Career Development Discussion Template: Questions & Agenda for 2026

Career development conversations are essential for employee engagement, retention, and growth. Yet most managers struggle to make them productive—either rushing through generic questions or turning them into performance reviews in disguise.

This template provides a focused framework for conducting effective 30-minute career development discussions that help team members envision and work toward their professional aspirations.

Before the Meeting

Preparation makes the difference between a meaningful conversation and a wasted 30 minutes.

For the manager:

Schedule 30 minutes in a private, distraction-free environment
Review the employee’s current role, strengths, and recent performance—tools like Windmill can surface accomplishments from Slack, GitHub, and Jira so you have concrete context
Identify 2-3 potential growth opportunities (projects, stretch assignments, training)
Consider what you know about their career interests and aspirations

For the employee (send this 2-3 days before):

Reflect on what energizes you in your current role
Think about where you’d like to be in 2-3 years
Consider skills you’d like to develop or strengthen
Come prepared with questions about growth paths

Career Development Discussion Agenda

Opening (5 minutes)

Set a positive, forward-looking tone that separates this from performance evaluation:

Today I’d like to focus specifically on your career development. This isn’t a performance review—it’s an opportunity for us to discuss your professional growth and aspirations, and how I can help you achieve them.

Key framing:

This conversation is about their future, not past performance
You’re here to support their goals, not evaluate them
Be explicit that there’s no “right answer” to career questions

Current State and Aspirations (10 minutes)

Understand where they are and where they want to go:

Essential questions:

“What aspects of your current role do you find most energizing?”
“What work would you do more of if you could?”
“Where do you see yourself in 2-3 years?”
“What skills would you like to develop or strengthen?”
“What roles or types of work interest you, even if they seem unrelated to your current path?”

Listen for:

Themes in what energizes vs. drains them
Clarity (or lack thereof) about future direction
Skills gaps they’re aware of
Concerns about growth opportunities

Development Planning (10 minutes)

Move from aspirations to concrete actions:

Focus areas:

Identify 1-2 specific development goals for the next quarter
Discuss concrete actions and realistic timelines
Define required resources and support
Consider immediate opportunities (projects, training, mentorship, shadowing)

Helpful questions:

“What’s one skill that, if you developed it, would have the biggest impact on your career goals?”
“Are there projects coming up where you could stretch into new areas?”
“Who in the organization does work you’d like to learn from?”
“What’s holding you back from pursuing this development?”

For each development goal, define:

The specific skill or experience to develop
How they’ll work on it (project, course, mentorship, etc.)
Timeline and milestones
How you’ll support them

Closing and Next Steps (5 minutes)

Summarize and establish clear commitments:

Wrap-up checklist:

Confirm 1-2 development goals in their own words
Agree on specific next steps (for both of you)
Schedule the next career check-in (monthly progress, quarterly deep-dive)
Document commitments from both sides

Close with:

To summarize, your main development focus is [goal]. You’re going to [their action], and I’m going to [your action]. Let’s check in on this in our next 1:1, and we’ll do another full career conversation next quarter.

After the Meeting

The conversation is just the beginning.

Within 24 hours:

Document the agreed-upon goals and actions
Share relevant resources (training links, contact info for mentors, etc.)
Add follow-up items to your 1:1 agenda template—Windmill’s 1:1 feature can automatically carry these forward so nothing falls through the cracks

Ongoing:

Reference development goals in regular 1:1s
Proactively look for stretch opportunities that align with their goals
Connect them with people and projects that support their development
Celebrate progress and recalibrate when needed

Monthly Progress Check-In Template

Keep career development alive between quarterly deep-dives with this 15-minute check-in structure:

Quick Progress Review (5 minutes)

What actions have you taken on your development goals?
What progress have you made?
What wins can we celebrate?

Challenges and Adjustments (7 minutes)

What obstacles are you facing?
Do we need to adjust timelines or approaches?
What additional support do you need?

Next Steps (3 minutes)

What’s your focus for the next month?
What do you need from me?

Career Development Discussion Questions by Scenario

For employees unsure about their direction

Some people don’t have a clear career vision—and that’s okay. These questions help them explore:

“What problems do you most enjoy solving?”
“When do you lose track of time at work?”
“What would you do if you knew you couldn’t fail?”
“What roles have you seen others do that looked interesting?”
“What skills do people often come to you for help with?”

For high performers ready for more

“What would make your role more challenging in a good way?”
“Are there leadership opportunities that interest you?”
“What’s the next role you’re working toward?”
“What’s the gap between where you are and where you want to be?”
“How can I advocate for your growth in the organization?”

For employees feeling stuck

“What’s getting in the way of your development?”
“What would need to change for you to feel like you’re growing?”
“Are there skills you want to develop but haven’t had the chance to?”
“What opportunities do you wish existed here?”
“What can we do differently to support your career?”

Common Pitfalls to Avoid

Turning it into a performance review. Keep the focus forward-looking. If performance issues need addressing, schedule a separate conversation.

Making promises you can’t keep. Be honest about what opportunities exist and what you can influence. False hope damages trust.

Doing all the talking. This is their career. Ask questions and listen more than you speak.

Skipping the follow-through. Career conversations without action are worse than no conversation at all. Track commitments and follow up.

One-size-fits-all development plans. Tailor development to their specific goals and learning style, not generic training paths.

Additional Resources

The Alliance by Reid Hoffman — Framework for honest career conversations
Designing Your Life by Bill Burnett and Dave Evans — Helps employees who are unsure about their direction

Make Career Development Easier

Career conversations work best when you have context about what your team members are actually working on and accomplishing. Windmill automatically surfaces accomplishments from tools like Slack, GitHub, and Jira—so you walk into career discussions knowing exactly where your employees are excelling and where they might want to grow.

Frequently Asked Questions

How often should you have career development discussions?

Career development discussions should happen quarterly at minimum, with lighter check-ins monthly. This cadence ensures goals stay relevant while providing enough time between conversations to make meaningful progress on development actions.

What's the difference between a career development discussion and a performance review?

Performance reviews look backward at accomplishments and outcomes against set expectations. Career development discussions look forward—focusing on aspirations, skill building, and future roles. The best managers separate these conversations so employees can focus on growth without the pressure of evaluation.

Who should lead a career development discussion—the manager or employee?

The employee should lead with their aspirations and interests, while the manager facilitates, asks probing questions, and connects development opportunities to organizational needs. However, the manager is responsible for ensuring these conversations happen in the first place and scheduling them at a regular cadence. The most effective career conversations are employee-driven but manager-supported.