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Ask Better Questions to Really Know How Others Are Doing


Have you ever been asked “how are you” and get a sense that the one asking really doesn’t want to know? Have you asked this question only to have the topic that is top of mind for you ready to go? Finally, we ask and hear “good… fine… ok…” and suspect we are not getting to the truth?


“How are you” is a natural question when we encounter others in the office, start a meeting, or even cross paths with those we know; then we get down to business. Understanding how people are doing is beyond “how are you” and it is during these moments that asking the right questions, at the right time, allow us to get to what is top of mind so we can effectively identify what is helping or hurting progress.


I am certainly not advocating to stop asking “how are you”. What I am proposing is that if we really want to know how people are doing, ask follow-up questions. The next time you are leading a meeting, connecting one-on-one with a co-worker or member of your team, consider these questions to get a sense of how people are really doing:

  1. How did it go with… (time to ask about personal/home/wellbeing events they have shared with you previously)?

  2. What is top of mind for you today/this week?

  3. What would make your job even more satisfying? What is important to you?

  4. What are you looking forward to?

  5. What is your outlook for today, the week, month, or project, task, change?

  6. What new idea or what part of your work is giving you energy this week?

  7. What is your biggest upcoming challenge and how can I/the team/the organization support you?

  8. What comes up that hinders progress and how can we work together to overcome?

  9. What helped you succeed with his project, task, etc. that we need to keep in place?

  10. What does success look like as you take the next step?


When engaging your team, show up with a curious mindset by using these tips to help everyone get the most out of the conversation:


  • Share why this input is important to you: demonstrating that you genuinely care for their wellbeing and connecting it to what they are looking to achieve.

  • Meet them where they are: withhold judgment and set aside your pre-conceived notions so you learn from the interaction.

  • Show empathy: we do this by putting ourselves in a place that generates similar feelings of another, and we refrain from giving unsolicited advice.

  • Demonstrate Interest: keep an open mind and resist distractions or the urge to write the “story in your head” or respond before you understand what the other person is trying to convey.

  • Check your understanding: restate what you believe is the message and ask clarifying questions to ensure understanding.


By incorporating these questions and showing up with the right mindset, you will set the tone for an open discussion about what affects the work of your team, understand what they find challenging and rewarding, and effectively check in on their wellbeing. All key to helping others feel fulfilled and show how they are doing and what they do, matters.


What other questions do you use to really know how people are doing?

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