The Hidden Trap of Quick Wins in Digital Transformation and AI

Over the years, I’ve had the opportunity to work with companies of all sizes as they embark on their digital transformation journeys. One of the first things leaders ask me is, “How can we show results quickly?” especially with AI on the rise.

I get it. Digital transformation can feel overwhelming. AI, automation, new workflows—it’s a lot to take in. Leadership teams want quick wins to prove they’re on the right track. Employees need to see immediate benefits to buy into the change. Investors and stakeholders expect tangible ROI early on.

And so, companies chase quick, easy projects—things they can roll out fast to show progress. I’ve seen it happen time and time again.

A company struggling with manual data entry in finance decides to automate invoice processing. Another integrates AI-powered resume screening to help HR hire faster. A sales team adopts an AI-driven lead scoring tool to predict which customers will convert.

At first, these wins feel exciting. Leadership gains confidence, employees feel optimistic, and the business gets to say, “We’re leveraging AI!”

But then, a few months go by.

The finance team now has automated invoice processing, but payment cycles are still slow because approvals are bottlenecked in another department. The AI resume screener is working, but hiring hasn’t improved because recruiters still struggle with candidate engagement. The AI lead-scoring tool is identifying high-value prospects, but sales conversion rates remain the same because the follow-up process is broken.

The problem? These companies weren’t choosing quick wins strategically. They were checking boxes instead of solving real business problems.

I’ve learned that quick wins can be incredibly powerful—but only when done right. If companies aren’t careful, they fall into the trap of false progress, thinking they’re transforming when they’re really just spinning their wheels.

The Power of Quick Wins—And Their Hidden Risks

Quick wins are essential in any AI or digital transformation effort. They:

• Provide fast, measurable value without long development cycles.
• Help leadership stay invested by showing early ROI
• Increase employee buy-in by proving AI and automation can enhance, not replace, jobs
• Reduce risk by starting small before scaling AI initiatives
• Create momentum, making people excited about the transformation journey

But as much as I believe in quick wins, I’ve also seen how they can derail a transformation if not chosen wisely.

The Wrong Quick Wins Can Create the Illusion of Progress

One of the biggest mistakes I see companies make is selecting quick wins that don’t impact core workflows.

Many organizations chase projects that:

1. Are not connected to real business processes.
2. Solve a small, isolated issue but ignore larger inefficiencies
3. Provide a short-term boost but don’t contribute to long-term transformation

This is where companies get stuck. They spend months implementing small AI tools, automations, and dashboards—only to realize that the fundamental business problems remain unsolved.

They celebrate quick wins that don’t move the business forward.

Breaking the Cycle: Choosing Quick Wins That Truly Matter

If you want to pick the right quick wins, don’t start by asking, “What can we automate?” Instead, ask, “Where are the biggest inefficiencies in our workflows?”

For example, I worked with a company that was struggling with its sales process. They wanted to introduce AI-powered meeting summaries to save time for their sales reps.

It seemed like a great idea. No more manual note-taking. AI would summarize key points, saving hours of work each week.

But when we looked at the bigger picture, we realized something crucial—note-taking wasn’t the real problem.

The real issue was that sales reps were slow to send follow-ups and proposals. Customers lost interest before deals could close.

If we had stopped at AI note-taking, we would have missed the real opportunity. Instead, we shifted focus to AI-driven proposal generation, which reduced turnaround times and helped the company close more deals.

That’s the difference between chasing any quick win and choosing the right one.

How to Choose the Right Quick Wins in Digital Transformation and AI

I always advise companies to take these three steps before implementing any quick win:

1. Break Down the Workflow First– Identify bottlenecks, inefficiencies, and areas of friction before choosing an AI or automation solution.
2. Optimize the Process Before Automating It – If the process itself is flawed, automating it won’t fix the problem—it will just make inefficiencies happen faster.
3. Pick a Quick Win That Creates Real Business Impact – Find a small but meaningful change that integrates into workflows and improves overall efficiency.

When companies follow this approach, quick wins don’t just prove AI works—they set the stage for long-term success.

From Illusion to Impact: Rethinking Quick Wins in AI and Digital Transformation

I’ve seen companies succeed when they choose quick wins that align with their broader transformation strategy. They don’t just chase small improvements for the sake of it—they make sure every quick win:

• Improves a core workflow, not just a standalone task
• Contributes to long-term transformation, not just a short-term win
• Builds momentum toward larger AI and automation efforts

Quick wins should never be about showing off AI—they should be about making AI work for the business.

So, the next time your company is evaluating a quick win, ask yourself:

Is this a real step forward—or just an easy checkbox to make us feel like we’re transforming?

If it’s not moving the business forward in a meaningful way, it’s not a quick win—it’s a distraction.