10 Power Questions to Ask a Loved One on Valentine’s Day

By Andrew Sobel

Hearts, Flowers…and Power Questions?  10 Relationship-Building Questions To Ask Someone You Love this Valentine’s Day

A token box of chocolates and reservations at a nice restaurant are, well, nice. But do they really deepen your relationship?  What really makes Valentine’s Day great is not the candy but the conversation, says Andrew Sobel. And if you find yourself mired in awkward silence, don’t worry—his power questions will do the hard work for you.

You’re all dressed up and sitting across from your sweetie at a fancy restaurant. The flowers have been given, the wine uncorked, the entrees ordered, the pleasantries exchanged. Now what? Unless you’re in the “can’t stop talking and gazing into each other’s eyes” throes of new love, right about now is when the awkward silence descends. It’s Valentine’s Day and expectations are high—so why can’t you think of anything meaningful to say?

It’s true. When you’ve just met ‘the one’ conversation seems to flow effortlessly. Add 10 years and couple of kids and the proverbial cat gets your tongue.

“Maybe laundry undone and bills unpaid have crowded out topics like childhood dreams and the meaning of life,” notes Andrew Sobel, author (along with coauthor Jerold Panas) of Power Questions: Build Relationships, Win New Business, and Influence Others (Wiley, February 2012, ISBN: 978-11181196-3-1, $22.95). “Or maybe you’ve just gotten lazy. But 9 times out of 10 the spark can be revived—and you don’t have to wow your partner with your insights or intellect. You just have to ask the right questions.”

Really showing someone you care has little to do chocolates or flowers, he insists. Relationships, whether at work or at home, deepen and grow when you take an sincere interest in the other person and invest time to learn about who they are and what they care about. Thoughtful questions are the way you do this.

“Power questions are called that because they give power to your conversations and to the other person,” explains Sobel. They make you stop talking and start listening. They help you learn things about a loved one that—I guarantee you—you didn’t know. And best of all they make the other person feel loved, valued and worthwhile.”

If you have a romantic partner, Sobel recommends you try these questions on Valentine’s Day. If you don’t, he assures you that they also impact anyone else you love—a parent, a child or just a good friend.


1. What are your dreams? Sit down with a cup of coffee–or a glass of wine–and allow some silence. Smile warmly. Ask this question with no elaboration–don’t mess it up with other words. Then wait.

“This is a deceptively simple question—deceptive because of its power,” notes Sobel. “Most of us are afraid to ask it. What if the answer is something we don’t want to hear? And yet, the conversation it sets in motion can transform lives in exciting ways.”

2. What would you say has been the happiest day of your life? (and Why did you choose that day?) Think of this question as the start of a much longer conversation. Why did the person choose that particular day? What other days have been happy ones? What is happiness, for him or her, anyway? Is it the same thing as joy or contentment? Allow an hour at least!

“Sometimes we have huge misconceptions about our partner—even if it’s someone we’ve lived with for 30 years,” says Sobel. “You may discover you have been projecting your own feelings and beliefs onto him or her.”

3. Can you tell me about your plans? We are all so FULL of our own plans, notes Sobel. Our own priorities. Our own goals. Our own stories. When we really, truly focus on our partner—not just use what he says as a springboard to talk about ourselves—we learn amazing things.

“Ask this about anything: The other person’s career, their upcoming vacation, their weekend,” Sobel suggests. “Instead of talking about your plans–or what you think the other person’s plans should be–ask this question and just listen.”

4. What do you think about…(this idea, news event, etc.)?My coauthor on Power Questions, Jerry Panas, calls these the FOUR WORDS,” explains Sobel. “They are very simple: “What do you think?” You’d be surprised how many people are never or rarely asked these four words. They can unleash a marvelous conversation–and help you make a warm connection.”

5. What do you wish you could spend more time on each week? Less time?  Actually, this is a good one to ask if you got a blank stare or an eye roll when you asked your partner about his or her dreams, says Sobel. In some ways you’re asking the same thing—just in more pragmatic language.

I ask this question a lot in business relationships and I find it gets the other person talking about what they really love and enjoy in their lives,” says Sobel. “I get to know them so much better. An added benefit, when you ask it about a partner, is that sometimes you can help them figure out a way to change their day-to-day reality..”

6. Can you tell me something about yourself that I don’t already know–and that might surprise me? This question can reveal surprising, even astonishing things about someone you thought you knew well. “A friend of mine once answered this by telling me “I spent a night in jail in Lubbock, Texas,” says Sobel. “Someone else said, “I rode on Air Force One with President Lyndon Johnson.”  Yet a third revealed they had been jilted the day before their planned wedding!

