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The Leadership Garden Newsletter – #41

The Lion Sleeps Tonight

Before you speak, ask yourself: Is it kind, is it true, is it necessary, does it improve upon the silence?


We’re a bit more than one month in the new year – how has it started for you? I’d love to hear about your joy, learnings, challenges from the first month of 2023 in the comments!

Can bossless management work?

Spoiler: Not according to B-school professors Nicolai Foss and Peter Klein, whose new book makes the case for functional hierarchy.

Why should you scale bottom-up in your organization?

Vânia Santos, Engineering Manager at OLX shares an overview of Team Topologies and walks through a practical example they use to help shape their organizational design.

Building a Great Relationship With Your Boss

Another gem from Paulo André – “If I could pick one skill, and one skill only, this would be it – for any relationship, but especially so for the relationship with a manager. So many difficult conversations become a lot less difficult if only you get curious about the other person’s challenges and needs before getting into yours.“

Skills that make a big difference — Empathy

Part 2 of a series of posts. While empathy is touted as a key leadership skill, one that helps collaborate with others in organizations, it is critical for engineers too. Empathy allows us to better understand our customers, stakeholders, and team members.

Playing Long Games: Focus on Companies With Moats and Relevant Products

Every company needs to figure out how to launch new capabilities to either strengthen their immediate value and, eventually, produce a new offering to create the next “S” curve for future revenues.

Product Enablement Principles

John Cutler: “A week in to my new role a Toast, I took some time to clarify my own principles when it comes to operations, enablement, and generally helping others. These may or may not become my team's principles, but it was a good exercise. Transitioning between jobs/roles is always a great time to reassess.”