Leadership Development¶

Leadership development is not a program you attend. It is a continuous practice of self-awareness, deliberate growth, and creating conditions for others to develop. This page covers all three: how to grow yourself, how to grow others, and how to build leadership depth that makes your organization resilient.

What Problem This Solves¶

Engineering organizations need leaders at every level. Not just managers—technical leaders, project leaders, domain experts who can align people and make decisions under uncertainty. Without deliberate development, this leadership either does not emerge or emerges unevenly, concentrated in a few people who become bottlenecks and burn out.

When leadership development is absent:

• Decisions bottleneck at senior levels because no one else feels empowered
• Promotions fail because people are elevated without preparation
• Knowledge and relationships concentrate in a few irreplaceable individuals
• Growth stalls because there are no paths to senior roles
• Teams struggle when key people leave, get sick, or take vacation

When leadership development works:

• Decisions happen at the right level by people with context
• Transitions are supported and succeed more often
• Leadership is distributed and resilient
• People see growth paths and stay longer
• The organization can scale without proportional increases in management overhead

When to Focus on Development¶

Actively invest when:

• You are preparing someone for a transition (IC to lead, lead to manager)
• You notice bottlenecks in decision-making or knowledge
• You have high-potential people who need stretch opportunities
• Turnover is creating leadership gaps
• You are scaling and need more leaders than you have

Maintain when:

• Things are stable but you want to stay ahead of attrition
• You have a healthy pipeline but want to keep developing it
• Onboarding new leaders who need context and relationships

Defer when:

• True crisis mode where survival is the focus
• The person is not ready or willing (development requires consent)

Ownership¶

Part 1: Developing Yourself¶

Leadership development starts with yourself. You cannot grow others if you are not growing. You cannot model continuous learning if you have stopped learning.

Self-Awareness¶

Self-awareness is the foundation. Leaders who lack self-awareness do not know their impact, do not see their blind spots, and cannot adapt to different contexts.

Practices that build self-awareness:

Seek feedback actively. Do not wait for performance reviews. Ask your team, your peers, and your manager: "What is one thing I could do differently that would make me more effective?" Ask regularly enough that people believe you mean it.

Reflect on interactions. After difficult conversations, meetings that went poorly, or decisions that surprised you, pause and ask: What did I contribute to that outcome? What patterns am I seeing?

Work with a coach or mentor. An outside perspective—someone who is not in your reporting line—can see things you cannot. Coaches ask questions that force reflection.

Use assessments thoughtfully. Tools like 360-degree feedback, personality assessments, or leadership style inventories can surface patterns. Treat them as data points, not verdicts.

Keep a leadership journal. Spend five minutes at the end of the day or week writing about what went well, what did not, and what you are learning. The act of writing forces articulation.

Energy Management¶

Leadership is demanding. If you do not manage your energy, you will burn out or become ineffective. Sustainable leadership requires attention to recovery, boundaries, and workload.

Principles for energy management:

Know your limits. Notice when you are depleted—irritability, poor decisions, withdrawal. These are signals, not character flaws. Respond by resting, not pushing through.

Protect recovery time. Weekends, vacations, and off-hours are not optional. Model this for your team. If you send emails at midnight, you are teaching others to do the same.

Manage your calendar ruthlessly. Not every meeting needs you. Not every decision needs your input. Delegate, decline, and batch meetings to create focus time.

Distinguish urgent from important. The inbox is full of urgent things. Leadership requires time for the important things that are not urgent—strategy, development, relationships. Schedule time for these explicitly.

Ask for help. Asking for help is not weakness. It is resource management. Build a support network—peers, mentors, friends outside work—who can provide perspective and encouragement.

Continuous Learning¶

Leaders who stop learning become obsolete. Technology changes, organizations change, people change. Staying effective requires ongoing investment in learning.

How to keep learning:

Read widely. Not just technical content—read about leadership, psychology, organizational design, and domains outside your own. Diverse inputs create novel insights.

Learn from failure. Your own failures are expensive education. Do not waste them. After something goes wrong, ask: What will I do differently? What system allowed this to happen?

Learn from others' experience. Talk to leaders in other companies, other industries, other stages of company. Join communities where you can share challenges and hear different perspectives.

Teach. Teaching forces you to articulate what you know, reveals gaps in your understanding, and reinforces learning. Mentor others, write, speak—whatever form suits you.

Experiment. Try new approaches in your work. Run small experiments in how you run meetings, give feedback, or make decisions. Treat your leadership as a system that can be improved.

