How to Have a Career Conversation With an Employee

Ask your employee where they want to go, even when you cannot promise a promotion or a new role. The conversation is not a contract. It is a way to understand what matters to them and decide what support you can offer now.

Managers often avoid this because they fear raising expectations they cannot meet. That concern is fair. Silence leaves the employee guessing, though, and makes it harder to support them with useful assignments or honest advice.

Set expectations before you ask

Be clear about what you can and cannot promise. You might say, "I want to understand what you are working toward. I cannot promise a particular role or timeline, but I can listen and look for ways to support your growth here."

Then ask open questions. Where would you like your work to lead? Which parts of your current role give you energy? What skill would you like to build? What kind of work would you like to do less often? If you are not sure yet, what would you like to explore?

You do not need to run through every question in one sitting. Let the employee decide where to start. Listen before you try to solve the problem. A career conversation is not a pitch for the next promotion.

If the employee is unsure, do not force a three year plan. Ask what they would like to test in the next few months. A small project, a shadowing conversation, or time to practice a skill can help them learn what fits before either of you talks about a longer path.

Turn interest into one concrete step

At the end, choose an action you can actually take. It could be finding a project that uses a skill they want to practice, introducing them to someone in a field they are exploring, or giving them clearer feedback on what the next role requires.

Be honest about constraints. A promotion may depend on an open role, business needs, and evidence the employee is ready. Say what you know and what you do not know. Avoid presenting a possible opportunity as a promise.

Write down what the employee wants to revisit. Bring it up again later. Following through on one agreed action will matter more than an enthusiastic conversation you never return to.

Keep the discussion going

Career goals can change as people learn more about the work and about themselves. Revisit the conversation periodically, perhaps during one of your regular one on ones. Ask what still feels important and whether the last step helped.

If the employee wants a path that does not exist on your team, say so directly. You can still help them understand the options, identify transferable skills, or prepare for a role elsewhere. Supporting someone's career does not mean promising that every next step will happen under your management.

Start by asking one direct question in your next one on one. Then listen closely, name the limits, and agree on a next step you can keep.

Make space for this in your next one-on-one. The free 1:1 Health Check shows whether your meetings leave room for development, clarity, and follow-through. It takes about three minutes, and you can use it without an account.