500 Sneaky Coaching Questions For Meetings

Transform Any Meeting from Awkward Assembly to Actually Useful Collaboration

Stop asking "Any questions?" and start getting real answers.

The Problem You Know Too Well

You've been there. That moment when you ask "Any questions?" and get hit with the kind of silence that makes you want to crawl under the conference table.

Everyone's staring at their phones. Jenny's examining her fingernails like they hold the secrets of the universe. Mike's clearly planning his weekend Ikea trip. And Sarah looks like she's calculating how many more meetings like this until retirement.

Your stomach does that weird thing. You know the one.

Here's what's actually happening: Your team isn't bored because they don't care. They're bored because you're treating them like an audience instead of participants.

Most meeting questions are terrible. They're either so obvious everyone zones out, so broad nobody knows where to start, or so loaded they shut down conversation entirely.

What If One Question Could Change Everything?

I learned this the hard way running team meetings at my radio station. After one particularly brutal session where I felt like a comedian dying on stage, I tried something different.

Instead of my usual agenda broadcast, I asked:

"What's one thing we do in these meetings that wastes everyone's time?"

The silence stretched. Then Jenny looked up from her fingernails.

"Well… we spend ages on updates we could just read in an email."

BOOM. Everything shifted.

Within minutes, we'd redesigned the whole format. The next meeting felt completely different. People arrived with actual issues to discuss. They engaged with each other, not just me.

The gap between "awkward team assembly" and "actually useful collaboration" is often just one honest question wide.

Introducing 500 Sneaky Coaching Questions

This isn't another book of meeting theory. It's 500 carefully crafted questions designed to slip past people's defenses and get to the stuff that actually matters.

What makes these "sneaky"?

They bypass meeting fatigue and corporate-speak to unlock real conversations. Instead of asking "How can we improve?" (boring), you ask "If these meetings were a Netflix show, would you binge-watch or cancel your subscription?" (honest answers incoming).

What You Get Inside:

10 Laser-Focused Chapters:

1. Getting People Actually Talking (50 questions) For when your meeting feels like performing to an empty room
2. Uncovering Hidden Problems (50 questions) For when everyone's smiling but nothing's really working
3. Getting to Real Solutions (50 questions) For when everyone agrees there's a problem but nobody knows what to do
4. Making Decisions That Stick (50 questions) For when you need to move from talking to actually doing something
5. Dealing with Difficult People (50 questions) For when someone's making everything harder than it needs to be
6. Creating Accountability (50 questions) For when everyone agrees but nothing actually gets done
7. Innovation and Creative Thinking (50 questions) For when you need fresh ideas instead of the same old solutions
8. Team Dynamics and Collaboration (50 questions) For when the team isn't working like a team
9. Managing Up and Stakeholder Relations (50 questions) For when you need to influence people you don't manage
10. Personal Reflection and Growth (50 questions) For when you need to look in the mirror and be honest

Plus: Complete usage guide with golden rules and practical tips for when to use each type of question.

Bonus: Now With Added Audio Of Each Chapter

Real Examples That Actually Work:

Instead of: "Any concerns about the timeline?" Try: "If you had to bet your own money on us hitting this deadline, what would worry you most?"

Instead of: "What do you think about this proposal?" Try: "If you could change one thing about this plan to make it actually work, what would it be?"

Instead of: "How can we work better together?" Try: "What's one thing we do well together that we don't do enough of?"

See the difference? These questions make people think instead of just respond.

Perfect For:

✓ Team Leaders who want meetings that people actually value ✓ Project Managers tired of status updates disguised as collaboration ✓ Anyone who facilitates meetings and wants real engagement ✓ Coaches and Consultants looking for fresh conversation starters ✓ HR Professionals dealing with team dynamics ✓ Startup Founders building team culture

What My Sneaky Coaching Clients Are Saying:

"Finally, questions that get to the real issues instead of dancing around them."

"I used three questions from Chapter 2 and uncovered problems we'd been tiptoeing around for months."

"My team actually looks forward to our meetings now. That's not something I thought I'd ever say."

