The Most Versatile Coaching Questions I Use Again and Again
There’s a lot of pressure in the coaching world to ask the perfect question — the one that unlocks instant clarity or creates a dramatic breakthrough.
But in real coaching sessions, that’s rarely how it works.
In this episode of The Coaching Edge, I’m sharing the most versatile, workhorse coaching questions I use again and again — not because they’re clever or flashy, but because they reliably open insight across nearly any topic.
These aren’t scripts or “magic questions.” They’re question types you can adapt moment-by-moment, depending on what your client actually needs.
In this episode, I talk about:
- Why coaches often over-hunt for the “perfect” question — and why that usually backfires
- Why versatility and timing matter more than clever wording
- How powerful questions work because of how and when they’re asked, not just what’s said
- Five core question buckets I return to again and again in real client sessions
- Simple go-to questions you can always use when a session feels stuck
You’ll hear examples of questions that:
- Gently surface limiting beliefs without arguing or fixing
- Reconnect clients to agency and choice
- Expose unspoken assumptions driving the problem
- Bring emotions and the body back into the conversation
- Widen perspective without minimizing the client’s experience
I also share why learning when to use these questions matters more than memorizing them — and how this skill is something I teach explicitly inside the Confident Coaching Skills Intensive (CCSI).
If you’ve ever left a coaching session with imposter syndrome and wondering whether you asked the “right” questions, this episode will help you trust yourself — and the simple questions that actually do the work.
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Author & Host
Wendy McCallum
Business Coach for Coaches, Burnout & Alcohol Coach for High Achievers
I’m Wendy McCallum — a coach, mentor, and former lawyer who’s spent the last 15 years helping people build lives and businesses they actually want to wake up to. When I first left law, I had no guidebook for how to do this coaching thing. I floundered — hard. I undercharged, overthought, and overinvested in shiny solutions that didn’t really move the needle. But every mistake taught me something, and eventually, I built the kind of coaching practice I once only dreamed about — one that’s profitable, sustainable, and full of work I truly love. Today, I coach two kinds of people: ✨ Busy professionals who are ready to make big, meaningful changes — whether that's finding balance, recovering from burnout, or rethinking their relationship with alcohol. ✨ And newer coaches who are building their businesses from the ground up and want a clear, sustainable path forward without all the gimmicks and noise. Whether I’m helping someone simplify their business or reclaim their personal life, the heart of my work is the same: giving smart, capable people the clarity, encouragement, and real-world tools they need to move forward — in a way that feels good, not overwhelming. If you’re ready for something better — in your work, your life, or your business — you’re in the right place. And I’m so glad you’re here. IMPORTANT: Blog content including Wendy's podcasts are for information purposes only and not intended in any way to be health advice. Please see full Terms of Use, by clicking on the link in the footer of this page, for details.
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