Career conversations with your reports: how to have one that goes somewhere

The first career conversation I ran as a manager went like this. I asked where the person saw themselves in two years, they said something about tech lead, I said great, let's work toward that, and we both went back to the sprint. Eight months later they left for a tech lead role somewhere else. Nothing had happened in between, and from their side the conversation had been a polite way of finding out that nothing would.

Most career conversations fail that way. Not badly, just emptily. Here is what I do differently now, and what I have seen work for other managers.

When to have one

Not in the review cycle. By the time the review arrives the decisions it depends on have been made, and a career conversation inside a review reads as a verdict. Not only when someone asks, either, because the people who ask are the ones who already feel safe asking. I put one on the calendar for everyone twice a year, named as what it is, in a separate slot from the weekly 1-1. The weekly meeting is where you hear the small signals. The career conversation is where you do something with them.

You also have one, unscheduled, the second time someone raises the same thing. One mention of wanting more architecture work is a comment. The second mention is a request, whether or not they say so.

Five questions that actually get an answer

• What do you want more of, and what do you want less of? Concrete work, not titles. People know this answer even when they do not know the title answer.
• What would you like to be trusted with that you are not trusted with today?
• Who does work here that you would like to be doing? Names turn a vague ambition into something you can look at together.
• What is the gap between where you are and the next step, in your words? Then say it in yours. The difference between the two answers is the whole conversation.
• What would make you say in a year that this was a good year? If the answer is only about promotion, ask what the promotion would let them do.

Skip where do you see yourself in five years. Nobody knows, and the honest answers to it are not things people say to their manager.

What to say back

Three things, and in this order. What you have seen, specifically: the design doc that changed a decision, the incident they ran well. What you think the gap is, also specifically, and if you cannot name it, say that you will come back with it in two weeks and then do. And what you can actually offer in the next quarter: a project, a review to lead, a room they are not in yet. Not a promise about levels. A level is a decision made by other people later, and promising one is how you end up in the eight-months-later conversation.

Writing it down

This is the part everyone skips and the part that decides whether the conversation counted. Keep one entry per person, dated, four lines:

• Wants: more of what, less of what, in their words.
• Gap: what you said the gap is. If you said you would come back with it, the date you promised.
• Next: the concrete thing you offered, and by when.
• Revisit: the date you will bring it up again, unprompted.

Wants: ownership of a service end to end, less support rota. Gap: has not run a project with another team depending on it. Next: lead the billing migration from the design review, starting next sprint. Revisit: first week of December.

The revisit date is the whole trick. A career conversation that nobody brings back is a career conversation that did not happen, and the person will not bring it back for you, because raising it twice feels like pushing.

The mistake that ends them

Asking about growth and then doing nothing visible before you ask again. It reads as theatre, and after two rounds people give you the polite version and take the real version to a recruiter. If you cannot offer anything this quarter, say that plainly, with a reason, and say when it might change. People handle an honest no far better than an enthusiastic nothing.

The career set in the free 1-1 question generator is a shorter version of the questions above. For the weekly meeting where the signals first show up, how to run one on one meetings covers the cadence, and the one on one meeting notes post has the format I keep the career entry in.