Career Performance Conversations That Matter
- Cristina Stensvaag
- Nov 20, 2025
- 2 min read
As the year winds down, many of us are sitting down with our directs to talk about goals, performance, and what comes next. And if we’re not careful, these conversations can turn into impersonal templates and timelines instead of real dialogue.
November 20, 2025
Originally published in One More Rep, our weekly leadership newsletter. 👉 Subscribe here
Slow down and have career conversations that actually matter -- the kind that help you understand the person behind the work and support who they’re becoming, not just what they’re delivering.
Read
The leaders people remember are the ones who cared enough to ask about their future. Not the future that fits neatly into a performance review, promotion track, or an org chart, but the future that matters to them.
Most people don’t want grand promises or perfectly mapped out career paths. They want a leader who’s curious about them. Who asks things like:
What lights you up?
What gives you energy?
What do you want more of in the year ahead?
People’s ambitions shift as their lives shift. Your job as a leader is to notice, to ask, and to understand what season they’re in right now. When you do that, you make better decisions and give better feedback.
Rep
Schedule a year-end career conversation. Keep it simple and human. Use these three questions to guide you, and share them with your direct in advance so they can prepare for the conversation.
“What work gave you energy this year?”
“What would you love to learn or grow into in the next 12–18 months?”
“How can I better support where you want to go?”
Then listen to what they tell you. You don't need to rush to solutions or answers. Just listen.
Afterward, send a short note capturing what you heard. It shows care, it builds trust, and it gives both of you a reference point in the months ahead.
Reflect
How well do I understand what my directs want for their future, not just their present?
Who might be craving more stretch?
Who might want more stability or mastery?
Who needs a different kind of support from me?
Where am I assuming instead of asking?
Career growth doesn't happen by following year-end procedures or filling out forms. It happens in real conversations. When you take the time to understand the future someone envisions for themselves, you're a better leader in their present.
