8 Tips to Ask Great Questions!

If I’ve learned anything in life and business, it’s how to ask better questions.

As a business leader, educator, and lifelong learner, I've found that asking the right questions is one of the most powerful skills you can develop. Whether you're leading a team, interviewing a candidate, negotiating a deal, or simply seeking to understand a situation better, your ability to ask better questions directly impacts your success.

In my years of supervising, hiring, and mentoring professionals, I’ve observed that great questions unlock insights, foster deeper connections, and drive meaningful conversations. So, how do we move beyond surface-level queries and ask better questions? Here are a few key strategies:

1.?Be Intentional About What You Want to Learn

Too often, people ask vague or unfocused questions that don’t get them the answers they need. Before asking a question, clarify your goal. Are you trying to gather information, challenge assumptions, encourage critical thinking, or inspire action? The clearer your intention, the more effective your question will be.

Example:?Instead of asking,?“How is the project going?”?try?“What challenges have you faced on the project so far, and how have you addressed them?”

2.?Use Open-Ended Questions to Encourage Thoughtful Responses

Closed-ended questions (those that can be answered with a simple “yes” or “no”) often limit conversation. Instead, opt for open-ended questions that invite deeper discussion and insight.

Example:?Instead of asking,?“Did the meeting go well?”?ask,?“What were the key takeaways from the meeting, and how do you think we can improve for next time?”

3.?Embrace Silence – Give People Time to Think

Many people rush to fill silence after asking a question, but great answers often take time. When you ask a thought-provoking question, allow for a pause. This gives the other person time to process and form a more meaningful response. And because silence is uncomfortable for many people they frequently blurt out something they didn’t intend to say.

4.?Ask Follow-Up Questions

One of the best ways to demonstrate active listening is to ask thoughtful follow-up questions. This shows you’re engaged and encourages the other person to go deeper.

Example:?If someone shares a new idea, instead of simply saying,?“That’s interesting,”?ask,?“What inspired you to come up with that approach?”?or?“How do you see this idea evolving over time?”

5.?Challenge Assumptions

Many questions come with built-in assumptions that can limit thinking. Instead of framing questions around preconceived notions, try to explore alternative perspectives.

Example:?Instead of asking,?“Why didn’t the project succeed?”?reframe it as,?“What factors contributed to the project's outcome, and what can we learn from it?”?This subtle shift encourages a more constructive and open-ended discussion.

6.?Use the Power of ‘What’ and ‘How’ More Than ‘Why’

While “why” questions can be useful, they sometimes put people on the defensive. Instead of asking,?“Why did this happen?”?try,?“What led to this situation?”?or?“How can we approach this differently next time?”?These alternatives encourage a more productive dialogue.

7.?Adapt Your Questions to Your Audience

People who ask great questions read the room and tailor their approach accordingly. The way you question an executive differs from how you question a new hire or a customer. Consider their perspective, background, and level of comfort when framing your questions.

8.?Practice Curiosity Over Judgment

Approach conversations with genuine curiosity rather than trying to “catch” someone in an error or confirm your biases. People respond better when they feel heard rather than interrogated.

Example:?Instead of asking,?“Did you make a mistake on this report?”?ask,?“Can you walk me through your thought process on this section?”?This encourages discussion and learning instead of defensiveness.

Conclusion: Asking Questions is a Skill You Can Improve

Asking better questions isn’t just about getting better answers—it’s about fostering richer discussions, building trust, and making more informed decisions. By refining your approach, you’ll strengthen your leadership, deepen relationships, and unlock new insights that might otherwise go unnoticed.

The next time you enter a conversation, challenge yourself: Are you asking the best possible questions? The quality of your questions shapes the quality of your outcomes.

Joe Barnes, Chief Communications Strategist, DIGITAL 3000, Seattle. https://www.dhirubhai.net/in/joebarnesseattle/

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