Here’s something worth sitting with as a practitioner — not just reading, but genuinely sitting with, because it’s easy to nod along and harder to feel the weight of.
Clients will answer the question you put to them — even when it’s not the question that actually helps them move forward.
The pattern
Ask a closed question, you get a closed answer. Ask a shallow question, you get a shallow answer. Ask the wrong question well — clearly, confidently, with good technique — and you’ll still get a perfectly good answer to the wrong thing.
That last part is the uncomfortable bit. A well-delivered question can feel like good practice even when it’s pointed at the wrong target. Confidence in how you ask doesn’t tell you anything about whether you asked the right thing.
A moment this might look like
A client says they’re unhappy in their current role. You ask, “What would you change about your job if you could?”
It’s a reasonable question. They’ll answer it — probably with something about hours, or pay, or a difficult colleague. And that answer will be true. It just might not be where the real work is.
A different question — “What does ‘unhappy’ actually mean here, for you?” — opens a different door entirely. Maybe it’s not the job. Maybe it’s a mismatch between what they value and what the role rewards. The client didn’t choose which door to walk through. You did, when you decided which question to ask.
This is the part that’s easy to miss: the client isn’t failing to go deep. They’re answering exactly what was asked. If the conversation stays shallow, the question was shallow — not the client.
Why this matters
- The client isn’t choosing what to explore — you are, whether you mean to or not. Every question narrows the field. That’s not a flaw in questioning; it’s what questions do. But it means the responsibility for where the conversation goes sits with the person asking, not the person answering.
- A poorly-aimed question can keep someone circling the same surface-level thinking for an entire session. Not because the client is resistant or stuck, but because the questions kept pointing at the same layer.
- Precision in questioning isn’t a nice-to-have — it’s the difference between a conversation that goes somewhere and one that doesn’t. Warmth and rapport matter, but they don’t substitute for aim.
- Generative questions don’t just get answered — they open up thinking the client hadn’t reached yet. The best questions don’t retrieve an existing answer. They create the conditions for a new one.
The real skill
The skill isn’t just asking questions. Anyone can do that. It’s asking the ones that actually move someone forward — which means paying constant attention not just to what the client says, but to what your own question just did to shape that answer.
That’s a different kind of listening. It’s listening to your own questions as carefully as you listen to the client’s responses.
Sharpening the aim of your questions is core work on our Level 6 Diploma in Career Guidance and Development. For more short reflections on practice, follow Sonder Training Group on LinkedIn.
