Adam Kalsey

This is the blog of Adam Kalsey. Unusual depth and complexity. Rich, full body with a hint of nutty earthiness.

"As a tech lawyer, the

20 Jun 2001

"As a tech lawyer, the thing that I do more than anything else is negotiate. Most people are so unskilled at it that sometimes it feels like taking candy from a baby." - Business 2.0 Improve Your Negotiating Skills

Recently Written

AI as Your Strategic Thinking Partner
Oct 12: AI becomes a lens on your own logic. It doesn’t replace your judgment—it sharpens it. By asking questions you wouldn’t think to ask yourself, it turns private reasoning into something visible and testable.
Your OKR Cascade is Breaking Your Strategy
Aug 1: Most companies cascade OKRs down their org chart thinking it creates alignment. Instead, it fragments strategy and marginalizes supporting teams. Here's what works better than the waterfall approach.
Your Prioritization Problem Is a Strategy Problem
Jul 23: Most teams struggle with prioritization because they're trying to optimize for everything at once. The real problem isn't having too many options—it's not having a clear strategy to choose between them. Without strategy, every decision feels equally important. With strategy, most decisions become obvious.
Behind schedule
Jul 21: Your team is 6 weeks late and still missing features. The solution isn't working harder—it's accepting that your deadlines were fake all along. Ship what you have. Cut ruthlessly. Stop letting "one more day" turn into one more month.
VC’s Future Lies In Building Winners
Jun 21: AI and megafunds are about to kill the traditional venture model, forcing smaller VCs to stop hunting for hidden gems and start rolling up their sleeves to fix broken companies instead.
Should individual people have OKRs?
May 14: A good OKR describes and measures an outcome, but it can be challenging to create an outcome-focused OKR for an individual.
10 OKR traps and how to avoid them
May 8: I’ve helped lots of teams implement OKRs or fix a broken OKR process. Here are the 10 most common problems I see, and what to do instead.
AI is Smart, But Wisdom Requires Judgement
May 3: AI can process data at lightning speed, but wisdom comes from human judgment—picking the best imperfect option when facts alone don’t point the way.

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