How do you hold a career conversation in a one-on-one?

Why hold career one-on-ones

Career conversations also tie into keeping people. In LinkedIn's 2018 Workplace Learning Report, 94% of employees said they would stay at a company longer if it invested in their career development (LinkedIn Learning, 2018). Even without a training budget, a career one-on-one is an investment a leader can make right away.

How is a career one-on-one different from a regular one-on-one?

A regular one-on-one covers work and wellbeing over the last week or two; a career one-on-one covers direction over years. So it needs to be run a little differently.

Adjust the cadence to your team. How to set the cadence of regular one-on-ones is covered in How often should you hold one-on-ones: weekly or every two weeks?. What matters is not to hold career conversations only during review season. When careers come up in the same meeting as ratings, team members tend to give answers that help their rating rather than their honest goals.

Three stages of a career one-on-one, with example questions

Russ Laraway developed a way of splitting career conversations into three while working at Google, and the approach became widely known through Kim Scott's book Radical Candor (Radical Candor). The order is past, future, present. Spreading them over three regular one-on-ones, rather than covering everything at once, gives the team member time to think.

Stage 1: Life story — what drives this person

The aim of the first conversation is not to review their résumé but to hear the reasons behind their choices. Ask “why did you make that choice?” at each turning point, such as school, first job, job changes, and role changes, and the values they care about come through.

• “What made you choose this line of work in the first place?”
• “When were you most absorbed in your work so far, and what made it that way?”
• “And in your hardest period, what was missing?”
• “When you left a previous company or team, what was the biggest reason?”

Note the words that keep coming up as you listen. If words like “recognition,” “autonomy,” “learning,” or “stability” come up two or three times, that is likely what motivates them.

Stage 2: Dreams — where they want to get to

The second conversation is about the distant future. Ask what they would like to be doing at the peak of their career, and help make that dream concrete. Focus on what work they want to be doing then, rather than a title like “I want to be a team lead.” Listen without cutting them off, even if the dream has nothing to do with your company.

• “When your career has gone as well as it possibly could, what do you think you'll be doing?”
• “If someone introduced you five years from now, how would you want to be introduced?”
• “If you named several dreams, what would they be? What skills does each need?”
• “Is there a field or role that draws you, even if it doesn't fit right now?”

Dreams change often. Don't stop after hearing them once; ask again about once a year.

Stage 3: Action plan — what to do now

The third conversation connects the first two. Look at the gap between the skills the dream needs and their current skills, and decide what they will learn and what work they will take on over the next 6 to 18 months. The plan must have owners and deadlines.

• “What skill should you build first to get closer to that dream?”
• “Which part of your current work could build that skill?”
• “Is there work or a project you'd like to take on next quarter?”
• “Who or what opportunity could I connect you with?”

For experienced team members, the plan often ties into a wider scope of decisions or a bigger role; see also How do you run one-on-ones with senior employees?. Questions on topics beyond careers are in What questions should you ask in a one-on-one?.

Sample career action plan

After the third conversation, have the team member fill in the table below themselves, and add what you as the leader will support. Writing it themselves makes the plan theirs. Two or three items are enough.

Once the plan is set, always bring it back up in regular one-on-ones, even briefly. How to follow up on the actions you agree is covered in How do you set and follow up one-on-one action items?.

What to watch out for in career one-on-ones

• Don't promise what you can't. Promotions and role changes often aren't the leader's call alone. “I'll help you head in that direction” is not the same as “I'll give you that role.”
• Listen to dreams outside the company, too. Don't get defensive if a team member says they hope to start a company or move into another field one day. If the skills that dream needs can be built in their current work, that helps the team as well.
• Don't push your team's path. Let go of the assumption that the path you walked fits them too. The management track is not the only kind of growth.
• Keep notes and agree on who sees them. Career conversations are often personal. Agree with the team member first on who can see the notes.
• Start with the people you've worked with longest. Radical Candor recommends beginning career conversations with the people you have worked with the longest. Practicing first where trust already exists makes the conversation come more naturally with others. With people you've just met, you first need conversations to get to know each other (see How should a new manager start one-on-ones?).