Part 2: Growing Others¶

Growing others into leaders is one of the highest-leverage activities a senior leader can do. One strong leader creates an environment where many people can do better work.

Identifying Emerging Leaders¶

Not everyone wants to lead, and not everyone who wants to lead is ready. Your job is to identify people with both potential and motivation.

Signs of leadership potential:

• Takes initiative without being asked
• Influences peers through ideas, not just authority
• Handles ambiguity without paralysis
• Takes ownership of outcomes, not just tasks
• Seeks feedback and acts on it
• Brings others along—does not succeed at others' expense
• Shows resilience when things go wrong

Signs someone is ready for a stretch:

• They are performing well in their current role
• They have expressed interest in growth or new challenges
• They have demonstrated relevant skills at smaller scale
• They have the bandwidth (not already overloaded)

How to have the conversation:

Do not surprise someone with a leadership role. Discuss their interests, aspirations, and concerns first. Some people who seem ready do not want leadership roles—and that is fine. Others want leadership but have unrealistic expectations about what it involves. Honest conversation prevents mismatched expectations.

Stretch Assignments¶

People develop by doing, not by reading about doing. Stretch assignments give emerging leaders real responsibility with real stakes, in a supported environment.

What makes a good stretch assignment:

Examples of stretch assignments:

• Lead a cross-team initiative or project
• Own an on-call rotation and improve it
• Represent the team in planning or roadmap discussions
• Mentor a junior engineer
• Lead a technical design for a significant feature
• Drive a process improvement from problem to solution
• Handle a stakeholder relationship that requires coordination

Supporting Transitions¶

Transitions—from IC to tech lead, tech lead to manager, manager to director—are high-risk moments. Many transitions fail because people are promoted without preparation or support.

The first 90 days matter. This is when habits form, relationships establish, and credibility builds. Provide extra support during this period.

Transition support practices:

Structured onboarding. Even for internal promotions, provide explicit onboarding to the new role. What are the expectations? What does success look like? Who are the key relationships?

Assign a mentor. Pair the transitioning leader with someone who has done this role successfully. This should be outside the reporting line—a safe space for questions and concerns.

Frequent check-ins. During the first 90 days, meet weekly to discuss how it is going. Ask about challenges, not just status. Be available.

Permit learning curves. The person will make mistakes. This is expected. Provide feedback quickly, but do not punish the inevitable stumbles of learning a new role.

Adjust expectations. A new tech lead will not deliver as much code. A new manager will take time to learn the people side. Make these trade-offs explicit so the person does not feel they are failing by not doing both perfectly.

See Coaching New Tech Leads for a detailed framework on the IC-to-lead transition.

Delegation as Development¶

Delegation is a development tool, not just a workload management technique. How you delegate determines whether people grow or just execute.

Levels of delegation:

For development, delegate at the highest level the person can handle. Start with problems, then outcomes, then portfolios as they demonstrate readiness.

The delegation conversation:

1. Context: Why does this matter? What's the background?
2. Outcome: What does success look like? What are the constraints?
3. Authority: What can they decide? What needs approval?
4. Support: What help is available? When should they escalate?
5. Check-ins: How will you stay informed without micromanaging?

Giving Developmental Feedback¶

Feedback is how people learn what is working and what is not. Without feedback, improvement is slow and misdirected.

Principles for developmental feedback:

Be specific. "You need to communicate better" is useless. "In yesterday's meeting, when you interrupted Maria twice, it made it harder for others to contribute" is actionable.

Balance reinforcing and redirecting. People need to know what to keep doing, not just what to change. Catch people doing things right and name it.

Connect to impact. Explain why it matters. "When you do X, the effect is Y" helps people understand, not just comply.

Focus on behavior, not character. "You were late to three meetings this week" is behavioral. "You're unreliable" is character. Behavioral feedback is actionable; character feedback is demoralizing.

Make it timely. Feedback loses value with delay. Aim to give feedback within days of the observation, not months later in a performance review.

Invite dialogue. After giving feedback, ask: "What's your reaction?" or "Is there context I'm missing?" Feedback should be a conversation, not a lecture.

See Feedback Frameworks for detailed models and scripts.

Part 3: Building Leadership Depth¶

Leadership depth means your organization has multiple people who can step into key roles when needed. It means you are not dependent on single individuals. It is the organizational equivalent of resilience.

Succession Planning¶

Succession planning is not just for executives. Every critical role should have at least one person who could step in if needed—even if imperfectly.

