“The thing that I had spent my whole life thinking was the kindest option for others was in fact putting all the work on them.”

Continue reading →

Since my tips to improve your writing in two minutes were so popular, I thought I’d share some similar tips to improve your next conversation.

Following are the simplest tips I can give you to ask better questions, which will make your conversations more valuable to you and the people you engage with.

Don’t ask yes/no questions.

Open-ended questions generate more interesting responses because they unlock more information from people.

Example: Don’t ask, “Do you like movies?” You’ll get a more interesting answer if you ask, “Why do you like movies?”

Ask “why” three times.

This is the easiest way to deepen the level of a conversation.

Example: If you ask a person why they like movies and they answer because it’s a good escape, you can follow up with, “Why do you feel like you need an escape?” If they answer because their job is stressful, you can follow up with “Why is your job stressful?” Repeated “Why” questions can turn a simple question about movies into a much deeper conversation.

Ask about specifics, not generalizations.

Questions about specifics lead people to give you answers that are not generic.

Example: Don’t ask, “What was fun about your trip?” Instead, drill down and ask, “What was the single most fun moment of the trip?”

Ask about reactions.

Frame questions around a person’s reactions to experiences in their life — what surprised them, challenged them, or changed their viewpoint.

Example: Don’t ask, “What’s it like to be a doctor?” Instead, ask “What’s the most surprising thing you’ve discovered about being a doctor?”

Ask follow-up questions.

When you ask a question, pay attention to the answer and ask a follow-up question about it to dig deeper.

Example: If a person says the most surprising thing about being a doctor is how uncomfortable people get in hospitals, follow up with a question like, “What do you do to help make them more comfortable?”

Ask about lessons.

If your goal is to learn from somebody, the easiest shortcut to do that is to ask them what they’ve learned.

Example: Ask questions like, “What did you learn from working with that client?,” “What do you wish you knew before you started working with them?,” and “What advice would you have for others who want to get into your field?”

Ask for a story.

The most interesting information is found in stories, so ask people to tell you one.

Example: Don’t ask, “What’s it like to be a teacher?” Instead, ask “What’s the craziest thing that’s ever happened to you in a class?”

Ask like a kid.

If you don’t fully understand something and want more clarity, ask a person how they would explain it to a kid or somebody with no experience on the subject.

Example: Instead of asking, “Can you explain that product feature again?,” ask “How would you explain that feature to somebody who’s never seen our product before?”

Ask what else you should ask.

When you wrap up your questions, give the other person an opportunity to tell you what you should have asked. They will likely suggest a question that provides valuable information.

Example: Ask, “Am I missing anything? What’s the question nobody ever asks you but you wish they would?”

One more thing…

Another great way to improve your conversations is to have more interesting things to talk about. This can help with that.

“The story becomes our memory, the story gets rehearsed ever more, and the story becomes the thing we tell ourselves the next time we need to make a choice. If your story isn’t helping you, work to rehearse a new story instead.”

Continue reading →