Question Everything

September 17, 2019
James Whittaker

Check out this episode on the Win the Day Podcast

"Seek first to understand, then to be understood."

Dr Stephen Covey

Over the weekend, my wife and I moved into a new house in Los Angeles, CA. As you know, an exciting part of any move is getting to know the new neighborhood. I noticed there was a gym a short walk away, and thought it might be interesting to check it out.

I walked in and the receptionist told me a gym manager would accompany me for a tour shortly. A few minutes later, the gym manager emerged and off we went. He pointed out everything — the female locker room, where the 90+ year old’s do their swim class, and many other things I literally had zero interest in.

But the interesting part is not in what he did, it’s in what he didn’t do. Not once was I asked:

  • Have I ever been to a gym before?
  • What result do I want from the gym?
  • What brought me in today to check it out?
  • What gym equipment do I usually use?
  • What is most important to me about a local gym?

Etc etc.

I tried to give him some clues, but to no avail.

At the end of the tour, he gave me a high five and enthusiastically asked, “Are you signing up today!?”

“No,” I responded.

The gym manager turned to the receptionist and proclaimed, “My man here wants to sign up TODAY!” then walked off.

I thanked the receptionist and left.

The following day, I had my six-monthly dental checkup. Before I’d even sat down in the chair, they’d hit me with question after question:

  • How’s your mouth feeling?
  • Are you keeping up the brushing / flossing?
  • Is anything concerning you today?

Etc etc.

I couldn’t help but laugh at the difference between the two scenarios.

The lesson? You cannot give someone a solution until you’ve figured out what their problem is!

So, what then is the simplest and most direct way to figure out what their problem is?


Ask as many tailored questions as you can, until you’re fully aware of what their need is, then you can offer your solution IF (and only if) there’s a good fit. That’s what Covey meant in the headline quote, “Seek first to understand, then to be understood.” By focusing so much on trying to get our own point across, we may ignore the other person completely.

What’s another benefit of asking questions? It builds rapport! The dentist would’ve pinpointed any issues when she looked in my mouth, but she knew that building rapport and having clients feel comprehensively looked after is what’s most important.

The most interesting topic in the world to any person is themselves. As Dale Carnegie, author of How to Win Friends and Influence People, said: “You can make more friends in two months by becoming interested in other people than you can in two years by trying to get people interested in you.”

This is a tenet of relationships that goes back thousands of years. In 500 BC, famed military strategist Sun Tzu said: “Know your enemy and know yourself and you’ll never be in peril.” Today, good professional services firms have their own version: “Know your product. Know your client.”

This applies for any business. Remember to only offer a solution when you’re clear on what the problem is.

How much time do you think is wasted from people selling to prospects who were never going to buy in the first place? A few simple questions upfront will:

  • Greatly enhance your ability to offer a real solution
  • Save you hundreds of hours each year
  • Significantly increase your income
  • Enable you to build trusted relationships

You’ll find that your trajectory in your career and in your personal life corresponds with the amount of value you’re able to provide for others. But how can you provide value if you don’t know the other person—what they want, where they want to go, and what problems they need solutions to?

Whether in business, relationships, or friendships, direct all your attention to knowing the other person’s motive. The best way to do that is to question everything.

Onwards and upwards always,
James Whittaker

In case you missed it:
Lessons from the Best

Back to Newsletters >

Ready to win the day®?

Get actionable tips from James and the world's leading experts. Delivered to your inbox every two weeks ?
linkedin facebook pinterest youtube rss twitter instagram facebook-blank rss-blank linkedin-blank pinterest youtube twitter instagram