Why This Works When Other Approaches Don't:

Most meeting advice focuses on process. Better agendas, clearer objectives, stricter timekeeping. That's not wrong, but it misses the point.

The real problem is conversation quality. When you ask better questions, everything else follows. People engage. Problems surface. Solutions emerge. Decisions get made.

These aren't random questions pulled from thin air. Each one is designed with a specific psychological purpose - to bypass resistance, encourage honesty, and unlock the conversations that actually matter.

Your Immediate Action Plan:

1. Download instantly - PDF format, ready to use
2. Pick your chapter - Jump straight to your biggest meeting challenge
3. Choose one question - Start with just one in your next meeting
4. Watch what happens - See how real questions create real conversations
5. Build your arsenal - Gradually expand your question toolkit

No theory. No fluff. Just 500 practical tools you can use immediately.

The Bottom Line:

You're going to run meetings anyway. You might as well make them useful.

For less than the cost of lunch, you get 500 ways to transform your most frustrating professional activity into something that actually moves things forward.

Your choice: Keep asking "Any questions?" and watching people check their phones, or start asking questions that make people think.

The next time someone leaves your meeting and actually looks forward to the next one, you'll know it was worth it.

Ready to Transform Your Meetings?

Get instant access to all 500 questions plus the complete usage guide.

£20 - Less than most people spend on coffee this week, but this will improve every meeting you run for years.

[DOWNLOAD NOW - INSTANT ACCESS]

About Phil Roberts: Author of "Imposter Syndrome" on Audible, radio professional, and firm believer that the right question at the right moment can transform any conversation from painful politeness to productive partnership. He lives with his cat Walter, who remains unimpressed with his coaching credentials but appreciates the regular meal schedule.

"The most powerful meeting strategy isn't better presentations. It's one sneaky question that makes them co-designers of the conversation."

EXCLUSIVE BONUS: My Complete Question Arsenal

When you grab the Meeting Questions today, you also get:

"500 Sneaky Coaching Questions: My Secret Comprehensive and Themed Collection"

(Worth £25 - Yours FREE)

This is my complete vault - every coaching question I've developed, tested with real clients, and refined through years of writing on Medium. The same questions that have helped hundreds of people break through their biggest blocks.

What I'm throwing in:

✅ 17 Complete Question Themes covering every situation I've encountered in coaching ✅ 425+ Additional Questions beyond the meeting-specific ones
✅ Daily Practice Questions I use myself for ongoing growth ✅ Meta Questions about questioning itself (yes, I went there) ✅ Complete Usage Guide based on what actually works

The themes I've included:

• Perspective-Shifting Questions (for when you're stuck in your own head)
• Values & Priorities (for when you've lost sight of what matters)
• Fear & Limitation-Busting (for when your brain is being unhelpful)
• Decision-Making (for when you're overthinking everything)
• Self-Discovery (for when you need to figure out who you actually are)
• Action & Momentum (for when you're procrastinating like it's an Olympic sport)
• Career & Professional Growth
• Leadership & Influence
• Money, Ambition & Status (the stuff we pretend doesn't matter but totally does)
• Creativity & Innovation
• Life Purpose & Meaning
• Plus 6 more themes that have saved my clients countless therapy sessions

This isn't just more questions - it's my entire coaching methodology in question form.

I use these with executives, entrepreneurs, and anyone who's tired of surface-level conversations. Whether you're coaching others, working through your own stuff, or just want better questions for literally any situation, you'll have exactly what you need.

Combined value: £45
Your price today: £20

You're getting my specialised meeting breakthrough system AND my complete question collection that I've spent years developing. It's like getting my entire coaching toolkit for less than most people spend on coffee this week.

Here's what you're really getting:

• 1000+ total questions that actually work
• 27 different themes for any situation life throws at you
• Instant PDF downloads - use them in your next meeting

I won't keep this bonus available forever. Eventually, I'll split these into separate products (because my Walter The Cat keeps telling me to), but right now you can grab both collections together.

The real value? Every difficult conversation, stuck moment, or "I don't know what to ask" situation you'll face - sorted.