Guest Post by Susanne Madsen

Asking questions is an essential component of leadership. Voltaire said that we should “Judge a man by his questions rather than by his answers” and Albert Einstein was obsessed with questions, or more precisely, with getting to the right question.

Another smart mind, Tim Brown (chief executive and president of IDEO) says, “It’s very easy in business to get sucked into being reactive to the problems and questions that are right in front of you. It doesn’t matter how creative you are as a leader, it doesn’t matter how good the answers you come up with. If you’re focusing on the wrong questions, you’re not really providing the leadership you should.” That interesting!

How often, for instance, have you seen organizations and projects waste time and money in the pursuit of ideas based on having asked the wrong question? When so many projects end in failure, is it fair to conclude that we have to some extent been asking the wrong questions?

The first step in asking better questions is to pause, and set time aside to observe and query what you and your team are currently doing. Consider questions such as:

  • What does our gut tell us about this project?
  • What would we do differently if we bet our own money on this?
  • What are we not seeing that is new or different?
  • Which bad decisions have we made that need to be reverted?

These types of questions challenge conventional thinking. Asking them shows that you are a leader who explores better ways of doing things, who acknowledges that you don’t personally have all the answers and who encourages others to share their views and ideas.

In her book, “Multipliers”, Liz Wiseman writes that good leaders “Ask the really hard questions that challenge people not only to think but to rethink. They ask questions so immense that people can’t answer them based on their current knowledge or where they currently stand.”

To ask a question that challenge people’s thinking, it is not always enough to ask a question that begins with who, what, how, when, and where. You also need to also ask “what if” questions as they tend to free our minds to focus on possibilities. Examples could be:

  • What if we could solve the problem better than anyone else?
  • What if we had no constraints?
  • What if we only had half the time?
  • What if we could start all over?
  • What if we couldn’t fail?

When you ask these great questions you will challenge your team to think beyond the status quo and into innovation and creative thinking. At first, you will have to show the way and share some of your own thoughts. But later, when the team becomes more familiar with generating and implementing ideas, you can start to take a step back and give space for others to lead and take responsibility.

As you evaluate new ideas be careful not to come across as negative or constrained. When we challenge others to think critically it’s easy to slip into a mode where we are too analytical and make people feel that their ideas aren’t good enough. What’s important is that you create a safe and inspiring environment and that people feel excited and motivated by the opportunity to make a difference. Your role is not to overrule anyone, but to listen, inspire and encourage people to share and think their best thoughts. Don’t give up if people are initially hesitating and not contributing. Be persistent and reward those who come forward and embrace a new and different way of thinking.

Imagine the impact you could have, if you started to ask those all-important questions.

Susanne Madsen is a project leadership coach, and the author of The Power of Project Leadership and The Project Management Coaching Workbook. She has over 18 years experience in leading large change programmes for global companies.  You can connect with Susanne @


Reporting Questions

Guest Post by Bobb Biehl Once your priorities (measurable problems, goals, opportunities) are clear, these...

13 CEOs Share Their Favorite Job Interview Questions

Interview questions: Everyone has them. And everyone wishes they had better...

15 Astute Questions To Ask Other Leaders

Guest Post By Indeed Editorial Team Previously posted at  Questions to Ask Leaders for Career...

Is It True?

Today - one day before Good Friday and 3 days before Easter - may I share with you the story of "3 Questions"...

Key Insights From “Good Leaders Ask Great Questions”

Guest Post by Artem Gurnov Growing as a leader means constantly challenging yourself to help raise your team...

Questions for Your Next Daddy-Daughter Date

Men, if you have been blessed with a daughter then you know that there is something really special about the...


Excerpted with permission from the 3rd Chapter of “Uncommon Greatness: Five Fundamentals to Transform...

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.