Reader situation
Most professional conversations stay at the level of current roles and projects. But some of the most useful insight comes from the moments when someone’s direction changed: a decision to switch fields, a setback that redirected them, an opportunity they took or turned down. Few people are asked about these moments, and many are glad to share them when asked well.
Central idea
A turning point can reveal how someone thinks, learns and chooses. Invite a story about a professional change, and listen without forcing it into your own experience.
Practical steps
- Invite a voluntary story. Ask in a way that makes it easy to decline or to share as much or as little as they like. For example: “I’m curious about how people end up where they are. Was there a moment that changed the direction of your career?” Make clear there’s no wrong answer and no pressure to share anything personal. Choose the right moment. This kind of question suits a one-to-one conversation or a small group, not a large meeting. It works best once you’ve established some rapport.
- Ask context. Once the person begins, ask about the situation around the turning point: “What was happening at the time?” or “What were you doing before?” Context helps you understand why the moment mattered and what options they had. Keep your questions open, and let the person choose which details to include.
- Explore choice. Ask about how they made the decision: “What made you decide to go that way?” or “What else were you considering?” This is often where the most useful insight lies. People’s reasons reveal what they valued, what information they had and how they weighed uncertainty. Be careful not to judge the decision. Questions like “Didn’t you worry that was risky?” can imply criticism. “How did you think about the risk?” invites reflection instead.
- Listen for meaning. Pay attention to what the person takes from the experience, not only the events. Some people describe a turning point as a lesson; others see it as luck or circumstance. Listen to how they make sense of it, rather than offering your own interpretation. Resist the urge to say “That’s just like when I…” straight away. Comparing too quickly can take the conversation away from them. If your experience is relevant, share it briefly later, once they’ve finished.
- Thank contributor. Thank the person specifically for sharing: “Thank you for telling me that. It’s helpful to hear how you thought through the move.” If something they said was useful to you, say what it was. Respect anything shared in confidence.
Worked example
Fictional example
The people and details are invented to illustrate an approach. It reports no outcomes.
During a peer call, Leah asks her peer Tomas whether there was a moment that changed his career direction. He says yes: ten years ago, he was a lawyer and decided to move into product management.
Leah asks what was happening at the time. Tomas explains that he’d been advising technology clients and realized he was more interested in their products than in legal issues. She asks how he made the decision. He describes taking a six-month secondment with a client first, which let him test the move without leaving law completely.
Leah notices she wants to share her own career change, but waits. She asks what he took from the experience. Tomas says the main lesson was that testing a change on a small scale made the larger decision easier. Leah thanks him and says the idea of a trial period is exactly what she needs to consider for her own possible move into consulting. She then briefly shares her own situation, and Tomas offers a few questions to ask before making the change.
Companion tool: Turning-point conversation guide
Opening questions (choose one)
- “Was there a moment that changed the direction of your career?”
- “What’s a decision that shaped where you are now?”
- “Is there a point in your career you think of as a turning point?”
Context questions
- “What was happening at the time?”
- “What were you doing before?”
Choice questions
- “What made you decide to go that way?”
- “What else were you considering?”
- “How did you think about the risks?”
Meaning questions
- “What do you take from that experience now?”
- “Would you make the same choice again?”
Thanking
- “Thank you for sharing that. The part about ________ was especially useful to me.”
Boundaries
- Turning points can involve personal difficulties such as illness, redundancy or loss. Don’t press for details, and follow the person’s lead.
- Keep what’s shared private unless you have permission to repeat it.
- Some people prefer not to discuss their history. Accept that without comment.
Member action
Ask a peer about a professional decision that changed their direction. Hold back your own story until they’ve finished theirs.
Discussion prompt
What’s a turning point in your career that taught you something you still use?
