June 19, 2025

Ten Dos and Don'ts of Career Conversations

by Our content team
Vitaly Gariev / Unsplash
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The career conversations you have with your employees reveal their work aspirations – and ways to achieve them. Sounds simple enough. But a survey from Right Management found that just 16% of employees have regular career discussions with their managers. [1] Many managers, it seems, are reluctant to have these talks in case employees bring up expectations they can’t satisfy.

But career conversations are about so much more than promotions. The survey found that simply having these chats boosted engagement for 82% of workers. And 75% said the catch-ups help convince them to stay on with an organization. [2] Let’s look at some dos and don’ts of career conversations.

Five Dos

1. Do... Get Their Life Story

Wondering where to start the conversation? Management guru and former military leader Russ Laraway suggests at the very beginning. So, “Starting with kindergarten, tell me about your life.” [3] Do that and you can uncover what’s motivated people so far – and get insights about where they want to go.

Laraway gives the example of an employee who switched from cheerleading to swimming in high school. During the conversation, he found out she loved improving her lap times and challenging for a podium spot. This gave him the insight that she valued hard work and tangible outcomes.

Top tip: Listen for the patterns in your employee’s story. Ask why they made life decisions with probing, “Tell me more…” style questions.

2. Do... Dream Big

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