Leadership in Tech
Leadership in Tech
#314 – May 24, 2026
how leaders can quietly fall into overload while still appearing successful
Barely treading water
11 minutes by Michael Lopp
Michael explores how leaders can quietly fall into overload while still appearing successful. Through a conversation with his chief of staff, Michael realizes he is failing at prioritization, delegation, and setting limits. He points out common warning signs of burnout and offers practical solutions: admitting failure, prioritizing honestly with trusted support, delegating important work, and learning to say no. It highlights that effective leadership requires self-awareness, honesty, and difficult decisions.
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Fix delivery first
10 minutes by Ant Murphy
Ant explains that many companies fail with OKRs, discovery, and AI because their real problem is poor delivery systems. Long release cycles, technical debt, and weak engineering foundations slow progress and reduce trust. Using the Theory of Constraints, Ant argues companies should first fix delivery bottlenecks before focusing on strategy, discovery, or AI. Strong delivery creates faster feedback, builds trust, and makes innovation and improvement possible.
On blunt feedback
2 minutes by Shreyas Doshi
Blunt feedback only helps when the giver has good intentions and real expertise in the area. In toxic workplaces, some feedback is designed to attach damaging labels to you through backchannels, not to help you grow. And even well-meaning feedback can miss the mark when the giver is less skilled than the recipient. For high performers, knowing when to ignore or adapt feedback is a rare but valuable skill.
You taught the company to overload you
4 minutes by Aviv Ben-Yosef
Tech leaders who always say yes create the same problems as those who always say no. Making the cost of every agreement visible is the real solution. Be honest about workload limits, avoid sudden pushback after long silence, and always present a range of options rather than a flat refusal. Boundaries need constant reinforcement, not just a one-time announcement.
The quiet power of presence
3 minutes by Andi Roberts
Most of us listen only to find a gap where we can speak. Real listening means paying attention to the values and hopes behind someone's words, not just the words themselves. Sitting with silence a little longer than feels comfortable often brings out what matters most. When you truly hear someone without judging or fixing them, you build the trust that holds relationships together.
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