Don’t Just Tell Me what You Think I Want to Hear

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If there’s one lesson I learned early in my teaching career, it’s that there are two questions that were totally useless if I wanted to know if my students understood whatever concept I had just taught:


1. “Do you understand?”

2. “Do you have any questions?”


This is, ironically, because students would often say “yes” in response to the first, when they really meant “no,” and would say “no” to the second when they really meant “yes.”


And what’s even more surprising is that this pattern is 100% the same now in the corporate training space, working with professionals, and even when onboarding new contractors.


Whether in the virtual realm or face to face, those two questions never seem to get to the heart of whether or not what you attempted to communicate was actually received, much less yield actionable insights.


First and foremost, the fact that both are yes-or-no questions essentially guarantees that no specific information will be given. Why would it? You gave them two one-word answer options, both of which satisfy the question, at least at face value. No thought or further information exchange needed.


But beyond that, there are many factors that may contribute to this pattern. To name just a few:


  • Ego/pride/shame – they don’t want to admit that there’s something they don’t understand
  • They don’t want to disappoint or anger you
  • They don’t want to look stupid in front of you
  • They are afraid of the possible repercussions (whether personal, private or public) of any of the above points
  • Cultural – in some cultures you’re not supposed to say “no” to the boss/client, no matter what.


A few options that are far more fruitful include asking:


  • What questions do you have?” (which presupposes that everyone has some, so it’s natural or appropriate to share them now)
  • I just gave you a lot of information. What do you need me to repeat or clarify?” (Again, this presupposes that something will need clarification, and helps the other person save face by acknowledging that the quantity of information would have created the need for the clarification, rather than due to any shortcomings of the listener.)
  • “I’m working on my own communication skills as a leader. Could you please tell me what you understood me to have said? I want to see where I wasn’t clear enough.” (This allows you to assess for yourself what was accurately received or missed, and it allows you to take the responsibility, so the listener doesn’t feel embarrassed for having failed to capture your message 100%.)


But no matter what the context is, there’s one thing that’s universally clear: asking the right questions makes all the difference.


And one person who is an expert in that subject is this week’s podcast, Jeff Wetzler, co-founder and co-CEO of Transcend, a nonprofit organization dedicated to transforming education, and the author of the brand-new, hot-off-the-press book, Ask: Tap Into the Hidden Wisdom of People Around You for Unexpected Breakthroughs In Leadership and Life.


In Ask, Jeff:


  • Dives deeper into what information people decide not to share and why,
  • Outlines the five key steps to the “ASK approach,” which
  • Asks better questions,
  • Creates a safe space for people to provide answers, and
  • Helps transform shared information into meaningful actiop\ion.


In this week’s Speaking to Influence episodeJeff also discusses the challenges of communication in leadership, the importance of listening, and how to create a safe space for open communication.



He also highlights the power of curiosity, and challenges us to practice what he calls “no BS listening.” (Sounds good to me!)


Listen to the full conversation here or watch the video on YouTube here.


PS. Don’t forget to rate the Speaking to Influence podcast on – thank you!

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