3 Lessons from Becoming a Manager of Managers

Every leader faces that pivotal moment when their team grows beyond their direct management capacity. For me, it came when I realized the daily tasks of reviewing work and troubleshooting process issues were crowding out the strategic thinking my team needed. My boss noticed too, gently suggesting it was time to delegate. What followed was a journey of creating job requirements, hiring managers, and making plenty of mistakes along the way.

Here are three crucial lessons I learned the hard way—so you don't have to.

1. Task Lists Aren't Enough: The Power of Values-Based Leadership

Like many first-time managers of managers, I started by creating what I thought was a comprehensive deck outlining responsibilities: hiring, team development, design reviews, documentation, project management, and more. For each area, I provided detailed task lists. Take "Design Reviews and Process Management," for example. I wrote things like:

- Maintain list of projects and manage approval processes

- Review projects at appropriate stages

- Ensure design convention compliance

- Guide teammates toward appropriate strategies

- Host design review sessions

Sounds thorough, right? But I made a crucial mistake. While I had always emphasized values like "proactivity and drive" and "product thinking" with designers, I failed to articulate the underlying values I wanted to see in my managers. I had inadvertently created process robots instead of empowered leaders.

A few months in, I gathered my three managers to share a broader framework—the values that should guide their decision-making:

- Anticipate and Plan: Think ahead about potential issues and take preventive action

- Collaborate Across Disciplines: Include designers, product, and engineering in process changes

- Show, Don't Just Tell: Provide templates and examples instead of vague directions

- Be Present: Give full attention through video calls and timely responses

- Stay Ahead: Keep up with industry trends to guide the team proactively

This shift from tasks to values finally gave them the confidence to think broadly and act independently.

2. Product Knowledge Needs Context, Not Just Features

My second mistake was confusing product familiarity with product understanding. I had my new managers complete user training, walk through each product, and even visit healthcare centers to see our software in action. Solid plan, right?

What I missed was the crucial context: the background, strategy, clinical knowledge, and current challenges of each product. Without this deeper understanding, my managers could only react to issues rather than guide meaningful improvements. Sometimes they even gave conflicting advice to designers, and I found myself answering the same strategic questions multiple times.

The solution? I created comprehensive briefings for our key products, covering their history, open questions, user feedback, and vision for the future. This context helped managers think strategically rather than just operationally. More importantly, I documented everything for future managers—learning from my earlier oversight.

3. Different Management Styles Need a Transition Plan

Here's where things got really personal. I had built strong relationships with my team, but I hadn't considered how this would affect new managers stepping in. One manager actually quit within weeks, citing in their exit interview that team members kept bypassing them to get my approval.

I had hired three managers with complementary strengths: one relationship-focused, one process-oriented, and one metrics-driven. In theory, this diversity would make the team stronger. In practice? The designers, accustomed to my style, struggled to adapt to different approaches.

Things got so bad with one manager that I nearly had to let them go. Their more directive, less democratic style clashed with the team's expectations, and people would come to me instead, knowing I'd take a more diplomatic approach.

My mistake? I hadn't prepared the team for different management styles or explained why these diverse approaches would benefit them. I should have actively introduced each manager's unique strengths and helped the team see the value in different leadership styles.

The Silver Lining

Today, I'm proud of the leadership team we've built and the growth I've seen in everyone involved. These lessons, though sometimes painful, helped create a stronger, more resilient organization. The key takeaway? Becoming a manager of managers isn't just about delegation—it's about creating an environment where different leadership styles can thrive and teams can adapt to change.

Remember, we're all learning as we go. The best we can do is share our experiences so others can learn from our mistakes. I hope these lessons help you navigate your own leadership journey more smoothly than I did.