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The Power of Asking Better Questions: A Guide for Leaders

Todler wearing harvard shirt using a laptop. raising his hand to show the importance of asking questions
01 November 2023

AT THE END OF THE DAY, the person who is most effective as a leader is NOT the smartest person in the room. It’s the person who asks the best questions.


Understanding the Need for Better Questions

You know what they say, "Knowledge is power!" And as leaders, we thrive on knowledge. By asking better questions, we open the floodgates to valuable insights and information. Not only that, but it also creates an environment of open communication and collaboration. So, get ready to tap into your curiosity and embrace active listening because that's where the magic begins.


Characteristics of Effective Questions

Now that we understand the importance of asking better questions, let's talk about what makes a question effective. Effective questions are like little gems that make people think and reflect deeply. They are open-ended, thought-provoking, and directly relevant to the situation at hand. So, instead of settling for simple yes or no answers, let's aim for questions that promote critical thinking and encourage meaningful discussions.


Strategies for Asking Better Questions

Active listening is about being fully present. It means hanging onto every word your team members say. This is key to understanding their thoughts and feelings. When you truly hear others, you can ask better questions. These questions can dig deeper and uncover valuable insights. For instance, don't simply ask, "Did you complete the project on time?". Instead, try asking, "What challenges did you face during the project? How did you overcome them?". This kind of question reveals more about the process and the challenges. It provides a richer understanding of your team's experiences.


  • Encouraging Participation: Building a safe and inclusive environment is key to getting everyone involved. When team members feel comfortable sharing their ideas, they'll be more likely to contribute their unique perspectives and insights. One way to encourage participation is by using questions like "What are your thoughts on this matter?" or "How would you approach this problem?". Create a space where everyone feels valued and heard.
  • Framing Questions Effectively: Open-ended questions are your best friends! They give people room to express themselves and share their thoughts freely. Don't be afraid to follow up with probing questions to dig even deeper. For example, instead of asking "Did you like the new product design?", ask "What aspects of the new product design do you find most appealing? How could we improve it?"
  • Understanding People's Feelings: It's important to understand others. By putting yourself in their place, you can ask questions that matter. Be kind and ask questions that show you understand their feelings or viewpoints. If someone seems unsure about sharing their thoughts, you can ask "What worries or doubts do you have about this plan?".


Overcoming Challenges in Asking Better Questions

We get it – asking better questions isn't always a walk in the park. Sometimes it can feel like pulling teeth! But fear not, my awesome leaders! Patience is key! Practice makes perfect, so keep at it. Adapt your questioning techniques as needed and never be afraid to experiment and learn along the way.


Case Studies: Examples of Leaders Asking Better Questions

Let's take a peek at some real-life examples of leaders who rock at asking better questions. By analyzing their techniques, we can see firsthand how their questioning skills contribute to their overall leadership success. Here are a few examples:


  • Mary, a team leader at a marketing agency, asks her team members questions like "What do you think our target audience needs right now?" or "How can we make this campaign more engaging?". By asking these open-ended questions, she encourages her team to think critically and come up with innovative solutions.
  • John, a CEO of a tech startup, actively listens to his employees' ideas during brainstorming sessions. He then follows up with probing questions like "How does this idea align with our company's goals?" or "What potential challenges do you foresee in implementing this solution?". This approach allows him to gather valuable insights and make informed decisions.


Leaders, the power of asking better questions is yours. Improve this skill to gain insights and boost collaboration. Become a more effective leader. Master the art of questioning and enhance your leadership.



Take a moment to reflect on your own questioning abilities. Commit to practicing and developing this skill further. Here are some actionable steps you can take in your business:


  • Schedule regular team meetings or one-on-one sessions where you encourage open dialogue and ask thought-provoking questions.
  • Practice active listening by giving your full attention to others when they speak.
  • Experiment with different questioning techniques and observe their impact on the quality of discussions.
  • Foster a culture of curiosity and continuous learning within your team.


And if you want to dive deeper into the world of leadership and effective questioning techniques, schedule a free consultation call with Brad.




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