How to ask smart questions

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This post is sponsored by the American Cancer Society.

After I realized that the most underrated skill is asking good questions, I realized that I am not very good at it. I don’t ask for help enough because I don’t know what question to ask. And also, I worry the question will be bad and then the person won’t want to help me again.

So I started forcing myself to ask for help. Like, I put myself on a schedule. And the result was not so much that I got good help (I did) but what I really got was good at asking questions. Because I thought so much about it.

Here are things I’ve been noticing about what makes a person good at asking questions:

1. Surround yourself with people who make you curious.
The first time we had a bonfire at the farm I was dating the farmer and he was winning over my boys with tree climbing and hot-dog roasting. I was concerned about fire safety, but I knew it was hopeless when I realized that the number-one rule I learned about building fires — put them out before you go to bed — does not apply on the farm. He just lets it burn out itself.

Here’s something I like about the farmer. He asks questions. When we were dating, and I had a fireplace in my house, he said he’d build a fire. But it turned out he had no idea how to make a small fire. You have to light kindling and then get the little sticks to catch, and then little logs, and the farmer lost interest after about three minutes.

I think this is what draws us to each other, though: We learn stuff we didn’t even know we needed to learn. It’s so hard to learn when you don’t know the right question to ask. Being around each other gives us the chance to learn stuff we’d never seek to learn. Like building fires.

It also gives us practice figuring out what question to ask.

2. Learn rules for asking questions.
Each industry has rules. Each circle of friends has rules. I think a reason I love work so much is that it’s all about rules. And there is no industry more full of rules than the venture capital industry. It has to be because it’s a matching system between two wildly different types of people: crazy, rule-breaking risk-taking entrepreneurs, and risk-averse, by-the-book, right-out-of-Wharton venture capitalists.

But the VCs are most valuable to startup founders when the founders are learning from the VCs. So there’s a lot of rule teaching going on. One of my favorite recent examples of this is how to ask for time from a busy person. Mark Suster, who is a VC, warns that you should never ask a busy person to lunch, because it’s too big of a time commitment. He has great examples of terrible ways to ask for time and also good ways, like, “grab a quick coffee” which is not so clearly defined, but clearly short in duration.

3. Get your timing right.
When my step-mom was in and out of the hospital getting chemotherapy, I learned a lot about how to deal with doctors. When it comes to cancer, once you pick a doctor, most people advise that you stay with that doctor. And then get to know the doctor well. Because ongoing quality of life depends, in part, on being able to ask good question of that doctor – asking what is happening, how things are going, and what is likely to come next. These are difficult questions for most people because this is an area where the vocabulary is new, and everything feels like a biology test you need to study harder for.

The best advice I got for asking questions was to not worry about asking too many questions, and instead focus on asking them in a good way for the doctor—ask in the morning, when doctors make their rounds. Leave questions at the nurse’s station, and then the doctor can pick up the question when they are starting their day. If you make it easier to answer your questions, you will get more attentive responses.

4. Your questions get better with more information.
The best questions are ones that come after a bunch of questions. The first question is never the real question.

I saw this in action with my sons. When we visited the Baha’i Temple in Illinois.

The first question was: “Can we play tag?” And they stepped on every step and jumped every railing and then asked if there’s an area for kids.

The next question was “Do Baha’i people celebrate Christmas or Chanukkah?”

By the end, my older son asked me, “Do you think that the B’hai people would mind that we’re Jewish?”

I liked that I could see his questions getting sharper and sharper as he figured out what really matters to him about the visit to the temple.

I thought to myself that I need to be the type of person who asks a series of questions rather than just one. I need to trust that questions are more interesting than answers, and people will not get annoyed as long as each question reflects a little more understanding on my part.

5. Be true to your passion.
Asking good questions means risking that the answer is totally obvious. That’s the scary part of asking a question. Here are tips for asking good questions in life, and here are tips for asking good questions in interviews.

But here’s something I’ve learned. If you ask a question about something you are passionate about and totally engaged in, the question will be good. Case in point: there are no stupid questions when you are asking a doctor about cancer treatment for a close relative.

But there are a lot of stupid questions from people who use the act of asking a question as a substitute for passion and engagement. Other people cannot do the work for you to make you care. When you genuinely care about a topic and have done honest investigation in that vein, trust that your question will be engaging to other people. Passion is always interesting.

41 replies
  1. Mark Wiehenstroer
    Mark Wiehenstroer says:

    I’ve found good questions need to be accompanied by careful and thoughtful listening. They need to exist together.

      • Penelope Trunk
        Penelope Trunk says:

        Yeah. I didn’t like it the other way. It was slow and some people didn’t like that comments on this site were tied to comments on all other sites.

        So we will have to just say “I agree” when we like a comment. That seems nice. I like that you did it here.


  2. my honest answer
    my honest answer says:

    I think a lot of people ask questions expecting to know the answer. You have to ask a question with an open mind, or it’s pointless.

