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The Art of Asking Questions: How to Ask Questions That Connect Ideas and Drive Deeper Insight

by Oct 25, 2020Career & Money0 comments

When it comes to inspiring and motivating others, it’s not about what you tell them. It’s what you ask. So, what makes a great question? What types of questions can overcome resistance in an organization? What will spark a thought-provoking dialogue?

Asking good questions is important because it elevates us beyond current thinking boundaries. As an employer, ask yourself: What am I hearing underneath the variety of opinions being expressed? What new connections am I making?

The most effective leaders know how to stimulate curiosity and drive reflective conversation. Through brainstorming and collaboration, they fortify learning and increase thought diversity. Most importantly, they know how to use the right language and communication skills to generate broad engagement.

Here are five tips to keep in mind during your next brainstorming session:

1. Don’t ask “yes” and “no” questions

Keeping questions open-ended is important. As you craft your question, ask yourself: will this generate multiple responses? Does it create space for diverse perspectives and follow up questions? What meanings and feelings do I imagine this question will evoke?

2. Listen

People who ask good questions are good listeners. They are not only listening to what you’re saying, but they are paying attention to your tone and language. This requires being mindful and fully present. By focusing on what’s happening in the moment, you will instinctively ask more thoughtful questions. 

3. Be genuinely curious

People always ask me why I do this work, and it’s because I am genuinely interested in what people have to say and love learning about their experiences and points of view. 

If you’re curious during a conversation – even if you don’t agree with everything the other person says – you get to the heart of the matter; you hear and understand what they are saying. And that’s all people truly want – to be heard and understood.

Getting curious gives others permission to let their guard down and connect with us in a more meaningful way. 

4. Push the other person to dig deeper

In a session, I often ask “can you tell me more about that?” I ask this when I feel like there’s something more to what they’re saying and I’m inviting them to make those deeper connections. 

For instance, if you’re brainstorming with an employee, but you aren’t liking their ideas, you can push them to expand their thinking with the question: “and what else?” 

There’s likely something more they aren’t telling you or perhaps scared to say. This type of question allows the other person to open up and share something they are reserved about. It’s an effective technique to uncover new possibilities. 

5. Be willing to ask questions you don’t have the answer to

Lawyers never ask questions they don’t have the answer to. Ever wonder why that is? It’s because they need to know what the answer is in order to stay in control of the conversation and direct it where they want it to go. 

Many managers get caught up in the thought process of “What’s your problem? Let me fix it.” But that’s not necessarily what your employees want you to do. Oftentimes they don’t want you to fix it; they simply want to be heard. They want someone to say, “that sounds difficult.” They want more empathy and compassion. 

At the core of great leadership is finding ways to influence and energize the people around you. Asking the right questions encourages contribution and collaboration. Most importantly, it invites your team to design the future they want to live in.



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