Leadership in Tech
Leadership in Tech
#270 – November 30, 2025
the original culture gets diluted through layers of management
How startups lose their edge
8 minutes by Ian Vanegas
Ian explains how companies lose their edge during rapid growth. As teams scale from 20 to 2,000 people, the original culture gets diluted through layers of management. Companies start hiring safe candidates with impressive resumes instead of culture fits, and adopt conventional strategies that contradict what made them successful. The post suggests keeping teams small, promoting from within, and continuing to take big risks to avoid becoming merely respectable instead of exceptional.
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The success trap
8 minutes by Mike Fisher
Success feels like freedom, until it quietly narrows your choices. The more you master, the less room you have to pivot. The real skill isn’t winning once, it’s staying free enough to win again.
The wanderer
6 minutes by Michael Lopp
Michael shares how a manager's tendency to tell stories during one-on-one meetings led to conflicting guidance when he agreed to something while in "story mode" but later denied giving that direction. Michael developed a three-step solution: prepare meeting topics in advance, write down decisions in real-time during conversations, and document the meeting immediately afterward.
Leading in low-trust times
4 minutes by Subbu Allamaraju
Recent layoffs and budget cuts have created a low-trust climate in tech companies. Employees no longer believe in leadership decisions and worry about job stability. This damages team collaboration and causes good people to leave. Subbu argues that the solution is authentic leadership through listening to concerns, being transparent about challenges, and involving teams in problem-solving.
Revisiting manager READMEs
6 minutes by Camille Fournier
Senior managers often struggle with getting the right information from their teams. Some try to solve this with manager READMEs that outline their preferences and communication styles. However, this approach creates a focus on managing up to the leader's personality rather than focusing on what matters most. Camille suggests that a better solution is creating lightweight templates and processes for specific types of work discussions.
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