25 Career Development Questions to Ask in Your Next 1:1
Career development conversations are the most impactful part of your 1:1s, yet they're often the most neglected. While it's easy to fill your one-on-ones with project updates and blockers, the engineers who feel supported in their growth are the ones who stay, perform better, and become your future leaders.
The problem? Most engineering managers don't know what questions to ask to spark meaningful career conversations. Generic questions like "Where do you see yourself in 5 years?" rarely lead to actionable insights.
This guide provides 25 powerful career development questions organized by category, along with why each question works and how to use the answers to actually help your engineers grow.
Try EliuAI's Career Development Tracking →
Table of Contents
- Why Career Development Questions Matter
- When to Ask Career Questions in 1:1s
- 25 Essential Career Development Questions
- How to Use the Answers
- Common Mistakes to Avoid
- Tracking Career Development Over Time
Why Career Development Questions Matter
The data is clear: Engineers who have regular career development conversations with their managers are:
- 3.5x more likely to stay at their company for 3+ years
- 2x more engaged in their daily work
- 40% faster to reach promotion milestones
- More innovative and willing to take on stretch projects
Yet research shows that 67% of engineers say their managers rarely or never discuss their career growth.
What Makes a Good Career Development Question?
The best career development questions share these characteristics:
✅ Open-ended: Can't be answered with yes/no
✅ Forward-looking: Focus on growth, not just current state
✅ Specific: Concrete enough to lead to action
✅ Safe: Engineer feels comfortable being honest
✅ Actionable: Answers can inform real decisions
Poor question: "Do you like your job?"
Better question: "What parts of your work energize you most, and how can we create more of that?"
When to Ask Career Questions in 1:1s
Don't save career development for annual reviews. That's too infrequent and too formal. Instead:
Ideal Cadence
- Monthly: At least one career-focused 1:1 per month
- Quarterly: Deep career planning session (60-90 minutes)
- Bi-annually: Major career trajectory check-in
- Annually: Formal performance review + goal setting
When to Go Deeper
- After completing a major project (reflect on learnings)
- When you notice disengagement or boredom
- Before promotion cycles
- After they've expressed interest in new areas
- When organizational changes create new opportunities
- After they've attended a conference or training
Pro tip: Block your calendar for "Career Development Month" where every 1:1 that month has extended time for growth conversations.
25 Essential Career Development Questions
Category 1: Understanding Current State (Questions 1-5)
These questions help you understand where your engineer is right now and how they feel about their current role.
1. "What parts of your work energize you most, and what drains you?"
Why it works: Identifies intrinsic motivations and helps you assign work that aligns with their interests.
What to listen for:
- Technical challenges vs people problems
- Building new things vs maintaining existing systems
- Independent work vs collaboration
- Specific technologies or domains
Follow-up: "How can we shift your work to be 70% energizing and 30% necessary-but-draining?"
2. "On a scale of 1-10, how challenged do you feel by your current work?"
Why it works: Reveals if they're bored (flight risk) or overwhelmed (burnout risk).
What to listen for:
- 1-3: Severely under-challenged, probably looking elsewhere
- 4-6: Could use more stretch, risk of stagnation
- 7-8: Sweet spot of productive challenge
- 9-10: Might be overwhelmed or stressed
Follow-up: "What would move you to an 8?" (if they're below) or "What support would help manage that challenge?" (if they're above)
3. "What's one skill you've developed in the past 6 months that you're proud of?"
Why it works: Helps them recognize their own growth (which they often overlook) and reveals what type of growth matters to them.
What to listen for:
- Technical skills vs soft skills
- Self-directed learning vs structured training
- Depth vs breadth of learning
Follow-up: "What's the next skill you want to develop?"
4. "If you could change one thing about your role tomorrow, what would it be?"
Why it works: Uncovers immediate friction points that might be preventing growth or causing dissatisfaction.
What to listen for:
- Process frustrations (you can fix these)
- Technology stack concerns (migration opportunities)
- Team dynamics (coaching opportunities)
- Scope of responsibility (potential for expansion)
Follow-up: "Let's talk about what it would take to make that change happen."
5. "What project or accomplishment are you most proud of in your career?"
Why it works: Reveals what they value and what types of impact matter most to them.
What to listen for:
- Technical complexity vs business impact
- Solo achievements vs team leadership
- Innovation vs execution excellence
- Scale vs craftsmanship
Follow-up: "What would it take for your current projects to feel equally impactful?"
Category 2: Exploring Future Direction (Questions 6-10)
These questions help engineers articulate where they want to go, even if they're not sure yet.
6. "When you imagine yourself in 2-3 years, what does success look like?"
Why it works: More concrete than "5 years" but still requires thought. Reveals if they're thinking about title, impact, skills, or lifestyle.
What to listen for:
- Title-focused ("I want to be a Staff Engineer")
- Impact-focused ("I want to build systems that affect millions of users")
- Skill-focused ("I want to be an expert in distributed systems")
- Balance-focused ("I want to do great work without burning out")
Follow-up: "What's one step you could take in the next quarter toward that vision?"
7. "Are you more excited by going deep in your current specialty or broad across multiple areas?"
Why it works: Helps distinguish between specialists and generalists, which dramatically affects how you should develop them.
What to listen for:
- Depth seekers: Want to become domain experts
- Breadth seekers: Want variety and exposure
- Hybrid: Want T-shaped skills (deep in one area, broad exposure)
Follow-up: "Given that, what projects should we prioritize for you?"
8. "Do you see yourself on an IC (individual contributor) track or interested in management?"
Why it works: Clarifies career trajectory early. Many engineers feel pressure to go into management when they'd be happier as senior ICs.
What to listen for:
- Clear preference (make sure you have a path for them)
- Uncertainty (provide exposure to both)
- Interest in hybrid (tech lead or staff roles)
- Pressure to choose (reassure them they don't have to decide now)
Follow-up: "What would you need to learn or experience to feel confident in that direction?"
9. "Who's career path do you admire, either here or elsewhere, and why?"
Why it works: Concrete role models reveal aspirations better than abstract questions.
What to listen for:
- Internal vs external role models
- What specifically they admire (technical skills, leadership, impact, work-life balance)
- Realistic vs unrealistic aspirations
Follow-up: "What's one thing they did to get where they are that you could start doing now?"
10. "What's a skill or area you've been curious about but haven't had time to explore?"
Why it works: Uncovers latent interests that could become growth opportunities.
What to listen for:
- Adjacent skills (easy to incorporate)
- Completely new domains (might need external learning)
- Technologies you're planning to adopt (perfect timing)
- Non-technical skills (leadership, communication)
Follow-up: "What if we carved out 10% of your time for exploration? How would you use it?"
Category 3: Identifying Growth Gaps (Questions 11-15)
These questions help pinpoint specific areas for development.
11. "What's the biggest gap between where you are and where you want to be?"
Why it works: Direct and forces specificity about development needs.
What to listen for:
- Technical skill gaps (training, projects, mentorship)
- Experience gaps (need specific types of projects)
- Visibility gaps (need to showcase their work better)
- Relationship gaps (need to build influence)
Follow-up: "Let's break that gap into 3 smaller steps. What's step one?"
12. "What feedback have you gotten that surprised you?"
Why it works: Reveals blind spots and how self-aware they are.
What to listen for:
- Positive surprises (strengths they undervalue)
- Negative surprises (areas for development)
- No surprises (might not be seeking feedback)
- Defensive reaction (coaching opportunity)
Follow-up: "How did that feedback change how you approach your work?"
13. "If you were promoted tomorrow, what parts of your new role would feel uncomfortable?"
Why it works: Identifies specific skills needed for next level without waiting for promotion cycle.
What to listen for:
- Technical gaps (architecture, system design)
- Leadership gaps (mentoring, influence)
- Scope gaps (cross-team work, strategic thinking)
- Confidence gaps (imposter syndrome)
Follow-up: "Let's create a plan to build confidence in those areas before promotion."
14. "What do you wish you were better at?"
Why it works: Simple, vulnerable question that often gets honest answers.
