Underrated career skill: Asking questions

It might be that the only useful thing you ever learned in school (besides how to make small talk at a party) is how to ask a good question.

Most of us didn’t learn that, though. Because it’s so hard to teach. I know it’s really hard to teach because people with Asperger Syndrome don’t understand how to ask a question, and I watched speech therapists (pragmatics specialists) try to teach my son, while I took notes for myself.

Children with Asperger’s often have to learn when to use Why, What, and Where because they don’t know how to ask questions, even though they often have through-the-roof IQs. They actually seem mentally slow because they cannot learn as fast as other children due to the lack of good questions – which is a great illustration of how important asking questions is.

I will answer almost any question someone asks, which makes me better at asking questions myself, but I am also very conscious of the fact that most questions people ask me are terrible.

So here are tips on how to ask good questions.

1. Trust that people are interesting.
Asperger’s children must learn that everyone can tell you something about the world that you don’t know, and learning things about the world is interesting. As adults, this is more of a respect thing—you need to take a leap of faith that each person deserves your respect and each person has an answer that will be really important to you, if you can just get to the topic they are interesting about. (This is hard when most people want to talk about the weather, or the price of gas or whatever. I am still working on that hurdle.)

2. Use a therapist to teach you to ask questions
Therapists almost never tell you what to do. They ask questions instead. And they ask such good questions that you can’t help learning about yourself. I realized, after about 20 years of therapy, that I had learned to internalize a therapist’s voice in my head—asking myself the questions that could help me to steer myself. So what therapy has taught me is to ask sharp questions of myself when I am lost, and to go back to a therapist when the questions I ask of myself are so broad and unfocused that they are not helping. It makes sense that everyone could do the same thing. And if you think you’re above this strategy, consider this: Companies do this all the time, they just call the temporary help consultants instead of therapists.

3. Recognize questions that are hard for you but easy for everyone else
I just had lunch with one of my board members, Erik. He is the guy the board sends in when I am losing my mind. (He’s the one who fielded the call when I was having a nervous breakdown from funding and maybe going blind.) Anyway, this week I asked Erik what do to because I can’t work because I’m so sad about the farmer breaking off our engagement. Erik told me to keep working. He said, “What else are you going to do?” He was right. The question seemed so large and complicated to me, but it was really that the question was emotionally charged for me. It was not a hard question.

4. Match the right question to the right person.
Seth Godin asked a group of people (including me) a few months ago to write a chapter for a new ebook. Usually stuff like this takes too much time, and, also, it’s usually boring to do. But Seth tailored his question so well that the answers he got were amazing. First, he said he needed “just 200 words.” That’s the amount of words that is easiest to write. Less than that starts looking like poetry and more than that starts being an essay. He also picked a great topic: “what matters now.” Of course, this would not be a good topic for most people. Most people would stress about it for months before deciding what matters now. But Seth asked people who ask themselves this question every day, and write about it every day. (Arianna Huffington, Dan Pink, Fred Wilson, for example) And he made answering fun, because, look, I love how this ebook turned out.

5. A question you never think of is one of the best surprises of all.
Tyler Cowen’s book, Create Your Own Economy is largely about getting a life in the information age. But he spends a lot of time talking about how interestingness in life might be an end in itself. I am not totally convinced of this because I think I’m long on interestingness and short on social skills and I’m not liking the balance. And I think, maybe if I could just be a little less interesting then things might be easier for me. But, anyway, Tyler is convinced, and Tyler is pretty darn interesting, and he makes me think that one of the things that most excites me is when I hear someone asking a great question that I had not thought of.

So here’s a question for today: We know that women get more interviews if the name on their resume sounds male. (Here’s one of a bazillion studies.) And we know that people do better in their careers if they are honest about who they are. (This applies to both your name and your sex orientation.) But here’s something I never thought of: What would it be like to pretend to be a man at work?