The Benefits of Deeper Questions

Why don’t you ask deeper questions? Are you more afraid of the questions or the answers?

Deeper questions

  • Uncover concerns
  • Shift the conversation
  • Invite transparency
  • Shift the mood
  • Provoke deeper thinking

Asking Deeper Questions

“Live your questions now, and perhaps even without knowing it, you will live along some distant day into your answers.”Rainer Maria Rilke

Asking Deeper Questions of Yourself

It starts by asking yourself deeper questions. In her TED Talk Christine Comaford, shares the importance of finding “your one big question.” The finding (and answering) of this “question” is a way to “intentionally evolve. She invites listeners to 1) reveal yourself 2) stand for yourself and 3) get still as you look for your questions.

Asking Deeper Questions Of Others

When, asking questions of others, pause and give yourself time to formulate the best question. Proactively plan your deeper questions as you plan your day. Make a point of asking at least one deeper question in any significant meeting you attend.

Power Questions by Andrew Sobel and Jerold Panas and StoryCorps are great resources to help you plan deeper questions for a variety of circumstances.

I asked Andrew Sobel to share the best questions for three of the most challenging topics for frontline leaders: dealing with disengagement, building confidence, and helping someone feeling overwhelmed.

“Sometimes the simplest question is the best. For example, ask your people often, ‘What do you think?’ Or, ‘How can I be helpful to you right now?’ Ask personal questions–‘How did you get your start?’ Turn statements into questions. Instead of, ‘We really need to burn the midnight oil if we’re going to hit our targets this month” ask “Here’s what we’re up against. What are your thoughts?”
~Andrew Sobel

Addressing Disengagement

  1. What is the one thing we could do to make it easier for you to do your job effectively? 
  2. What can I do to help you be more effective in your job? 
  3. What makes you proud—or not proud—to work here? 
  4. What’s the most and least engaging part of your work? 

Building Confidence

  1. What options are you considering right now? 
  2. What do you think are the pros and cons? 
  3. What do you think you should do? 
  4. What is most puzzling or difficult about this?
  5. What have you done in the past in similar or analogous situations? 
  6. What’s your biggest unanswered question about this situation?
  7. Who do you think has the right experience to help you with this? 

Helping the Overwhelmed

  1. What’s something that’s very hard to do for you but which would really help you be more successful? If there were no constraints—what could help make it happen? 
  2. How can I help you right now?
  3. What people or resources would be helpful to you right now?