Career & work
Was there a turning point in your working life — a moment things changed direction?
Why this question matters
Most careers look linear in the retelling and were anything but in the living. There is almost always a moment — a layoff, a bad boss, a chance conversation, a phone call from someone they had not heard from in years — that changed the trajectory. Asking for it gets you past the resume version of the story and into the part that actually shaped who they became.
If they pause, try this
Ask if they could see it happening at the time, or only later.
What people often remember when asked this
- 01
Sometimes the turning point is a person — the mentor who pulled them up, or the boss who pushed them out. Ask how that person ended up in their life in the first place.
- 02
Sometimes it is a moment of failure — getting fired, missing a promotion, watching a project collapse. The story behind those moments tends to be the most honest career advice you will ever get.
- 03
If they say they had no turning point — that they just kept doing what they were doing — ask whether they wish there had been one. The answer to that is often more revealing than the original question.
A small tip for the conversation
Pair this with the question: did you see it coming? Most turning points feel inevitable in hindsight and were invisible at the time. The gap between those two versions is the real story.
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