One Simple Way to Ask Better Questions

Do you tend to ask specific or generic questions? 

The answer to this question could make or break your leadership.

Recently, while I was speaking to a group of executives about subtle shifts in communication, I learned that 80% of the people in the room never considered this subtle shift.  

While many of them knew that it was important to ask better questions, very few of them considered what that meant, and none of them considered the shift between specific and generic questions.

I found this surprising and wanted to share this simple idea that will help you be a more effective leader.

Specific or Generic Questions

There is a big difference between specific and generic questions.

Generic questions are broad, open-ended inquiries that allow for a wide range of responses, and lack depth. Questions like: “How are things going?”, “How do you feel?”, “How is your workload?”, and “Do you have any updates for me?” often lead to superficial answers that fail to provide insights into specific issues, challenges, or successes. 

This can result in missed opportunities for meaningful dialogue and problem-solving, limiting a manager’s ability to effectively support and guide others.

But specific questions like “What specific challenges are you facing with the project x?” or “Can you walk me through the steps you’re taking to resolve the specific issue you mentioned?” prompt more detailed and actionable responses. 

By asking for specifics, managers encourage team members to delve deeper into their tasks and reflect more critically on their work. 

It also helps you provide better support and guidance because specific questions lead to proactive problem solving, increased accountability and a culture of continuous improvement.

Making this Subtle Shift

Adopting a practice of asking specific questions may require some adjustments in your communication habits. 

Here are three practical suggestions to help you make this crucial shift from generic to specific questioning:

  1. Prepare and Reflect: Before entering any meeting or one-on-one session, take a few minutes to prepare specific questions related to the objectives of the encounter. Reflect on the goals, the issues at hand, and what you need to understand better. For instance, instead of asking “Are you on track with your tasks?”, consider asking “What progress have you made on the key components of your project this week, and what obstacles are you encountering?”
  2. Focus on the ‘How’ and ‘Why’: Enhance the depth of your questions by focusing on how things are done or why decisions are made. These types of questions encourage detailed responses and critical thinking. For example, replace a question like “Is the project moving forward?” with “How are you ensuring the project meets the next milestone, and why have you chosen this particular approach?”
  3. Encourage Follow-Up: When you receive an answer, make it a habit to ask a follow-up question to dig deeper. This shows genuine interest and often leads to discovering underlying issues or ideas that weren’t initially apparent. If a team member reports a delay, follow up with, “What steps are you taking to address this delay, and how can I support you in mitigating similar issues in the future?”

By integrating these strategies into your daily interactions, you can shift towards asking more specific, insightful questions that not only enhance communication but also drive better outcomes. 

This subtle shift can significantly impact your leadership effectiveness, promoting a culture of openness, detailed feedback, and proactive problem-solving within your team.

How to Get Started Today

If you’re eager to refine your questioning skills and cultivate a more engaging leadership style, there’s no better time to begin than now. 

The process of asking better questions can significantly enhance how you interact and connect with your team, leading to more effective leadership and improved team dynamics.

Let’s work together to unlock your full potential and achieve new heights in your leadership journey.

If you’d like to elevate your communication skills and make impactful changes in your communication style, I invite you to explore my Subtle Shifts Coaching Program. This program isn’t just about broad leadership principles—it’s a bespoke solution designed to refine your specific capabilities and enhance your influence.  To learn more schedule a meeting here.

If you have a team that would benefit from communication training I also offer a 90 minute masterclass called Subtle Shifts in Communication.  To schedule a masterclass connect with me here.

Reach out today to begin this transformative experience and see why so many leaders have trusted this program to enhance their executive presence and effectiveness.

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Matt Cross

Matt Cross is a speaker, author, and advisor with expertise in leadership, change, and teamwork. He is the author of Subtle Shifts: A Simple Strategy for Leading Change, which explores the power of small, intentional adjustments to inspire lasting change.
 Matt regularly speaks at Fortune 500 companies and works with executives, entrepreneurs, and emerging leaders from some of the world’s leading non-profits. His popular email newsletter, The Subtle Shift, helps leaders unlock new possibilities and navigate change with clarity and purpose.