Ask "What’s the real challenge here for you?"
The presenting problem is rarely the actual problem — this question cuts through to what really matters.
Why it works
People often present the problem that is easiest to articulate, not the one that is hardest to solve. Adding "for you" is critical — it personalizes the question and moves from the objective situation to the person’s actual experience of it. The subjective challenge (fear, uncertainty, interpersonal tension) is often where the real coaching leverage exists, while the stated challenge (the project, the deadline) is just the surface.
How to do it
- After understanding the situation, ask: "And what’s the real challenge here — for you?"
- Pay attention to whether the answer shifts when they add "for me": the shift is the useful signal.
- If they name a people problem, stay there: "Tell me more about the [person] piece."
- If the real challenge seems to be about their own capability or confidence, name it tentatively: "It sounds like the challenge might be about…"
Evidence
Distinguishing the presenting problem from the real problem is a foundational principle in clinical and coaching psychology. Adding "for you" is Stanier’s contribution — a small word that reliably personalizes the exploration and surfaces the subjective challenge. (clinical)
The value of surfacing the real challenge is established in clinical and coaching practice. Stanier’s specific phrasing is practitioner design; the underlying principle is from clinical and counseling psychology.
Common mistake
Asking "What’s the real challenge?" without "for you" — the missing personalizer makes the question feel like you are questioning whether they’ve identified the right problem, rather than inviting deeper exploration.
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More practices for The Coaching Habit: Seven Questions to Be More Coach-Like
- Open with "What’s on your mind?"
The best opening question is also the most open — it invites exactly what the person most needs to talk about.
- Ask "And what else?"
The first answer is rarely the most important one — "And what else?" pulls out the one that actually matters.
- Ask "What do you want?"
People often know what they want but haven’t said it — asking directly surfaces it and shifts from complaint to intention.
- Ask "How can I help?" instead of assuming
Telling people how you’ll help before finding out what kind of help they want is one of the most common management errors.
- Ask "If you’re saying yes to this, what are you saying no to?"
Every yes is a yes-at-the-expense-of-something — making the trade-off explicit is the most useful thing a coach can do.
- Close with "What was most useful for you?"
The closing question turns the conversation into a learning that sticks — and teaches you what is actually valuable.
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