Facilitator's Dilemma: Help That Builds Capacity

Fri, 13 Mar 2026 17:03:48 -0600

Day 278 of corporate infiltration: My role is that of a leader. My job, in the words the upper echelon gave me during the offsite, is to make this stick.

They handed me a team, a transformation, and the quiet implication that if the team fumbled it, I had fumbled it. So I sat with that, and I slowly considered all of the potential traps.

The primary trap was this: the fastest way to make the thing work is to do the thing yourself. You have done this before. You could have everything running in an afternoon if you just, you know, grabbed the wheel.

Don't Expect the Codebases to fall in Love

Thu, 17 Oct 2024 10:09:00 -0600

The silly creatures are at it again. They have merged two companies and expected the codebases to fall in love. They expected the databases to hold hands and the APIs to understand each other because the marketing department said “synergy.”

They are wrong.

Welcome to Mergers, Acquisitions, and the Art of the Unplanned API.

Conway’s Law is the ghost in the machine

You cannot merge two organizations and keep the old architecture. It does not work that way. The system’s architecture reflects the communication patterns of the organization that built it. Structure is not an accident. It is a direct output of how teams interact.

Best Leadership and Management Books

Mon, 15 Jul 2024 22:01:00 +0000

My leadership and management book recommendations. These books are curated based on my own experience building high performing teams, values, biases, and my dedication to continuous growth as a leader.

My top picks I’ve chosen for their ease of reading and ability to serve as quick references.

Drasner, Sarah. Engineering Management for the Rest of Us. 2022.
- If you’re pressed for reading time and can only pick one book from my list, read this one. It covers many aspects of management in plain language that are broadly applicable. Easy to read with some unique insights.
Hogan, Lara. Resilient Management. Book Apart, 2019.
- Staying grounded, growing teams, effective communication, and adapting energy. Really good reference guide.
Flyvbjerg, Bent, and Dan Gardner. How Big Things Get Done: The Surprising Factors That Determine the Fate of Every Project, from Home Renovations to Space Exploration and Everything In Between. Crown Currency, 2023.
- Alternate title: How Jodie’s Brain Works. This is the first book I’ve found that aligns with my thought processes and explains how I’m able to continuously stay ahead. I naturally adapt a lot of things in this book to my leadership styles.
Friedman, Ron. The Best Place to Work: The Art and Science of Creating an Extraordinary Workplace. 2014.
- A conversational book all about psychological factors that affect businesses. When reading this, you may dismiss it as common sense, but ah, turns out it’s not so common. TL;DR a book that I wish more people had read before they begin spouting off about work-life balance.
Scott, Kim. Radical Candor: Revised Edition. 2019.
- Kim is always learning and incorporating the lived experiences of others, while dispensing practical advice. See also Radical Respect.
Stainer, James. Become an Effective Software Engineering Manager: How to Be the Leader Your Development Team Needs. Pragmatic Bookshelf, 2020.
- Incredibly practical and easy to read. From getting yourself organized, how to have effective 1:1s, writing good job descriptions, performance reviews, how to mentor vs coach, breaking silos, bias, team culture, deciding how to gatekeep certain information, etc. This book has a bit of everything.
Zhuo, Julie. The Making of a Manager: What to Do When Everyone Looks to You. Random House, 2019.
- This reads similar to The Leadership Challenge (Kouzes and Posner), but is more digestible and practical. While the ideas are not new, the concise way in which it is written make it stand out.

Worth mentioning…

Tackling bias

Eubanks, Virginia. Automating Inequality: How High-Tech Tools Profile, Police, and Punish the Poor. St. Martin’s Press, 2018.
Noble, Safiya Umoja. Algorithms of Oppression: How Search Engines Reinforce Racism. NYU Press, 2018.
Perez, Caroline Criado. Invisible Women. Random House, 2019.

Leadership ecosystems

These books come with supplemental material to make the most out of their content. They can be fairly academic and information dense. They’re all great first steps into something more.