5 Reasons IT Leaders Fail

 In Leadership

Leaders set direction even when the future isn’t defined. They provide clarity and confidence that the path they’ve chosen to follow is specifically engineered to make the business better and make their customers better.

You can only do that if you know how to communicate and communicate well.

It’s nearly impossible to be proactive in IT. New technology keeps entering the market at exponential rates adding to the already overcrowded market of tech vendors. Not to mention, all the new technology, and the feature updates from the existing companies to keep up with the startups, is causing nightmares for security specialists who see new attack vectors everywhere they look.

That means it’s more critical than ever that IT leaders know how to interpret and communicate the changes they’re seeing to upper management and the rest of their teams.

Even if you communicate flawlessly, there are still five obstacles that keep good IT leaders from being great.

They don’t have a purpose or vision.

No matter where you work, or what type of business you work for, your IT department has one goal: to support the business’ overall mission. Knowing what your company is working to achieve helps you define how you fit into the plan and grounds the decisions you make moving forward.

The great leaders don’t settle with just knowing their purpose, though. Great leaders have vision. They see the ways technology can make that mission go further.

It’s one thing to hit your goals. It’s another to be able to forecast, look at what’s being done in the industry and say this is how we’re going to take new advancements in technology and improve our business.

When you combine your business’ mission with your vision for how your department fits into and becomes integral to it, you’ve created a finish line that you and your team can chase after. It’s a guidepost that helps you make quick decisions you can be confident in, and it’s a way to gauge your team’s effectiveness.

They don’t question top-level decisions.

The CEO sets the direction and lays out the mission. You execute to it. That doesn’t mean you don’t have a say in where you’re going or how you’re going to get there.

If you’ve made it to a leadership position, it’s because someone (your boss) thinks you’re an expert in your field. It’s now your job to help them make the best strategic decisions for your business. If you’re a part of those conversations, it’s easy to provide your input.

Once a decision on a direction has been made, you can still make suggestions on the best way to execute to that mission. Constantly validating your CEO’s decisions, even when you disagree, limits the success you could see as a business and erodes the trust your employees have placed in you.

You live and breathe technology. It’s your world every day. You know what’s working, what isn’t and where there are issues. You have a unique insight into how your business runs from a technical side that could and should inform critical business decisions. If you keep your comments or suggestions to yourself, you’re not giving your CEO or other leaders a chance to find a way to achieve their goal in a way that’s better for your business, your employees and your customers.

On the other end of the spectrum, if all you do is repeat the same line from your executive leadership team to your employees, and you don’t believe it, they’ll know. It’s crystal clear when someone doesn’t believe in what they’re doing or saying. You erode a little bit of the trust and respect your team has for you when you don’t stand up for what you believe is best for your business.

They can’t delegate.

Great leaders hand off the basic troubleshooting and minor projects to their team and instead focus on the leadership and managerial sides of their job.

Most IT leaders came up through the ranks as technicians or engineers, so it’s difficult – especially for new leaders – to delegate the little things. They get so bogged down wanting to fix everything that they neglect their responsibilities.

Delegation does more than just spread out the workload; it builds trust between you and your team.

When leaders hoard projects they should be delegating, it makes their team feel like they’re not trusted. In most cases, that’s not how it’s intended, but almost always how it’s perceived.

It all comes down to trust. When you’re the one accountable, it can be easy to want to keep the project for yourself because you think you know how to get it done most efficiently and effectively. Really, it creates a perception in your team that you don’t believe they’re smart enough, fast enough or good enough to do fix the issue.

Let’s say you’ve got a new guy on your team. He’s still learning the ropes and you’re not sure he’s up to handling the project yet. If you don’t let him try, even if he fails, why did you hire him in the first place?

It’s got to be okay for technicians to try new things, and occasionally fail, because that’s how you learn what works and what doesn’t. If it’s not okay to fail, you’re creating obstacles that stunt your team’s growth and keep you from seeing real progress in your business.

They don’t know how to manage people.

Managing people is hard. It’s a constant balancing act of skillsets, communication styles and personality types.

