14 Powerful Questions That Will Transform Your Conversations!

Upon starting my new position as VP/Chief of Staff at a previous job, my boss asked me to meet with all his other direct reports. He wanted me to get to know them and to start building relationships with them as I would be working closely with them. The problem was that there were 50 of them! The fact that one person should not be managing almost 50 people is neither here nor there. Seeing that I enjoy meeting new people and successful people at that, I was excited. I did a bit of preliminary research on each of them and had my assistant schedule 30-minute ‘meet and greets’ with them over the span of a couple of months.

I ended each meeting by asking the person 2 specific questions which they all answered graciously; that is except for one person.

We will come back to that a little later!

I recently read a great, thought-provoking book by Andrew Sobel and Jerold Penas called ‘Power Questions: Build New Relationships, Win New Business and Influence Others’. The book consists of 34 short chapters that each share a powerful question or powerful questions and then recounts how it was used to transform a certain situation. They then illustrate how and when to utilize the question to help transform your life.

In this post, I will discuss 14 of the powerful questions that they presented, as well as when you can use them in your life:

(1)  “What would you like to know about me?”

When to use it: This is a great and different way to answer the question, “Tell me about yourself?” Let’s face it, most of us could talk about ourselves for hours. But how do we know we are giving the other person the information they want? However, by asking this question we can discuss a part of our background that interests them the most.

(2)  “How will this further your mission or goals?”

When to use it: This is a question you can ask yourself or a question you can ask others. It can be used when you are making a tough decision or when you are mentoring someone else who is making a tough decision or doing something inconsistent with their mission. Remember, your personal mission statement is your true north and can help you avoid attractive distractors.

(3)  “How did you get started?”

When to use it: Anytime you really want to engage with someone and learn their story. It is a great question in that it will help draw the excitement, passion, and inspiration out of the other person. You will get to learn something and possibly hear some exciting stories.

(4)  “Do you mind if we start over?”

When to use it: It has happened to all of us – being involved in a conversation that has got off to a very bad start. What do we do? One gutsy and bold strategy to use when a conversation has gotten off on the wrong foot is to simply ask: “Do you mind if we start over?”

(5)  “Why do you do what you do?”

When to use it: When you want to uncover what motivates, inspires or drives someone. It can also be a good question to ask yourself to ensure that you are doing the right thing. As Friederich Nietzsche said: “He who has a ‘why’ to live can bear almost any ‘how’.”

(6)  “What has given you the most fulfillment in your life?”

When to use it: This type of question can uncover something that the other person has deep satisfaction with and is very special to them. Ask this question when you want to build a powerful and deeper connection with someone.

(7)  “Is this the best you can do?”

When to use it: This is a question used by both Steve Jobs and former Secretary of State Henry Kissinger to push people to maximize their abilities. A cautionary note – use it sparingly and strategically as it can drive people crazy. However, if used on the right person at the right time it can help someone push their potential to the maximum.

(8)  “What are your dreams?”

When to use it: Thoreau said, “Dreams are the touchstones of our characters.”, while Van Gogh once told a friend, “I dream my painting, and then I paint my dreams.” Dreams are something that we all have and by asking someone this question it will help you connect and get closer to them. It may also help them rekindle their passion and aspirations.

(9)  “What did you learn?”

When to use it: When you or someone you are working with has completed a task, it is a good idea to stop and reflect on what you have learned. Asking “what did you learn?” will help you and others get the most out of your experiences. As the great management guru Peter Drucker once said: “Follow effective action with quiet reflection. From the quiet reflection will come even more effective action.” If you would like to ask this question using a more structured methodology see our recent post on after-action reviews.

(10)  “Can you tell me more?”

When to use it: Asking the other person this question is a great way to draw them out and open the information floodgates during a conversation. Remember, it’s not all about you, and sometimes you need to step out of the spotlight and empower the other person.

(11)  “If the circumstances were turned around, how would you like to be treated?”

When to use it: When you are trying to decide how to handle a delicate situation with someone or counseling someone else in a similar situation. By asking how you would like to be treated and reversing the roles you will usually come up with the right solution.

(12)  “What have we decided today?”

When to use it:  To get clarity and commitment at the end of a meeting or discussing an important issue with a family member or friend. Many of us like to procrastinate and are afraid to make decisions. By asking this question it helps bind the group or individuals with an affirmation and a commitment to follow through on next steps.

(13)  “Exactly, what is your question?”

When to use it: When someone comes to you for advice but cannot get to the point. While it can be a ‘tough love’ question, it helps clarify and crystallize their thoughts on the issue. It also helps give you the information you need to give them the best advice possible.

(14)  “if you knew you had only three years to live, what would you hope to achieve personally and professionally?”

When to use it: To shake up your own and other people’s thinking, ask this powerful question. It will force you and others to really think about how you are spending your time and who you are spending it with. It will also help you uncover some unexpected responses and thoughts that no other question will elicit and seize the moment!

At the Conclusion of Each of My 50 Meetings

I asked each person the following two questions:

(1)  What are the 3 things that have contributed the most to your success?

(2)  What do you do for fun outside of work?

The first question was a bit selfish as I wanted to see if I could uncover some nuggets of success that I could use for myself. The second question was to start developing a more personal bond and rapport with the people I was meeting with.

In case you were wondering, the 3 things that came out on top in terms of what has contributed most to their success were: an obsession with their craft or discipline, having a key mentor or mentors along the way, and being curious.

As for the second question about what they do for fun – most of them went on and on about their hobbies, which really helped me start to build great rapport and relationships with them. That is, except one scientist who answered my question by saying, “it is none of your business what I do outside of here, what I do on my own time is not something I will discuss with you.”

“No worries!” I said, “I hear you. Thanks so much for your time”

Unfortunately, it was too late in the conversation to use #4 of the powerful questions above: “Do you mind if we start over?”!!

Until next time, keep using those powerful questions and as always…PYMFP!
–Rick

When to Use These Powerful Questions 

Use these powerful questions in the situation where each question works best.

What Do You Think?

Have you used any of these powerful questions? Do you have any other powerful questions that you use? Please share in the comments below!

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References

Sobel, A., & Panas, J. (2012). Power questions: Build relationships, win new business, and influence others. Hoboken, N.J: Wiley.