Leadership in Tech
Leadership in Tech
#265 – October 26, 2025
Should leaders prioritize team happiness over company performance?
Stop caring so much about your people
3 minutes by Aviv Ben-Yosef
Leaders often prioritize team happiness over company performance. When you avoid tough conversations and sugarcoat feedback, you build a team that can't handle reality or accountability. Companies are more resilient than leaders think. The key is choosing the right pain now rather than letting problems compound over time.
Context Engineering: Why LLM’s need more than prompts and MCP servers
sponsored by Unblocked
AI coding agents can’t solve real engineering problems with prompts alone — it needs institutional knowledge. Context engineering puts together the right mix of your code, docs, tickets, and conversations so AI generates code that works in your system.
Prioritization starts with strategic prioritization
12 minutes by John Cutler
John connects strategic frameworks to practical prioritization by linking business benefits to competitive advantage. All business investments fall into four categories: increase revenue, protect revenue, decrease costs, or protect costs. Then you go through discovery, growth, extraction, and erosion phases. Understanding where your company sits in these cycles helps prioritize investments that create the most lasting leverage rather than just short-term gains.
On innovation and 20% time
19 minutes by Phil McKinney
HP invented "20% time" in the 1950s, decades before Google. They abandoned it when they realized it didn't work. Google later copied the concept from 3M, who had unknowingly copied HP's failed policy. Phil nearly made the same mistake at HP in 2007 until Art Fong, HP's employee number nine, explained the real cause of innovation. It wasn't structured project time but personal relationships, deep trust, and removing barriers to creativity.
Navigating the risks in leadership
4 minutes by Corbin Crutchley
After 10 years in, Corbin finally reached VP of Software Engineering. This new role brought both excitement and fear. The position offered a chance to care for people at all levels, from team members to customers. However, it also carried significant risks and responsibilities. Corbin compares leadership to keeping a poisonous dart frog. It's beautiful but dangerous, requiring careful handling to create a thriving environment.
What if hard work felt easier?
8 minutes by Jean Hsu
Jean argues that work which feels natural and joyful can be more effective than forced effort. She shares examples of building apps and coding projects that felt effortless yet produced significant results. The key insight is finding alignment between what energizes you and what needs to get done. This approach leads to higher output and greater sustainability than traditional "grind culture" methods.
Turn engineering prompts into full stack internal apps at enterprise scale
sponsored by Tooljet
Running enterprise engineering is hard with shifting priorities, complex systems, and constant delivery pressure. ToolJet helps you turn natural language prompts into secure full stack internal apps that connect across your organization. Build faster and ship with confidence.
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