Leadership in Tech
Leadership in Tech
#290 – March 01, 2026
real strategy means picking one good option over another good option and owning all the consequences
Strategic choices: When both options are good
14 minutes by Jason Cohen
Jason says that real strategy means picking one good option over another good option, then owning all the consequences. Vague values like "customer first" or "great design" are not strategy because no one argues for the opposite. A real strategic choice has a smart alternative, creates real trade-offs, and shapes decisions across the whole company. When those choices reinforce each other, teams move faster and stop relitigating the same debates.
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sponsored by Meticulous
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Your supportive, disengaged manager is a slow poison
10 minutes by Judd Antin
A supportive but disengaged manager feels great at first, like trust and freedom. Over time though, the lack of real engagement quietly stalls your growth, weakens your relationships, and leaves you without anyone to truly advocate for you when it matters. To fix it, focus on your boss's top worries, communicate in short and sharp messages, and build allies among other leaders so your boss feels social pressure to pay attention.
What is compensation planning and why do you care?
10 minutes by John Pfeiffer
Compensation planning means balancing a fixed budget across your whole team while keeping people motivated and fairly paid. John suggests to start by understanding what your company needs for the coming year, then gather data on each person's pay history and what they value most. Build a clear framework using salary bands, performance ratings, and career levels to guide your decisions objectively. Once approved, deliver the news individually, listen carefully, and be ready to explain your reasoning.
Systems thinking
7 minutes by Paul W. Homer
Paul explains that big software systems can be built two ways: design everything upfront, or grow it gradually. Each approach has real tradeoffs. Planning ahead handles complexity better but requires heavy coordination and experience. Evolving code is faster and more enjoyable at first, but dependencies pile up and the mess compounds over time. Most projects likely need some mix of both, matched to how well the problem is already understood.
Executive amplification
7 minutes by Mike Fisher
Mike explains “executive amplification,” the powerful effect leaders’ words and actions have on their organizations. Even small comments or casual behaviors can shift priorities, shape employee identity, and waste time. Research shows that employees internalize leaders’ expectations and treat signals as direction. Because of this, leaders must communicate clearly, act intentionally, and understand that everything they say or do influences performance, culture, and strategy.
Why nearshore is replacing traditional scaling models
sponsored by AssureSoft
Scaling engineering once meant a simple choice: hire locally or outsource offshore. Today, both options reveal tradeoffs as teams grow—from burnout and attrition to misalignment and slow feedback loops. This report explores why nearshore models are gaining traction with CTOs who want to scale capacity while keeping teams aligned, decisions fast, and momentum intact.
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