Avoiding IT Project Failure: Lessons from Colby Anderson

IT projects are essential to how businesses expand, function, and compete in the modern digital environment. A successful implementation of a new internal tool, cloud migration, or infrastructure upgrade requires more than simply strong code or powerful servers; it also requires the correct strategy.

I’m Colby Anderson, and over the years, I’ve led IT projects across different industries, from small startups to major enterprises like Bank of America. Along the way, I’ve seen what works—and more importantly, what doesn’t.

The reality? Many IT projects fail. Deadlines get missed. Budgets explode. Teams burn out. But with the right planning and mindset, most of these problems are completely avoidable.

In this post, I’ll share some of the most common reasons IT projects fail—and what you can do to make sure yours succeeds.

1. Not Clearly Defining Objectives

Starting a project without a clear idea of what success looks like is one of the biggest mistakes I see. Too many teams begin development without having a clear idea of their goals.

Rather than stating, "Let's upgrade the system," be more precise: "We need to improve performance by 30% and migrate to cloud infrastructure with zero downtime."

Everyone can stay focused and in sync when you have clear, quantifiable goals that also allow you to monitor your progress.

Colby Anderson taught us that every endeavor should begin with clearly defined objectives. The project isn't ready to start if you can't sum up the results in a single sentence.

2. Ignoring the Planning Phase

Planning might not feel exciting, but it’s where success begins. Without proper planning, teams often run into surprises later: missing resources, unclear timelines, or dependencies no one thought about.

A good plan includes:

• A clear scope
• Defined roles and responsibilities
• A timeline with realistic milestones
• A communication plan
• Risk management strategies

Spend more time upfront planning than you think you need. It’s far easier to solve problems on paper than in production.

3. Not Involving the Right People

Too many IT projects are driven by one department, with little input from others. This leads to misalignment, overlooked requirements, and unhappy end users.

Whether it’s operations, finance, legal, or frontline employees—bring them into the conversation early. They’ll help you identify risks and design a solution that actually works for everyone.

Stakeholder input isn’t optional. Good communication leads to better design, fewer surprises, and stronger buy-in across the company.

4. Underestimating Complexity

IT projects are often more complicated than they seem. There may be legacy systems to deal with, integrations with other platforms, or compliance requirements to meet.

Many teams rush through scoping, only to realize halfway through that they need to rebuild something or buy a new tool. That leads to delays, extra costs, and frustration.

Be realistic about what’s involved. Take the time to audit systems, dependencies, and risks before writing a single line of code.

5. Poor Communication

If there’s one thing that will sink an IT project faster than anything else, it’s poor communication. When updates are missed, decisions aren’t shared, or feedback loops break down, small problems become big ones.

Successful projects have clear communication channels, regular check-ins, and a shared understanding of priorities. Everyone knows what’s happening, what’s expected, and where things stand.

Keep people talking. Transparency and consistency turn good teams into great ones.

6. No Testing Until the End

It’s tempting to wait until everything is built to test it—but that’s a trap. By then, fixing issues is more difficult, time-consuming, and expensive.

• I always recommend testing early and often:
• Unit testing during development
• Integration testing across systems
• User testing for feedback
• Load testing to check performance

7. Skipping the Post-Project Review

Once a project goes live, many teams simply move on to the next thing. But without reviewing what worked and what didn’t, you miss out on valuable lessons.

I always run a post-project review with the team. We talk about wins, struggles, and ways to improve. That feedback is used to make the next project better.

Final Thoughts

IT projects are never just about technology. They’re about people, communication, planning, and problem-solving. While no project is completely risk-free, most failures can be prevented with the right approach.

As someone who’s been in the trenches, I can tell you this: the more effort you put into understanding your goals, communicating with your team, and planning every step, the smoother your project will go.

Success doesn’t happen by chance—it happens by design.

If you're gearing up for an IT project and want a proven approach, take these lessons to heart. I’m Colby Anderson, and I’ve learned that the best tech projects are the ones that start with clarity, end with confidence, and stay flexible every step of the way.