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Why Simplify?
In 2025 my company completed dozens of projects that reduced Technical Debt. Basically, all the “stuff” that accumulates over the course of doing business that creates friction for your employees, clients, and leadership team.
For the companies we helped, it wasn’t obvious that they had a problem or that it was even related to years of small decisions that piled up into a tapestry of complicated technical “one-offs”.
For them, it looked like reduced margins, longer lead times, more employees, overtime, and rework. It was miscommunications, data entry errors, work-arounds, and customer complaints. Naturally, those in-charge looked to their employees and management team to just DO BETTER. (Hardly a thoughtful solution.)
We came into these projects because tech was reaching end-of-life, or they were looking a yet another new tool that promised to create more organization. So we took the opportunity to do more than just fulfill an order. We asked the right questions and looked at the problem through first principles thinking. Why are you doing it this way?
MANY companies have shadow IT that leads to increased complexity and quite literally eats your margins.
If you run a business or are responsible for IT within your business, it is imperative to re-evaluate your tech continuously. Great tech enables high-performing teams.
So to answer the question, Why?
Almost universally businesses run on a foundation of information technology. If an interstate highway had potholes and debris, no one would be going 70MPH. If your tech can’t help your employees deliver efficient solutions, then you can’t get better.
Sometimes it’s the driver, but when it comes to SMBs, it’s almost always the road.
How do I Simplify?
This is always the more nuanced question, because for many companies the result of simplification looks wildly different. However, the approach to get there is universally the same.
10 Steps to Simplification
Create a clean map of the landscape
Inventory applications, infrastructure, integrations, vendors, and data flows. One page that shows “what talks to what” usually exposes 50% of the mess.
Tie everything to a business purpose
For each system, note which process, team, and revenue or compliance outcome it supports. Anything without a clear owner or purpose is a simplification candidate.
Measure complexity, not just cost
Score systems on age, customization level, integration count, support burden, failure impact, and skill scarcity. High-friction systems create hidden drag even if they’re cheap.
Find duplication and overlap
Look for multiple tools doing similar jobs (CRM, HR, reporting, file storage, ticketing). These are the fastest wins for consolidation.
Trace process pain back to technology
Identify where workarounds, spreadsheets, manual re-entry, or delays exist. These are symptoms of unnecessary system complexity.
Assess data flow and ownership
Find where data is copied, rekeyed, or reconciled. Each break in data flow adds risk, time, and errors.
Evaluate integration quality
List all point-to-point integrations and manual exports/imports. Fragile or custom integrations are major complexity multipliers.
Rank by business impact vs. effort
Prioritize what to simplify based on risk reduction, user impact, and speed to improve—not just technical elegance.
Define the target state
Decide what “simple” means for this company: fewer platforms, fewer vendors, cleaner data, or fewer workflows. Without this, you just reshuffle complexity.
Build a phased simplification roadmap
Sequence changes so quick wins fund and enable larger cleanups, while avoiding disruption to core operations.
If you don't do some of these tasks continuously, this project will look daunting. But, just remember, your scale and margin depends on it!
I’ve helped dozens of companies do this from ZERO, and then maintain and iterate year-after-year. I have seen it transform businesses.
The results my clients have lead me to create this newsletter. I think it is vitally important to keep friction low, keep employees happy, hit great margins, compete in your market, and drastically reduce security incidents.
If you’re unsure where to begin, give me a shout. I work with companies that value progress.
Until next week,
—Jared
Text Me: 314.806.3912
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