Managing Managers: A Very Short Director's Guide to Engineering Leadership

After more than a decade leading engineering teams and managing dozens of managers across multiple companies, I’ve learned that managing managers is fundamentally different from managing individual contributors. The leverage is enormous. A great manager can multiply the effectiveness of an entire team. A struggling manager can create cascading problems that take months to resolve.

Here’s a short essay on what I’ve learned about the key challenges and strategies for successfully managing engineering managers.

Getting Real Information from Your Skip-Level Reports

Your managers are your primary source of information about their teams, but they’re also a filter. Sometimes that filter is helpful, sometimes it obscures critical issues. Skip-level conversations are essential for understanding what’s really happening.

I schedule regular skip-levels with every IC on my teams—not to go around their manager, but to get a fuller picture. The key is establishing psychological safety in these conversations. I always start by being clear about my intent: “I’m not here to catch anyone doing something wrong. I want to understand how we can better support you and your manager.”

The most valuable skip-level conversations happen when engineers feel comfortable sharing their real challenges. I’ve found that asking specific questions yields better results than generic “how are things going?” Try: “What’s the biggest blocker slowing down your team right now?” or “If you could change one thing about how we work, what would it be?”

When skip-levels reveal concerning patterns, I don’t immediately escalate to the manager. Instead, I use the information to ask better questions in my 1:1s with managers and create opportunities for them to identify and address issues themselves.

About Manager Accountability

Accountability in management isn’t about catching people making mistakes—it’s about creating clear expectations and supporting managers in meeting them. I’ve seen too many directors who either micromanage their managers or give them complete autonomy without guidance. Both approaches fail.

Effective accountability starts with clarity. I work with each manager to establish specific, measurable outcomes for their team: delivery commitments, quality metrics, team satisfaction scores, and career progression goals for their reports. We review these regularly, but the conversation isn’t “did you hit your numbers?” It’s “what’s working, what isn’t, and how can I help?”

When managers consistently miss expectations, I dig into the root causes. Is it a skills gap? Unclear priorities from above? Inadequate resources? External dependencies? Most performance issues stem from systemic problems, not individual failings. My job is to identify and address those systemic issues while coaching the manager through the specific challenges they’re facing.

The hardest part of accountability is knowing when to step in directly versus letting a manager learn from their mistakes. I generally err on the side of letting managers own their decisions, even when I might have done things differently. But I draw clear boundaries around anything that affects people’s careers, team psychological safety, or major customer commitments.

Are you Experienced?

New managers need structure and frequent feedback. They’re often overwhelmed by the transition from individual contributor to people leader, and they need concrete guidance on everything from running 1:1s to making difficult personnel decisions.

For first-time managers, I increase 1:1 frequency to weekly and focus on skill-building. We role-play difficult conversations, review their approach to delegation, and discuss specific team dynamics. I also pair them with experienced managers as mentors and encourage them to attend management training programs.

Experienced managers need different support. They don’t need me to teach them how to run a team meeting, but they do need strategic context, resources to tackle complex problems, and autonomy to lead their teams their way. My 1:1s with experienced managers focus more on organizational alignment, career development, and removing obstacles.

The trap you can fall into is treating all managers the same. A manager who just stepped into their first leadership role needs hands-on coaching. A manager with five years of experience needs strategic partnership, not basic management advice.

Hiring Managers Who Actually Manage

Hiring engineering managers is one of the highest-leverage decisions you’ll make. A great manager hire can transform a struggling team within months. A poor manager hire can set a team back by years.

I’ve learned to be extremely selective about manager hiring. Technical skills matter, but they’re table stakes. The real differentiators are: genuine interest in developing people, ability to make decisions with incomplete information, communication skills that work across all levels of the organization, and demonstrated ability to build high-performing teams.

My interview process for managers includes scenarios that test their approach to common management challenges: dealing with underperformance, managing conflicting priorities, handling team conflict, and making technical tradeoffs. I also have them meet with several ICs on the team they’d be joining to assess cultural fit and leadership style.

One common mistake people make, especially early in their director careers is hiring managers primarily based on their technical expertise. Some of the best engineers make terrible managers because they haven’t developed the people skills or learned to achieve results through others rather than through their own individual contributions.

Debugging Orgs

When teams consistently miss deadlines, produce buggy code, or experience high turnover, the problem usually isn’t individual performance. It can be caused by many things, but organizational dysfunction and systems issues are often at play. My job as a director is to identify the root causes and address these issues.

The most common dysfunctions I encounter are: unclear or constantly changing priorities, inadequate tooling and infrastructure, poor communication between teams, misaligned incentives, and inadequate planning processes. These problems create stress and inefficiency that cascades through the entire organization.

I use several diagnostic techniques to identify organizational issues. Regular team retrospectives reveal recurring friction points. Skip-level conversations surface problems that managers might not see or report. Cross-team project post-mortems highlight integration and communication challenges. And tracking metrics like deployment frequency, lead time, and incident resolution time can reveal process bottlenecks.

The key insight is that organizational dysfunction rarely has a single root cause. It’s usually a combination of structural, process, and cultural issues that reinforce each other. Fixing it requires systematic changes across multiple dimensions, not just tweaking one process or replacing one person.

Cultivating Technical Strategy Across Teams

As a director, I’m responsible for ensuring our technical decisions align with business goals and that we’re building sustainable, scalable systems. But you can’t create technical strategy in isolation. You must cultivate it across your teams.

I work with my managers and senior engineers to establish technical vision and principles that guide decision-making. This includes architectural standards, technology choices, quality practices, and tradeoff frameworks. The goal is to create enough alignment that teams can make good technical decisions independently while ensuring consistency across the organization.

Regular technical reviews help maintain this alignment. I hold monthly architecture reviews where teams present significant technical decisions and get feedback from peers. We also conduct quarterly technical strategy sessions where we step back from day-to-day execution and evaluate whether our technical direction still serves our business goals.

The balance is crucial: too much centralized control stifles innovation and slows down teams, while too little coordination leads to fragmented systems and duplicated effort. I aim for clear principles and lightweight processes that guide decisions without micromanaging them.

The Multiplier Effect

Managing managers is ultimately about multiplication. Every improvement you make in a manager’s effectiveness ripples through their entire team. Every organizational dysfunction you eliminate benefits dozens of engineers. Every strategic decision you get right affects multiple products and services.

The work is challenging because you’re operating at multiple levels simultaneously: individual coaching, team dynamics, organizational systems, and strategic direction. But when it works—when you see a first-time manager successfully developing their team, when cross-team collaboration improves, when your organization consistently delivers high-quality software—the impact is enormous.

The most rewarding part of this role is watching the managers you develop become exceptional leaders themselves, building great teams and solving important problems. That’s the ultimate measure of success as a director: not just what your organization achieves today, but the leaders you develop for tomorrow.