What to listen for:
- Self-awareness about weaknesses
- Realistic vs perfectionist standards
- Technical vs interpersonal skills
- Fixed mindset vs growth mindset
Follow-up: "What's one experiment you could run to improve in that area?"
15. "What's something senior engineers on the team do that you'd like to learn?"
Why it works: Identifies concrete role models and specific skills to develop.
What to listen for:
- Observable behaviors (easier to coach)
- Technical skills (can create learning opportunities)
- Soft skills (may need different development approach)
Follow-up: "Would you like me to set up mentorship or pairing sessions with [senior engineer]?"
Category 4: Understanding Motivation (Questions 16-20)
These questions dig into what drives your engineer beyond just career progression.
16. "What would make you excited to come to work every day?"
Why it works: Gets at intrinsic motivation and ideal work conditions.
What to listen for:
- Type of work (problems to solve)
- Team dynamics (collaboration style)
- Autonomy level (how much direction they want)
- Learning opportunities (growth velocity)
- Impact (connection to users or business)
Follow-up: "Which of those factors is most missing right now, and how can we change that?"
17. "What's something you'd regret not learning or doing in your career?"
Why it works: Reveals aspirations they might not have articulated as "goals" yet.
What to listen for:
- Specific technologies or domains
- Types of companies or products
- Leadership experiences
- Creative or side projects
Follow-up: "Is there any way to incorporate that into your work here?"
18. "When do you feel most proud of your work?"
Why it works: Identifies what type of achievement matters most to them.
What to listen for:
- Solving hard problems (love technical challenge)
- Helping teammates (natural mentor)
- Shipping features (product-minded)
- System design (architect inclination)
- User impact (impact-driven)
Follow-up: "How can we create more opportunities for those moments?"
19. "What would you do if you weren't worried about money or practicality?"
Why it works: Reveals pure passion and interests that might inform career direction.
What to listen for:
- Still engineering-related (strong fit)
- Adjacent fields (could inform unique career path)
- Completely different (might have retention risk)
- Teaching/mentoring (leadership potential)
Follow-up: "Are there small ways to incorporate elements of that into your current role?"
20. "What's the best professional development experience you've ever had?"
Why it works: Shows what learning style works for them.
What to listen for:
- Formal training vs self-directed learning
- Conference attendance vs reading
- Mentorship vs independent projects
- Classroom vs hands-on
Follow-up: "How can we recreate that type of experience for your current growth goals?"
Category 5: Creating Action Plans (Questions 21-25)
These questions turn conversations into concrete development plans.
21. "What's one thing you want to be known for on this team?"
Why it works: Helps them articulate their personal brand and how they want to contribute.
What to listen for:
- Technical expertise (domain specialist)
- Reliability (execution excellence)
- Innovation (creative problem-solver)
- Mentorship (team builder)
- Leadership (influence and direction)
Follow-up: "What would you need to do consistently to build that reputation?"
22. "If you could shadow anyone for a week, who would it be and why?"
Why it works: Identifies specific people and roles they want to learn from.
What to listen for:
- Cross-functional roles (product, design)
- Senior technical roles (staff, principal)
- Leadership roles (VP, CTO)
- Customer-facing roles (sales, support)
Follow-up: "Let's set up a few hours of shadowing or informational interviews."
23. "What project or responsibility would feel like a meaningful stretch?"
Why it works: Directly identifies next-level work they're ready for.
What to listen for:
- Appropriate stretch (challenging but achievable)
- Too big a leap (need intermediary steps)
- Specific vs vague (shows readiness)
- Aligned with team needs (win-win opportunity)
Follow-up: "Let's map out how to prepare you for that and when we could make it happen."
24. "What's one thing you'd like to accomplish in the next 3 months that would feel like real progress?"
Why it works: Creates concrete, near-term milestone that builds momentum.
What to listen for:
- Realistic timeline (shows planning ability)
- Measurable outcome (can track progress)
- Aligned with growth goals (part of bigger picture)
- Mix of technical and soft skills
Follow-up: "Let's put that in your goals and check in monthly on progress."
25. "How can I better support your career development?"
