6 signs an IT manager is struggling — and how to help

IT managers increasingly find themselves oversubscribed, challenged, and in many cases floundering, and it’s little wonder why.

Pressured to do more with less, faster, in flatter organizational structures, IT middle managers serve as a company catchall, with too much time spent on lower-value tasks such as administrative work and planning rather than high-value work such as actually managing and executing plans, according to a recent survey from McKinsey.

And, perhaps most importantly, they are less likely to have time to foster talent by assisting their reports with upskilling, a crucial part of any IT department.

Meanwhile, IT managers are increasingly feeling unfulfilled in their roles and suffering burnout, leading them to be far more open to finding a new job elsewhere.

“IT middle managers play a critical role, and companies often neglect and underinvest in them,” says Dan Roberts, host of the Tech Whisperers Podcast and author of Confessions of a Successful CIO. “That suggests why they’re struggling.”

What can be done to help? Tech leaders say relationship building is the key. Middle managers need strong mentors and a network of colleagues who understand their problems and can offer advice based on their own experience when things get tough, so the manager can learn how to cope, get back on track, and thrive.   

But it starts with identifying a middle manager who needs an assist and then stepping in to intervene. Here are some of the red flags.

Low team morale

Alan Clark, senior vice president of strategy at staffing agency Randstad USA, says a low-energy team that’s missing deadlines is a sign that an IT manager isn’t clearly communicating to their team or to management. An IT middle manager who struggles to get their message across may also make the problem worse by leaning into micromanagement, hurting morale. 

Part of the problem, Clark says, is that middle managers in IT need to get up to speed quickly on new technology and integrate it into existing systems. This can lead less experienced managers to have difficulty balancing technical requirements and business objectives, he says. 

Employees need upskilling to be effective in this scenario, but the middle manager is too stressed out to provide it to their reports — and these problems will likely continue until they’re addressed by upper management. 

Clark recommends seeking out the manager’s boss and having a frank conversation about their challenges and struggles. 

“Work with their manager or mentor to establish short-term goals that are clear and achievable,” Clark says. “Break down the goals into smaller tasks and prioritize them. Focus on time management and proper delegation of assignments. This will allow the middle manager to start to regain momentum and reengage with their team. Focus on small daily improvements and foster open communication with the team.”

Customer complaints

Listen to your customers internally and externally and you’ll hear plenty about a manager who’s struggling. When a middle manager’s performance is flagging, the number of complaints will increase, and it won’t be subtle, says SelectQuote CIO Floyd May III.  

“If the manager is part of a team that directly interacts with customers, they will quickly escalate issues to the leadership team above the middle manager,” May says. “In addition to customers, the manager’s employees will send a distress signal up the chain of command to express their concerns. In most companies, middle managers are the closest to the information technology team’s customer base — the results of their struggles will be noticed immediately.”

Today’s customers are increasingly tech savvy and know what they want, May says, which keeps those middle managers on the hot seat when things go sideways. 

“In the past, most customers focused on the what’s and why’s of their needs,” he says. “Today, they come to IT already knowing what they want and why they want it, and they direct IT on how to deliver. A seasoned manager knows how to navigate that conversation and refocus the requestor on what’s and why’s. That’s not the case with a less experienced one.”

May says that at the middle management level, the focus is often squarely on completing tasks with little attention paid to relationship building. And a middle manager who hasn’t built relationships will find success difficult.

“The worst-kept secret is that being a manager, along with all of the associated trials and tribulations, is an open book test,” he says. “Your failure or success will be highly dependent on your network. You need to focus on developing relationships so you have a network to call on when you are struggling.”

Productivity takes a hit

Vikas Kaushik, CEO at TechAhead, says the team of a struggling IT manager is probably missing deadlines and their output may be measurably decreasing.

“It might be time to conduct additional research if you observe regular project deadline delays, less teamwork, or an increase in personnel turnover,” Kaushik says. “A struggling IT manager may also appear overburdened and struggle to adjust to new difficulties in the quickly changing tech industry.”

In this scenario it’s time to make sure you’re calling attention to the problems directly and openly so that you can help a tech manager get back on track. 

Kaushik also recommends strategically assigning tasks, combined with a healthy dose of constructive criticism, which can help a tech manager develop the skills they need to run their team effectively. 