For each key role, answer:

• Who could step into this role today if needed?
• Who could step into this role with 3-6 months of development?
• What development would they need?
• What is blocking their readiness?

See Succession Planning for the full framework and templates.

Knowledge Distribution¶

Leadership depth requires that knowledge and relationships are distributed, not concentrated.

Practices for distributing knowledge:

• Rotate ownership of systems and processes
• Document decisions (see Decision Making & ADRs)
• Include multiple people in key meetings and relationships
• Cross-train during stable periods, not just during transitions
• Use pairing and shadowing to transfer tacit knowledge

Avoiding Single Points of Failure¶

A single point of failure (SPOF) in leadership is a person whose absence would cause significant disruption. SPOFs are risky—people get sick, leave, or burn out.

Signs of leadership SPOF:

• One person is the only one who can make certain decisions
• One person has all the relationships with a key stakeholder
• One person holds critical knowledge that is not documented
• The team is paralyzed when one person is on vacation

Mitigations:

• Delegate decisions and authority to multiple people
• Include backup people in key relationships
• Document decisions, context, and processes
• Practice having someone else lead when the usual leader is available (not just when they're gone)

What Good Looks Like¶

Failure Modes and Mitigations¶

The Reluctant Delegator¶

Symptom: The leader does everything themselves. Team members do not grow. The leader is overloaded.

Root cause: Fear of loss of control, perfectionism, or lack of trust. Sometimes the leader does not know how to delegate effectively.

Mitigation: Start small. Delegate one thing well, with support and clear expectations. Build confidence through success. Get coaching on delegation skills.

The Sink-or-Swim Culture¶

Symptom: New leaders are thrown into roles with no support. Some succeed; many struggle or fail.

Root cause: "I figured it out, so should they" mentality. No investment in transition support.

Mitigation: Implement structured transition support: onboarding, mentoring, frequent check-ins. Track transition success rates and treat failures as system problems.

The Feedback Void¶

Symptom: Leaders do not receive feedback. They do not know how they are perceived or what to improve.

Root cause: Hierarchy makes feedback upward feel risky. No channels or norms for peer feedback.

Mitigation: Leaders must ask for feedback explicitly and repeatedly. Create safe channels (skip-levels, anonymous surveys, peer feedback rituals). Model receiving feedback gracefully.

The Development Squeeze¶

Symptom: Development gets deprioritized for delivery. There is never time for stretch assignments or learning.

Root cause: Short-term pressure crowds out long-term investment. Development is seen as nice-to-have.

Mitigation: Budget time for development explicitly. Include development in planning. Measure and celebrate growth, not just delivery.

The Clone Army¶

Symptom: All leaders look and act the same. Leadership development produces conformity, not capability.

Root cause: Leadership is defined too narrowly. Only one style is valued.

Mitigation: Define leadership by outcomes, not style. Value different approaches. Ensure diverse representation in leadership development programs.

Copy-Paste Artifact: Leadership Development Plan¶

Use this template for a development conversation and follow-through.

## Leadership Development Plan

**Name:** [Name]
**Current role:** [Role]
**Manager:** [Name]
**Date:** [Date]
**Review date:** [Date, typically 90 days]

### Development Goals

**What are you working toward?**
[E.g., Preparing for tech lead role, strengthening cross-team influence, building coaching skills]

### Strengths to Leverage

**What do you do well that you can build on?**

1. [Strength]
2. [Strength]
3. [Strength]

### Development Areas

**What do you need to develop?**

1. [Area] — [Why it matters]
2. [Area] — [Why it matters]
3. [Area] — [Why it matters]

### Development Actions

| Action            | Type                          | Timeline | Support Needed               |
| ----------------- | ----------------------------- | -------- | ---------------------------- |
| [Specific action] | Stretch / Learning / Feedback | [Date]   | [What help from manager/org] |
|                   |                               |          |                              |
|                   |                               |          |                              |

### Stretch Assignment (if applicable)

**Assignment:** [Description]
**Ownership:** [What they own]
**Success criteria:** [How we'll know it worked]
**Support:** [Who will help, how often to check in]
**Timeline:** [Start and end dates]

### Feedback Plan

**Feedback sources:**

- [Manager — ongoing]
- [Peer — quarterly]
- [Skip-level — quarterly]
- [Team — [mechanism]]

**How feedback will be gathered:** [1:1s, surveys, direct asks]

### Check-in Schedule

| Date   | Focus                                                   |
| ------ | ------------------------------------------------------- |
| [Date] | [E.g., Progress on stretch assignment, feedback review] |
| [Date] | [E.g., Mid-quarter development review]                  |
| [Date] | [E.g., Plan review and next quarter planning]           |

### Notes

[Any additional context, constraints, or considerations]

Copy-Paste Artifact: Transition Support Checklist¶

Use when someone is transitioning into a new leadership role.

