The Leadership Ceiling You Hit Before You See It

After several years of leading engineering teams, I learned something unexpected. The hardest leadership transition isn’t the one most people prepare for.

Books, courses, and talks focus on the move from individual contributor to manager. Everyone sees that coming. The less obvious ceiling shows up later—when you move from leading a single team to coordinating how multiple teams work together. Instead of just solving delivery problems, you start debugging the organization itself.

I’m navigating this transition firsthand, leading across multiple teams and seeing these challenges surface daily—not as isolated delivery issues but as patterns shaped by the system’s design. I don’t have all the answers, but the pattern keeps showing up:

The habits that make you a good manager—like moving fast, asserting answers early, and getting involved—can quietly cap your effectiveness at the next level.

From Speed to Agency: Designing for Time and Uncertainty

The trap: Focusing on quick wins while waiting for perfect clarity that never really comes.

As your responsibilities grow, feedback takes longer to show up. At this level, agency means shaping how decisions get made rather than making every decision yourself. Small problems can quietly build up until they suddenly turn into big issues.

I watched a team defer critical work in a high-volume payments system to hit a quarterly target. They made the number. Six months later, accumulated issues forced a rushed rebuild under regulatory pressure. They missed a market window and two teams burned out.

The failure wasn’t about technology. It was about leadership choices that delayed hard work until timing ran out.

Leadership decisions don’t fail the way code does. If a function is broken, you see an error right away. But a weak system might look fine at first, pass reviews, and only show problems months later when things change or pressure increases.

The warning signs are subtle: slower progress, more incidents, or lower morale. It’s hard to see how these connect to decisions made months earlier unless you’re paying attention.

When you manage tasks, you get quick and precise feedback. When you design systems, feedback is slower and less noticeable. The challenge is learning to act before problems become impossible to ignore.

During a reorganization across three time zones and several product lines, some leaders waited for answers that never came. Others pointed out the uncertainty, set up temporary roles, and gave teams a plan within days. It wasn’t perfect, but work moved forward. Teams didn’t love it, but they knew what to do.

Systems often settle around the first person who names reality—and has enough credibility and authority to make it actionable.

To do this, you need two skills that many leaders don’t develop enough:

• Make decisions before you have complete certainty. Waiting doesn’t remove risk; it just changes when and how it shows up.

• Bring structure to uncertain situations. When roles are unclear and priorities keep changing, teams can fall apart. Leaders who succeed at a larger scale add just enough order to keep things on track.

Building something that lasts comes with a cost. Sometimes you create the right system but miss the right timing. The key isn’t choosing between speed and durability, but knowing which you’re aiming for and being honest about the risks if you choose wrong.

From Contribution to Leverage

The trap: Judging your value by how much you personally get done.

Great engineers still want to contribute after they become leaders. That urge often gets stronger. You jump in because you can solve problems quickly, give better feedback, and make clearer decisions.

But something important changes.

On a platform team that managed money movement and reconciliation, I saw a leader who excelled at getting things done. Problems were solved fast, but decisions started to pile up around them. It became unclear who owned what. When this leader took time off, work didn’t just slow down, it became unstable.

The system worked well, but it wasn’t built to last.

The shift: Measure success by how well things run when you’re not there.

You see this most clearly when leaders use silence on purpose.

When you first start leading, speaking up is encouraged. But as you lead larger groups, always having the answer puts all the authority back on you.

In a design review, I watched a senior architect stay quiet while two mid-level engineers debated API versioning. When they stalled, she asked one question: “What happens to clients if we break backward compatibility?”

That one question changed the whole discussion. Her silence wasn’t about not being there. It was about holding back so others could take responsibility. This only works once you’ve built credibility; without trust it just looks like disengagement.

Silence can be a powerful tool. If you use it well, it helps others grow. If you use it poorly, it can feel like you’re not supporting your team. Silence stops being a tool the moment values, safety, or irreversible decisions are at risk.

Accept the Asymmetry of Responsibility

The trap: Moving up to get recognition.

Leading at a higher level isn’t about status. It’s about facing more challenges and risks.

When systems break, customers complain, or promises fall apart, you feel the responsibility directly. Great leaders give credit to others and take responsibility themselves.

But here’s what most advice leaves out: At a senior level, you’re responsible not just for your own decisions, but also for other people’s.

When executives set unrealistic deadlines or suddenly change priorities, your job is to turn that confusion into clear direction for your team. Sometimes you have to support strategies you don’t fully agree with. You take on the problems, so your team can stay focused.

I once had to publicly support a technical direction I believed was flawed. I raised concerns early, supported by data and alternatives. Once the decision was made, I focused on de-risking execution instead of creating organizational churn. The hard part wasn’t letting go of the idea—it was deciding the issue wasn’t worth spending more organizational capital on. Reversing it would have disrupted three teams and damaged a critical partnership. I quietly put guardrails in place, documented risks, and took responsibility when issues came up months later.

That imbalance isn’t unfair. It’s just part of the job.

Authority isn’t about status. It’s about taking on pressure instead of passing it along.

The Transition Most Leaders Miss

Many skilled leaders stop growing, not because they lack ability but because they keep focusing on the wrong things.

They keep improving execution in jobs that now require designing systems. They work harder when they should step back. They become the key person when they should build the bigger picture.

Moving forward isn’t about learning new skills. It’s about letting go of old habits that no longer work.

If you want to move up, stop wondering if you have enough skills. Instead, ask yourself:

• Are you building systems that work without you, or are you still the bottleneck?

• Are you choosing durability over visibility, even when it costs you short-term wins?

• Have you accepted that you’ll own decisions you didn’t make and defend strategies you privately question?

At this level, leadership isn’t about being right more often. It’s about building systems that keep working even when things change, especially when you’re not at the center anymore.

Sometimes, these systems work so well without you that you lose critical context. The best leaders I know always balance this. They step back from daily decisions but stay close enough to understand what is really happening and make important choices.

None of this comes from a playbook or a course. It comes from living with the consequences of your decisions long enough to see the system respond.

That tension isn’t a problem. Designing and operating systems at this level is the work.