The best managers don't map out every career path for their team. They teach people how to navigate their own career path.
When employees own their own development, they're more engaged, more motivated and more likely to stay. And you get to focus on coaching instead of tracking every skill gap and growth goal.
This shift from manager-driven to employee-owned development works. Here's how to make it happen.
Why self-directed development works
When you're the only one thinking about someone's career, you become a bottleneck and they don't build the skills to manage their own career.
Benefits when employees own their development:
- They're more motivated because they chose their direction
- They take initiative instead of waiting for direction
- They develop career management skills they'll use their entire life
- They stay engaged even when promotion opportunities are limited
Self-directed doesn't mean unsupported. It means they're in the driver's seat and you're the coach.
Teach them to identify their own skill gaps
Most employees don't know how to assess their own capabilities objectively. They either overestimate their skills or underestimate them.
Simple framework for self-assessment:
Have them rate themselves on key skills for their role:
- 1-2: Learning (need significant support)
- 3-4: Developing (can do with occasional help)
- 5-6: Proficient (can do independently)
- 7-8: Advanced (can teach others)
Then ask: Where do you want to be in six months? What would it take to get there?
This creates a gap they can see. "I'm at a 4 in strategic thinking and want to be at a 6" is actionable. "I need to get better at strategy" is vague.
Practice this in one-on-ones. Walk through it together a few times. Eventually, they'll do it on their own.
Help them connect work to what they actually want
Many employees have never thought about what they want from their career. They just know they want "growth."
Questions that clarify what they actually want:
- What parts of your job energize you? What drains you?
- What do you want to be really good at?
- What kind of problems do you want to solve?
- Do you want to manage people, projects, or stay hands-on?
These questions reveal patterns. Someone who lights up talking about solving complex problems but zones out discussing people management probably shouldn't aim for a management role.
When people understand what energizes them, they can design development plans that actually fit.
Show them how to seek feedback strategically
Employees often wait for formal reviews to get feedback. Teach them to go get it themselves.
How to seek useful feedback:
- Ask specific people for specific feedback on specific things
- "Can you give me feedback on how I handled the client meeting?" works better than "How am I doing?"
- Ask within 48 hours of the thing they want feedback on
- Follow up with what they're working on based on the feedback
When employees actively seek feedback, they improve faster and show initiative.
Model this yourself. Show them how you ask for feedback. Make it normal, not scary.
Teach them to create their own stretch goals
Don't be the only one setting development goals. Teach employees how to set their own.
Framework for self-created stretch goals:
Pick a skill or area to develop. Then identify:
- What "good" looks like (be specific)
- One thing to practice this week
- One bigger project to apply it in this quarter
- How they'll know they're improving
Example: "I want to get better at presenting to executives"
- Good looks like: delivering a clear message in under 10 minutes without rambling
- This week: practice my pitch with a peer and get feedback
- This quarter: present the Q4 roadmap to leadership
- I'll know I'm improving when: executives ask fewer clarifying questions
When employees can create goals like this, they don't need you to map out every development step.
Give them reflection prompts, not answers
Instead of telling employees what they should learn, ask questions that help them figure it out.
Powerful reflection prompts:
- What's one thing you did really well this month? Why did it work?
- What's something that didn't go as planned? What would you do differently?
- What skill would make the biggest difference in your work right now?
- Who in the organization has a skill you want to develop? What makes them good at it?
- If you were coaching someone in your role, what advice would you give them?
These questions build self-awareness and pattern recognition. Over time, employees stop needing you to ask the questions. They start asking themselves.
Connect them to resources and people
Self-directed doesn't mean figuring everything out alone. It means knowing how to find help.
Teach employees to identify who has the skills they want to develop, reach out for conversations or shadowing opportunities, and find relevant training programs.
Give employees access to continuous learning through programs like Electives Membership, where they can choose from live, expert-led classes on leadership, AI, communication, and manager development. When employees can browse a catalog and pick what matters to them, they own their development path.
Point them to AI simulations where they can rehearse difficult conversations before trying them in real situations.
Give them the tools, then let them use them.
Normalize experimentation
Employees often think development means being perfect at something new. Teach them that development means trying, failing, adjusting, and trying again.
Create psychological safety by celebrating attempts, asking "What did you learn?" when something doesn't work, and sharing your own experiments.
When people feel safe experimenting, they take more risks. When they're afraid of messing up, they stick to what they already know.
Build the check-in habit
Self-directed development still needs regular check-ins. Just shift what you're checking.
Monthly career development check-ins should cover:
- What are you working on developing right now?
- What progress have you made?
- What's harder than you expected?
- What support do you need?
Notice these are all questions, not directives. You're helping them think through their development, not managing it for them.
What success looks like
You'll know employees are becoming their own career coaches when they come to one-on-ones with their own development goals, seek out stretch assignments without being prompted, ask for specific feedback, and can articulate why they're working on certain skills.
This doesn't happen overnight. It's a gradual shift from you driving their development to you supporting their self-directed growth.
The start of the new year is the perfect time to start this shift. People are naturally reflective. Teach your employees to coach themselves now. They'll be better equipped to own their growth in 2026.
Ready to give employees continuous growth opportunities? Explore Electives Membership for live, expert-led classes employees can choose from to build the skills they want to develop.


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