Leading what you’ve never done before

#281 – January 29, 2026

many try to become experts in everything or completely disengage

Leading what you’ve never done before
6 minutes by Kevin Goldsmith

Technology leaders often find themselves managing teams and domains they've never worked in before. Many try to become experts in everything or completely disengage from unfamiliar areas. Both approaches fail. Instead, Kevin argues leaders should focus on understanding the big picture, asking good questions, and trusting specialists to handle the details while staying accountable for outcomes.

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Should you include engineers in your leadership meetings?
3 minutes by Will Larson

Will now includes senior engineers directly in his top leadership meetings alongside managers. This prevents leaders from managing around reality instead of managing reality itself. The practice improves decision making and creates better information flow throughout the organization.

How I bankrupted two companies
10 minutes by Phil McKinney

TeraPlex built a revolutionary microprocessor that could run software five times faster than competitors using just a dozen simple instructions. Phil tells the story of a startup that failed not because of bad technology, but because of indecision. As young president, facing fear and impostor syndrome, he delayed key choices while waiting for certainty. The company slowly collapsed.

How I estimate work as a staff software engineer
12 minutes by Sean Goedecke

Accurate software estimates are usually impossible because most work involves unknowns. Estimates are not for engineers, but political tools for managers. Instead of predicting time, he starts with the expected deadline and finds technical approaches that could fit it. Good estimation focuses on risks, tradeoffs, and options, not precise timelines.

Creating momentum when an employee is stuck
9 minutes by Lara Hogan

People often get stuck in unproductive patterns during difficult times. When having tough conversations with struggling teammates, Lara suggests to balance empathy with clear direction. Start by identifying your core goal or "why" for the conversation. Give specific guidance on what to stop doing and what to start doing instead. Begin by acknowledging their concerns honestly before delivering your message. This approach usually helps people move forward without creating conflict.

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