Archive / Collection

Strategy

15 Entries

2025

Nemawashi and the Meta of Meetings

5 min read

A few weeks ago I walked into a meeting room to discuss my solution to a fork in the road problem. We’ve been roadblocked for two weeks with two clear paths forward. One of them I preferred; a …

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2025

Teams Outlast Projects

4 min read

In my startup days, we often had these dead marches where we had to implement a massive new feature in time before some kind of trade show happened. We worked long hours and even weekends to make it …

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2025

Pace layering an application portfolio

8 min read

In every organization I’ve worked with, there’s always been a handful of core applications, central, timeworn systems that quietly hold the business together.

Knowledge of these systems often lives in …

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2025

Choosing where to spend my team’s effort

6 min read

It’s the start of a new fiscal year. Strategy season. That time when all the grand ideas come out and everyone is still hopefull.

Over the years, I’ve settled into a structure that helps me define …

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2025

Business strategy is like a lizard

7 min read

Well, the real title was going to be “Business strategy is like a lizard: It leaves behind its tail while it grows a new one,” but that was just too long.

Strategy never exists in …

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2025

Enterprise architectural skunk works

9 min read

Most big organizations I’ve worked with are more akin to an ecosystem of multiple smaller companies. These smaller companies all share the same umbrella of the bigger total but internally …

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