Sam Shar on

Modernization that makes sense

When to modernize, how to handle technical debt, and why most transformations fail on people, not technology.

1 newsletter, 1 video. Updated 30 Oct 2026

Sam's approach

What I do

I start with the business problem and work back to the technology, never the other way round. The first pass is an inventory of what the business actually runs on, which systems hold the work up, and what the cost of leaving each one alone really is. Then I sequence the moves so the smallest useful one goes first and gets used before the next is funded. For clients in regulated industries that often starts with getting off legacy fax and print onto secure cloud delivery, with the people whose daily work changes signing off each step.

How I work

A legacy modernization expert is paid for sequencing and for adoption, not for picking products. Technical debt is a business decision. Some of it I pay down, some of it I leave alone for years because nothing downstream is waiting on it, and saying which is which is the judgement the work turns on. UPS built ORION as a staged routing rollout and it stuck. Lidl ran SAP as one program and went back to the old system. At Trend-Setters Consulting I took the same small steps with automation and cloud inside my own operation before taking Fortune 500 clients through bigger moves.

When to bring me in

Bring in a legacy modernization expert when someone has proposed a big-bang replacement, when a vendor has set an end-of-support date, or when a CMO is being asked to approve a martech and CRM overhaul in one go. You do not fit a bigger engine before you have sat in the driver's seat. A sequence that holds up:

  • Name the business problem before naming any system.
  • Pick the one change users will notice and ship it.
  • Measure adoption, not go-live.
  • Fund the next step from what the last one proved.

If that is the decision on your desk, I am happy to talk it through.

Questions about modernization that makes sense

Why do digital transformations fail?
Most digital transformations fail for reasons that have little to do with the technology. Companies pick the tool before they understand the problem, try to change everything at once, and underinvest in training and support after launch. Lidl abandoned a huge SAP program after bending the software around its business instead of fixing the process. Start with a specific problem, modernize in steps, and keep supporting people after go-live.
How do you decide which legacy systems to modernize first?
Start with the pain, not the age of the system. Ask which systems are costing you the most in money, risk or lost opportunity, and which ones the business can't grow without. An old system that works quietly in the background can wait. One that slows your people down, blocks customers or can't be supported any longer should go to the top of the list. Pick a first move that is small enough to finish and valuable enough that people notice. That earns the trust you need for the harder steps that follow.
Is technical debt always a bad thing?
No, technical debt is not always a bad thing. Like financial debt, it can be a sensible trade when you take it on deliberately. Shipping something imperfect to meet a real deadline or test an idea can be the right call, as long as you know what you owe and plan to pay it down. The trouble starts when the debt is ignored and the interest builds up in slower projects, fragile systems and people afraid to touch anything. Keep an honest list of it, and fix the items that are getting in the way of the business first.
How do you get employees to adopt new technology?
To get employees engaging with new technology, the best thing you can do is involve them early and give them a reason to care. People resist a new tool when it is dropped on them, when training is thin and when it makes their day harder before it makes it easier. Ask the people who will use it what slows them down today, and build the change around that. Train close to go-live, put someone on hand to help in the first weeks, and keep checking whether people are actually using it months later. If adoption fades, the project hasn't finished.
How should a CMO approach a martech or CRM overhaul?
Start with the customer journey and the questions you can't currently answer, then choose the technology. Many overhauls go wrong because a CMO buys the platform first and works out the purpose afterward. Map what you need to know about your customers, check the data you already have and how clean it is, and agree with sales and IT on who owns what. Then move in stages rather than all at once, so each step shows results before you commit to the next. An independent adviser can also help you resist a vendor's pitch for features you won't use.

What Sam is saying

On working with an independent

"When a consultant is independent of the third-party solutions they are offering, the only incentive they have is for what works."
Sam SharSam Shar, CEO, Trend-Setters Consulting (TSCi)30 Oct 2026
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