    People send questions to my advice blog, and I find so many of them are rhetorical. But it makes me wonder: if they are so sure of themselves why do they need my opinion? (I think it’s because the ones who are surest of themselves are the most likely to get entrenched in situation they can’t get out of without admitting they were wrong. And boy do they hate doing that!)

  3. Reid
    Reid says:

    Good suggestions, every one.

    One “question” I have had a lot of luck with is to simply sit and listen some more, with a stare. If you want to put it too words, you can say, “Tell me more.”

    I’ve been continually surprised by the power of silence. Most people cannot stand a pause in conversation.

  4. Anne
    Anne says:

    Hi Penelope,
    What a nice surprise seeing pictures of the Baha’i House of Worship this morning! I am so happy that you and your family enjoyed your visit. The Baha’i Faith embraces diversity of religion, and not only would we not “mind that you are Jewish” but we would cherish your presence and be grateful for your friendship. Because the Baha’i Faith is an independent world religion, we celebrate holidays associated with our own Faith, but would joyfully partake in celebrations with others because we value our connection with all people. You might be interested to know that Baha’is view the House of Worship as not being primarily for people of the Baha’i Faith but for all of humanity. Thanks so much for visiting and posting your pictures. I’m happy to see your boys asking such inquisitive questions.

  5. chris
    chris says:

    And I’ve learned not to answer questions that have not (yet) been asked. If you homeschool, or if you are just really into raising your children to be insightful, you will prompt the questions from your children–then point at the answers obliquely. You will tease the kids into asking and then show them how to find out . . . It is a journey–and yes, the questions refine themselves, it seems, as Penelope says.

  6. Lora Stevenson Obrohta
    Lora Stevenson Obrohta says:

    I love #1, and it has taken me a long time to learn this. Surrounding yourself with curious people means not over-thinking (or apologizing) for asking questions for fear they’ll person I’m asking will be threatened or insulted.

  7. O
    O says:

    Asking questions is also a refining process. It is a system of checks and balances. When a group of passionate, intelligent people get together and each ask questions from their own perspective, the result is a more streamlined, refined, and ultimately superior product, process, or idea.

  8. Erin
    Erin says:

    Great suggestions, Penelope.

    And I love seeing the Baha’i temple here! I love visiting that place in the summer. Such an interesting faith and a really beautiful and intricate building.

  9. Angela Palmier
    Angela Palmier says:

    I agree 100%…questions, and especially good questions are critical for any type of learning/personal growth, etc. In my opinion, this is the single biggest reason for the failure of the US public school system. The system is set up to require our children to answer questions that have already been answered…regardless of their relevance. When we stop asking questions, or fear asking them because it threatens the “way it’s done around here” we all lose. Great post, and thanks (again) for your insight.

  10. Carmen
    Carmen says:

    This was great… Perspective is everything. What better way to gain new perspective other than asking honest questions.

  11. pfj
    pfj says:

    You said, “It's so hard to learn when you don't know the right question to ask . . .”

    And I add — it’s hard to learn when you (we) don’t have any idea of what we don’t know.

    Some examples:

    We did a house exchange to France, which meant grocery shopping along with everything else. We didn’t know – and therefore didn’t ask – that some small things were different about the “hypermarche'” as compared to the US grocery stores.

    Produce had to be bagged and tagged (with price) on the spot, before taking anything to the checkout up front.

    And the carts required a coin. We thought it was to ‘rent’ the cart; but it was returned upon leaving. That is, pushing the cart into stack of carts outside the store caused the coin to pop out. Voila.

    In Japan, they say that some people are so much at ease and comfortable in the world, they are like a fish IN water. In the U.S., we say that someone who is uncomfortable and awkward is like a fish OUT OF water.

    How can a fish, in water, have any idea to ask a question about the nature of water?

    We have to find out something about what we don’t know — before we can ask the right question(s).

    Therefore, indeed, a series of questions it will be.

    • Mark Wiehenstroer
      Mark Wiehenstroer says:

      It’s true that Penelope wrote – “It's so hard to learn when you don't know the right question to ask.” However, prior to that sentence she wrote – “I don't ask for help enough because I don't know what question to ask. And also, I worry the question will be bad and then the person won't want to help me again.” So, really, one aspect of being able to ask good questions is to be vulnerable. Good questions require a person to take a certain amount of risk. They’re showing another person how much they know (or don’t know) about a subject.

      • chris
        chris says:

        Back to doctors . . . I wish everyone in the medical community, doctors AND nurses and others, could believe in what you have said here, Mark. That is, stop pretending that we know it all and are so unreasonably sure of ourselves. Doctors and nurses need to show their vulnerability . . .

      • Mark Wiehenstroer
        Mark Wiehenstroer says:

        Chris, I think the medical community is trying to better the relationship with their patients. I think you’ll find the Radio Health Journal podcast of 11/23/11 ( ) titled “Do women make better doctors?” to be encouraging. Within that podcast mention is made of a new foundation at the University of Chicago ( ) – “The Matthew and Carolyn Bucksbaum Family Foundation is giving $42 million to the University of Chicago to create the Bucksbaum Institute for Clinical Excellence, a unique initiative that will focus on how to improve doctor-patient interaction.” As far as people in the medical community and vulnerability are concerned, I think they have to walk a tightrope. They need to be upfront and approachable and yet confident with their medical knowledge. I think Penelope gives some good suggestions for asking doctors questions in this post. The best advice was “Leave questions at the nurse's station, and then the doctor can pick up the question when they are starting their day. If you make it easier to answer your questions, you will get more attentive responses.”

