Leading Without Chaos: Avoiding Common Pitfalls That Undermine IT Success

Oct 23

In my experience as both a contributor and a project manager, I’ve seen firsthand how senior leadership can drive a team’s success. Unfortunately, when leadership is chaotic, the organization mirrors that chaos, especially at the team level. No leader intentionally injects disorder into their processes, yet it’s easy to make decisions that have unseen ripple effects—particularly in the fast-paced, complex world of technology. Even well-meaning leaders can inadvertently sabotage their teams, leading to low morale, employee turnover, inefficiency, and increased costs. This post explores a few common ways this happens and offers practical solutions to prevent it.

Misaligned Priorities and Unrealistic Expectations

One of the most common ways leadership can derail IT teams is by constantly shifting priorities or setting expectations that don’t align with reality. In many organizations, sales are king, and when sales are on the line, everything feels like it needs to be fast-tracked. Unfortunately, when leadership demands sudden changes mid-sprint or pressures IT to meet arbitrary deadlines, it disrupts more than just the timeline.

What’s the Impact?

Constant context switching exhausts the team and leads to unfinished work piling up. The IT department ends up scrambling, trying to put out fires instead of delivering well-thought-out solutions. Employees have said, “Burnout is real, and it’s not just about long hours—it’s the frustration of feeling like you’re never able to finish anything before another priority gets dropped on your desk.” This results in delays, decreased productivity, and a demoralized team.

How to Avoid it?

To prevent these issues, it's crucial to involve IT leaders in discussions early on so they can understand the vision and strategy. Crafting clear problem statements allows the team to assess feasibility and provide realistic timelines. This upfront planning fosters buy-in and ensures that the team feels supported rather than blindsided. Leaders should have a comprehensive understanding of what is needed before engaging the team.

Additionally, leaders should communicate priorities clearly and concisely, minimizing the number of channels through which messages pass to maintain clarity. It may be necessary to refrain from contacting team members individually about tasks; instead, work with project managers or IT managers to ensure everyone stays aligned with the overarching goals.

Bypassing Established Processes

Process matters in IT. Whether the team uses Agile, Scrum, Kanban, or a custom method, these systems exist for good reasons. They manage workloads, ensure timely project delivery, and prevent team burnout. But what happens when senior leaders bypass these processes? Chaos ensues.

EXAMPLE: An executive needs something urgently. Instead of following protocol (submitting a ticket or adding to the backlog), they directly message the individual team members or drop the request into an active sprint without consultation. This creates havoc, forcing the team to derail planned work for an urgent (but possibly not critical) request. Additionally, different team members end up with a different understanding of what is required.

What’s the Impact?

Instead of making progress, the team will now shift from proactive planning to reactive firefighting. Ongoing projects will face delays or remain half-finished. Efficiencies will be lost from constant context switching.

Each bypass sends a clear message: "The process is optional." Others in the company may follow leadership’s example and ignore processes as well. It can become the “Wild Wild West” in the IT Group; whomever has the loudest gun gets all the attention. Not only does this thwart project success, It's also extremely challenging to build an efficient culture when the systems designed to protect it are routinely undermined. The costs show up in turnover, lost time, failed projects, and eventually even sales.

How to Avoid It?

Respect the process. If you lack confidence in the current system, collaborate with IT to improve it, don't circumvent it. Have trust in the team to get things done according to the processes. Allow the team to prioritize based on the bigger picture, not just today's crisis. Strive to set an example to others in the organization, so they’ll do the same. Not only do things get done better and more quickly, but this approach also fosters a more productive, less chaotic IT environment that better serves the entire organization.

Lack of Understanding or Respect for IT Workloads

A common disconnect between senior leadership and IT often stems from a misunderstanding of technical complexity. I've witnessed scenarios where leaders request "quick fixes" or "small changes" from IT, unaware of the potential ripple effects across interconnected systems.

For instance, a leader might ask IT to deliver something "by tomorrow," not realizing that what seems simple on the surface could require extensive testing, careful integration, or coordination with multiple systems. This gap in understanding can lead to unrealistic deadlines and unnecessary pressure on IT teams. It can also drive leaders to mistrust their teams.

This disconnect not only creates stress but can also compromise the quality and security of solutions.

What’s The Impact?

Unrealistic deadlines force IT teams into a corner, often leading to compromised solutions and increased technical debt. Like financial debt, technical debt compounds over time, creating a snowball effect of issues.

These "quick fixes" might seem cost-effective in the short term, but they often result in higher costs down the line. Systems become brittle, prone to breaking, or require extensive reworking. It's a classic "pay now or pay later" scenario, where "later" typically comes with a much steeper price tag.

Moreover, this approach can lead to:

Decreased system reliability
Increased security vulnerabilities
Higher maintenance costs
Technical Debt
Reduced team morale and productivity

In essence, pushing for rapid solutions without understanding the full scope of work doesn't only affect the current project, but it can undermine the entire IT infrastructure and the team's ability to innovate effectively in the future.

