The Iterative Leader

Leadership Lessons I Took From Education to Tech

Written by webs | Dec 17, 2024 3:00:00 PM

I spent a decade teaching before I stepped into leadership roles in tech. On paper, they look like completely different worlds—chalkboards and classrooms vs. APIs and sprint boards. But the truth is, education shaped the kind of leader I am today in ways I couldn’t have anticipated.

Teachers are systems thinkers, facilitators, and builders of trust—exactly what great leaders need to be. Here are the leadership lessons I carried from education into tech, lessons I still use to help teams thrive.

1. Facilitation is Leadership

In a classroom, you’re not the center of attention—your students are. You’re there to guide conversations, pose questions, and create an environment where people learn and grow. It’s the same with tech teams.

Good leaders don’t just give orders; they facilitate collaboration. They create the space for their team to ask questions, explore solutions, and take ownership.

Example:
In education: I once guided a group of students through a debate about how to solve a community problem. My role wasn’t to decide for them—it was to keep the conversation moving, ask the right questions, and ensure every voice was heard.

In tech: I used the same approach in sprint planning with a team that had stalled on prioritizing their backlog. Instead of making the call myself, I facilitated:

  • “What’s our highest-risk area right now?”
  • “What happens if we don’t tackle this problem in the next sprint?”
  • “What trade-offs are we comfortable making?”

By shifting the focus from me to the team, they reached clarity and built alignment they wouldn’t have achieved if I’d made the decision for them.

2. Iteration Is at the Heart of Growth

Teachers iterate constantly. Lessons get adjusted mid-class. Feedback loops happen daily. You plan, execute, reflect, and improve—sometimes in a single hour. Sound familiar? It’s the backbone of Agile, but teachers have been doing it forever.

I learned early on that perfection is an illusion. Instead, you focus on growth:

  • Start where you are.
  • Reflect on what worked and what didn’t.
  • Adjust and try again.

Example:
In tech, I led a team that was trying to automate a manual workflow. The first version was messy. It didn’t solve everything, but instead of scrapping it, we treated it like a draft:

  • “What’s working in version 1?”
  • “What’s the next improvement we can make?”

Just like in teaching, we didn’t wait for the “perfect plan.” We started small, reflected, and iterated until the system delivered massive results.

Key Takeaway: Iteration is progress. The goal isn’t perfection—it’s continuous improvement.

3. Psychological Safety Drives Performance

In a classroom, if students don’t feel safe to ask questions, make mistakes, or share their ideas, learning stops. The same is true for teams. Without psychological safety, innovation dies, collaboration stalls, and teams end up playing it safe.

Teachers build trust every day. They set norms, model vulnerability, and celebrate mistakes as learning opportunities. Great leaders do the same.

Example: The Power of Wild Ideas
In one of my tech teams, I noticed people weren’t pushing back on ideas during design reviews. The team looked “collaborative,” but really, they were avoiding risk.

I borrowed a tool from my teaching days: the wildest ideas session. I encouraged team members to share the most ridiculous, over-the-top ideas they could think of—ideas that were almost laughably impractical.

The effect?

  • It brought humor into the room, disarming the tension and creating a sense of play.
  • By comparison, realistically risky ideas felt safe and reasonable, making it easier for team members to speak up.

Wild ideas broke the ice and sparked some genuinely innovative solutions. The key was creating a space where no one felt judged, and everyone felt safe to contribute.

4. Clear Systems Create Freedom and Innovation

In education, routines and systems make the classroom work: students know what to expect, what’s expected of them, and how they’ll be supported. Those systems don’t stifle creativity—they enable it.

The same holds true in tech. Clear systems and expectations aren’t micromanagement—they’re the foundation for trust, shared understanding, and better performance.

What the Research Shows
In my research on collaborative problem-solving, I found that clear systems and expectations:

  • Build psychological safety by removing ambiguity.
  • Foster shared mental models, where teams align on goals, processes, and roles.
  • Lead to more efficient and innovative solutions because the team spends less energy navigating confusion and more energy solving problems.

Example:
In one cross-functional team, handoffs between engineering and QA were riddled with errors. The system was unclear: expectations for “done” were vague, and each team assumed the other would catch critical gaps.

Instead of adding complexity, we simplified:

  1. Defined what developer “done” meant, with clear handoff criteria.
  2. Ensured user stories had well-documented acceptance criteria agreed upon by the whole team.

The results? Fewer mistakes, faster feedback loops, and a stronger shared understanding of the team’s goals.

When teams know what to expect, they have more bandwidth for creativity and innovation. Systems don’t limit people—they enable them.

5. People Over Everything

Teachers know one thing better than anyone else: relationships drive results. You can have the best tools, the smartest strategies, and the most innovative systems, but if you’re not prioritizing the people doing the work, none of it matters.

In leadership, your team is your classroom. It’s your job to:

  • See the strengths in every team member.
  • Build trust and safety.
  • Coach, mentor, and guide—not just manage.

Great teachers don’t just deliver content. They build confidence, ignite curiosity, and create conditions where students can thrive. Great leaders do the same.

From Classroom to Tech—Leadership is Leadership

The best lessons about leadership don’t come from strategy books or corporate workshops. They come from experiences where systems meet people, where trust enables growth, and where iteration creates progress.

Whether you’re leading a classroom or a tech team, the principles are the same:

  • Facilitate, don’t dominate.
  • Create systems that empower and align.
  • Foster psychological safety and curiosity.
  • See people’s potential, and help them reach it.

Because leadership isn’t about you—it’s about the space you create for others to thrive.

Ready to create systems and strategies that empower your team?
Let’s connect to unlock your team’s full potential.