Luis Peralta is CEO of ParallelStaff, a nearshore engineering firm helping digital transformation teams execute faster.
Every year, technology leaders pour billions into digital transformation: new platforms, cloud migrations, AI pilots and modernization road maps. The ambition is real, and so is the investment. And yet, the results continue to disappoint.
A Gartner study tracking more than 3,100 CIOs and technology executives found that fewer than half of digital initiatives actually deliver on their intended business outcomes. Gartner’s own researchers have described this pattern as “the curse of random success.” After spending years placing engineers with companies navigating these exact challenges, I’d argue the word “random” is the most telling part of that phrase.
The real culprit isn’t the technology.
When a transformation initiative stalls, the instinct is to question the tool, the platform or the vendor. But in my experience, the technology is rarely where things go wrong. What breaks down is execution, and execution requires the right people.
Gartner’s research makes this concrete: “IT executives see the talent shortage as the most significant adoption barrier to 64% of emerging technologies, compared with just 4% in 2020.” Organizations aren’t failing because they chose the wrong stack. They’re failing because they don’t have enough of the right people to build, deploy and sustain what that stack demands.
This is a structural problem, not a hiring problem. The demand for engineers skilled in cloud-native development, DevOps, data platforms and AI integration has far outpaced what traditional hiring pipelines can supply. A company can have a sound digital strategy, executive alignment and a reasonable budget, and still find itself stuck, waiting on headcount approvals, watching candidates accept competing offers or trying to ramp new hires who need months before they’re productive.
What separates the engineers who truly move the needle?
After more than 100 placements across industries, I’ve stopped being surprised by which engineers make the biggest impact. It’s rarely the ones with the most impressive resume. The ones who consistently deliver share a few traits that aren’t always easy to spot in an interview.
The first is genuine autonomy—not the kind where someone works independently because they prefer to avoid meetings, but the kind where an engineer can look at a problem, form a view and drive toward a solution without needing constant direction. In fast-moving transformation projects, that quality is worth more than any specific technical certification.
The second is what I’d call structured pushback. The best engineers we’ve placed don’t just execute—they challenge. One of our clients, a SaaS platform in the entertainment industry, was initially resistant when a senior product manager we deployed started questioning how their SCRUM ceremonies were run and how epics and user stories were being written. He proposed changes. There was friction. But within a couple of sprints, the client recognized that those changes were directly responsible for a measurable increase in developer productivity. The pushback wasn’t noise—it was a signal.
I saw something similar with a DevOps engineer we placed at a software development firm. Early on, the client read his directness as arrogance. He wasn’t being arrogant. He simply knew what he was proposing and why. After a few initiatives launched and delivered, the client’s perception shifted entirely. What felt like friction at the start turned out to be exactly the kind of technical conviction the project needed.
What are these engineers looking for?
Understanding how to identify strong engineers is only half the equation. The other half is knowing what they want, because the best candidates have options, and they’re evaluating you as much as you’re evaluating them.
In my experience, the top performers we work with aren’t primarily motivated by compensation alone. They respond to remote work flexibility, yes, but more specifically to schedules that treat them as professionals rather than resources to be managed by the clock. They want to see that a project is well-organized, that leadership has a clear vision and that the team they’re joining has real structure.
That last point is more important than most clients realize. I’m currently watching a retail client struggle to get traction on an AI initiative aimed at improving productivity within their product engineering team. The technology isn’t the problem. The problem is that there’s no clear leadership guiding the initiative, no defined KPIs and no shared understanding of what success looks like. The result is that a strong team is spinning, not because they lack ability but because the environment isn’t giving them anything solid to push against. Great engineers don’t just need a task. They need a structure worth contributing to.
Being flexible matters.
The organizations consistently hitting their digital targets tend to treat workforce flexibility as a strategic asset, assembling teams around the initiative rather than shaping the initiative around whoever happens to be available. They can add three engineers with specific API integration experience in days, not months, and scale back just as quickly when a workstream wraps.
If half of all digital transformation initiatives are falling short, and the data consistently points to talent execution as the root cause, then the next planning conversation probably shouldn’t start with tooling. It should start with capacity, and more specifically, with the kind of people you’re building that capacity around.
In a market where speed of execution is a competitive differentiator, how you staff a transformation matters as much as how you scope it.
Forbes Technology Council is an invitation-only community for world-class CIOs, CTOs and technology executives. Do I qualify?
