The Ultimate Guide for Leading With Questions: 36 Sample Questions

“Judge a man by his questions rather than his answers” – Voltaire

If you want to inspire creativity, drive engagement, and get better results… you need to ask a great question.

Telling someone what to do might get you some nice short-term improvement. But, asking open-ended questions opens the door to empowerment, ownership and self-learning.

In my executive coaching practice, the most powerful tool I use is to ask the right questions, listen deeply and help my clients discover how to grow as leaders.

Asking powerful questions helps us “Stay Curious,” one of the seven practices of authentic leaders I wrote about in Wired for Authenticity.

The trick is to ask the right question! Here are ten ways asking questions can help us be more effective leaders and create breakthroughs in our impact.

1)  Inspire Creativity & Innovation – When you make a statement like “We need to follow up with new clients” causes people to judge (agree or disagree) and can bring up resistance. When you ask the right open-ended questions you help people tap into the creative, solution-making side of the brain.

Examples of questions to inspire creativity:

• If we were to totally delight our customers, what would that look and feel like to them?

• What does success look like in this situation?

• If resources were not constrained what could be possible here?

2)  Sell Your Product or Idea – What is the biggest barrier to you selling your product or idea? In my experience it’s always about not knowing the buyer’s needs, wants and constraints.

Questions help us better understand the needs of our customers and align ourselves with those needs:

• What are the most pressing issues or challenges you face?

• If we were to create the perfect solution for you what would that look like?

• Why is this area of need important to you?

3)  Improve Decision-Making – As companies move to flatten authority and widen span of control, leaders can no longer afford to hold on to decision making authority or expect to be an expert in every situation.

Questions allow us to learn and tap into the expertise of our people who are closest to the issue at hand. They help us challenge our assumptions about a situation.

Examples of good decision-making questions are:

• What are your criteria for making this decision? Why?

• What options did you consider?

• What is your recommendation and why?

• What options did you reject and why?

• What assumptions have we made that we need to test?

4)  Create a Culture of Learning – When we start with “a beginner’s mind” we open to learning more. The opposite is also true: if think you know everything you are closed to learning.

Creating a culture of learning opens the door for taking calculated risks and rapidly test new ideas. Great examples in recent history include: YouTube (was a dating site), Nokia (was a paper mill) and Nintendo (made playing cards).

Examples of questions are:

• What did we learn from this situation?

• What would we do differently in the future?

• How and where else can we apply this learning for greater success?

5)  Direct the Discussion – Great questions lead to great answers. And every question takes you closer to where the conversation needs to go: from what is the problem to what is the solution.

As a leader and coach your have great power to direct the conversation in a way that builds capacity in people and creates a positive vision of what’s possible.

Examples of questions to direct the conversation are:

• What’s working well in this situation?

• What did we do to create that positive outcome?

• What could be a vision for this project that would really excite you?

6)  Engage and Influence – You can’t lead if you don’t have a healthy relationship.

In particular, working across organizational boundaries can sometimes feel like the battle lines are drawn as each area has unique goals. Your questions can move the conversation from what is different to what is common.

Examples of questions to engage and influence:

• What are your goals in this situation?

• What are some constraints you’re facing?

• What could be possible if we were able to remove these constraints?

• How can we work together to make this happen?

• How can I support you in your goals?

7)  Coach to Fuel Growth – As leaders, how we make people feel about themselves can be as important as the direction we inspire them to take. As Maya Angelou wrote, “People will forget what you said, people will forget what you did, but people will never forget how you made them feel.”

Your questions can unpack years of resentment and frustration and instill confidence. Learn more about the steps to effective coaching tips for managers in this article.

Examples of good leadership coaching questions are:

• What does success look like in this project to you?

• Which of your strengths will be critical to leverage?

• How can we make sure this project helps you develop?

• What support do you need from me?

8)  Get Commitment to Change – Great leaders inspire a desire to achieve more—a commitment to change. They instinctively know lasting behavioral changes only happen when people want to change – not because they were told to change.

By helping others identify their own motivators, constraints and barriers you give permission for real change to begin.

Examples of good questions to inspire a commitment to change:

• What are your objectives and goals? Why are they important to you?

• How can we make sure that this initiative helps you achieve your goals?

• What do you see as the barriers to implementation?

• How do we work together to resolve them?

9)  Challenge Your Own Actions – How are you doing? Are you motivating others, but falling behind personally?

To be great leaders we need to always start with ourselves—challenging ourselves to improve and to be slightly better than we were yesterday.

Ask yourself these questions:

• Why is this goal really important to me? What’s already working well?

• What have I done to create that success?

• What special talents or strengths do I have that can help me achieve my goals?

10)  Grow in Our Self-Awareness – Are you aware—noticing what is working and what constantly gets in your way? This is hard work: to be both the leader of others and the leader of yourself.

And it is essential work.

Ask yourself these questions:

• What are strengths I have that can be leveraged at work?

• What brings me joy in the work that I do? What is a personal brand I can create for myself that inspires me?

• How can my strengths taken to an extreme become derailers for me?

These 10 ways to use coaching tips for managers to challenge behavior and promote new directions, for others and yourself. I encourage you to print this out – create your own list.

Here’s the real challenge to asking good questions.

It requires a shift in our own mindset as leaders. We have to let go of three ego needs that hold us back. This is where executive coaching works to uncover limiting beliefs and stuck paradigms so we can let our curiosity naturally flow.

Do these apply to you?

• Let go of the need to be superior or to prove ourselves (e.g. I’m the smartest person in the room so let me tell you everything I know.)
• Let go of the need to control outcomes (e.g. The best and most efficient way to do this is my way, so let me just help you by telling you what to do.)
• Let go of the need for perfection or need to succeed without any tolerance for failure (e.g We have to do this perfectly because anything less than success will make us or me look bad.)

My executive coaching clients find this Socrates method of learning and teaching a key driver of growth in leadership, engagement, and results. Try it for yourself!

A version of this post first appeared on my Forbes.com blog in 2013 and was updated in 2019.

If this resonated for you, please comment, subscribe, and share with others.

Enjoyed this article? Here are three more of my most popular leadership articles:

What’s your leadership practice?
Ten ways great coaches overcome resistance to change.
The 5 C’s of great coaching conversations.

This article was written by Henna Inam, C-level executive coach, global speaker, and author of the book Wired for Disruption. She helps leaders grow their agility to be a force for good and thrive in times of change. They create organizations that drive breakthroughs in innovation, growth, and engagement. In roles including Head E-Innovation and Chief Innovation and Marketing Officer, Henna drove transformation throughout her 20-year corporate career as an executive with Fortune 500 companies. Join the thousands who follow her blog here. Connect on Linkedin.