How to Have a Career Conversation With an Employee

People stay where they can see a future. When they cannot see one, even a good job starts to feel like a waiting room. That is why career conversations matter so much, and why it is worrying how rarely they happen. LinkedIn’s 2025 Workplace Learning Report found that only 15% of employees say their manager helped them build a career plan in the past six months, down from the year before.

At the same time, organizations know development matters. The same report found 88% of organizations are concerned about retention, and providing learning opportunities is their top strategy for keeping people. And Gallup reports only 32% of U.S. employees say they had opportunities to learn and grow at work in the past year. The intent is there. The conversations often are not.

Why do managers avoid career conversations?

Usually for understandable reasons. Some worry that talking about the future will make someone want to leave. Some do not know what opportunities exist and do not want to promise something they cannot deliver. And many are simply too busy, with career talks always falling behind today’s urgent work.

In my experience, the fear of losing people is backwards. People are much more likely to leave when nobody talks with them about their future. When a leader genuinely invests in someone’s growth, even growth that might eventually take them elsewhere, it builds a loyalty that is hard to compete with.

How do you run a career conversation?

Development does not always mean promotion

Not everyone wants to be a manager, and that is a good thing. Some people want to become the best in the organization at what they do. Others want to learn a new area, take on a project they care about or build skills for a future they have not fully defined. A good career conversation honors all of those paths and does not assume the only way up is into leadership.

For those who do want to lead, I give the same advice every time: start developing the people around you now. It is the one leadership skill that requires no title, and it is the clearest signal that someone is ready. I wrote about that in How to Decide Who to Promote Into Leadership.

Make it a rhythm, not a one-time event

A career conversation once a year during a review is better than nothing, but it rarely changes much. A short check-in every few months, even ten minutes during a regular one-on-one, keeps the plan alive. Ask what progress they have made, what is getting in the way and whether their goals have changed. People’s ambitions shift, and that is fine.

Development is the K in SPARK, Knowledge & Growth, one of the five drivers in my culture keynote, You Are Capable of a Better Culture. It is also why I tell leaders the risk of training people and losing them is smaller than the risk of not training them and keeping them. See What If You Do Not Train Them And They Stay?