These unrealistic deadlines force IT to cut corners, which leads to increased technical debt. And just like financial debt, technical debt compounds over time. The “quick fixes” end up costing more down the line when systems break or need reworking. It’s a classic case of “pay now or pay later,” and paying later usually comes with higher interest.

How to Avoid It?

To avoid the pitfalls of unrealistic IT requests, it’s essential to understand the complexities involved. Leaders should take the time to learn about the intricacies of IT tasks, and if not technically inclined, ask for explanations in business terms. This will help to make informed decisions that align with both business goals and technical realities.

Some other ways to help are as follows:

Trust the IT experts when they provide time estimates; they are accounting for necessary steps to ensure quality and security. Foster a partnership with the IT department by involving them in strategic discussions early on, which helps align technology initiatives with business objectives.
Prioritize quality over speed. Resist the urge to impose unrealistic deadlines that may compromise outcomes, as robust solutions often save resources in the long run. Encourage transparency so that IT feels comfortable discussing challenges and risks associated with rushed projects.
Consider hosting regular “open house” sessions where IT can share insights with leadership, building mutual understanding and respect.
Balance short-term needs with the long-term health of your IT infrastructure. By implementing these strategies, you can support your IT department and foster effective, innovative technology solutions that drive your business forward.

Neglecting IT’s Need for Resources and Support

IT departments aren't mere cost centers; they're vital business assets that require ongoing investment. I've witnessed environments where IT was chronically underfunded, understaffed, and reliant on outdated tools. It's akin to expecting a chef to create a gourmet meal with only a can opener and a microwave. When teams aren’t provided with essential resources, be it updated software, adequate staffing, or continuous training they’re being set up for failure.

What's the Impact?

When IT lacks the necessary resources, the consequences are far-reaching. Projects drag on beyond deadlines, quality suffers, and employee turnover increases as frustrated team members seek better opportunities elsewhere. The exodus of a company’s best talent means valuable institutional knowledge walks out the door, further escalating costs as a new struggle begins to onboard and train new personnel.

Moreover, an under-resourced IT department struggles to keep pace with evolving technology trends and security threats, potentially exposing the organization to risks and missed opportunities for innovation.

How to Avoid It?

Invest strategically in the team. This means:

1. Providing up-to-date software and hardware

2. Offering ongoing training and professional development opportunities

3. Ensuring adequate staffing levels to manage workload effectively

4. Fostering a culture of innovation and continuous improvement

5. Establishing and consistently adhering to repeatable processes and policies

The Toxic Culture of Unspoken Expectations

While perhaps the most subtle, the creation of unspoken expectations can be the most insidious form of unintentional sabotage due to its indirect nature.

One growing trend in many organizations involves the establishment of implicit expectations that inadvertently foster a challenging work culture. It often begins innocuously - a late-night email here, an "urgent" request there, but over time, it can create an environment where employees feel compelled to be constantly available. Even when the overall company policy might stress a strong work-life balance, employees often feel that only those who make themselves available gain promotions or pay increases. It’s often the high performing team members who suffer the most. High performers have been known to burn out due to perceived pressure to respond to communications at all hours, even when officially off the clock.

The same can be said of vague job descriptions and goals. When team members don’t understand what is expected of them, how can they know if they’re meeting expectations? It’s maddening to report to several different managers who all have varying expectations, yet nothing is documented and agreed upon. A team member might feel like he is always missing the mark.

What’s the Impact?

This always-on culture can lead to burnout, decreased productivity, and increased turnover. It may also send an unintended message to the rest of the organization that boundaries are flexible and work-life balance is elusive. In the long term, such a culture is often unsustainable and potentially detrimental to both employees and the company. Vagueness and lack of reporting structure sows confusion and creates conflict within team members who strive to meet all their obligations. This results in burnout, turnover, failed projects, mistakes, double work, technical debt, wasted work, and lost sales.

How to Avoid It?

Establishing and adhering to clear boundaries can be beneficial. Fostering a culture where employees are encouraged to work diligently during business hours without facing implicit judgment for not responding after hours can lead to a healthier work environment. For genuinely urgent matters, appropriate escalation procedures can be put in place, but these should be the exception rather than the norm. By consciously cultivating a balanced approach to work expectations, organizations can support their employees' well-being while maintaining high standards of productivity.

By having clear expectations of different team member roles, a leader can eliminate some of the confusion and help teams stay focused and leverage their skills in the right places. Having a clear chain of command and work funneling system provides team members with a sense of safety and helps them feel as though they are part of the overall strategy.

Conclusion

The relationship between leadership and IT departments is crucial for fostering a productive and innovative environment. By recognizing the potential pitfalls of unintentional sabotage, leaders can take proactive steps to support their teams effectively. Investing in IT resources, respecting established processes, and setting clear boundaries not only enhances team morale but also drives long-term success for the organization. A collaborative approach that values communication and understanding will empower IT teams to deliver high-quality solutions that align with business goals. Ultimately, when leadership prioritizes the well-being of their IT departments, they set the stage for sustainable growth, innovation, and a thriving workplace culture that benefits everyone involved. Leaders have the power to elevate their IT teams to success, but it requires intention, trust, and investment.