Pushing oneself to ask great questions is extremely important. It forces you to think critically, accelerates your learning, improves decision-making, and helps build trusting relationships. Here are some things that have helped me ask better questions:

Tell yourself a story and use questions to fill in the gaps.

When I'm interviewing someone, being interviewed, or just having a conversation with a colleague or founder about a business problem, I typically take what the other person is saying and try to tell a story that makes sense in my mind. If someone is explaining a new company they'd like to start, I'm listening, but as I hear them talk, questions pop into my head about things I want to know more about or inconsistencies with my preconceptions. This is the trigger for most of the questions I ask, and it’s a useful way to generate dozens of questions in a single conversation.

Of course, you have to temper your questions and prioritize the most important ones so you don't sound like a nut. But forcing yourself to tell your own story based on what you're hearing—and fitting it into your worldview, or using it to learn something new and adjust your worldview—is a great way to ensure you're asking high-value questions.

Be ruthlessly authentic and ask “dumb” questions.

Have you ever noticed that whenever you ask a “dumb” question, it often turns out to be a great one? Dumb questions are wonderful. They typically simplify the topic, challenge assumptions, align the conversation at a high level, and enhance inclusivity. The trick is having the humility and courage to risk showing that you don’t know something that others do. This is definitely a risk worth taking. Try to never hesitate to do this. Be authentic. The best questions are about the things you really want to know. As someone once said, “Not knowing is not ignorance; not seeking to know is.”

Ask what people think, feel, or would do—not what they know.

I almost always find that opinions based on facts are way more interesting than simple facts. Instead of asking a job candidate, “What is our competitor's product strategy?” try asking, “What do you think of our competitor's product strategy?” Similarly, don’t ask your real estate broker, “How can I get a better price?” Instead, ask, “How would you go about getting a better price?”

This tactic encourages the person to really think about the answer and provides you with genuine insights rather than just reciting what they know. Also, give them time to think and express their full answer. Rushing them only leads to less interesting responses.