Why Most Digital Transformation Projects Fail Before They Start

digital transformation projects shown with light trails at night

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By Matt Lhoumeau, CEO of Concord

Fifteen years ago, I spent six miserable months digging through filing cabinets for contracts at a $6 billion telecom company. The CEO asked me to find a thousand vendor agreements and renegotiate them to save millions. What should have been a straightforward business process turned into an archaeological expedition through decades of poorly organized paperwork—a painful reminder of why transformation projects are so critical in large organizations.

Fast forward to today, and I see companies making the exact same mistake – but now they’re calling it “digital transformation.” They’re trying to digitize broken processes instead of fixing them first.

The Automation Trap That Kills Digital Transformation Projects

Here’s the uncomfortable truth about digital transformation projects: most of them fail not because of bad technology, but because companies automate dysfunction. They take manual processes that are already inefficient, confusing, and wasteful, then spend hundreds of thousands of dollars making them digitally inefficient, confusing, and wasteful.

I see this constantly at Concord. Companies approach us wanting to implement contract management software, but when I ask about their current process, they describe something like this: “Well, Sarah creates the contract in Word, then emails it to three different people for approval, then someone prints it out for the CEO to sign, then we scan it and save it in a folder called ‘Contracts 2024’ on the shared drive, and then we hope we remember to renew it next year.”

Their solution? “We want to automate all of that.”

That’s not digital transformation—that’s digital preservation of chaos. What they need is contract compliance management software built around a logical, streamlined process, not a digital recreation of their current mess.

Why Companies Get This Backwards

The reason this happens is simple: broken manual processes are often invisible to leadership. When everything is done through emails, spreadsheets, and informal conversations, executives can’t see how many steps are redundant, how many approvals are unnecessary, or how much time is wasted on administrative busy work.

But the moment you try to automate these processes; every inefficiency becomes glaringly obvious. Suddenly you need to map out every step, define every approval threshold, and account for every exception. The technology forces you to confront the dysfunction you’ve been living with for years.

I learned this lesson the hard way during my telecom days. We weren’t just dealing with missing contracts—we were dealing with a system where nobody knew who was supposed to approve what, where documents lived in a dozen different formats across multiple systems, and where the same information had to be entered manually into three different databases.

The problem wasn’t that we needed better filing cabinets. The problem was that we had no coherent business process for managing vendor relationships.

The Right Way to Approach Digital Transformation

Here’s what I wish I had known fifteen years ago, and what I tell every company considering digital transformation projects today: start with the process, not the technology.

Before you buy any software, before you talk to any vendors, sit down and design how things should work in an ideal world. What steps are actually necessary? Who really needs to be involved in each decision? What information do you actually need to collect, and when?

At Concord, we’ve learned that the most successful implementations happen when companies take what we call the “greenfield approach.” Instead of trying to replicate their existing workflow digitally, they ask: “If we were starting this company today, how would we handle contracts from scratch?”

The answer is usually dramatically simpler than what they’re currently doing. Instead of six approval steps, they need two. Instead of three different review cycles, they need one. Instead of saving documents in seventeen different places, they need one centralized system.

The Cost of Getting It Wrong

When companies try to automate broken processes, the failure is expensive and demoralizing. I’ve seen organizations spend millions on digital transformation projects that ultimately get abandoned because the technology couldn’t overcome the fundamental process problems.

The worst part is what happens to company culture. When employees go through a failed digital transformation, they become skeptical of future technology initiatives. They start to believe that “digital” means “more complicated” rather than “more efficient.” This creates a vicious cycle where good digital tools get rejected because people have been burned by bad implementations.

The Simple Test for Digital Readiness

Here’s a quick test for any digital transformation projects: can you explain your ideal process in five sentences or less? If you can’t, you’re not ready for technology. You need to simplify first.

Most business processes that have evolved organically over years are like archaeological sites—layer upon layer of ad hoc solutions stacked on top of each other. Digital transformation isn’t about preserving these layers digitally. It’s about excavating down to the core business logic and building something clean from the ground up.

The Strategic Advantage of Simplicity

Companies that get this right don’t just save money on technology—they create a competitive advantage. When your business processes are logical and streamlined, you can adapt quickly to market changes. When they’re a digital recreation of organizational chaos, every change becomes a complex project.

The telecom company where I learned this lesson eventually did transform their contract management—but only after they threw out their existing process entirely and redesigned it from scratch. They went from six months to renegotiate a thousand contracts to six weeks. The technology made it possible, but the process redesign made it powerful.

Your digital transformation projects will either amplify your organizational strengths or amplify your organizational dysfunction. The choice is yours but make it before you buy the software.

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Matt Lhoumeau is the co-founder and CEO of Concord, a contract management platform used by over 1,500 companies worldwide. Before founding Concord, Matt worked with Nicholas Sarkozy during the 2007 French presidential campaign and later for a major telecom company, where his frustration with manual contract management inspired him to transform how businesses handle agreements.

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