Why it works: Shows you're accountable for their growth and invites feedback on your management.
What to listen for:
- Specific requests (training budget, time for learning)
- Visibility asks (introductions, presentations)
- Feedback needs (more frequent, more specific)
- Project assignments (exposure to new areas)
- Nothing (might not feel safe yet or unsure what they need)
Follow-up: "Let me commit to [specific action] by [specific date]. Let's check in on whether it helped."
How to Use the Answers Effectively
Asking great questions is only half the battle. Here's how to turn answers into action:
1. Listen More Than You Talk (80/20 Rule)
Don't: Jump in with solutions after every answer
Do: Ask follow-up questions, let silence sit, take notes
Example:
- Engineer: "I want to learn more about distributed systems."
- Bad response: "Oh great, I'll assign you to the cache migration project!"
- Good response: "Tell me more. What aspect interests you most? What have you already learned on your own?"
2. Document Everything
Create a career development tracker for each engineer:
- Their stated goals and aspirations
- Skills they want to develop
- Projects that would stretch them
- Timeline for major milestones
- Your commitments to support them
With EliuAI: This tracking happens automatically with AI-generated career development insights and progress visualization.
3. Create Concrete Action Items
Every career conversation should end with:
- Engineer action items: Specific things they'll do (take course, lead design review, etc.)
- Manager action items: Specific things you'll do (make introduction, find project, approve training)
- Timeline: When you'll check in on progress
- Success metrics: How you'll know it worked
Example action plan:
- Goal: Develop distributed systems expertise
- Engineer actions: Complete MIT 6.824 course by March, read "Designing Data-Intensive Applications"
- Manager actions: Pair with Sarah on cache project, nominate for architecture review group
- Check-in: Monthly progress discussions, reassess in Q2
4. Connect Development to Current Work
Don't: Treat career development as separate from daily work
Do: Design projects and assignments that align with growth goals
Example:
- Engineer wants to improve leadership skills
- Assign them to mentor junior engineer on current project
- Have them lead next sprint planning
- Ask them to present at engineering all-hands
5. Follow Through Religiously
Your credibility as a manager depends on follow-through.
If you say you'll:
- Make an introduction (do it within 48 hours)
- Approve training budget (get answer within a week)
- Find stretch project (present options within 2 weeks)
- Check in on progress (set calendar reminder, don't skip)
Track your own action items as rigorously as your engineer's. EliuAI does this automatically with manager accountability tracking.
6. Revisit Quarterly
Career goals evolve. What excited them in January might not matter in April.
Quarterly career check-ins should cover:
- Progress on previous goals
- New interests or aspirations
- Changes in life circumstances
- Market changes affecting career path
- Updated timeline and action plan
Common Mistakes to Avoid
Mistake 1: Only Asking During Performance Reviews
Why it's bad: Once a year is too infrequent. Engineers need ongoing development, not annual check-ins.
Fix: Monthly career-focused 1:1s, quarterly deep dives.
Mistake 2: Asking Questions Without Follow-Up
Why it's bad: If you ask about their goals but never reference them again, they'll stop trusting you.
Fix: Create visible documentation, review it together, track progress.
Mistake 3: Making It About Your Needs
Why it's bad: "We need someone for this project, so let's call it career development" is manipulative.
Fix: Align when possible, but be honest when it's a business need vs their development.
Mistake 4: Having All the Answers
Why it's bad: You're not their career counselor. Telling them what they should want is patronizing.
Fix: Ask questions, share observations, offer options, let them decide.
Mistake 5: Ignoring External Aspirations
Why it's bad: If they want to do something your company can't offer, ignoring it won't make them stay.
Fix: Help them grow even if it means they eventually leave. They'll stay longer and perform better.
Mistake 6: Not Being Honest About Opportunities
Why it's bad: Leading them on about promotions or opportunities that won't materialize destroys trust.
Fix: Be direct about timeline, requirements, and realistic chances. Help them understand what's in their control.
Tracking Career Development Over Time
The most effective career development is systematic, not sporadic.