Try it out yourself, he suggests. You may not find out anything that dramatic—but then again, you might!

7. Right now, what are you most passionate or excited about in your life? “This is what I call a “Passion Question,” says Sobel. “When you tap into people’s passions, they come alive and the conversation comes alive. All of a sudden you’re not just chit-chatting about mindless trivia. You’re talking about the stuff that lights us on fire!”

8. What would you say gives you the most fulfillment in your life? This comes at passion from a slightly different angle than the previous question. Maybe the answer will be the same. Maybe not. But a conversation about what fulfills us in our lives is always a rich and rewarding one.

9. What are you doing this week that I could help you with or support you on? Even if the answer is nothing, you’ll make the other person feel supported and loved. If there is something–well, it’s a good day when you can identify how to help someone else.

“Remember, ‘from everyone to whom much is given, much shall be required,’” says Sobel. “Maybe you can run an errand for your spouse. Or help a friend with an unpleasant task. It could be that simple.”

10. Can I share with you the reasons why I love you so much? (or, value you so much as a friend?; or, enjoy spending time with you?; or, am so proud of you?; etc.) Think this one through beforehand, suggests Sobel. Really ponder it. One of the greatest gifts you can give someone–a spouse, a child, a friend–is to share with them why you think they are so special. Why you treasure them. Why you love being around them.

“This one is powerful, and it’s truly in the spirit of Valentine’s Day” he says. “Go for it.”

So….pick a question (or two or three of them) and give it a try.

“It may feel a little alien to you at first but it will get amazing results,” promises Sobel. “And it sure beats carrying on a monologue about your workday, discussing your child’s C in Geometry, or sitting in uncomfortable silence. Power questions create power conversations… which create power relationships.”


About the Authors:

Andrew Sobel is the most widely published author in the world on client loyalty and the capabilities required to build trusted business relationships. His first book, the bestselling Clients for Life, defined an entire genre of business literature about client loyalty. His other books include Making Rain and the award-winning All for One: 10 Strategies for Building Trusted Client Partnerships.

For 30 years, Andrew has worked as both a consultant to senior management and as an executive educator and coach. His clients have included leading corporations such as Citigroup, Xerox, and Cognizant; as well as professional service firms such as Ernst & Young, Booz Allen Hamilton, Towers Watson, and many others. His articles and work have been featured in a variety of publications such as the New York Times, Business Week, and the Harvard Business Review. Andrew is a graduate of Middlebury College and earned his MBA at Dartmouth’s Tuck School.

Andrew is an acclaimed keynote speaker who delivers idea-rich, high-energy speeches and seminars at major conferences and events. His topics include Developing Clients for Life; Creating a Rainmaking Organization; Collaborating to Grow Revenue; The Beatles Principles; and Power Questions That Win New Business. He can be reached at https://andrewsobel.com.

Jerry Panas is executive partner of Jerold Panas, Linzy & Partners, one of the world’s most highly regarded firms in the field of fundraising services and financial resource development. His firm has served over 2,500 client-institutions since its founding in 1968. Jerry’s clients comprise many of the foremost not-for-profit institutions in the world. They include every major university, museum, and healthcare center in the United States. Internationally, Jerry has advised organizations as diverse as the University of Oxford, The American Hospital in Paris, and Nuestros Pequeños Hermanos in Mexico, the largest orphanage in the world.

Jerry is the author of 13 popular books, including the all-time bestsellers Asking and Mega Gifts. He is founder and chairman of the board of the Institute for Charitable Giving, one of the most significant providers of training in philanthropy.

Because of the prominence of the firm and the impact of Jerry’s writing, few have had a greater influence in the history of the profession. He is a favorite speaker at conferences and workshops across the nation and internationally. He can be reached at http://jeroldpanas.com.

About the Book:

Power Questions: Build Relationships, Win New Business, and Influence Others (Wiley, February 2012, ISBN: 978-11181196-3-1, $22.95) is available at bookstores nationwide and all major online booksellers.

Founded in 1807, John Wiley & Sons, Inc., has been a valued source of information and understanding for 200 years, helping people around the world meet their needs and fulfill their aspirations. Wiley’s core business includes scientific, technical, and medical journals; encyclopedias, books, and online products and services; professional and consumer books and subscription services; and educational materials for undergraduate and graduate students and lifelong learners. Wiley’s global headquarters are located in Hoboken, New Jersey, with operations in the U.S., Europe, Asia, Canada, and Australia. http://www.wiley.com/

The Company’s Web site can be accessed at www.wiley.com. The Company is listed on the New York Stock Exchange under the symbols JWa and JWb.





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