Dealing with IT Cowboys: The Importance of Process in Scaling Your Business

Every industry has its version of the cowboy—that lone ranger who charges in, guns blazing, determined to solve problems their way. In IT, these renegades can initially seem like heroes, swooping in to resolve tickets quickly and making clients happy. But when you dig deeper, IT cowboys often leave a trail of chaos, undermining the processes and systems critical for a company’s long-term success.

What Is an IT Cowboy?

An IT cowboy is an IT professional who resists following established processes and procedures, preferring to “wing it” instead. While they may appear competent and even charming, their refusal to adhere to standard practices can wreak havoc on a company’s operations.

Some common characteristics of IT cowboys include:

• Ignoring Documentation: They skip updating documentation, making it hard for others to understand what’s been done.
• Ad-hoc Problem Solving: They fix issues but in ways that are inconsistent or undocumented.
• Resisting Collaboration: They prefer to work independently and reject team-oriented workflows.

The Case of the Maverick Engineer

A few years ago, we hired a skilled engineer at our managed IT company who seemed like a great addition to the team. Clients loved her. She was quick to resolve tickets, and she always had a smile. But it didn’t take long to notice that she wasn’t following our documented processes or adhering to our procedures.

This wasn’t just a minor issue. Our processes are the backbone of our operations, ensuring that we deliver consistent, reliable service. But this engineer wanted to do things her way.

Here’s what happened:

• Lack of Trust: We couldn’t trust her with critical tasks because we never knew if she’d follow the agreed-upon steps.
• Scalability Issues: Her ad-hoc approach didn’t align with our goals of scaling the business.
• Documentation Gaps: Without proper documentation, handoffs became difficult, creating bottlenecks and inefficiencies.

Ultimately, we had to let her go. It wasn’t an easy decision—she was skilled, nice, and popular with clients. But the needs of the business came first.

Why Processes Matter in IT

For IT teams, processes are not bureaucratic red tape—they are essential for maintaining efficiency, ensuring quality, and enabling growth.

1. Consistency: Processes create predictable outcomes, ensuring every client receives the same high-quality service.
2. Transparency: Clear documentation means anyone on the team can understand what’s been done and why, reducing reliance on any one person.
3. Scalability: A process-driven approach makes it easier to onboard new team members and handle increasing workloads.
4. Accountability: Processes define roles and responsibilities, minimizing finger-pointing when things go wrong.

How to Handle IT Cowboys

Dealing with an IT cowboy requires a proactive approach. Here’s how to manage the situation:

1. Set Expectations Early: During onboarding, emphasize the importance of following processes and explain why they matter to the company.
2. Provide Training: Sometimes resistance comes from a lack of understanding. Offer training to ensure everyone knows how to follow procedures.
3. Monitor Performance: Keep an eye on whether processes are being followed and address deviations immediately.
4. Have a Zero-Tolerance Policy: Make it clear that failing to follow processes is a dealbreaker, no matter how skilled or personable someone is.

The Bigger Picture

It’s tempting to hold on to IT cowboys because they often bring passion and problem-solving skills to the table. But in a team environment, no one individual should operate above the system. As we learned with our maverick engineer, failing to address these behaviors early can undermine the very foundation of your business.

The key to success in IT isn’t just technical skill—it’s the ability to work within a framework that ensures long-term growth and scalability. Processes may not be glamorous, but they’re what separate a chaotic IT team from a thriving one.

So, the next time an IT cowboy rides into town, be ready to rein them in—or show them the door. Your business depends on it.