4 Types of questions get us in trouble

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How far you get, in almost anything, is limited mainly by your ability to ask good questions.

The problem is that we are not taught to ask good questions. We’re trained to answer questions. But only answering questions doesn’t make an interesting life. After all, if you have all the answers, and you’re spewing them all the time, then you are not learning anything new.

Asking questions is how we get smarter. One of the earliest signs of a child with Asperger syndrome is that they fall behind in their learning because they do not understand how to ask a question. It doesn’t occur to them that someone would have information.

And maybe all my blog posts are actually about my obsession with a good question. For example, my recent rant about how blogs need topics is really about how a good blog is based on a good question. (My question is: how can we make the the intersection of work and life better?)

Today I’m going to focus on the kinds of questions that back us into a corner.

1) The question that asks: What is the meaning of life?

I think a lot about how people ask questions because I get them all the time. Often, the questions are so vague and poorly framed that I can’t believe the person actually sent an email. Here’s an example of one:

Hi Penelope,

I am from Bangalore India and an avid reader of your blog. I have recently quit my job at [big, international tech company] after working with them for many years. I would like to start something of my own but do not know how to go about it.

Can you guide me please?

Thanks for taking time out to read my mail. I will look forward to your response.

I sent a reprimanding email back to this person. In hindsight, I should have directed him to the post titled How to Write an Email that Generates a Good Response. Instead, I told him that there is no answer to this question. The question is so vague that it is not actually a question but a plea for respite from the inherent difficulties of adult life.

2. The question that reveals that you don’t care.

The questions that are most interesting are ones that create a conversation. My friend, Marci Alboher is great at these questions, because I love the conversations we have, even though she never likes my answers.

One of the most frequent mistakes people make in a job interview is when you switch to complete BS when the interviewer asks, at the end, “Do you have any questions for me?” Face it: the best way to ask questions in an interview is to ask them the whole time, not just at the end, so you can create the conversation that the interviewer needs so she can learn that yes, you are the right person with the right ideas for this position. If you wait until the end of the interview, it’s obvious that you don’t care—you have already had your conversation, based only on you answering the questions and having nothing to contribute on your own.

3. The question that generates an answer you can’t cope with.

I like to think that I’ve learned to be great at asking questions. I spend days dreaming up the perfect question for my mentor who I haven’t spoken to in a month. I want to make sure I ask a question that is interesting, and engaging to him and useful to me.

And I hear so many bad questions that I think I have become immune to asking them.

But it turns out that I’m not. Because I knew I was going to have a hard time getting myself to write a blog post today. Last year, I’d often go five days with no post. But that was when I was CEO of Brazen Careerist, and traveling every week, and also worrying that the company had no money.

Today I have a relatively calm life. The company is going great, and there is a new CEO, and my job is to write this blog, be a thought leader about the workplace, and talk to the press. So I need to be posting more regularly.

I know that having a trick works for me, from days when I can’t get myself to go to the gym. Like, I tell myself I will go to the gym and just sit in the locker room and listen to my ipod and then go home. Invariably, if I convince myself to do that, I don’t actually stay in the locker room. I end up doing some sort of exercise.

So I thought of a trick for blogging. I told myself that I’d make a game of it. I asked my Brazen Careerist chat group (sign-up required) for a topic. I told them I’d write about the first three topics people suggested.

But here’s what happened: I didn’t like the topics. Well, some of them I liked a lot. Like, Karen Gaustad and Mara Lunaria both asked why we link to Facebook profiles from Brazen Careerist. It’s a good question, because I talk all the time about how Facebook is a network for personal –and often unprofessional — aspects of your life, and Brazen Careerist is for building your professional network. So I actually don’t know why we link to Facebook. I keep asking Ryan and Ryan and they say something which I will summarize like this: Wait. Hold it. I can’t even summarize what they say, because I can’t remember exactly, but I think it’s something like “You’re too old to understand” but I don’t want to write that.

Okay. So I asked a good question that generated good questions in return. But I don’t like that question. I try to spend my life not hiding from hard questions. You’d think it’d be the abortion stuff that flummoxes me. But I’m pretty clear on how I feel about that. Why to link to Facebook, though? That’s a tough one.

4) The question that has unintended consequences.

Melissa Mansfield asked me to write about how companies that are highly ethical and also highly profitable. She will think I didn’t write about this topic. But I did. Because we can’t control companies. We can only control ourselves. So I’m always more focused on how I can change the world personally than how I can try to require institutions to change the world.

