Run a Career Conversation - Mentora Documentation

Run a Career Conversation with Your Employee

A career conversation is a focused 1:1 about your employee's career development. Instead of status updates, you'll discuss their vision, progress, obstacles, and next steps.

Before the Conversation

Step 1: Ask your employee to set their Career Vision if they haven't already

Step 2: Review their goals, milestones, and progress:

Open Mentora
Go to the Dashboard
Click on their name in the Team Overview
Review their goals and recent activity

Step 3: Note any areas to discuss:

Goals that are on track or at risk
Milestones due soon
Comments or feedback they've left

Step 4: Think about 2–3 questions you want to ask them about their development

During the Conversation

Opening (5 minutes)

Start by asking about their career vision:

"Tell me about your career vision. Is it still accurate?"
"How are you feeling about your direction?"
"What's changed since we last talked?"

This sets context for everything else.

Progress Review (10 minutes)

Walk through their goals:

"Let's look at your goals. Which are you most excited about?"
"This goal is at risk — what's blocking you?"
"You completed this milestone ahead of schedule. Great work! What's next?"

Use Mentora to show the Roadmap or Goals list.

Obstacles & Support (10 minutes)

Ask what they need:

"What's one thing that would help you move faster?"
"Are there any skills you need to develop to reach your goals?"
"How can I support you better?"

Next Steps (5 minutes)

End with clarity on what happens next:

"Let's create these two new goals together"
"I'll help you schedule that training course"
"Let's check in on this milestone next week"

Update goals and milestones in Mentora during the call so you both see the changes.

After the Conversation

Step 1: Update any goals or milestones based on your discussion

Step 2: In Mentora, leave a comment on their goals summarizing the conversation:

"Great discussion! We agreed to focus on completing the leadership course (new milestone by Q2) and leading the Q3 project. Let's check in on progress in 2 weeks."

Step 3: Send a summary email with:

New goals/milestones
Agreed-upon timeline
Your commitment to support them

Step 4: Schedule the next career conversation (every 4–6 weeks is good)

Tips

Use Mentora during the call — Show them their progress visually
Celebrate wins — Point out milestones they've completed
Be specific about next steps — "Let's create that goal today" beats "I'll help you someday"
Ask more than you tell — Let them drive the conversation about their career
Document the conversation — Comments in Mentora keep everyone on the same page
Follow up — If you said you'd help with something, do it and mention it in the next conversation

Example Conversation Flow

You: "Hey Sarah. Before we jump in, how's your career vision feeling? Still want to become a Tech Lead?"

Sarah: "Yeah, but I've been thinking I might want to focus more on architecture. Maybe move into a principal engineer role instead."

You: "Got it. Let's update your vision. [You both edit it in Mentora] Perfect. Now let's look at your goals. You've got three active — let's talk about each."

[You review goals. One is on track, one is at risk.]

You: "The infrastructure refactor goal is marked at risk. What's happening there?"

Sarah: "I lost two weeks to production issues. I'm catching up, but I'm worried I'll miss the June deadline."

You: "Let's extend the deadline to July — that's more realistic. And I can help you get some team support for the refactor so you're not blocked on production work. Sound good?"

Sarah: "Yes. That would help."

You: [Updates milestone date in Mentora] "Done. Let's check progress next week. Any other obstacles?"

[Continue with other goals...]

Troubleshooting

My employee doesn't have a career vision set

Ask them to set one before the next meeting. If they're stuck, offer to discuss it together in a shorter call.

They're not updating their progress in Mentora

Remind them (nicely) that status updates help you support them better. Offer to help them get comfortable with the tool.

I don't have time for regular conversations

Even 30 minutes every 4 weeks helps. Short, regular conversations beat rare, long ones.

The conversation feels awkward

That's normal. These conversations get easier with practice. Focus on listening and asking questions.