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15 June 202416 min read

Technical Leadership: Lessons from 20 Years of Building Teams

LeadershipCareerTeam ManagementMentorship

Insights on growing from individual contributor to technical leader. Delegation, mentorship, and balancing hands-on work with strategic thinking.


Technical Leadership: Lessons from 20 Years of Building Teams

Technical leadership is fundamentally about enabling others while maintaining technical credibility. After two decades of building and leading engineering teams across telecom, healthcare, banking, and energy sectors, I've learned that the skills that make great individual contributors are different from those that make great leaders.

The Transition Challenge

Moving from individual contributor to technical lead means success is now measured by team outcomes, not personal output. This transition is harder than it sounds.

What Changes

Before: Your impact = Your code + Your designs After: Your impact = Team output × Team growth × Strategic decisions

Common Struggles

The hero trap: Jumping in to fix problems instead of teaching others The control trap: Reviewing everything instead of building trust The abstraction trap: Spending all time in meetings, losing technical depth The friendship trap: Avoiding difficult feedback to stay liked

Signs You're Struggling

  • Your team waits for your decisions instead of making them
  • You're the bottleneck for code reviews and approvals
  • You can't explain what your team members are working on
  • You feel exhausted while your team seems underutilized

Effective Delegation

Delegation is the highest-leverage activity for leaders, yet most struggle with it.

Delegate Outcomes, Not Tasks

Poor delegation: "Write a function to validate email addresses" Better delegation: "We need to reduce invalid email signups by 80%"

When you delegate outcomes, you empower problem-solving. The team might find solutions you never considered.

Provide Context, Not Just Instructions

People do better work when they understand why:

  • What problem does this solve?
  • Who benefits and how?
  • What constraints matter?
  • How does this fit the bigger picture?

Accept Different Approaches

Your way isn't the only way. Unless there's a clear technical reason (performance, security, maintainability), let people solve problems differently.

The goal is outcomes, not clones.

Create Growth Through Stretch Assignments

Match challenges to people's growth edges:

  • Ready for more responsibility? Lead a project
  • Need technical depth? Own a complex component
  • Want visibility? Present to stakeholders
  • Learning new skills? Pair with experts

Stretch without support is stress. Provide scaffolding.

Know What Not to Delegate

Keep these for yourself:

  • Hiring and firing decisions
  • Performance feedback and career conversations
  • Strategic technical decisions affecting multiple teams
  • External stakeholder relationships
  • Crisis management

Staying Technical

Leaders who lose technical depth lose credibility and make poor decisions.

The Credibility Connection

Your team watches whether you understand their challenges:

  • Can you discuss technical trade-offs knowledgeably?
  • Do you ask good questions in design reviews?
  • Can you help debug difficult problems?
  • Do you stay current on relevant technologies?

Practical Ways to Stay Technical

Code reviews: Not all of them, but enough to understand the codebase Architecture discussions: Participate actively, not just as approver Spikes and prototypes: Pick up occasional small technical tasks Learning time: Block time for reading, courses, experimentation Pair programming: Occasionally pair with team members

Knowing Your Limits

You don't need to be the best coder on the team. In fact, you probably shouldn't be. Your role is different now.

Know enough to:

  • Ask the right questions
  • Spot red flags
  • Understand constraints
  • Make informed trade-offs

Trust your team for deep technical execution.

Mentorship That Works

Effective mentorship accelerates careers and builds loyalty.

1-on-1s Are Not Status Meetings

Status belongs in standups and project updates. 1-on-1s are for:

  • Career development and aspirations
  • Feedback (both directions)
  • Obstacles and frustrations
  • Growth opportunities
  • Personal check-ins

Questions That Open Conversations

  • "What's been on your mind lately?"
  • "What's frustrating you about the project?"
  • "What would you like to be doing more of?"
  • "What feedback do you have for me?"
  • "What does success look like for you this year?"

Giving Difficult Feedback

Avoiding difficult feedback helps no one. Use the SBI model:

Situation: "In yesterday's design review..." Behavior: "...you interrupted Maria three times..." Impact: "...which made it hard for her to explain her proposal."

Then discuss: "What was going on for you?" and "How might you handle it differently?"

Creating Sponsorship

Mentorship is advice. Sponsorship is advocacy.

Sponsors:

  • Recommend people for opportunities
  • Advocate in rooms where decisions are made
  • Connect people with influential networks
  • Take reputational risk for their people

Look for opportunities to sponsor your team members.

Building High-Performing Teams

Psychological Safety

People do their best work when they feel safe to take risks:

  • Admit mistakes without punishment
  • Ask "dumb" questions without ridicule
  • Challenge ideas without retaliation
  • Experiment without career risk

Leaders set the tone. If you punish failure, you'll get hidden problems.

Clear Expectations

Ambiguity creates anxiety. Be clear about:

  • What success looks like
  • How performance is measured
  • What decisions they can make independently
  • When and how to escalate

Removing Obstacles

Ask: "What's slowing you down?" Then actually fix it:

  • Process bottlenecks
  • Missing tools or access
  • Unclear requirements
  • Organizational friction

Sometimes the best thing a leader does is remove barriers.

Managing Up and Across

Technical leadership isn't just about your team.

Executive Communication

Executives need different information:

  • Lead with outcomes, not technical details
  • Frame in business terms (cost, risk, time)
  • Provide options with trade-offs
  • Be honest about uncertainty

Cross-Functional Partnership

Your team depends on others:

  • Build relationships before you need them
  • Understand other teams' priorities
  • Find win-win solutions
  • Share credit generously

Managing Conflict

Conflict is inevitable. Handle it directly:

  • Address issues early before they escalate
  • Focus on interests, not positions
  • Seek to understand before seeking to be understood
  • Involve others only when direct resolution fails

Key Takeaways

  1. Measure yourself by team outcomes: Your impact is through others now
  2. Delegate outcomes, not tasks: Empower problem-solving
  3. Stay technical enough: Maintain credibility without competing
  4. Invest in people: Mentorship and sponsorship build loyalty and capability
  5. Create safety: People do best work when they can take risks
  6. Communicate across levels: Adapt your message to your audience
  7. Keep learning: The best leaders never stop growing

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