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10 Tips For How to Start Asking Better Questions

Effective communication is important in all relationships. These tips and links will help you to ask better questions, improve relationships, and get the information you need to succeed. Communicate with FINESSE.
Effective communication is important in all relationships. These tips and links will help you to ask better questions, improve relationships, and get the information you need to succeed.

“I can’t believe you asked him if he married a trophy wife,” my colleague stated. “Even more, I can’t believe he answered it without getting mad. Or that he told you so much about his first marriage."

“Well, the key was that I kept the questions short and followed where he took the conversation,” I replied. “On its own, the trophy wife is a bit over the top. But in the larger context, it flowed with everything he described and his comfort in discussing it with me."


10 Tips for Better Questions in Business Environments

Effective communication is important in all relationships. The opening story was among business colleagues after a professional association meeting. While it is a bit personal, it reminds us that asking good questions – including in business environments – is personal.


Knowing what questions to ask can help you collaborate better with team members, improve your leadership skills, and communicate better with professional colleagues. These are my top 10 tips on how to start asking better questions.


1 Listen Carefully

Pay attention when someone answers your question or explains something. If you don’t empathetically listen, you might ask questions that have already been answered directly or indirectly. Make eye contact and use body language, like nodding, to show you’re engaged.



2 Don't Be Afraid to Ask

Don't hesitate to ask for clarification if you’re confused about something. And technical professionals should ask questions even if they think they know the answers. Asking helps you avoid mistakes and learn more.



3 Do Your Research

Understand what you’re asking and why. This helps you ask more focused questions. Think about your goals. Are you looking for data or an opinion? Is your question formal or informal? Are you seeking confirmation or new insights? Clear, specific questions get better answers.


4 Follow the Conversation

It's okay for conversations to go off-topic. Let the conversation flow naturally. This leads to more questions or answers to questions you haven't asked yet. Relax and let the conversation guide you.


5 Use Silence Wisely

Don’t rush to respond. Pausing after answers gives you time to think and ask better follow-up questions. Silence can help you and others gather your thoughts and contribute more meaningfully.



6 Ask Probing Questions

Asking probing questions encourages deeper thinking and understanding. They show you're curious and help you explore emotions and ideas. Examples include:

  • What do you think is the best solution?

  • How did you decide on this course of action?

  • What are you worried might happen?

  • What will we do if our worst-case scenario comes true?



7 Keep Questions Short

Long questions can be confusing. Keep your questions brief and to the point. One-sentence questions can still lead to good conversations. An interactive, conversational flow of short questions is more effective than long-question interrogations.



8 Sequence Your Questions

Start with easy, basic questions before moving on to more personal or challenging ones. End with easier questions to re-establish any tension created by the string of questions. A good rule is to use easy questions to warm up, piercing questions in the middle, and easier questions at the end.


9 Use the Right Tone

Adjust your tone based on the situation. Some questions need to be serious, while others can be light-hearted. Being too formal all the time can make people uncomfortable. Pay attention to the mood and adapt your style accordingly.


10 Show Empathy

Understand the feelings of the person you’re talking to. Show that you care about their perspective. This helps build a connection and makes them more willing to share.



Bonus: Make Questions Part of a Conversation

There is nothing more powerful than a good question. There is no better way to ask good questions than in a conversation. In technical and business settings, the trick is to drive a conversation with questions rather than an exchange of statements.

The next time you are about to say something, turn it around by forming it as a question. You will understand more from the feedback. Others will want you to be around more because it shows you care more about their needs than yours.



Start Asking Better Questions

These are 10 tips (actually 11) for asking better questions. These tips are true in all environments, but their focus in this series is on technical and business environments. The next article will focus on “what pisses people off when you ask them a question.” I could have called that one “what not to do when asking questions,” but I realize that sometimes you may want to piss people off when you ask them a question. More on that next time. Are you Communicating with FINESSE?


Communicating with FINESSE is a not-for-profit community of technical professionals dedicated to being highly effective communicators and facilitators. Learn more about our publications, webinars, and workshops. Join the community for free.


JD Solomon is the founder of JD Solomon, Inc., the creator of the FINESSE fishbone diagram, and the co-creator of the Solomon-Oldach Asset Prioritization (SOAP) Method. He is the author of Communicating Reliability, Risk & Resiliency to Decision Makers: How to Get Your Boss’s Boss to Understand and Facilitating with FINESSE: A Guide to Successful Business Solutions.


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