  12. Posey
    Posey says:

    Well, if you want to be able to stick with one doctor as you recommend, don’t go to a female doctor. I have been through at least five. They all quit as soon as they have a child, or leave to follow their husbands when they get a new job. I know this isn’t politcially correct, but why do women even become doctors if they aren’t committed to their patients? I am sick of having to start all over every time. Woemn don’t take their careers seriously. I say this, and I am a female.

    • KateNonymous
      KateNonymous says:

      I wonder how common it really is, because I’ve had both male and female doctors, and both times a doctor has left the practice, it’s been a man. In fact, one of my female doctors had her fourth child while I was in her care, and she came back to work afterward.

      Based on a statistical sample of two patients, we have inconclusive data to draw gender-based conclusions on this topic.

      • Posey
        Posey says:

        It would make an interesting study, wouldn’t it? I have had male doctors leave their practices too, but either because they finally retired after 30 to 40 years of serving their patients, or because they died!

  13. TR
    TR says:

    I found that passion and a willingness to listen to the people giving advice can cover some rule breaking. When I was working towards my IT degree I was in a non IT job at a very large company. We had some internal IT forums that I posted some very noobish questions (looking back) but I always received positive responses from the IT veterans. I think this was the result of me demonstrating some enthusiasm for their areas of expertise as well as I asking follow up questions that demonstrated I was taking their suggestions seriously.

    • Penelope Trunk
      Penelope Trunk says:

      The American Cancer Society is sponsoring posts to encourage people to write about experiences of living with cancer. I actually think it’s a totally cool campaign — that they want to influence the online conversation.


  14. Chloe
    Chloe says:

    I was taught as a child not to ask questions because questions were considered rude.

    Blogging has been good for me because I can ask my questions behind the protection of being sort of a journalist.

    • Ron
      Ron says:

      Asking questions *can* be rude. Naturally, you just need to know *when* to ask them and in what tone.

  15. Brent
    Brent says:

    I need to remind myself of #4, that questions get better the more you ask. Your story captured that perfectly. I sometimes spend so much time editing and perfecting my first question that I miss the opening to ask. I’m going to remind myself not to be afraid to ask a first question, even if it isn’t perfect.

  16. BellatrixLestrange'sWand
    BellatrixLestrange'sWand says:

    Ok ok….1st Penelope….4 sum reason ur “schmoozing” the farmer, his mother…Maybe with your history of abuse you’ve created what use to be known as Multiple Personality Disorder and your in a nice/good personality today. I see your “making up for past actions” with your “schmoozing”. So what’s the real deal?? Or, be honest as to why your “schmoozing”
    2nd…If your gonna play the card of “I’m PENELOPE AND I’M SO SUCCESSFUL BECAUSE IM HONEST AND FORTH-COMING, DO AS I DO” Then just be honest and spit out why your buttering up the farmer and his mother who screwed over the farmer with the whole land deal that your not happy about. ……………I’m waiting

  17. Laura
    Laura says:

    Oh, I’m so glad you changed the comments back to how they were. Thank you. Now I want to read them again.

  18. Garth Beyer
    Garth Beyer says:

    I have the problem of asking too many questions. 75% of them are irrelevant to the topic. I ask the other questions to get a better understanding of the person so I can better understand the answers to the important questions. Just a little tactic that I did not know I did until I thought about it after reading this post. Thanks Penelope

  19. Jason Max
    Jason Max says:

    Yup, even asking question need a lot of thinking. Sometimes even when I am thinking how to ask, I find the answer before asking itself.
    That’s the rule before asking, think first and ask later. People just doesn’t like to be questioned with something that is without much thinking.

  20. Debbie I
    Debbie I says:

    I work in a profession where everyone who comes into our office is nervous, wonders what will be required of them and anxious about the outcome ( ok- well of course it has to do with permits). It has taken forever to convince people I work with that the first thing they have to do is listen and then ask questions. because people coming in are afraid and usually they don’t know what questions to ask – they can’t really use our services fully unless we do ask questions- in a kind, non-threatening , way. After all we know our regs- most of them don’t – they just have an idea of what they want to do. If we ask the right questions we can often save people money, get people what they want or close to it or help them re-design to make it work. And I agree with those above that say it takes listening- it saves everyone time and in the end makes your questions more productive. Great post.

  21. Gail Kasper
    Gail Kasper says:

    Thank you so much for this, Penelope! This is great information that can be applied in any situation… Coming from place of such helplessness, I lacked the confidence to ask any question at all. As I grew as a person, asking questions and continuous learning became a part of my life and continue to today. This transition is the basis for my autobiography.

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