The thing is, though, that ethical workplace behavior is based on asking good questions. They lead to honest conversations and meaningful connections and the world of good behavior is build on relationships like these.

Not that every good question leads to a great relationship. The world is not perfect, of course. Because sometimes you ask a question that reveals only that the person you’re asking is useless.


42 replies
  1. Melissa Mansfield
    Melissa Mansfield says:

    Hi Penelope,

    I actually really liked how you answered my triple bottom line question b/c it reflected the way you think about things and approach career/life issues. It wasn’t a typical green response that I’m used to b/c I work in that field. I was surprised you chose it as a topic, and I loved seeing how you played with the idea.

    On another note, your observations about good blogs answering interesting questions really got me thinking. I’m struggling with my blog – figuring out the focus, the goals, how to keep up with it – and I think looking into what questions I’m asking and answering could be a good approach.


  2. KateNonymous
    KateNonymous says:

    I do #2 with a twist. At the end of the interview, when someone says, “Do you have any more questions?” a good answer is not “No.” So while I do ask questions as we go, I save one for the end. And I phrase it as something like, “I’ve already asked most of my questions, but I wonder if you could tell me about X.” Or “…could you tell me a little more about how you do Y.”

    That way I’m reminding them that we have had a conversation throughout, but I’m also demonstrating that I can ask a follow-up question at the end when prompted.

    • MJ
      MJ says:

      I’ve always found “No, I have no questions” at the end of an interview to be a nice way to convey the fact that I’d rather cut my head off with a butter knife than take THAT job. It has its purposes.

  3. Andrew
    Andrew says:

    Loved this post, this line especially had me laughing out loud, “The question is so vague that it is not actually a question but a plea for respite from the inherent difficulties of adult life.” I’m an engineer and I get those type of questions from time to time, although they are usually from people trying to get respite from the hard work required to actually learn the technology they are working on.

    I actually think meaning of life type questions have a strong component of showing that the questioner doesn’t care as they show a complete lack of respect for the time of the person being asked.

  4. Chris
    Chris says:

    You link to FB from Brazen Careerist because if BC is work and FB is life, you are all about their intersection. Yes? Though it is inconsistent with what you preach.

    Also, you have a typo in this sentence:

    “Melissa Mansfield asked me to write about how companies that are highly ethical and also highly profitable.”

    • Matt Secor
      Matt Secor says:

      It sounds like a typo to me too. Either the word ‘how’ needs to be dropped from the sentence, or it should read like this:

      Melissa Mansfield asked me to write about how companies that are highly ethical can also be highly profitable.

  5. Jacqueline
    Jacqueline says:

    “Why to link to Facebook, though?”

    Are you talking about the option people have to link to their Facebook profile from their Brazeen Careerist profile, or the option to login to Brazen Careerist using Facebook Connect?

    The former is just an option. Some people have two Facebook accounts (one personal, one professional), or keep their Facebooks very professional (since so many employers search it these days), or don’t mind integrating their professional and personal lives that way. If they don’t want to link their Brazeen Careerist profile to their Facebook profile, they just don’t have to enter the link. It’s a nice option for those who want to, though.

    The latter (Facebook Connect) is a MUCH-appreciated feature. I don’t want to remember another login for another site. Being able to click “Facebook Connect” and sign in is such a huge convenience because I’m already logged into Facebook all day. If you hadn’t offered that feature, I may not have registered a Brazen Careerist profile at all because it’s just not worth it to me to keep track of yet another social networking profile. So please keep that feature.

  6. Mark W.
    Mark W. says:

    “I spend days dreaming up the perfect question for my mentor who I haven't spoken to in a month. I want to make sure I ask a question that is interesting, and engaging to him and useful to me.”

    I think there isn’t a way for us to know what that really good question is to ask a mentor just as there isn’t a way for us to know what will make us happy without taking some form of action. It isn’t the one perfect question that needs to be formulated beforehand and asked but rather a series of questions that will eventually lead to the question that really needs to be addressed and hopefully answered. That’s my approach.

  7. Jim
    Jim says:

    The email from the preson from Banglaore was a perfect opportunity for you to “Change The World.” You could have at least given that person some advice on where to start to help him / her determine what they want to do next.

    This person took the time to reach out to you and looked to you as an expertise in their respective field.

    If you were a rock star or and actress and a fan asked you for an autograph, would you dismiss them out of hand? This is similar to what you did.

    Who knows, this person could have given you some great insight into the economy in Bangalore and it could have been an opportunity to write about common experiences and differences in employment around the world.