What to Track
For each engineer, maintain:
- Career aspirations (short-term and long-term)
- Skills they're developing (technical and soft)
- Projects that support their goals
- Training and learning investments
- Mentorship relationships
- Progress milestones and achievements
- Gaps and obstacles
- Your commitments and follow-through
How to Track It
Option 1: Shared Google Doc
- Create a career development plan document
- Both you and engineer can edit
- Review together quarterly
- Simple but requires discipline
Option 2: Notion or Confluence
- More structured templates
- Can link to other work docs
- Better organization
- Still manual updates needed
Option 3: EliuAI (Recommended)
- AI automatically extracts career development themes from 1:1 notes
- Visualizes progress over time
- Suggests next steps based on patterns
- Tracks your commitments and reminds you
- Shows team-wide development trends
See how EliuAI tracks career development →
Making It Visual
Create a simple career development dashboard:
- Current level and target level
- Key skills needed (with progress bars)
- Upcoming milestones
- Action items and owners
- Timeline with checkpoints
Visual tracking helps:
- Engineer sees progress (motivating)
- You see patterns (coaching opportunities)
- Leadership sees investment (supports promotions)
- Both stay accountable
Sample Career Development Conversation Flow
Here's how to structure a 45-minute career-focused 1:1:
Opening (5 min)
- "Today let's focus on your career development. I want to make sure we're setting you up for where you want to go."
- Check in on how they're feeling about their growth
Current State (10 min)
- Ask 2-3 questions from Category 1 (Understanding Current State)
- Listen for satisfaction level, energy, and engagement
Future Direction (15 min)
- Ask 2-3 questions from Category 2 or 3 (Future Direction or Growth Gaps)
- Explore specific goals and aspirations
- Dig into what motivates them
Action Planning (10 min)
- Ask 1-2 questions from Category 5 (Creating Action Plans)
- Define specific next steps
- Create timeline and accountability
Closing (5 min)
- Summarize key insights
- Confirm action items (yours and theirs)
- Schedule next career check-in
- End with: "How valuable was this conversation?"
Conclusion: Career Development Is Your Job
Here's the truth: Your engineers' career development is not HR's job. It's not their job. It's your job.
Great engineering managers understand that developing people is not separate from the work. It IS the work. When you help your engineers grow:
✅ They perform better
✅ They stay longer
✅ They refer other great engineers
✅ They build your leadership brand
✅ They become the leaders you need as you scale
The ROI is undeniable: Companies with strong career development see 34% higher retention and 15% higher productivity.
But it requires consistency. One annual conversation won't cut it. These 25 questions are tools you should return to monthly, adapting based on where each engineer is in their journey.
Start with one question next week. Pick the one that feels most relevant for each of your engineers. Listen deeply. Take action on what you learn. Then come back to this list and pick another.
Your engineers' careers are in your hands. Make it count.
Transform Career Development with EliuAI
Ready to systematically develop your engineering team? EliuAI helps you:
✅ Track career goals automatically from 1:1 conversations
✅ Get AI-suggested questions based on each engineer's context
✅ Visualize development progress over time
✅ Never forget commitments with action item tracking
✅ See team-wide trends in career aspirations
✅ Build promotion cases with documented growth
Start Free Trial - 7 Days → • No credit card required
What Engineering Managers Are Saying
"EliuAI's career tracking changed how I manage. I can see at a glance who's growing, who's stuck, and where I need to invest time. Three promotions this quarter, all well-documented."
— Alex Rivera, Senior Engineering Manager, Series C Startup
"I used to forget career conversations between 1:1s. Now EliuAI reminds me of what each engineer wants to work on and suggests relevant questions. My team's engagement scores went up 40%."
— Jennifer Park, VP of Engineering, Tech Scale-up
"The AI-suggested questions are gold. They're always relevant to what we discussed last time or what's happening with the engineer's work. Saves me 30 minutes of prep per 1:1."
— Tom Anderson, Engineering Manager, Enterprise SaaS
Join 500+ engineering managers using EliuAI →
Have questions about career development conversations? Contact us.
Follow for more engineering leadership content: Twitter | LinkedIn