Ask Great Questions

Note from Yann:?? Hey readers! I’m Yann A?tBachir . Each week, I share practical tips to help you grow in your career.

Today's article, the 19th in this series, is arriving late. While I was writing on a bullet train to Shanghai, my LinkedIn account was restricted for security reasons. LinkedIn's algorithm likely flagged the multiple VPN connections as suspicious activity.

I'm back in Singapore now, and I've just recovered my account, so I can finally hit Publish.

I’ve read plenty of articles on how to boost leadership by asking great questions. But what makes a question "great"? In this article, I’ll share what I’ve learned on the subject.

I’d love to hear your thoughts! Feel free to share them in the comments so we can learn together.

?? If you enjoyed this content, share it with your connections.

Ever wondered why some leaders seem to have all the answers?

Truth is, nobody does! ??

The real secret? Great leaders are masters at asking the right questions to find out.

?? What if asking the right questions is the key to unlocking success?

Let me share how I levelled up my leadership game by becoming better at question-asking.

The Power of Questions ??

Questions aren't just for gathering information. They're the spark that ignites innovation, builds trust, and uncovers hidden opportunities. ??

The way we frame our questions significantly impacts our relationships and outcomes. ??

The simple act of asking a question can transform a mundane interaction into a meaningful exchange, fostering learning, collaboration, and growth. ??

?? Example: When onboarding new hires, ask "What's one thing we could do to make your first week better?" It shows you value their input from day one.

Question-Asking 101: My Cheat Sheet ??

?? Be Prepared

Know why you're asking and what you hope to learn.

The quality of your questions often hinges on preparation.

Be intentional with your words and timing. Before posing a question, consider your objective and the desired outcome. ??

The more clarity you have about your purpose, the more focused and effective your questions will be.

If you're seeking a colleague's opinion on a project, frame your question with context: "Given your expertise in [area], I'd love to hear your thoughts on [specific aspect of the project]."

?? Be Brave

Don't shy away from asking tough questions, even if they cause a bit of discomfort.

Often, the most valuable insights come from challenging the status quo and pushing boundaries. ??

Effective questioning requires courage and a willingness to apply first principles thinking - breaking down complex problems into their fundamental truths and rebuilding from there.

Thought-provoking questions, rooted in first principles, can lead to breakthroughs and uncover solutions that may have otherwise remained hidden.

In a meeting where a decision seems rushed, don't hesitate to ask, "What are the underlying assumptions behind this approach, and how do they align with our long-term goals?"

?? Be Open-Ended

Go beyond simple yes/no answers and encourage meaningful discussion.

Open-ended questions invite deeper exploration, spark curiosity, and can lead to unexpected discoveries and innovative solutions.

These questions typically start with words like "what," "how," or "why," and they avoid leading the respondent towards a specific answer.

They also demonstrate your genuine interest in the other person's perspective and encourage them to share their thoughts and feelings more freely.

For example, instead of asking, "Are you happy with the project's progress?", try asking, "What aspects of the project's progress are you most satisfied with, and what areas do you think we could improve?"

This invites a more nuanced response and opens up a conversation about potential opportunities for growth and development.

?? Be Curious

Go beyond the surface and dig deeper.

Ask follow-up questions that show you're genuinely interested.

The best question-askers are inherently curious, always seeking to uncover new information and perspectives.

They go beyond the basics, prompting others to think critically and provide thoughtful responses. ??

The ability to ask insightful follow-up questions demonstrates not only your attentiveness but also your desire to truly understand the topic at hand.

For example, instead of asking, "How are you settling into your new role?", try asking, "What's been the most surprising aspect of your new role so far, and how has it impacted your perspective?".

You will learn much more about the person and go beyond the general polite answer "fine".

?? Be an Active Listener

Pay attention to the answers. Really.

It's not just about asking; it's about understanding.

The cornerstone of good questioning is active listening.

Maintain eye contact, use encouraging body language, and demonstrate genuine interest in the responses you receive. ??

When someone shares something with you, show them you're fully engaged by paraphrasing or mirroring their words back to them. This ensures you understand their perspective and makes them feel valued and heard.

After a colleague shares a concern, respond with, "It sounds like you're feeling [emotion] about [situation]. Is that accurate?"

??♀? Be Flexible

Adapt your tone and approach to the situation and the person you're talking to.

Flexibility is key. Tailor your questioning style to the context and the individual.

An overly formal tone can stifle open communication, while a casual approach may not be suitable for every situation. ??

By reading social cues and adapting your communication style, you can create a more comfortable and productive environment for dialogue.

In group settings, be mindful of how dynamics can influence question-asking and answering. The presence of others can impact individuals' willingness to share. Consider starting with less sensitive questions and using a casual, conversational tone to create a safe space for open dialogue.

In a team meeting, encourage participation by asking, "What are some initial ideas we can explore, even if they're not fully formed?".

If a team member seems hesitant to speak up in a large meeting, try approaching them individually later and asking, "I noticed you were quiet during the meeting. Did you have any thoughts you'd like to share with me?"

?? Be Silent

The sIlence after a question is also part of the question.

Don't rush to fill the gaps. A well-timed pause can lead to more thoughtful responses.

Embrace silence as a tool for deeper reflection.

After asking a question, especially a particularly thought-provoking one, I count to five in my head before saying anything else. It allows space for the other person to gather their thoughts and provide a more comprehensive answer. ??

Resist the urge to jump in with your own thoughts immediately. Give the other person time to process and articulate their ideas fully.

Beyond the Workplace ??

The art of asking the right questions isn't limited to your 9-to-5.

It can enrich your personal relationships, foster deeper connections with your friends or family, and boost your overall communication skills.

By actively engaging with the world around you and seeking to understand different perspectives, you'll cultivate a lifelong habit of learning and growth. ??

Conversations are a two-way street. By mastering the art of asking, you unlock your full potential as a leader, a communicator, and an individual. ???

Note from Yann: ?? Hey folks! Thanks for reading. It was the 19h edition of the Simple Leader's Playbook.

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