The Great Transition: Scaling Leadership in Yourself and Others

In building ambitious things, we spend a lot of time thinking about how to scale systems. But the most critical scaling challenge is often human: scaling leadership. The transition from managing individual contributors to managing managers—the leap from Manager to Director—is one of the most significant and failure-prone inflection points in an organization. Getting it right is a form of leverage that compounds. Getting it wrong creates a drag that can cap a company’s potential.

This isn’t just a promotion. It is a completely different job. The failure to recognize this is the primary reason so many struggle. The skills that made you a great manager of engineers can actively work against you when your job is to lead other managers.

Your Job Is No Longer Your Job

As a frontline manager, you’re close to the work. You’re in the stand-ups, you might review code, and you are deeply involved in the daily execution of your team. When you become a director, those tasks are now the responsibility of the managers who report to you.

Continuing to do them is a failure mode. At best, you disempower your managers. At worst, you cause chaos.

In a key story shared by a friend on his own experience in this transition about his own friction points and difficulties. He drove an agile transformation, spending all his time internally focused on his engineering teams. By his measure, the teams were improving. But when his performance review arrived, it was one of the worst of his career. He had completely neglected his new primary team: his peers, the other directors. He hadn’t built relationships or aligned his vision with the leaders of project management, QA, or other groups.

He was still doing his old job, and failing at his new one. The new job is not to be the best manager, but to build a system of managers who can succeed.

The Paradox of Control

A common motivation for seeking a director role is the desire for more control; to finally be able to fix the problems you see. But the reality is that you often have much less direct control, not more. You trade direct control for broader influence.

Your success is no longer about your direct actions. It’s about getting alignment, managing relationships, and connecting your team’s work to the company’s mission. You now operate in a system of leaders, and you cannot just do what you want. Your primary team shifts from the people who report to you to the leadership team you are now a part of.

The Three Failure Modes

There can be three common reasons why this transition fails.

1. Failure to Stop Doing the Old Job: This is the story above. The skills are different, the expectations are different, and the context is different. You have to learn the new role.

2. Failure to Manage Yourself: A director with their “hair on fire” (who is constantly in meetings and gives off an air of being stressed) does not inspire confidence. You cannot manage a large organization if you cannot manage your own calendar and energy. Your new, broader scope means your time is your most valuable resource. If you don’t control it, you can’t make time for the high-leverage work: coaching your team, solving systemic problems, and connecting with stakeholders.

3. Failure to Take the Leadership Role: The most significant shift is in mindset. You are no longer only responsible for your team; you are responsible for shaping the world around your team. I’ve seen new directors wait for the company to define their function or solve their team’s problems for them. In a conversation, one leader had a breakthrough when asked if the VP was thinking about defining the specifics of his function. He realized he was the one hired to do that. The job is to create the conditions for success, not wait for them.

The Tools for Leverage

To succeed, you need to master a new set of tools built for leverage.

• Management Fundamentals as a Teacher: You must have solid management fundamentals not just to practice, but to teach. You are now responsible for coaching your managers on everything from hiring and performance management to giving feedback.

• Delegation and Coaching: You have to learn the art of letting go. This can be deeply uncomfortable, but allowing your managers to learn, and even make mistakes, is essential for their growth and your own sanity.

• Communication as Culture: As a director, you are a cultural beacon. You are always communicating—through your words, your actions, and the questions you ask. You have to be incredibly intentional about the culture you are signaling to the organization.

• Giving Hard Feedback: Leadership is not about being liked; it’s about being effective. Servant leadership includes the responsibility to give direct, hard feedback when necessary for the good of the individual and the company. Avoiding this is an abdication of duty.

Why Bother?

This sounds hard. And it is. One could listen to the challenges and wonder why anyone would want the job.

The reason is that this journey is one of immense personal growth and scaled impact. To become a better leader, you have to become a better person. It’s a journey of self-discovery, of learning about people, and of understanding how organizations truly function.

When you successfully make the transition, you get to see the unlocked potential in your teams and the impact you can have on an entire company. It is difficult, but it is one of the most rewarding journeys you can undertake. Building great leaders is how we build great companies that can solve the world’s hardest problems.