Stop It With Your Stupid Questions

Patrick_Lor_profile_pic 2YES, there are stupid questions. And who knows that better than CEO and Co-Founder, Patrick Lor. He has an extensive list of experiences which include:

  • Being the pioneer behind microstock industry, as co-founder of iStockphoto, the world’s first crowd sourced stock photography community (acquired by Getty Images for $50M)
  • An advisor, mentor, angel investor, teacher, and community leader for various organizations including:,,, University of Calgary, Mount Royal University, GrowLab, and FounderFuel… to name a few
  • Entrepreneur-in-Residence at iNovia Capital, and Partner at Flightpath Ventures, a seed stage accelerator fund

In the post below Patrick goes over some of the stupid questions he’s encountered as an entrepreneur, investor and mentor. He also shares with us his secret on how to respond to stupid questions.

You’ve been told all your life that there are no stupid questions. For the most part, that’s true. But, as with all things in life, there are no absolutes. There are exceptions to the rule. Here are a few of the stupid questions I have come across, and why I think they’re stupid:

1. What’s more important – the entrepreneur, or the idea?

(or, substitute any two other necessary ingredients)

This question is essentially: “Can I have a great idea and be a lousy entrepreneur, or be a great entrepreneur with a lousy idea and still get investors?“. The answer is obviously no. And you’ve killed the conversation.

Every entrepreneur understands that the world is full of constraints, and building a company involves sacrifices. By definition, every successful startup entrepreneur has done the impossible by challenging giants with a small team of talented and dedicated people. They, like most entrepreneurs, started out as newbie entrepreneurs with average ideas. Over time, they became great entrepreneurs with great ideas.

Instead of asking “Do I need A or B?“, assume that you need both. Your question then becomes “How do I build a better A? How do I do it faster, more efficiently, and with almost no resources?” – that starts off a great growth hacking conversation with almost any entrepreneur in the world.

2. What was the one thing that you did to become successful?

This question assumes that it only takes one thing to bring success – which we know is impossible. For example, the answer you’ll get from one person might be “education” – and, as we all know, education is necessary, but not independently sufficient in producing success. Worse yet, you’ll get different answers from every entrepreneur you ask.

Another thing I hate about this question is that it’s generic and lazy. If you want a meaningful conversation with a busy, successful person, you have to put some effort towards it. Great interviewers do a ton of research to ensure that their conversations are rich and meaningful. So, aside from knowing that it takes more than one condition to achieve anything meaningful, you should know a little about what the entrepreneur you’re talking to went through to find their success.

The bottom line is this: when you ask generic questions, you’ll get generic answers. So, the answers you’ll get to this question are education, hard work, family, dedication, passion, and other generic stuff you already know about. It’s a question that can’t yield a useful answer.

Instead, go deep. Your research might reveal a similar childhood, education, or work experience as the entrepreneur you’re speaking with. So now, you might ask:

I’ve read that we’ve gone through a similar upbringing and education, but I’ve found myself encountering resistance in getting to the next level. Tell me, did you experience the same difficulties?

3. So hey, let me tell you about myself and my business. [insert 5 – 10 minutes of background here]. Did you find the same thing?

There’s only two ways to answer this question – yes or no. Either way, it’s a conversation killer. The problem: they don’t know what the question is, so they’ve shotgunned their life story in hopes that you’ll be able to counsel them.

This question isn’t really a question. It’s really just a chance for the other person to talk about themselves. Which, depending on the situation, might be just fine. In a business situation, you’ll want to practice dropping short, information-rich and interesting little conversation nuggets that will encourage a 2-way conversation about entrepreneurship. Eliminate any question that could possibly evoke a yes or no response.

And finally, relax. It’s hard to have a great conversation when you’re trying to gain knowledge, impress the other person, line them up as a future investor/advisor, and seek life-altering advice at the same time. Every entrepreneur starts somewhere, and if someone puts you down because they’ve forgotten that, then they’re not worth talking to. However, if you’re the one that sounds so impressive that you don’t need any advice, then you’ve committed the same crime.

What to do when you’re asked a stupid question?

1. Reject the question. Tell them that you think they’re asking the wrong question, and ask them to restate it, or restate it for them. In certain instances, when I sense that entrepreneur is ready for it, I’ll tell them that their question isn’t great, because it’s leaving me with a negative impression – and show them how to correct it.

2. Dig deeper:before I answer that, let me ask you this . . . ” I find that most people have already answered their own questions, and are just looking for someone to agree with them. In cases like these, I’m useless as an advisor unless I can find the true question.

3. Relax. I forget to to do this most of the time. And remember that we all used to (and continue to) ask stupid questions.

Ask Patrick Lor about your questions on business development, marketing and pitching on Clarity.

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  • raehanbobby

    I’m afraid to ask any question now because it might be perceived as “Stupid”.

    Sadly, I am now also questioning whether the same attitude will be applied to my comment too.

    • Patrick Lor

      Let’s face it, we’ve all got stupid questions. The point is that with a little research, and a slight adjustment in the way we ask these questions, you can become a great conversation starter and interviewer.

      Here’s an exercise that helps me: I observe how effective leaders ask questions and discuss issues with people. They’re essentially the same questions we all have – however, they seem to able to ask them in a way that gets a great conversation going.

  • raehanbobby

    Thank you Patrick for responding (and so quickly too! I love that) to my comment. Here is my take…

    Ultimately, I approach every situation with the values of Leadership, Gratitude and Love. I have to believe that there are no stupid questions, only stupid attitudes. The question is posed to me and I am grateful that they felt I could answer it. I use love to feel empathy for their lack of knowledge or understanding and my willingness to be generous and helpful. Finally I use leadership to encourage them to keep asking, create an environment where any question is asked or supported, and allow people to fail, whether it’s a question or a lack of experience.

    While I applaud Patrick’s method for gaining traction with the idea of stupid questions (it definitely got my attention!), I think leadership should always seek to be inspirational and positive. You are definitely using honesty, which is a good thing, but then so am I. (There are no stupid questions, only stupid attitudes). If you truly and genuinely want to know something from me then ask away. Just be ready to take responsibility for getting a response that you may not like.

    One of the challenges of categorizing some questions as ‘stupid’ is that it may exclude or demotivate some further questions or comments. Please don’t get me wrong, the insight in the article and the tips given are excellent. I just don’t want people to stop asking those questions because some of the most important conversations or my life (and theirs) started because they had the courage to even ask that question.

    Just my two cents. All the best and thanks for sharing! 🙂

  • buttonbeats

    I like this advice – “Reject the question. Tell them that you think they’re asking the wrong question, and ask them to restate it, or restate it for them.”

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  • Robbin Block

    I may not have your entrepreneurial cred, but I’ve seen my share of stupid questions. As if there’s only one answer to, for example, “What is the best way to market my business?” So it makes me wonder what the real value of Q&A sites like Quora, and now Yabbly, really are.

    P.S. It would be great if people would do a little research on their own before asking questions. That’s what makes for a great interview. I was recently asked, “What is marketing?” Uh, start with Wikipedia if you have to…