HeyJaredThe Strategy Trap Newsletter
Strategy fails when execution is an afterthought. This newsletter helps leaders close the gap with practical tips, operator insight, and occasionally a little fun.
- Indexed issues, last 90 days
- 12
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- Sep 28, 2026
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- Jul 13, 2026
Latest issues
Fool’s Gold: The Success Measures That Don’t Measure Success (opens the original)
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If your team hit every success measure in the plan, would you know whether the strategy actually worked?In a lot of plans I’ve seen over the years, the answer is “not really.” A lot of success measures tell us the work got done, and that’s about it. So this week I’m digging into how to define success in a way that actually tells you whether you got the results you were hoping for. I added in a couple of great articles that build on the idea, including a simple ratio you can use to score your own
Seven things to get clear on before you launch a strategy (opens the original)
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Every season, legendary basketball coach John Wooden started by taking time to teach his players how to put on their socks.Yes, socks. His reasoning was that wrinkles cause blisters, and blisters get in the way of practice and games, so a little care at the start saved a lot of trouble later. That’s basically the thinking behind this week’s Featured Musing on why a short, focused stretch of preparation up front is the fastest way to get results from your strategy.We also dig into why change can
Your Company Values Should Actually Do Something (opens the original)
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Enron’s core values were Integrity, Communication, Respect, and Excellence. Oops.Values can and should be powerful execution drivers. But all too often they’re meaningless posters and not much else. This week we dive into how to make them (and their good buddies “guiding principles”) key tools to make your team faster and more consistent. And there’s even a free worksheet download to help you fine-tune yours right away!Cheers,KevinFEATURED MUSING<a class="image-link image2 is-viewable-img" href=
The Expert Trap: When Success Makes You Stop Asking Questions (opens the original)
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Expertise ain’t always what it’s cracked up to be.This week, I came across a quote from Henry Ford saying he didn’t have experts in his company because they were too sure of themselves. I was fascinated, so I dug into it, and even more fascinated when I discovered he became a victim of the expert trap himself.I’ve also got an excellent HBR article highlighting why we can all fall prey to this problem. Another on Edgar Schein’s humble inquiry technique to help us get out of it. And of course, I’v
Stop Hiring the Hero (opens the original)
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Ever hired someone who crushed the interview and then spent the next two years making everyone else’s job harder?Your hiring process might be built to reward the hero’s story, when the job actually needs someone who’s good at handing the mic to someone else. This week I dig into why resumes, job descriptions, and standard interview questions all train candidates to highlight individual triumphs, and what to do instead if you want people who make the whole team better. Then I found two great comp
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