## Transition Support Checklist

**Name:** [Name]
**New role:** [Role]
**Transition date:** [Date]
**Manager:** [Name]
**Mentor:** [Name]

### Before the Transition

- [ ] Role expectations documented and shared
- [ ] Success criteria defined for first 30/60/90 days
- [ ] Mentor assigned (someone who has done this role)
- [ ] Key relationships identified (who they need to build relationships with)
- [ ] Handoff from predecessor completed (if applicable)
- [ ] Workload adjusted (they may need to drop some previous work)

### First 30 Days

- [ ] Onboarding meeting: Role, expectations, support
- [ ] Introductions to key stakeholders
- [ ] Weekly check-in scheduled with manager
- [ ] First meeting with mentor
- [ ] Initial observation: What's working, what's surprising?

### 30-60 Days

- [ ] 30-day check-in: How is it going? What's hard?
- [ ] Feedback gathered from team/stakeholders
- [ ] Adjustment to expectations if needed
- [ ] Development areas identified from experience

### 60-90 Days

- [ ] 60-day check-in: Progress on goals
- [ ] 90-day review: Success against criteria, lessons learned
- [ ] Development plan created or updated
- [ ] Transition from "new" to "established" — reduce check-in frequency

### Ongoing Support

- [ ] Regular 1:1s continue
- [ ] Mentor relationship continues (if valuable)
- [ ] Development plan reviewed quarterly
- [ ] Feedback mechanisms established

### If the Transition Struggles

- [ ] Diagnose: Is it skill, will, or fit?
- [ ] Increase support: More coaching, more check-ins
- [ ] Adjust expectations: Maybe the timeline was too aggressive
- [ ] Consider alternatives: Can they step back without shame?

Copy-Paste Artifact: Leadership Self-Assessment¶

Use quarterly for self-reflection or as input to a coaching conversation.

## Leadership Self-Assessment

**Name:** [Name]
**Date:** [Date]
**Period covered:** [E.g., Q4 2025]

### Self-Awareness

**How well do I understand my impact on others?**
[Rating: Strong / Adequate / Needs work]
[Evidence/examples:]

**What feedback have I received this quarter?**
[Summary of feedback and my response:]

**What patterns am I noticing in myself?**
[E.g., triggers, blind spots, recurring challenges:]

### Energy and Sustainability

**How is my energy level?**
[ ] Sustainable — I have capacity
[ ] Stretched — Manageable but tight
[ ] Depleted — I'm running on fumes

**What's draining me?**
[List:]

**What's energizing me?**
[List:]

**What will I do to protect my energy?**
[Commitment:]

### Learning and Growth

**What have I learned this quarter?**

1. [Learning]
2. [Learning]
3. [Learning]

**What am I currently developing?**
[Skill/capability and how I'm developing it:]

**What do I need to learn next?**
[Skill/capability and why:]

### Impact on Others

**Am I developing my people?**
[Evidence — stretch assignments given, growth observed:]

**Am I delegating effectively?**
[Evidence — what I've delegated, how it's going:]

**Is my team doing better work because of how I lead?**
[Honest assessment:]

### Key Questions for Coaching

**What would I like to discuss with my coach/mentor/manager?**

1. [Question]
2. [Question]
3. [Question]

### Commitments for Next Quarter

1. [Specific commitment]
2. [Specific commitment]
3. [Specific commitment]

Further Reading¶

• The Making of a Manager by Julie Zhuo — Practical guide to new managers
• Radical Candor by Kim Scott — Framework for feedback and caring personally
• An Elegant Puzzle by Will Larson — Systems thinking for engineering management
• Turn the Ship Around! by L. David Marquet — Intent-based leadership and empowerment
• Thanks for the Feedback by Douglas Stone and Sheila Heen — How to receive and use feedback
• The First 90 Days by Michael Watkins — Navigating leadership transitions

Related¶

• Coaching New Tech Leads — Detailed support for the IC-to-lead transition
• Succession Planning — Building leadership depth organizationally
• Growth Plans — Structured career development framework
• Feedback Frameworks — How to give and receive feedback effectively
• One-on-Ones — The primary venue for development conversations
• Core Principles — The values that underpin all leadership