    It is obvious from this email you have an international following that values your opinion.

    I would not only rethink how I responded to that person but send an email apologizing and try to glean some insights as to why this person did what they did.

    It is obvious this wasn’t a spam email, but someone trying to reach out to you. If you can’t give them the right advice, maybe you could have pointed them in the right direction.

    • oldfeminist
      oldfeminist says:

      I’m fairly new to this blog, and I must say I’m a little surprised how many people spend their time admonishing PT to be nicer to everyone all the time. The degree of handholding expected here seems absurd to me.

      Jim, I guess you have time to answer every single detailed question anyone asks you with a series of incisive, deeply-thought-through questions, and then spend time lovingly crafting a long, detailed guru-like answer that will change the questioner’s mind?

      I don’t think you have the slightest idea how much time it would take for PT to do this with every single question someone asks her — and expects her to answer for free.

      You’re someone’s special snowflake, sure, but not hers. If you want emotional validation or in-depth individual career counseling, you’re in the wrong place.

  8. Jay
    Jay says:

    The thing I love about your posts, Penelope, is also the thing I hate: You leap so well around and among prior posts that I end up spending an inordintate amount of time reading and reincorporating their wisdom.

    Personally, I like that in your July 14, ’08 post, whose date I remember but not name, you said, “It’s not about having good answers, it’s about having good questions,” which is a neat paraphrase of words I penned almost 30 years ago: “It’s not whether you have the answers, but whether you know the questions.”

    Also enjoyed link back to “inherent difficulties of adult life.”

  9. Gayle
    Gayle says:

    How you frame a response to an answer, trying to reframe from judging it good or bad thus dismissing it out of hand, is equally important. For example with the guy from Bangolore, I’m going to take cultural differences in account (Socio-culturally aware interviewers understand this btw).

    Second, using follow-up questions as part of a conversaion helps us learn more (I learned this in sales)and build connection (which is how you get beyond canned answers in interviews) as well as giving us the opportunity to improve our social and emotional intelligence.

  10. chris keller
    chris keller says:

    Penelope, I found it hard to follow, especially #3 and #4. Under each of your 4 types of questions, I would have wished you had given a concrete example of the question.

    Re: #1, questions that ask the meaning of life. When I find myself asking a question like this, it is because I am trying to see the “big picture”. “How does _____ fit in to the big picture, the long-range goal or value, the mission/vision/values?” I ask. Do you believe that is inappropriate?

    Also, I think there should be a #5 where the question is perceived as a sign of stupidity by the expert or long-term employer or member of the interviewing team. How do you defend your question and reverse the perception that your question reveals your inexperience or stupidity?

    And perhaps also a #6, where you want to revisit an issue after you’ve worked at a place for a while. You then ask a question, which may be considered basic. And yes, it IS basic. But you want to 1) hear the rationale, which you don’t remember or was never discussed during your “basic training;” OR 2) you want to question the rationale. For example, “Let me get this straight–I handle this particular variety of customer complaint by using this scripted response? I am allowed no other discussion with the client? I need to refer to a manager if the client wants more discussion? Why have we chosen a scripted response? I would like to use some active listening techniques before referring on to a manager . . .”

  11. chris
    chris says:

    One other thing:

    In my organization, we use a model called the “Novice to Expert” model, originally designed for airline pilots and adapted for nursing by Patricia Benner. In this model, a proficient nurse questions authority and does not go by the book, but by her own assessment of the situation at hand. She may see fit to bend the rules . . . This level also engenders lots of ethical questions.

    I wish you would write more, Penelope, about questioning authority, questioning the status quo, and fitting one’s practice into an ethical framework.

  12. Laura
    Laura says:

    You link to Facebook because, if you didn’t, people would bug the crap out of you asking you, “Why don’t you link to Facebook? Everyone else links to Facebook, so there must be something wrong with you.” Those people don’t understand why they link to Facebook either.

  13. Kye
    Kye says:

    Penelope, Jim, Chris, and Bangalore reader,

    I concur with Jim. There is a cultural component to the problem of the ‘bad’ email. (An interesting side-point related to Chris’ comment is that in training aircraft crew to question authority, overcoming cultural constraints to asking such questions is a big job.) In the US we are trained to think along certain lines. Some of us do it with more ease than others, of course–but we have been trained in certain kinds of thought. I could point to that training pretty easily by asking you to notice how you would feel if someone said to you, ‘that was a very incisive question!’

