Leadership in Tech
Leadership in Tech
#316 – May 31, 2026
they help leaders spot cultural problems before they become serious
The secret to skip-level one-on-ones
14 minutes by Mark Grebler
Regular skip-level one-on-ones help leaders spot cultural problems before they become serious. Simply asking broad questions often isn't enough, as people fear social risk from speaking up. Naming your concern directly removes that burden and unlocks honesty. But probe carefully, since raising an issue can plant it, so always validate across multiple conversations and look for evidence that contradicts your suspicion.
eBook: A Leader's Guide to De-Risking the Move from Jenkins
sponsored by Jetbrains
Migration is a big decision. The Migration Decision Framework eBook gives you a structured way to assess your current setup, quantify the risks, and move forward with confidence – whatever you decide.
Our uncertain uncertainties
7 minutes by Kevin Kelly
Kevin shares the idea that rapid advances in AI, global politics, media, and technology may create a long-lasting “Age of Ambiguity.” Instead of reducing uncertainty, progress could deepen confusion about truth, work, identity, and the future. He argues that society may face years of instability and unclear answers, making adaptability, open-mindedness, and flexibility more important than certainty or fixed predictions.
The role of body language
7 minutes by Wes Kao
Your body language and facial expressions shape every conversation as much as your actual words do. Learning your personal "tells," matching your face to your message, and keeping calm through slow breathing helps you come across as genuine and trustworthy. Small adjustments, like keeping your head straight or leaning forward, signal authority or openness depending on what the moment needs.
Why your releases feel harder than they should
5 minutes by Marcos F. Lobo
Marcos explains why software releases often feel stressful and risky. The main issue is usually not the deployment itself, but weaknesses in the system behind it, such as unclear ownership, inconsistent environments, and poor visibility. Instead of adding more release checks, teams should focus on building systems that are easier to understand, operate, and trust, making safe and confident releases a natural outcome.
Why I don’t have a manager README
6 minutes by Suresh Choudhary
Manager READMEs seem like a smart way to help teams align quickly, but they often backfire. They present an idealized version of you that your actions may not match, ignore real power dynamics, and push new team members to adapt to you rather than the other way around. Better options include intro meetings, regular one-on-ones, open Q&A sessions, and a shared team working agreement. Trust comes from behavior, not documents.
And the most popular article from the last issue was: