feedback if I am approaching this right?
  • Observe first and then ask: You may find the question you want to ask will be asked by someone else, or eventually explained contextually. Just don’t wait till the topic of conversation changes. Asking later could be tricky and you lose the opportunity to understand the conversation.
  • Give context to why you are asking: Ask for context: ‘Just so we are on the same page, can you explain what you mean in by that in the context of adtech’
  • Show you made some effort beforehand to comprehend: In asking questions about a topic with which you are largely unfamiliar, show the audience that you’ve done some work. If you are talking about the benefits of PHP vs Python, say “In preparation for this meeting, I read that… I didn’t quite understand that. Can you explain why Python will be better in this context?’
  • Repeat a point and ask for an example: Don’t ask for clarity through details, ask for details that clarify. “Could you give me an example?” is a great stock question when you are worried about looking dumb.
  • Make questions more open-ended: As you seek clarity through detail you’ll get more of both if you ask open-ended questions that encourage a longer answer. “What do you think about… ?” is a good one, as is, “What do you see as the reasons for that?”
  • Ask them to explain it to a child: When I really don’t understand what someone is saying, I ask the speaker to explain their point to a third party imaginary person. A child is the go to. “For the sake of clarity, can you pretend you are explaining this to a child.”
  • Summarize what they say into 3 bullet points: An ex-MD in banking said to me “there is always the rule of three. “Everything can be explained in three bullet points. Repeat what was said in three points and ask if that is a proper summary. Then ask “is that what they are saying?” Read this blog to understand the Rule of Three
  • Ask dumb questions early: You get a grace period in any interaction of job. The earlier you ask the better. It is understood you don’t know how to work the coffee machine on your first day. After a year they will sneer at you. Ask early and often
  • Think before you ask: The obvious answer or question is often not the best one. Read this great article from the New Yorker. “In a lake, there is a patch of lily pads. Every day, the patch doubles in size. If it takes 48 days for the patch to cover the entire lake, how long would it take for the patch to cover half of the lake?” I always played lateral thinking games with my family. I took this up a notch when I fancied the idea of working at one of the big 3 consultants and studied complex questions. Over time I learned to not answer quickly and assume my first answer was wrong. It often is. I learned to think more and if I wasn’t clear to ask more questions. Ask dumb questions to challenge your assumptions before giving a dumb answer, which is way worse.

“Mine was the Depression generation of journalists. Many of the best people were not educated. When I went to London as a sportswriter, I didn’t even know the difference between the Baltic states and the Balkans. But I learned the advantage of the dumb-boy technique. I found that people love to talk about themselves. You get more news by trust than by tricks.

But that is not a very popular idea with this generation. Because they went to college, they think that they know more than the guys who run the joint, and that’s a pretense that doesn’t work. Also they like big shots. I always felt that the way to gather news in Washington is at the periphery not at the center. You get it from the people who tell the big shots what to say.”

James Reston, interviewed by Alvin P. Sanoff, US News and World Report


At the end of the day, most people are dumb. Who cares if they think you are too. You can only be dumb once. What matters is that you don’t stay dumb. Asking dumb questions is one pitch deckof the great ways to change that, in addition to Googling everything you don’t get.

Near the start, I mentioned the founder who shared his candidness. I appreciated that he asked a dumb question because I knew he didn’t understand fundraising, no one really does. But most don’t ask questions to get smarter faster. I like that.

I also told him it is ok to Google. He was worried he would learn something and thinks in the wrong way, opposed to figuring out an answer himself. That’s an eminent opinion but fallacious. It’s almost always better to stand on the shoulders of others that have thought about a common question and hack forward. In this case, he should have Googled first- he would have gotten better insight than a quick response from me.

Was his question dumb? Yes, a little. But he is going to get ahead because he is learning. Do the same. Be dumb. Get smarter. Win.

Video on YouTube

If you want to watch the video version of ”How asking dumb questions is the smartest thing you can do?” You can watch below:


pro cap table model magnet


Comments 2

  1. Good article; very helpful.

    I got hung up on the point referencing the lake and lily pad. I’d suggest reducing the number of days it takes to cover the lake by a *lot*. Do you have any idea how unbelievably small a lily pad would need to be to double every day for 48 days to only cover a “typical” lake, and not the *entire earth*? Anything larger than about 1 square inch would fully cover the earth. Yikes! 🙂

    Also, one minor typo: ‘you’ should be ‘your’ in the bullet point on competence. Not saying it’s ironic, just pointing it out. 🙂

    1. Post

      Hey Joel –
      I c/p from the New Yorker article. Point is knowing it is 47 days not challenging the question asked, which I have to ironically caveat given the topic of the post…
      Thanks for reading.

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.