Benjamin
Charity

Published:

The Leadership Transition That Trips Up Most Engineers (and How to Survive It)

Reading time: 4min

The toughest leap in an engineering career is not learning a new language or scaling a system. It is stepping into leadership for the first time. Most engineers underestimate just how different the job becomes once you stop being judged on your commits.

Eight rowers in a racing shell move in sync while a coxswain at the back calls direction on calm water.
Eight rowers in a racing shell move in sync while a coxswain at the back calls direction on calm water.

The Problem

Many engineers approach the move from senior IC to director as if it is a straightforward promotion. They assume they will simply scale their impact. In practice, they either:

  • Keep trying to lead by being the super-engineer, reviewing every PR and making every big decision.
  • Or they overcompensate, leaning so hard into process that their team feels micromanaged and disconnected.

Both approaches fail. The real challenge is that the skills that made you valuable as an IC do not map neatly to leadership. In fact, they can actively work against you.

Why This Transition Is So Tough

The trap is simple: you try to keep doing what made you successful. But leadership is a different sport entirely.

  • Managing peers who are no longer peers. Yesterday you were shoulder to shoulder in the trenches. Today you are setting their growth paths.
  • Changing your scoreboard. As an engineer, success is building. As a director, success is enabling. If you do not adjust your lens, it can feel like you are doing nothing.
  • Earning trust in new rooms. Technical mastery earns credibility with engineers. In executive discussions, the currency is alignment, tradeoffs, and business impact.

This is why so many stumble: they keep trying to win the old game while playing a new one.

How to Survive (and Thrive) in the Transition

1. Redefine Success

Your value is not in writing code anymore. It is in creating the environment where others do their best work. Shift your scoreboard from "what I built" to "what my team accomplished."

2. Expand Your Time Horizon

Engineers solve for sprints. Directors solve for quarters. You need to anticipate hiring needs, technical debt cliffs, and roadmap collisions months in advance and shield your team from being blindsided.

3. Learn to Say No

Focus is oxygen. Your credibility as a leader grows when you protect your team's bandwidth. Saying no, or "not yet," is one of the most valuable tools in your kit.

4. Manage Relationships, Not Tasks

Former peers do not need you in their tickets. They need clarity, fair evaluations, and honest career conversations. Your new job is building trust and alignment, not logging more commits.

5. Speak the Language of the Business

Executives do not care about story points. They care about revenue, risk, and runway. Learn to translate technical debt into opportunity cost and roadmap risk. That is how you secure budgets and headcount.

The Hard Truth About Technical Depth

Technical mastery is necessary, but it is rarely what makes or breaks a company.

I have seen technically pristine teams collapse because they could not align with product, retain talent, or agree on priorities. I have also seen beautifully engineered, technically complex products fail simply because no one wanted to use them. On the other hand, I have watched teams with scrappy, imperfect systems thrive for years because leadership kept them aligned, trusted, and focused.

Technical depth gets you in the room. Staying in the room, and moving the company forward, comes from clarity, focus, and trust.

Looking Ahead

This transition is not going away. As companies grow, the gap between technical depth and organizational leverage only widens. The leaders who thrive will not be the ones out-coding their teams. They will be the ones who connect engineering effort directly to business outcomes while keeping their teams motivated and focused.

The biggest trap in moving from engineer to director is trying to scale yourself. You do not scale, you change. Success is no longer what you build, but what you enable.

Call to Action

If you are staring down this transition, start small. Pick one thing this week you will stop doing yourself and instead enable someone else to own. That is the beginning of the shift.

Build, Scale, Succeed

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