Managing Skillsets

Technicians and engineers come to the field in many ways. Some have four-year degrees, while others went to a trade school. There’s now a growing base of technicians who didn’t go to either but sharpened their skills on their own time. Some came up through MSPs or call centers, while others started their careers at an internal IT department or outside the industry altogether.

Everyone brings their own unique experiences and backgrounds to this job. One of the most interesting aspects of it is that it causes them to do the same job a little bit differently, and all without compromising the two main benchmarks in our industry: speed and accuracy. They still get the job done fast and with precision, but they don’t necessarily follow the same script.

Managing Communication Styles

You also have to manage communication styles. You will have employees who are list-makers and task-followers who require a clear direction with status checks throughout the process. You’ll have those employees who need to be coached and taught the best ways to do their job. On the flip side, you’ll find the employees who just need you to point in a direction, and they’ll run at the problem head-on until they fix it.

As a leader, it’s up to you to make sure your team is as successful as possible. When it comes to communication styles, that means you need to be intentional in how you communicate the tasks you want employees to complete. If you walk up to someone who needs a clearly defined map, point in a direction and tell them to go, you’re not setting that individual up for success. Similarly, if you give a map to the employee who just wants to run, you’re limiting their ability to a confined list of tasks.

Managing Personalities

The last thing you have to manage for is personality. There are certain stereotypes for technicians and engineers. What we know, though, is that there are so many different types of people who come to this job. From the highly intelligent know-it-all, who seems to truly know it all, to the hands-on, head-down introvert, getting a group to work together as a cohesive unit is challenging in the best of circumstances. When you’re under a deadline or in a crisis, though, that ability to work as a group can make or break your team.

One of the easiest ways to manage all these simultaneously is to be mindful of the position you’ve placed each of your employees in and the responsibilities you’ve given them. When you match those positions with skillsets, communication styles and personalities, you’re setting your entire team up for success.

Let the introvert get their hands dirty. Put the energetic people-pleasers on the front lines with your other staff and vendors. Use what makes each of them different to your benefit, and, in turn, theirs.

They make blanket statements.

Generalizing problems or making blanket statements to your team is a way for leaders to feel like they’ve addressed a problem, without ruffling any feathers or calling out specific individuals.

That’s not what’s happening in the real world, though. Instead, the employees who are doing the right thing start to doubt, and the ones who are causing the problems think you’re talking to someone else. No matter how much some leaders dislike confrontation, the best way to address problems is in person, one-on-one and sooner rather than later.

You don’t have to be confrontational, but you do have to be direct. You can’t just talk about what’s going wrong, you also have work on solutions. It’s called the sandwich technique, and it’s used by leaders across the world for every type of negotiation and tough conversation there is.


Using the Sandwich Technique

You start with something positive about their work performance, a project they just completed or how they helped someone else with a tough issue. You want them to know you recognize the good things they’re contributing to the team before you move into the criticism.

The meat of the meeting needs to be spent addressing the issue. Be direct and clear, but don’t get personal. Once you’ve identified the issue, ask the employee for context. There may be something happening that you don’t know about. Armed with all the information, you can create a plan to resolve the issue with measures for improvement.

Before you leave the meeting, reaffirm something positive about the employee. This leaves them with a good feeling about you, the meeting and what they can do to modify their actions moving forward.


It’s natural to shy away from this type of confrontation and hope it’ll fix itself if you just make a few comments or suggestions, but if you let the negative activities draw out, they’ll start to form habits. And habits are harder to break.

You don’t get to the end of a quarter, pat yourself on the back and say you did it. Leadership is an all-day, everyday battle to make sure your team stays focused on their work, aligned toward your mission and ready to go to work for your business and your customers. It’s easy to fall into ruts. It’s easy to get caught up in the weeds.

As a leader, though, it’s your job to stay future-focused and to create the strategies and plans that are going to make your business better. That means, letting go and trusting others. It means knowing your strengths and finding people to complement your weaknesses. More than anything, though, it means taking up a mindset of ownership and giving your best every single day, so your team wants to do the same.

Recent Posts