Look, I’ve been selling, architecting, and deploying IT systems for over 20 years. I have a story arc that is the same with small businesses and enterprises that I’ve noticed and is so predictable that I almost want to shake the person on the other side of the table to save them from years of pain. (and possibly their job)

It’s this…

THE CAGE

1. Buy — Company picks a platform/vendor because it solves the immediate pain (or a salesperson closed well).

2. Integrate — Data, workflows, and headcount get built around it. Custom fields, trained staff, dependent processes.

3. Outgrow — The tool stops fitting. New need emerges the platform wasn't built for. Leadership knows it's the wrong tool now.

4. Justify — Instead of switching, they add a bolt-on, a workaround, another tool duct-taped to the first. Migration cost (real + perceived) always looks bigger than the workaround cost. So they never leave.

As you can imagine, it seems preventable, but short-term thinking and pain avoidance keeps organizations trapped. Good IT people and executives are blind to seeing a small add-on or a work-around as a long-term cost.

This is where thinking like a CIO can help you. Someone needs to see the bigger picture. Someone needs to hold the decision makers accountable to the long-term vision of the company. Though it remains a sneaky trap, you don’t have to fall into it. You simply have to plan for it and filter decisions through an avoidance framework.

Charlie Munger the famous investor next to Warren Buffet once said, “All I want to know is where I am going to die, so I never go there.” If most people knew they were building a cage they couldn’t escape from, they would avoid building it.

Well here’s how to avoid it…

Freedom Framework — four checks, applied at the moment of every tech buy:

1. Reversibility check. Before buying, ask: "What does it cost to leave this in 18 months?" Not "can we leave”, but actual dollars and actual time. If you can't answer that number before signing, you don't understand what you're buying. Vendors will happily quote onboarding cost; make them (or yourself) quote exit cost in the same conversation.

2. Boundary check. Define what the tool is NOT for, in writing, at purchase time. Cages get built one bolt-on at a time because nobody drew the line on scope up front. "This tool owns X. Anything outside X gets evaluated fresh, not bolted on." Write it down where the next person making a bolt-on decision will actually see it.

3. Integration ceiling. Cap how deep a tool gets woven in before it's re-evaluated. Example: "No custom integration gets built on top of Tool X without a standing review at 12 months." This is the mechanism that stops step 2 (Integrate) from silently becoming permanent.

4. Named owner of total cost. Someone has to own "cost of staying" as a tracked number from day one, not just cost of switching. If nobody's job is to periodically ask "what is staying costing us now, compared to the day we bought this," the risk perception goes to zero, which is exactly how the cage becomes invisible.

The cage organizations build for themselves can be dismantled, but as you can imagine, avoidance is much less expensive. My company has been doing this for years and we have seen it all. If you don’t know you’re trapped, but you see tech costs continuing to rise, frustration mount, and tools that were supposed to help your team become barriers, then you may have fallen victim.

I created the Mission Assessment for this very scenario. We align YOUR mission with technology. Many times we remove systems, because “complicated” isn’t efficient.

If you’ve never heard a technology partner talk like this, then you were talking to a vendor. We don’t sell software, we help frustrated companies use technology to become badass.

If you think we should talk, just reply to this email.

Until next week,

—Jared

Text Me: 314.806.3912

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