500 Sneaky Self-Aware Coaching Questions At Work

Disarming prompts to help you think sharper, lead better, and dodge workplace drama without sounding like a TED Talk in khakis.

🟨 What Is This?

You don’t need more leadership theory.
You need better questions.

This PDF toolkit gives you 500 sneaky, self-aware coaching questions you can use in 1:1s, team meetings, coaching sessions — or those "I'm the bottleneck again" moments staring at your laptop at 9:07am.

They’re called “sneaky” for a reason.
These prompts slide under the surface of polite workplace chat and go straight to the stuff that actually matters:

• Why your feedback keeps getting ignored
• Why your team is smiling but disengaged
• Why you’re stuck in overthinking loops
• Why your confidence still wobbles after the promotion
• Why that meeting could’ve been an email (but wasn’t)

💡 Use it for:

• Coaching yourself out of a rut
• Kicking off deeper conversations
• Giving feedback without starting a war
• Cutting through office noise with real clarity
• Sounding like the leader you secretly wish you were

📚 What’s Inside?

• 12 themed sections including:
  • Leadership Without the Ego
  • The Art of Honest Feedback
  • Dodging Drama with Style
  • Confidence Without the Cringe
  • Meetings vs Meaning
• 500 smart, edgy, reflective questions
• No fluff. No filler. No jargon.
• Just you, your brain, and a better way forward.

🎯 Who It’s For:

• New managers with imposter syndrome and a team staring at them for answers
• Team leads who want real conversations, not just updates
• Workplace coaches who want better questions in their back pocket
• You (yes, you) if you're secretly the go-to person, the fixer, or the one who feels too much and says too little

💬 Feedback so far:

“These aren’t just questions. They’re flashlights.”
“My team meetings sound different already.”
“It’s like therapy, but cheaper.”

🟢 Yours for £5

(You’ll use it more than you think. Promise.) Yes download it , print it, use it. Simple.