Five principles for successfully managing managers

Saumil Mehta, former CPO of Square, argues that the "skip lead" (the manager of managers) is pivotal to organizational health, since most manager problems trace back to how the skip leads hires, reviews, and coaches them. He contends that moving from managing individual contributors to managing managers is a fundamentally different job that many leaders underestimate. He offers five principles: recognize the role change, run an "API endpoint" thought experiment that forces reliance on managers alone, never undermine your managers with off-the-cuff directives, never cover for their underperformance, and use task-relevant maturity to match and review delegated work. The piece matters because middle-management is often dismissed, yet well-run skip leads multiply team effectiveness.

01Key takeaways

• Treat the move from line manager to manager of managers as a distinct role change with a steep learning curve, not just more of the same work.
• Practice the API endpoint thought experiment: ask how you would create value if you could only interact with your direct managers.
• Hear unfiltered feedback from skip reports, but route follow-up and direction through their direct manager instead of issuing your own verdicts.
• Escalate underperformance early with a course-correction plan rather than quietly doing the manager's job yourself.
• Match projects to managers using task-relevant maturity, then scale your review cadence to the project's uncertainty and impact.

02Key sections

Why the skip lead matters

Complaints about a manager usually reflect the skip lead's hiring, feedback, and coaching, so the author asks people about their manager's manager instead.

Recognize the different role

Managing managers loses direct context, filtered information, and the clear IC-maker versus manager-coach division, so it demands a distinct skill set that leaders often fail to acknowledge.

The API endpoint experiment

Imagining you can only work through your managers, not their ICs, reveals how to delegate, review, and intervene effectively, though the exercise is a thought experiment rather than literal practice.

Never undermine or cover

Off-the-cuff opinions disempower managers and confuse their reports, while covering for underperformance hides problems; instead, skip leads should coach, surface issues, and set clear expectations.

Task-relevant maturity for delegation

Drawing on Andy Grove, skip leads should match each project's scope and uncertainty to the manager best suited for it, then review high-uncertainty, high-impact work closely.

03From the post

“If you aren’t a paid subscriber, here’s what you missed this month: 1. Make product management fun again with AI agents 2. State of the product job market in 2025 3. The ultimate guide to negotiating your comp Annual subscribers also get a free year of Perplexity Pro, Notion, Superhuman, Linear, Granola, and more. Subscribe now. Saumil Mehta is the former CPO and Head of Business for Square. He most recently ran Product Management, Marketing, and Partnerships across Square while reporting to the CEO. Over a nine-year tenure, he also held various General Manager roles with full P&L responsibility, including the flagship Point of Sale business. Along the way, he helped Square scale from a late-stage pre-IPO startup to $3.6 billion in annual gross profit, expand globally, and build out a full suite of products across payments, banking, and SaaS. Prior to Square, Saumil was a startup founder for LocBox, a marketing automation company that was acquired by Square in 2015. After stepping down a few weeks ago, he’s spending his newfound time crystallizing his most important leadership lessons learned…”

04Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.