How often should managers hold career conversations?

Twice a year suits most people, with shorter check-ins on the agreed steps in between. Hold one sooner after a change: a new manager, a reorganization, or the end of a large project.

How is a career conversation different from a performance review?

A performance review assesses results over a past period and often feeds into pay. A career conversation is about the person's future and has no rating attached. Mixing the two makes people guarded, so hold them at different times.

What if there is no promotion available?

Say so plainly, then look at what is available: a larger project, a sideways move, a new skill, mentoring someone, or more say over how the work is done. Growth is wider than a title.

What if the employee wants a path the company cannot offer?

Thank them for being open and be honest in return. Help with the parts you can, such as skills and exposure, and accept that they may leave one day. The person does better work while they are with you, and they may speak well of you, or come back, later.

Retention conversations

Career conversation template

A career development conversation guide in five parts, with nine questions and a table of next steps, to fill in together, copy or print.

TemplateWhat you type stays in your browser.

Employee

Manager

Date

Looking back

Which work in the last six months gave you the most energy?

Which work drained you?

Strengths

What do people come to you for?

What would you like to be known for?

Direction

What kind of work do you want more of a year from now?

Is there a role here, sideways or upward, that interests you?

Which direction fits best right now?

Go deeper in my current role
Move toward leading people
Move sideways into a new area
Not sure yet

Gaps

What skill or experience is missing for that step?

What would help you build it: a project, a course or a mentor?

Next steps

Last updated October 14, 2026

A career conversation is about where the person wants to go next.

A career conversation is a meeting between a manager and an employee about the employee's future: what they enjoy, what they are good at, where they want to go and what stands in the way. It is separate from a performance review, which looks back at results, and from a pay conversation.

People often leave for a move they would have taken internally if someone had asked. This guide gives the conversation a shape: two questions about the recent past, two about strengths, three about direction, two about gaps, and a short list of next steps.

Here is how to use the career conversation template in five steps.

How to use it

1Give notice and the questions
2Start with energy
3Accept the answer you get
4Be honest about what exists
5Agree two or three steps

Give notice and the questions. Book 45 minutes a week ahead and share the questions, so the person arrives with answers and not with guesses about why you are meeting.
Start with energy. Begin with the work they enjoyed and the work that drained them. It is easier to answer than a question about a five-year plan.
Accept the answer you get. Not sure yet is a real answer, and so is wanting to stay in the same role. Do not steer people toward management.
Be honest about what exists. Say which moves are open here and which are not, and roughly when. Do not promise a role you cannot give.
Agree two or three steps. Write down small steps with dates, and come back to them in one-on-ones during the quarter.

Here is a worked example with invented names.

Take an invented company, Brambleworth Logistics. Tomas Lindqvist manages Noor Aziz, who has been a route planner for four years, and books a career conversation with her.

Noor says the work that gave her the most energy was redesigning the Monday loading schedule, and the work that drained her was the daily exception reports. People come to her to make sense of messy data. She picks a sideways move into a new area, analytics, and names the gap herself: she has never built a dashboard for other people to use.

Worked example

Brambleworth Logistics, an invented company: one career conversation

EmployeeNoor Aziz, route planner, 4 years
ManagerTomas Lindqvist
Gave the most energyRedesigning the Monday loading schedule
Drained herThe daily exception reports
DirectionMove sideways into a new area: analytics
GapHas never built a dashboard for other people to use

Next steps

Build the depot delay dashboard with the analytics team this quarter, and shadow an analyst one afternoon a week

They agree two steps. Noor builds the depot delay dashboard with the analytics team this quarter, and she shadows an analyst one afternoon a week. They will talk again in three months.

These mistakes spoil a career conversation.

Holding it only at review time, when pay and ratings crowd out everything else.
Assuming everyone wants to manage people. Many want to get better at the craft.
Talking about the company's needs first and the person's wishes second.
Promising a promotion or a date you do not control.
Having a good conversation and never mentioning it again.

People ask these questions about career conversations.

A career conversation is a planned discussion between an employee and their manager about the employee's direction: what they want to do more of, which roles interest them and what they need to learn. It looks forward, and it is separate from reviews of past performance.

These glossary terms explain the ideas behind it.

Internal mobility
Internal mobility is people moving into new roles inside the company, sideways or upward, instead of leaving to get the same move elsewhere.
Employee value proposition (EVP)
An EVP is the whole deal an employer offers in exchange for work: pay, growth, flexibility, the work itself, the people and the mission.
One-on-one
A one-on-one is a recurring private conversation between a manager and a direct report about the work, the obstacles and the person's growth.
Employee retention
Employee retention is a company's ability to keep the people it wants to keep, for as long as the business needs them.
Boomerang employee
A boomerang employee is a former employee who is rehired by the same company after working somewhere else.

These pages on this site go deeper.

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