    The Bangalore reader is at such a fertile moment in his life. He is ready to step outside the system where he would be told what to do, and offer something independently. But he hasn’t learned anything about how to do that.

    For a long time now I’ve regularly worked with people who are asking ‘meaning of life’ kinds of questions. When one of my clients is at this point, I might frame a question like the following:

    “In the job you just left (and others), some things gave you energy when you did them, while others drained your energy. What are some of the things you did which gave you energy?”

    This would be just one question of several (in one sense that is what my job is, is to know the right questions to ask to open up the too-vague questions where someone doesn’t know what to do next), but until I heard the answer to the first one I wouldn’t know the next question (kind of like a computer program which branches in different directions, depending on what just happened). But a safe possible second question might be, “And what was the value to your employer and their customers, of each of these things it gave you energy to do?”

    I hope that if you, reader-from-Bangladesh, are reading these comments, these questions give you a little more traction.

  14. Grant Crow
    Grant Crow says:

    I absolutely agree with the key messages in this post. In my view, there are 2 common reasons for the poor questioning problem: The first is that the questioner lacks the insight to ask a good question. If you don’t know what you don’t know, its hard to ask a good question. Secondly, pure laziness is a factor. I believe that a person needs to be genuinely interested in the other person in order to ask good questions. People without empathy aren’t going to be good questioners.

  15. Damian
    Damian says:

    I am a philosopher by background. It’s so difficult to say what question is interesting. And you are a good proof that religion influence or even create our way of thinking. I’ve read all available posts to make sure. I can say the same think about myself. You just helped me to realize that.

  16. chris Keller
    chris Keller says:

    I used to be a teacher. And this is the most important educational principle: Do not answer questions that have not been asked. The answers (will) fall on deaf ears. Which is to say, teaching will be ineffective . . .

    Instead, prompt the learner to ask the question.

    News shows do this well. They “tantalize” you with a photo, or a headline about the news item. Then they take a commercial break to let the question linger or bug you, as you wait out the commercial. They then return to the newscast to lay out the full story. All inservicing and training should adopt this model, I believe.

    A good interviewer or manager or CEO will adopt this teaching principle. S/he will coach the employee to wonder, to ask, to be curious, or to challenge the status quo “answer” that we all have lived by up till now. Penelope has, in this post, done just that–challenged us to ask, to be curious, to wonder. It is the way of growth.

    Thanks, P!

  17. Brian
    Brian says:

    I got on the FB kick for a while and friended a lot of strangers because I really didn’t think it through. I ended up putting those friendly strangers into a special category so I don’t have to see them, their ugly kid or their witty remarks about Obama. Maybe I should just dump them?

  18. Rose Jeudi
    Rose Jeudi says:

    Thanks for an insightful post! It will definitely help me write my monthly newsletters.
    I find that the key to asking great questions is being able to listen well (both to what’s being said and what’s being implied). Our culture tends to struggle with this task. So, perhaps that’s why we struggle with asking good, intelligent questions.


  19. Rachel Esterline
    Rachel Esterline says:

    Another potential question that can cause problems could be the ones that you can easily answer yourself. Sometimes people ask questions that can easily be Googled or looked up in a book.

    I don’t think this is always bad, but in some professional situations you can end up wasting people’s time by asking “stupid questions.”

    High school teachers might say there is no such thing as a stupid question, but there definitely are some. I try to do research on things before I start bugging my supervisors for answers on the simpler things.

  20. Tamar
    Tamar says:

    I think the difficulty of coming up with a good question is related to many people’s difficulty with how to think. Our whole lives we are not what to think, not how to think. But, really, that ends up limiting our ability to come up with original thoughts and responses to dynamic situation. That’s part of why I loved my liberal arts college education so much. The importance of a question was drilled into me almost daily for four years.

  21. Dale
    Dale says:

    Two points Penny,
    I’ve always found that asking questions is an effective way to help others understand my point of view. The main problems with this for me are when the other party thinks me clueless and doesn’t take my questions seriously, or when they become so focused on answering the question that they do not listen to their own answers.
    Secondly, life is short and often painful. Be kind to those who reach out to you seeking to reduce some of their uncertainty. You are very goal oriented and focused so in your impatience you may not realize how fragile or very much in need the person reaching out to you might be.

    My 2cents worth.

  22. Wang Moli
    Wang Moli says:

    Do people really not know the answers to the questions they ask? Most of the time in our adult life when we ask a question, we already know the answer.

    Q: Why did you do that?

