Asking questions may be the most important, yet least developed, skill for personal and professional success.
But, we live in a show and tell world, don’t we? C’mon, you’ve noticed it too. Everybody’s so busy talking, they’ve forgotten the value of listening. It all starts with asking one question (and then another, and another). Here’s the trick though, if you want to learn new things and build strong relationships; you have to CARE about hearing the answer. Really care, not fake care. Most of us know the difference.
In the work I do coaching executives, we discuss how they are using questions. You’d be surprised at how many smart leaders are great at giving answers, but fall short on asking questions.
One popular belief holds that we win friends and new business by being clever and quick on our feet and that our brilliance saying just the right thing is what attracts others. But knowing the right question to ask is actually far more valuable than having a ready answer.
Power questions, the kind that make you think and open up the conversation can be life-changing.
They can help you:
- Reframe and redefine a problem
- Challenge underlying assumptions
- Force us to examine new perspectives
- Innovate for the future
- Forge important relationships
- Gather information
- Focus us on what’s most important
Transformational teachers like Socrates, Jesus, Mohammed and Buddha were masters at using powerful questions as teaching tools, forever changing the lives of their disciples. Albert Einstein and Peter Drucker were 20th-century intellectuals who were known for asking provocative questions.
In the book Power Questions: Build Relationships, Win New Business, and Influence Others (Wiley,2012), consultants Andrew Sobel and Jerold Panas present more than 200 significant questions, along with stories about how to use them.
The questions we select have the power to give life to conversations in unexpected and delightful ways, they are powerful tools to get directly to the heart of the matter. They are the keys to opening locked doors.
Here’s an example of a powerful question that can help you improve relationships, manage priorities and enjoy greater influence.
What would you like to know about…?
When people ask you to describe your company, job or services, clarify their intent before you start talking. What are they interested in learning? Don’t assume you know. There’s nothing worse than giving a five-minute answer to the wrong question. If time is tight, make sure your answer is brief and on target. After you respond, ask if you’ve answered the question and if there’s anything else they want you to cover.
Many smart executives are great at giving answers. They get interviewed and give speeches frequently enough. But asking powerful questions is a skill worth developing.
In the work I do coaching executives, we work on raising their curiosity and skills for asking the right questions.
Here are three power questions that, in my opinion, aren’t used often enough:
What do you think?
These four words are key to initiating conversations. Many of us expend too much energy making sure our opinions are heard and understood. Few of us provide adequate care and attention to others’ opinions. Many people talk too much, and too few know how to listen effectively. As Henry David Thoreau once wrote in his diary, “The greatest compliment was paid to me today. Someone asked me what I thought and actually attended to my answer.”
Studies repeatedly demonstrate that we care most about people who listen to us. People crave appreciation, and they seek out those who will listen to them. There is nothing more potent than asking, What do you think?? How will this further your mission and goals??
Human nature makes us hungry to achieve wealth, power and fame. This applies to both individuals and organizations. We become engrossed in the day-to-day challenges associated with winning at all costs, but this doesn’t necessarily nurture our hearts and souls. Before you invest time and energy in pursuing the wrong goals, ask yourself, Is this consistent with my values and beliefs?? Focus on what’s really important in your life.
What do you mean?
Ask people for specifics when they use cliché terms: What do you mean by “more innovation” or, “better teamwork” or “What would this look like to you”? Ask people to describe, in specific detail, what they’d like to see happen.
Instead of assuming there’s shared meaning, ask for clarification. You’ll be surprised at how people answer. By asking fundamental questions, you take the conversation to a deeper level. You engage people and make them think. Instead of imposing your views, encourage others to examine their assumptions.
Here are some more of my favourite power questions that executives can use to help motivate and influence their people.
In Power Questions: Build Relationships, Win New Business, and Influence Others (Wiley,2012), consultants Andrew Sobel and Jerold Panas present more than 200 significant questions, along with stories about how to use them.
Out of the 200 questions, it was hard to choose the best ones, but these are my favourites that
really work.
How did you get started?
Ask people how they got their first job or decided to go into a particular field. Background questions provide a better understanding of another’s frame of reference. Everyone has a story, and unless you ask, you’re missing key pieces of the human puzzle.
Is this the best you can do?
You’d be surprised at how many people actually appreciate it when you encourage them to do better. Instead of accepting their first efforts, give them an opportunity to improve. Don’t let them coast. Call attention to their strengths, and suggest that
they’re capable of doing more. Don’t let mediocrity or convenience replace stretch goals.
Management guru Peter Drucker posed five questions to his corporate and organizational clients, which can be applied to your personal and professional life:
- What is your mission?
- Which are the most important relationships you want to invest in?
- What are the essential priorities and goals of those closest to you?
- What are your expectations of the people around you, and what do they expect of you?
- What is your plan?
Use these and other power questions to add excitement and meaning to your conversations.
You’ll be surprised at the stories that unfold, thereby deepening your relationships. I really do think there’s magic in asking the right question at the right time.
I’d love to hear about the questions you ask when you want to get to know and understand someone better. Got any tips? Post a comment!

Author: Cathy Shaughnessy
Cathy Shaughnessy is an ICF Assessor and PRISM award-winning ICF Master Certified Coach. Cathy mentors credentialed coaches and she creates tools and programs to assist coaches to successfully earn their ICF Credentials. Get more information on Cathy’s group mentor coaching programs here. Check out the latest resource for coaches, How to Learn the ICF Competencies – 32 Fun Activities to Get You Started.
Click the image below to download the Free Easy Tracking Form for Coaches and get tools and resources from Cathy!

Cathy Shaughnessy is an ICF Assessor and PRISM award-winning ICF Master Certified Coach. Cathy mentors credentialed coaches and she creates tools and programs to assist coaches to successfully earn their ICF Credentials. Get more information on Cathy’s group mentor coaching programs here. Check out the latest resource for coaches, How to Learn the ICF Competencies – 32 Fun Activities to Get You Started.
Click the image below to download the Free Easy Tracking Form for Coaches and get tools and resources from Cathy!