Strategy on Andrew Healey

Kanter's Law: everything can look like a failure in the middle

Tue, 29 Sep 2026 08:06:18 -0500

Kanter’s Law: everything can look like a failure in the middle. Starship launching, reaching orbit, and coming home yesterday was a good reminder that the middle is where we make our money. It never looks like progress while you’re standing in it. Too many of us skip it now, because a polished product page, a quick dashboard, or kneejerking to Claude or ChatGPT takes a few minutes before we ask if anyone actually needs the thing. Meanwhile an HVAC tech who bet everything on her own shop is spending another night away from her family to get somebody’s air back on, and she doesn’t need one more tool in her inbox. Before you chase the next one, ask what problem you’re actually trying to solve.

The context trap

Tue, 20 Jan 2026 08:27:42 -0600

The context trap. Netflix popularized microservices. Google invented Kubernetes. Amazon built their own everything. Spotify gave us the squad model.

These are real innovations from smart people solving real problems. They’re also almost certainly wrong for your organization.

I know that sounds harsh. Let me explain.

Netflix runs a global streaming platform serving hundreds of millions of users. Their engineering team is measured in thousands. When a monolithic architecture became a bottleneck to their ability to deploy independently and scale specific components, microservices made sense. For them.

The cargo cult of "Enterprise"

Sat, 17 Jan 2026 07:24:38 -0600

The cargo cult of “Enterprise”. From Seattle to Bentonville, I keep hearing this phrase in meetings: “That’s how they do it at [insert Fortune 500 company].”

It gets used like a trump card. Like the name itself is evidence. Like having worked somewhere successful means you understand why it was successful.

Here’s the problem. During and after World War II, some Pacific Island communities observed military planes landing with supplies. After the war ended and the planes stopped coming, they built wooden control towers and runways out of straw. They mimicked the forms they had seen, believing these structures would summon more planes. They didn’t understand logistics, manufacturing, or global supply chains. They just knew what it looked like when planes showed up.

Stop chasing tools, start measuring maturity

Thu, 15 Jan 2026 08:31:28 -0600

Stop chasing tools, start measuring maturity. Here’s a pattern I see constantly.

Team identifies a problem. Team sees a demo of a shiny tool. Team convinces leadership the tool will solve the problem. Tool gets purchased. Tool gets partially implemented. Tool gets blamed when problems persist. Cycle repeats.

Gartner estimates that 90% of organizations invest in ITSM tools without first assessing their maturity. We buy solutions before we understand where we actually are.

Invest in your own judgement

Mon, 12 Jan 2026 10:40:11 -0600

I’ve spent the vast majority of my career in manufacturing. They haven’t all been the companies that show up in Harvard Business Review case studies, something I’ve come to see that as an advantage.

When you’re not at a company with infinite resources and a thousand engineers, you learn to be deliberate. You accept constraints while still delivering results. No excuses. You can’t buy your way out of problems. You can’t throw headcount at complexity. You have to understand what actually matters and focus there.

Escaping the hype cycle

Fri, 09 Jan 2026 09:34:12 -0600

Escaping the hype cycle (and the vendor noise). Your vendors want you to buy. Your peers want you to succeed. These are not the same thing.

I don’t say that to be cynical. Vendor relationships matter. Good vendors genuinely want to help you succeed because your success is their success. But their incentive structure is optimized for sales. The information they share is filtered through that lens. The case studies they present are their best outcomes, not their typical ones.

Don't rush to tear down a fence

Mon, 30 Jun 2025 15:21:30 -0600

Don’t rush to tear down a fence just because you don’t see its purpose.

As G.K. Chesterton said: ‘There exists a certain institution or law; let us say a fence across a road. The modern reformer says, “I don’t see the use of this; let us clear it away.” To which the wise reformer replies, “If you don’t see the use of it, I won’t let you clear it away. Go and think. Only when you understand its purpose may you touch it.”

Complexity Kills

Tue, 12 Sep 2023 15:14:24 -0600

Complexity kills.

… the startups we audited that are now doing the best usually had an almost brazenly ‘Keep It Simple’ approach to engineering. Cleverness for cleverness sake was abhorred. On the flip side, the companies where we were like ”woah, these folks are smart as hell” for the most part kind of faded.

https://renegadeotter.com/2023/09/10/death-by-a-thousand-microservices.html*