“As a leader, invest the time in one-on-one discussions to learn about the difficulties the manager is encountering,” he says. “Their abilities and confidence can be improved by providing mentorship programs, training sessions, and professional development opportunities.”

Active listening is also key. Identifying the problem is a start — but it’s only half the solution. 

“Fostering an atmosphere of open communication and empathy is essential,” he says. “Any firm that relies on technology must recognize failing tech managers and act quickly to help them. Excellence in digital transformation requires fostering the growth and well-being of our middle managers.”

They’re overwhelmed

IT pros, confident in their technical skill, can often be accelerated into management roles, particularly in rapid scale-up environments such as startup, says Alex Christie, CTO and co-founder of Attio. But the skills that helped them succeed in their previous role, especially without management training, doesn’t always translate to success in middle management. The promotion results in a bad fit, and it’s clear to all observers this former star, in a new managerial role, is no longer thriving in the company.

“There are generally two types of struggling middle managers: those who just aren’t great at the job, and those who are simply overwhelmed,” he says.

Christie recalls that early in his own career he found himself in a management role without a full understanding of what it means to lead. 

“I think that’s where a lot of the struggles that managers I have worked with or spoken to face,” he says. “They just landed in the job, and this happens at industry scale in startups. Management as a career and a discipline needs to be taught and learned.”

And the best way to learn the necessary skills, he says, is to develop good connections in the company with smart leaders who can advise when things get tough.

“If the struggling manager works with experienced managers, perhaps their boss or peers, they should ask for help and consider getting a mentor to guide them through how to improve on some of the basic skills that a manager needs,” he says. “Often the key is in refining the basics.”

In some cases, the best path forward may be to return to what was working before. Some tech pros, developers in particular, may be inclined to give management a shot as their career progresses. When it’s clearly not working out, the manager’s — and the company’s — best interests may lie elsewhere. 

“There’s nothing wrong with trying it out, learning that it’s not for them, and returning to their previous role,” he says. “Some of the best engineers I know have gone on that journey.”

They’re disconnected 

When a middle manager isn’t in sync with their team, an array of problems may show up simultaneously. Mushfiq Sarker, founder of WebOperators, says it’s an unfortunate mix of missed deadlines, unmet targets, and a disengaged team. The front-line staff may also be confused about their objectives because they’re not being identified clearly.

“The tech field presents unique challenges due to its rapid pace of change and innovation,” Sarker says. “For a less-experienced manager, keeping up with technological advancements, managing increasingly complex projects, and ensuring team members have the necessary skill sets can be overwhelming.”

Just as tech staff are expected to upskill around new technology, their managers need to continue to grow their skills around leadership and management, he says. 

“Training courses, mentorship, or coaching can provide valuable insights and tools for better team management,” Sarker says. “It’s also crucial to foster a culture of open communication. Regular check-ins and feedback sessions can help identify issues early and allow for timely intervention.”

Without intervention, a struggling IT manager may be headed for burnout, he says. 

“The tech industry can be demanding, and continuous stress without proper management affects both the individual and the team’s performance,” he says. “Encourage provide support for mental well-being in the workplace.”

They take on too much

Beyond the more obvious red flag of missed deadlines, Brent Skalicky, executive vice president of human resources for Arcserve, says when a middle manager delays making commitments, it may signal a need for better time management.

“There are a variety of tasks and challenges coming at an IT manager daily,” Skalicky says. “More experienced managers can often handle this fluidity and prioritize their workload more effectively, whereas a less experienced manager might struggle. Regular meetings can help open the lines of communication and ensure IT managers are aligned with the rest of the organization.”

These meetings can be a touch point to discuss prioritization, he says. IT managers should review upcoming critical tasks and consider how to manage their time most effectively going forward. They also need to be aligned with their direct reports, knowing what they are working on and their priorities to ensure everyone is on the same page, he says. 

And some middle managers tend to struggle because they’re not adept at delegating. Encourage the manager to share their load, Skalicky says, so their work is both more manageable and more impactful for the business.  

“Managers shouldn’t be afraid to delegate,” Skalicky says. “In fact, they should focus on value-added tasks, and delegate less critical tasks to team members.” 

Staff Management