How to ask smart questions

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.