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Let's talk about the questions you never ask.
You know, the ones that stick in your throat like a chicken bone.
The ones that make your palms sweat and your voice crack.
The ones you rehearse in your head but never let past your lips.
Yeah, those.
I’ve noticed all too often that:
The questions you're most afraid to ask are usually the ones that matter most.
They're the keys to doors you didn't even know were locked.
The bridge between surface-level chit-chat and actual connection.
But we don't ask them.
"He who asks a question is a fool for five minutes; he who does not ask a question remains a fool forever."
Why?
Because we're terrified of looking:
Stupid
Weak
Unprofessional
Needy
Out of our depth
Too emotional
So we stick to safe questions:
"How's the project going?"
"What are the next steps?"
"Does anyone have any questions?" (While praying nobody does)
Gif by fallontonight on Giphy
Meanwhile, the questions that could change everything stay buried:
"I don't understand this at all. Can we start from the beginning?"
"Am I meeting your expectations?"
"This strategy scares me. What if we fail?"
"I'm struggling. Can you help?"
"Why do you really think this isn't working?"
Here's what happens when you finally ask the scary questions:
1. People respect your courage
Nobody thinks less of you. They think, "Thank god someone finally asked that."
2. You get real answers
Not corporate BS. Not polite deflections. The actual truth that moves you forward.
3. You build deeper trust
Vulnerability fast-tracks connection. When you drop the facade, others feel safe to do the same.
4. You learn faster
"Stupid" questions often reveal the deepest insights.
Growth lives at the edge of discomfort.
5. You give others permission
Your courage creates safety. Suddenly, everyone's asking better questions. The whole team levels up.
So, how do you ask the questions that scare you?
Here comes another framework: The BRAVE method
Breathe and prepare mentally
Recognize your fear is normal
Ask with genuine curiosity
Value the response you receive
Engage with follow-up questions
Let’s get it:
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B - Breathe and prepare
Take a moment to center yourself.
Acknowledge that the discomfort is normal.
Remember: courage is fear plus action.
R - Recognize what you're really afraid of
Name your fear to tame it.
Is it looking stupid?
Being judged?
Appearing weak?
Say: "I'm worried this might seem basic, but..."
A - Ask with genuine curiosity
Frame it as a learning opportunity.
Use phrases like "Help me understand..."
Focus on getting clarity, not being right.
V - Value the response
Listen without defending.
Take notes to show you value their input.
Say "thank you" and mean it.
E - Engage with follow-ups
Ask clarifying questions.
"Can you give me an example?"
"How does this connect to...?"
Every expert was once brave enough to ask the "stupid" questions.
POLL
What stops you from asking important questions at work?
LEVEL UP
7 Days to Vulnerable Curiosity Challenge:
Day 1: Write down three questions you've been avoiding.
Day 2: Pick the scariest one and ask it.
Day 3: Ask for clarification on something "everyone" understands.
Day 4: Ask someone for feedback on your biggest weakness.
Day 5: Question a process that "we've always done this way."
Day 6: Ask about the elephant in the room at your next meeting.
Day 7: Ask someone you admire how they really achieved their success.
CURATED ROUNDUP
What Caught My Eye This Week
Read: The Coaching Habit: Say Less, Ask More, and Change the Way You Lead Forever" by Michael Bungay Stanier
Watch: The Power of Vulnerability by Brené Brown, TED
This digital daily planner helps you feel calm and stay focused.
The questions that scare you are usually the ones worth asking.
They're scary because they matter. Because they might change things. Because they require vulnerability.
But here's the thing about vulnerability: It's not weakness. It's the ultimate professional courage.
The most respected leaders I know ask the "dumb" questions.
They admit what they don't know.
They seek help when they're struggling.
And their teams love them for it.
So what's the question you've been avoiding? The one that makes your stomach flip? The one you rehearse but never ask?
Ask it. Today.
Thanks for reading. Be easy!
Girvin
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