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How Can I Avoid Turning Talented Workers Into Crappy Managers?

Learn how to tell who is a great worker, and which of your workers can be great leaders

Osman (Ozzie) Osman
Index
Published in
11 min readSep 9, 2019

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Illustrations: Thomas Hedger

GGrowing teams need managers, and who better to manage a team than someone who is already part of one? While that may be true, picking the right person to become a team manager can be a lot harder than it looks. While this piece will focus on engineers, the lessons within are applicable to all kinds of worker-to-leader transitions.

There’s some pretty great literature on making that transition, on being successful in a new managerial role, and on avoiding common mistakes. There are even some great reads on transitioning back and forth between engineering and management. Having advised startups on this, overseen engineers transitioning to management, and personally become a manager, I’ve read it all. But before any of that can happen, a company’s management needs to decide: Which engineers should they ask to become managers?

This is no simple task, as I’ve learned the hard way. Through failure, I’ve been able to take what I’ve learned and put it into a framework for successfully choosing potential managers. Before we talk about what works, let’s talk about what doesn’t.

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