Asking Questions that Stick!

There I was, logged onto a virtual call with eight professionals from a large, multinational organization. They were representing an extensive European region with one task at hand: making the meeting a success. The keynote speaker was yours truly, focusing on asking the right questions, connecting the dots between company core values and the meeting’s theme. Most importantly, I wanted to build rapport and inspire trust.

In both business and casual settings, we ask questions of our clients and coworkers. It may not occur to you, but such questions can be used to create connections and build rapport. Whether it’s a meeting, interview or a casual conversation, questions can help us better understand contexts, details and intentions. As my wise ancestor Socrates once said, “The only true wisdom is in knowing that you know nothing.”

Consider the next occasion where you’ll need to gather information by asking questions. Which of the following types of questions will be the most helpful to you? You may choose all types, but take time to establish an order which will give you the best results and understanding.

Clarifying: “Can you tell me more?” “Does this mean…?” These questions provide you insight and help the speaker summarize their thoughts. In my meeting, I specifically asked, “Tell me more about this new core value. Where do you see it come to life in your organization? How would you describe it to a new hire?” In your context, you may preface this question with a brief reasoning statement of, “what’s in it for your audience”. It sounds like this: “So that the project is a success can you help me understand…?”

Connecting: “How does this relate to…?” “Is this similar to…?” You need to have some basic context to ask this type of question which is one level above an introductory clarifying question. It results in a deeper context and fuller understanding. In my meeting I asked, “Help me understand, how does this core value link with the overall mission of the company?” For you, this question may sound like this: “We all know of the importance of project X, but could you tell us how it ties to the strategic initiatives?”

Focus: “What are three takeaways…? “What would be the optimal outcome of…?” These types of questions dig into concepts and help you learn about your audiences’ expectations. For example, in our virtual meeting I asked, “If the keynote I delivered was a smashing success, what would be three learning objectives we would have covered?” Focus questions often involve asking for numbers or other data to provide additional clarity and establish expectations.

Big Picture: “How did you decide…?” “What inspired this direction?” In many situations, this type of question is best for gaining the broadest perspective or general understanding. These questions can also be crafted to provide you with relevant historical background or a general philosophy perspective. In my case, I was trying to see where my talk would fit into the overall philosophy and leadership initiatives. In an interview you might ask, “How does this position contribute to the overall values of the organization?”

Besides planning your types of questions, be sure to consider the interpersonal aspect of question asking. As an example, you might attend a cocktail hour at a conference which executives or clients are attending, or part of your interview includes a lunch. Here are some things to consider:

1. Start with building rapport. This may be a professional compliment to the person, their company or positive news you’ve read in the media. Like a ‘warm-up,’ the question will show that you’re interested and have done your homework.

2. At the start, keep your questions indirect. At a conference, you can say: “The keynote speaker drove home the message of time management. How do you train for that in your division?” But, asking direct questions too soon may give the perception of you being too aggressive in your approach such as, “Why did you decide to grow in this market?” A side note on style: some industries expect directness and efficiency, so choose your strategy accordingly.

3. Ask open-ended questions that allow your listener to elaborate on the topic, giving you further information. Begin a conversation with added hedge phrases such as, “Mr. Hodge, tell me more about that... what went into that decision?”

4. Ask questions that go beyond basic knowledge to show you understand the context, company and the industry. For example, if someone tells you that they work for an established pharmaceutical company, you might ask, “How did your research and development strategy change after the pandemic?” or “How is artificial intelligence influencing your day-to-day in sales?”

5. Mind your non-verbals. Giving a positive impression during your question-asking period involves standing tall and maintaining open body language without fidgeting or looking distracted. Some social settings might be loud and crowded which make listening a challenge. I often position myself facing my speaker with a wall behind them so I’m less visually distracted.

6. Finally, when the other person is speaking, actively show that you’re listening. Nod, maintain eye contact, smile, repeat part of the question, take mental notes, and use verbal encouragers such as, “I see” or “very interesting.” If you’re listening in a virtual setting, check out last month’s issue of Stronger for specific tips.

Whether you’re asking questions in a one-on-one office conversation, an interview, a networking event with people you’ve just met at a conference, or a formal Q&A session at the end of a presentation, use each question to build your credibility and positively impact your professional brand.

My virtual meeting with the multinational professionals allowed me to gather information resulting in a more relevant and personalized keynote address which was a success because of the questions I asked. Focus on your audience, prepare by doing your homework and, most importantly, use questions to help you build a relationship — ask questions that stick!

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