    Q: Did you get my email? (Did you get my voice mail?)

    Q: Is this job for me?

    Q: Should I ask for a raise?

    Q: Should I vaccinate my kids?

    Q: Is my spouse cheating?

    99% of the time, we already know the answer. Many times the purpose of asking a question is to force the respondent to verbalize the answer. As an attorney, you learn very early on that you should never ask a question you don’t already know the answer to. ;)

  23. Lea
    Lea says:

    “Advice is what you ask for when you already know the answer but wish you didn’t.”
    — Erica Jong, novelist

    Interesting post, and even more interesting comments. I think the people who are complaining about how you shunted aside the writer of the “bad e-mail” are missing the point. Cultural differences aside, YOU are not here to serve as a career counselor to everyone who writes to you. You help people who help themselves, and you’ve given us many, many, many tools in your blog posts. You’re an expert in this topic, and by this point, you should be picking and choosing which questions you answer. Good questions get answered. Makes sense.

    The writer of the e-mail needs to do his/her research and reading and make decisions about what he/she wants out of life, work and career. Those are things no one can help with anyway.

  24. S.
    S. says:


    What are the two best questions you’ve ever asked people, and what are the two best questions anybody has ever asked you?


  25. maeve
    maeve says:

    Sick, sad, slutty narcissist. Yuck. Bye, “brazen opportunist, oops- “brazen careerist.” I could just puke at all of the “way to go, thank you for opening up a dialogue to empower women” comments, just loved the really intelligent interview on CNN- really? Really, people? Are you that stupid? Don’t answer that, please. I’ve read enough comments about the hair to know.

  26. MikeK
    MikeK says:

    Interesting post. My question to you is what makes a good question? I think there’s a trap in being too analytical. Being afraid to ask questions is not a good predicament to be in.

  27. jesse
    jesse says:

    Regarding the first question: there is no meaning to life. Only symbols and signs carry meaning, and life is not a symbol. Being a symbol is a difficult weight to shoulder; the human act of representing must be accompanied with increased power and resources in order to be worthwhile to most unless one is a masochist or some other something-or-other.

    Life is meaningless. Have fun or die.

  28. Jonasfreebies
    Jonasfreebies says:

    I would be more interested in finding out what motivates someone to ask specific question in the first place, one can ask questions to make other people feel miserable, arouses curiosity even chaos. Sometimes people ask question not because they want to get smarter, because they already knew the answer, but they want to challenge you, they tested your limit and hit your soft spot in the gut and leaves you bewildered.


  29. New York
    New York says:

    Hi Penelope, I found your article meaningful one. But I somehow don’t completely agree with you. How can we consider a question bad or good? If you consider from your point of view then you are free to think so.But it all depends on the person who asks.I am talking about the serious questions not about the silly questions like may I go with you.I am talking about questions related to life, carrier or problems faced by someone. When a question represents the missing part of our chain of thinking process. We miss that part so it appears as a question in our mind. So if someone asks you a question, try to find what he or she actually wants; the direct answer or needs that missing part. It is all about the game our mind played with us. Like can you tell me the calmness you feel is due to the company going great or due to your new CEO.OK, I will write you later about this topic.

  30. Jonha
    Jonha says:


    I have developed a habit of reading your blog everyday (more than the times I eat)because I find your thoughts very refreshing. Sometimes I don’t ask questions because I’m afraid it might reveal something about myself that I won’t like.


  31. Nick Vita
    Nick Vita says:

    Hi Penelope,

    I enjoyed reading your thoughts on asking questions during the actual interview process, and not just at the end. Asking questions while the interview is taking place levels the playing field and creates a conversation-type environment instead of the typical question and answer (which can make people nervous). It develops a more personal relationship between the interviewer and the interviewee.

    Thanks for suggestions, I found them very helpful. For more strategies on interviewing and asking questions that you may find interesting, my blog is listed below.

    Nick Vita

  32. Andrew Walker
    Andrew Walker says:

    1) Facebook means different things to people under 26 to those over the plimsole line…
    Get with the programme, young people seem to blur the edges between work rest and play far more suvcessfully than those who remember John Lennon & Kurt Cobain when they were alive.
    2) The final question in an interview is designed by HR departments to keep you on track. Otherwise, how you twist it or it twists you will be irellevent as the decission would have been made in the first four minutes anyway.
    3)a Question you can’t cope with is the question that needs to be asked to realise that the person asking you has either moved on intellectually, lost respect for you or both and
    4) the meaning of life is natures way of keeping food fresh.

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