Ask the Question You're Afraid to Ask

In partnership with

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.

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)

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: