Most IT decisions don't make a big fuss when they fail.
They just silently operate at a mediocre level to avoid criticism. When the decisions are made, they seem quite reasonable, even necessary sometimes. Budgets are limited. Timelines are tight. The business must keep going.
Working with organizations that have experienced the consequences of their decisions, Ive seen that in almost all cases, the regrets are not about what they did, but about what they didn't take time to think about deeply. Five years down the line, the company is bigger, more complex and more technology, dependent. It is then that the problems start to show.
Speed beats structure, until it doesn't
In the beginning, speed is rewarded. Get the system up and running. Deliver the solution. Address the problem immediately.
Shortcuts make perfect sense because we will sort it out later. It is only that the later doesnt show up. Gradually, temporary solutions become integral parts of the system. Complex custom logic that nobody really understands. Integrations that work only because one person knows exactly where they are breaking. Every change is intimidating because the architecture was never meant to be flexible.
Leaders dont regret moving fast. It is that they regret not securing the base while doing so.
The convenience of a supplier gradually turns into a covert reliance.
Typically, vendor operations are regarded as operational decisions. But they are actually a departure from the strategy most of the time.
A situation that appears to be quite flexible in the first year may become extremely restrictive by the fifth. The financing of the licensing models is outpaced by the revenue scale. What were once thought of as standard features are now paid add-ons. Data extraction becomes more challenging than anticipated. When you feel like you can't stop switching, it's not because the alternative isn't better; rather, it's because the cost of leaving is too great.
Knowledge leaves long before systems fail
This is one of the most expensive blind spots.
Organizations underestimate how much operational stability lives in people’s heads. Senior engineers, architects, and long-tenured IT staff don’t just know how systems work; they know why they were built that way. When that knowledge walks out the door, through layoffs, burnout, or quiet attrition, systems keep running. For a while. Then something breaks. Or needs to change. And suddenly, no one can explain the dependencies, the edge cases, or the decisions that shaped the environment.
Documentation helps.
But documentation never captures intuition.
Treating IT as execution instead of strategy
Many leadership teams involve IT after decisions are made. The business defines direction. IT is asked to “support it.” Five years later, leaders wonder why systems don’t align with processes, why reporting is unreliable, or why transformation feels harder than expected.
IT wasn’t absent.
It just wasn’t invited early enough to shape the outcome. Organizations that avoid this regret treat IT as a design partner, not a delivery function.
Delaying resilience because nothing has gone wrong yet
Security incidents. Extended outages. Data loss. Almost every organization that experiences them says the same thing afterwards:
“We knew we should have addressed this earlier.”
Resilience work is easy to defer because success looks like nothing happening, until it does. The regret isn’t underestimating risk. It’s overestimating how long luck would last.
The common thread behind every regret.
None of these decisions comes from poor leadership.
They come from short-term thinking applied to long-term systems.
Technology compounds. Complexity accumulates. And once decisions are embedded into daily operations, reversing them is expensive, disruptive, and emotionally draining.
The leaders who get this right don’t aim for perfect systems. They aim for clarity, optionality, and continuity — knowing their organization won’t look the same five years from now.
A final thought
If your IT environment still makes sense only to a few people… If changing systems feels riskier than staying stuck… If growth keeps exposing new cracks instead of creating momentum… Those are signals worth listening to.
At Annexus Technologies, we work with organizations that want IT decisions to age well — not haunt them later. Our focus is on building environments that are understandable, resilient, and aligned with how the business actually operates.
If you’d like a practical conversation about where your current setup may create future regret, reach out:
📧 sales@annexustech.ca
📞 (403) 879-4371
No pressure. Just clarity before the next five years are decided.
