Leading with Questions
- ellen9074
- Apr 3, 2024
- 3 min read
“When you are an individual contributor, you try to have all the answers. When you are a leader, your job is to have all the questions. You have to be incredibly comfortable looking like the dumbest person in the room.”

This quote from Jack Welch, former CEO of General Electric, captures a fundamental challenge for leaders: the imperative to completely shift their concept of the value they contribute to an organization, from having all the answers to asking the right questions.
Why is it so important to lead with questions? Here are my top 10 reasons.
#10: dialogue rather than directives make meetings more engaging and fun
#9: it reduces your stress; you don’t need to know everything!
#8: you teach others by example to develop their skills of curiosity and listening
#7: with more input you can better assess risk
#6: you help your team develop in many ways, especially critical thinking skills
#5: asking questions helps evaluate the talent on your team
#4: you shape an inclusive environment where everyone feels heard and valued
#3: done right, it creates psychological safety where people feel free to speak up
#2: better solutions come through diverse opinions and healthy debate
#1: you improve the bottom line with greater innovation, adaptability, and impact!
In my coaching and leadership development programs, this crucial transition sparks a lot of dialogue. For individuals inclined towards instructing rather than inquiring, altering this entrenched habit can be challenging.
The first step involves evaluating your current position by seeking feedback. I assess this for leaders with 360 degree feedback interviews. And you can do this yourself. Be brave and openly communicate with your team about your goal to ask more questions and give fewer directives. Solicit their input regarding specific strategies for improvement, including how, when, and where you can enhance your approach.
Use that feedback to tame the telling beast! Here are some ideas my clients have tried with success:
Asking the team to call them out on specific behaviours (based on their feedback).
Committing to always speaking last in team meetings.
Committing to ask each person’s opinion on decisions.
Writing a sticky note reminder on their computer for virtual meetings.
Reflecting after meetings to celebrate the wins and learn from the setbacks.
Getting coaching training (effective coaching relies on asking great questions).
And my favourite – taking on a role that is out of their zone of expertise. When you are not the expert, you have to lead differently and it’s easy to be the dumbest person in the room.
When you begin resisting the urge to have the answers and ask more questions, you multiply your impact. And the types of questions you ask are important.
Start with some simple questions, like:
What do you think?
What factors went into your recommendation?
Who else should be involved?
What roadblocks might get in the way?
What is the next step?
Good questions allow people to contribute their thoughts without fearing judgement. They open conversations, and they inspire bigger, bolder thinking.
The best questions are:
SHORT – 5 to 7 words or less. Shorter questions elicit bigger answers and help avoid leading the witness.
OPEN – start with “how”, “where”, “what”, “when”. Use why questions with caution. “Why did you make that decision?” can put someone on the defensive. Whereas “What factors went into your decision?” feels more like its coming from a place of curiosity.
BIG – Big questions encourage people to think differently, they prompt the exploration of new perspectives and ideas. “What would you do if there were no budget constraints?”, “What does the world need from us?”, “What are we willing to risk to _____?”, “What would you do if you knew you couldn’t fail”.
FOLLOW UP – “What else?”, “Say more”, “What did that feel like?”, “What was the result?”, “How do you think that will work out?”, “What makes you think this?” With follow up questions you dig deeper and get the most interesting and important information. And they are great to use when you feel yourself getting defensive – resist the urge to jump to your solution and ask one more question.
And the #1 question for leaders: “How can I help?”
In no way am I advocating that a leader only asks questions. Certainly, there is a time to set expectations, share your opinion, and make decisions but for many those skills comes more easily than inquiry.
So practice looking dumb, ask great questions, and shift your leadership!
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