How To Use Questions To Change Your Life

If you want a great life, ask great questions. Questions can be catalysts. They’re challenges, inspirations, road maps, and hints of something better.

My first assignment as an FBI undercover agent was to identify a KGB officer who was a member of Russian delegation visiting a Silicon Valley company for six months. The company was involved in a joint venture with the Russian government. Of particular interest to the FBI was the fact that the American company was conducting high tech research. While some aspects of the research could be used for commercial use, there were other aspects that were classified and restricted for use by the U.S. Military.

Therefore, it was no surprise when Oleg showed up among the delegation—click HERE for an earlier post on how I identified Oleg as a KGB officer. The first step in an FBI counterintelligence operation is Identify the Target; there are, however, many levels of identification.

The first level is name, rank, and serial number—little more than a legal description of a person. The second and third levels go much deeper and attempt to more fully identify the spy. The FBI’s goal is to prompt the target of their investigation to answer questions like, “What is the purpose of your life?” and “What is your higher calling?”

Oleg was no longer finding fulfillment or purpose in his life as a KGB officer. The thrill was gone. But what do you think would be my chances of getting an honest and thoughtful answer if I walked up to him and asked, “Hey, Oleg! What is the purpose of your life?”

That is not an answer that is at the tip of most people’s tongues. It takes time to excavate the significance of our own stories and experiences. The most effective way to begin this process is to begin probing with questions. As I stated earlier, questions can be catalysts that hint of something better to be found in us. Most of us find our past experiences help us to recall how our strength and resilience got us through the tough times.

The power of our own stories and experiences can encourage us to move beyond the limits we set around ourselves. We yearn to connect the threads of our life story to help us interpret our present circumstances. Questions can be a magic wand that probes deeply into our mind.

I didn’t fire the following questions at Oleg all at once; but over time, I asked the following:

  • Who is the happiest person you know?
  • Who are the people you like and respect the most? Why?
  • What are you curious about?
  • When does time seem to fly?
  • What bores you?
  • What makes you different from other people or members of your family?
  • How do you want to be remembered?
  • What is in your bucket list of things to do in life?

Questions are entry points into significant conversations about issues, values, and goals that are most important to us. If you want to start a significant conversation, ask a significant question. These questions do not have to be brilliant or well crafted; instead, they need to be from the heart and wrapped in genuine curiosity.

If you start asking yourself questions like these, the answers will quickly uncover whether or not you’re leading the kind of life you want. The truth is, most of us are so busy doing what we think we have to do that we never get around to doing what we really want to do.

Oleg rarely had an answer off the top of his head, but my use of patience, pacing, and timing allowed him to mine deep to find the answer. So many times we ask questions of individuals and then don’t allow them the luxury of moving at their pace. Instead, we expect them to move at our pace.

Give people the time to explore their thoughts and relive their memories. In a fast-paced world, sometimes the greatest luxury in the world is the ability to tell you own story at your own pace. Help them by asking:

  • What does hope feel like?
  • What does courage sound like?
  • What does action look like?
  • How do things get better?

How would you answer these questions? What additional questions would you add? What tips do you have for getting people to open up to you?












Erin shows overscheduled, overwhelmed women how to do less so that they can achieve more. Traditional productivity books—written by men—barely touch the tangle of cultural pressures that women feel when facing down a to-do list. How to Get Sh*t Done will teach you how to zero in on the three areas of your life where you want to excel, and then it will show you how to off-load, outsource, or just stop giving a damn about the rest.

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