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The Art of Asking Critical Questions in Leadership Meetings

“Wanted to ask something, but I held back.” 

AK attended the town hall meeting today, seemed unsure.

GK: “What’s going on?”

AK: “I didn’t want to come off as challenging the leadership.”

GK: “You seem like you’ve got something on your mind, AK.” inquired while picking his coffee.

AK: Sighed, “I wanted to ask something during the meeting about the company’s growth plans and roadmap, but I held back.”

GK: “That sounds like an important topic.”

AK: “Yeah. We’ve been growing too fast, but I don’t see a clear direction for how we’re going to sustain it long-term. I didn’t want to sound like I was questioning the leadership’s vision.”

GK: Smiled, “I’ve been there. The kind of question that can move things forward. Leadership needs to hear perspectives from all levels, especially when it comes to growth strategies.”

AK: “I wasn’t sure if it was the right time.”

GK: “Meetings like these are the perfect opportunity to raise critical questions. When you ask the right questions, it shows you’re thinking about the bigger picture.”

AK: “I wasn’t completely confident if it would be well-received.”

GK: “It’s also about HOW you ask.”

AK: “So, how should I have approached it?”

GK: “Frame it in a constructive way, be prepared and have relevant data around it. Asking questions is a way to contribute, not criticize.”

AK: “That makes sense. Can you elaborate.”

GK: “Just for example, you could say, ‘I’m excited about the direction we’re heading and would love to explore how we’ll ensure this growth remains sustainable in the long run.’ That way, you’re showing support while opening the conversation to broader discussions.”

AK: “That makes sense. So it’s not just about voicing our point, but more about shaping them into productive questions that keep the focus on solutions?”

GK: “Exactly. When it comes to topics like growth and roadmaps, leadership appreciates people who are thinking strategically.”

AK: “I see. It’s also about showing that I care about the future of the company but also being mindful of how I present my question.”

GK: “You got it.”

AK: “Thanks, GK. I’ll make sure to speak up next time — will craft it well-received.”

GK: “That’s the way to go, AK. The key is to be constructive and forward-thinking.”

 

Have you ever found yourself in a meeting, eager to ask tough questions, but held back? How did you handle it?

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The Art of Asking Critical Questions in Leadership Meetings
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