The Sneaky Coaching Question That Transforms Terrible Managers
Making Self-Awareness The Secret Weapon
Hi, I’m Phil, Thanks for joining another edition of Sneaky Coaching Questions For New Managers
❓ “What qualities in others make you lean in and listen?”
Here’s a great addition to your leadership toolkit for coaching future superstars.
Use this gem in your next chat with a struggling manager and see their reaction.
That moment of “huh?” followed by actual thinking. Beautiful stuff.
Because here’s the secret…
Most rubbish managers have NEVER considered this question before.
They’re too busy thinking about what THEY want to say. Not what makes THEM actually listen to others.
Sneaky, right?
Like Blabbering Barbara. Yes I told her this after a few frustrating sessions. We were in fun mode and laughing so don’t panic.
“You’re blah blah blah Barbara” I said.
Why I’m not doing this but this…
Now , when I ask this question, I’m not teaching them communication.
I’m prompting them to reflect on what they value in others and how it aligns with their own actions.
Aha! Yes that cheeky intervention.
I’m basically saying:
“Hey, show me your listening blueprint without realising you’re showing me your listening blueprint.”
This works because it sidesteps defensiveness.
I’m not saying “You’re a terrible listener” (even if they are). I’m inviting them to describe the communication style they respond to.
And here’s where the magic happens…
They’ll describe qualities they rarely demonstrate themselves.
❎ “I listen when people are concise.” (Yet they ramble for 20 minutes in meetings)
❎ “I appreciate when someone acknowledges my expertise.” (Yet they dismiss others’ input constantly)
❎ “I value authentic communication.” (Yet they hide behind very bad corporate speak)
Is it foolproof? Nothing is
Some managers will give you textbook answers they think sound good.
Others get uncomfortable because they’ve never actually thought about what makes them listen.
That’s when I follow up with:
“Think about the last conversation where you were fully engaged — what was that person doing?”
The standard alternatives just don’t dig as deep:
❎ “Are you a good listener?” (They’ll say yes)
❎ “How would you improve your listening?” (Assumes they know they need to)
❎ “What’s your communication style?” (Too abstract)
This sneaky approach has evolved beyond the old “active listening tips” nonsense.
It’s not just about teaching listening skills. It’s about building self-awareness, which sparks real change.
I used this with a radio station tech manager named Dave (not his real name, obviously).
He claimed communication problems were everyone else’s fault. After this question, he saw he only listened to those who agreed with him first.
This was exactly what he never did for his team.
Boom. Self-awareness unlocked.
The beauty is they believe they’re describing others, but they’re really writing their own guide.
So try it. Watch as they connect their own dots.
Because creating exceptional communicators isn’t about communication rules.
It’s about mirror moments.
Sneaky Coaching Question: ❓ “What qualities in others make you lean in and listen?”
(Walter the cat just walked across my keyboard and deleted three paragraphs. He doesn’t believe in drafts. Pure confidence. Another leadership lesson from my feline CEO.)
Till Next Time
I’m the Author of the Imposter Syndrome on Audible, love local radio and coaching my cat Water.