Man looking pensively and asking tough questions steve white
March 15, 2021

What’s the Most Powerful (and Painful) Question You Can Ask Yourself?

Why is it important to ask yourself thoughtful questions? Because those are the moments you’re stepping up and taking responsibility for your own learning. It’s also when you’re opening yourself up to the idea that you can learn something new if you work at it.

I’m an inquisitive guy, so I’m passionate about asking questions. I learn a lot by throwing a thought out to the room and tuning in to hear how people respond. Curiosity is one of the many ways you can invest in yourself and those around you. The great advantage of curiosity is that you can craft a self-reflective question that triggers personal growth or focus on the art of inquiry to learn from others.

For instance, you might have heard me say, “Invest in You, Inc.” That means I want you to treat your own future as a business. If you were a company, what investment would you make in yourself to drive your own success? I love this question because it prompts people to answer differently than if I had said, “Where do you see your career in five years?”

Upstart founder and CEO Dave Girouard has a question that he began asking himself while he was an executive at Google. He relies on this question because it pushes him toward a growth mindset. Girouard says, “One mental exercise I’ve invested in is thinking about what would happen if tomorrow my board got together and fired me.” Then Girouard imagines the sequence of events that led the board to hire the very best CEO, and then he ponders what that new leader would do differently.

Girouard thinks about that for a while and then asks himself, “Why the hell aren’t you doing those things? It’s just a weird game I play to get myself to recognize that while I’m doing some things okay, I can be lulled into a place of feeling good about myself when I’m probably not doing some other things very well.”

While this question can be a bit painful, it’s incredibly powerful. You’ll be surprised at how quickly you respond with ways that you can improve on the job you’re currently doing. Why is it important to ask thoughtful questions like Girouard’s? Because those are the moments you’re stepping up and taking responsibility for your own learning. It’s also when you’re opening yourself up to the idea that you can learn something new if you work at it.

After you ask yourself the tough questions, don’t forget to look outward. There’s always someone around you—the board’s next hire or the person working with you on a project—who knows something you don’t. It’s on you to ask them questions. It’s up to you to engage them in a conversation.

What do effective questions look like? It often depends on what your conversational goals are, but here are some tips to get you started in a cooperative versus competitive setting, according to Harvard Business School Professors Alison Wood Brooks and Leslie K. John:

1. Follow Up

Great questions start with good listening. When someone shares something with you, ask a detailed follow-up question about what they’ve said. It shows you care, and that you value a connection with them.

2. Avoid close-ended questions

Open-ended questions cultivate a dialogue more quickly than yes-or-no questions that can cause someone to feel manipulated. These begin with phrases like, “What do you think about…” or “Tell me more about…”

3. Think about the order of disclosure

Begin with the least-sensitive questions if you’re trying to build rapport and then escalate slowly.

The art of questioning is not only powerful for self-reflection, but also for learning from others.

If you adopt my question, consider what investment you need to make in yourself—just like you would in a business. Should you sign up for training or enlist a would-be mentor? If you choose Dave Girouard’s question, you’ll ponder what your successor would do and make a list of how you’ll up your game.

Maybe you have a question of your own. Think about a prompt that will get you the helpful response you’re looking for, that speaks to your heart and purpose in life. I’d love to hear what gets you motivated to push, to grow, and to learn!

Live your why,


P.S. I’ve created a tool that can help prompt life-changing questions of your own. It’s called The 10Daily Wins. Over the next 10 days, I’ll send you my favorite life and business advice from some of the world’s most inspiring minds. Ready to make the next leap forward? Sign up for The 10 Daily Wins.

More Like This…

A Big Win for All of Us

A Big Win for All of Us

Receiving this week’s honor as an inductee into Syndeo Institute’s Cable Hall of Fame is a big win for everyone on my journey.

1 Comment
  1. James

    I’ve always enjoyed your leadership and inspiration, Steve. I remember feeling the lull in my job and COVID made it worse. Perhaps others noticed because I was part of a “transition” where my job was eliminated. I kept trying to apply for other positions within the same company to try and ignite that spark, but it just never happened. Losing that job forced me to refocus. Now I have a great job with a new company! It may not pay as much, but it challenges me and gives me something to look forward to. Pay isn’t everything. That DEFINITELY is a lesson learned.

Submit a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.