Most Common Headaches for IT Managers and How to Solve Them

In today’s landscape, IT managers and their teams are essential for all business functions. IT is no longer just about support and infrastructure maintenance, but about operational performance, business objectives, employee productivity, and the customer experience.

This evolution of the IT function has brought along new challenges, while also exacerbating challenges that have existed for a long time. Here are some of the most common headaches that IT leaders face, along with some tips on how to deal with them.


1. Overwhelmed IT Team

This headache will be familiar to IT managers and professionals in all industries. You know the challenges:

  • Weakness in your organization’s IT infrastructure
  • The stop-start nature of IT strategy implementation
  • Slow transformation progress


The problem is you have practically zero time to focus on these essential issues. 

Instead, you and your team spend time on day-to-day tasks, firefighting, compromising, and holding everything together as best you can. 

You are successful in the primary objective, as demonstrated by the fact your organization continues to operate, but you know that with the right support and resources, you could implement initiatives, improvements, and strategies that would take your company to a whole new digital level – a level that accelerates growth, improves productivity, and creates new opportunities.

The solution is as challenging as the headache itself. Increased investment in IT is one answer, as it would enable you to expand your IT team in strategic areas, speed up the introduction of new infrastructure, and move faster with digital transformation.

You should also carefully analyze your current workflows, processes, risks (IT and business), and pressure points to identify the priorities for outsourcing to an MSP. Understanding these priorities will help focus the conversation and ensure the MSP’s solution aligns with your requirements.


2. Not Enough C-Level Focus on Strategy Development and Implementation

Following on from the previous point, not having enough focus on IT strategy in the organization is a headache. You’re aware of the need to align IT with wider business goals and objectives, but there is not enough c-suite buy-in or vision. 

This trickles down through the organization, making it challenging to deliver the behavioral change needed for your business to achieve digital transformation success.

A proactive MSP can help with these challenges by assisting with digital maturity and readiness assessments. Your MSP could also help create business cases, and they may even be able to attend IT strategy meetings with the senior leadership team alongside you.

At the very least, you should have regular meetings with your MSP to ensure the service is delivering the business outcomes you need.


3. Outdated Infrastructure & Lack of Digital Transformation Investment

Companies that don’t embrace things like the need for digital transformation, technologies like the cloud, and the importance of IT for future growth and prosperity, are going to be left behind. That isn’t just a random opinion, as it is increasingly backed up by facts. Research by Deloitte, for example, found that companies with higher levels of digital maturity reported three times as much revenue and profit growth than those with low levels of digital maturity.

As an IT professional, this research is unlikely to be a surprise. The challenge – the headache – is getting other senior executives behind the need for digital transformation investment and a comprehensive strategy and roadmap.

The solution is to get buy-in based on outcomes, benefits, and business impacts, rather than technology features and functionality. In other words, talking their language. Your MSP can assist with this process, by helping to formulate a roadmap for improvement.


4. IT Staff Turnover

IT staff turnover causes a lot of frustration, in addition to the practical challenges it presents. There are several steps you can take to alleviate this headache:

  • Create and maintain IT process documentation and training materials. After all, IT is a competitive recruitment landscape in Eugene and beyond, so an element of staff turnover is inevitable. Planning for it helps make the transition to a new employee easier.
  • Identify must-have, in-house skills. Niche IT skills can be difficult to retain, so focus on the skills that are most important. You can outsource the rest to your MSP.
  • Cross-train your team and continuously develop the skills of your staff, ensuring they have capabilities in all priority areas.

5. Evolving Cybersecurity Threats

Cybersecurity threats always evolve, but there is evidence that evolution is ramping up. A survey by VMware of enterprises around the world is a good example. It found that 91 percent of respondents were experiencing an increase in cybersecurity attacks, with the move to higher levels of remote work exacerbating the issue. The same survey found that attacks are also now more sophisticated than before.

The big challenge facing IT managers when it comes to cybersecurity, is that it is difficult to keep up with new threats and other developments.

Protecting your organization against cybersecurity threats also requires multi-pronged proactive defenses. This can be challenging for small IT teams in Eugene to plan, implement, and manage. 

Support from an MSP, particularly in relation to the technical aspects of cybersecurity (password management, firewall management, threat detection and response, etc.), can significantly reduce risks. 

An MSP can also help with cybersecurity awareness training, security policy management, and more.


6. Skills Gaps

Skills gaps are another headache faced by IT managers, and the situation is not getting any better. UK government research, for example, found that two-thirds of organizations are suffering from skills shortages in one aspect of IT – cybersecurity. A survey of cybersecurity professionals in the US had similar findings, as 57 percent of respondents said the organization they work for has suffered from the skills shortage in cybersecurity.

Add everything else that falls under the concern of IT in small and medium-sized enterprises, while also considering the pace of change in the sector, and the scale of the challenge starts to take shape.

The risks aren’t just about cybersecurity, either. Without a properly functioning IT infrastructure, a proactive IT strategy, and an effective digital transformation roadmap, companies struggle to stay competitive, growth can be limited, and the customer experience can be negatively impacted.

Training is one way to deal with skills gaps, but a low barrier solution is to augment your team with expertise from an MSP. Your MSP will offer a broad range of skills, including advanced IT skills in niche areas, making it possible to bridge multiple skills gaps in one go.


Challenging but Effective (and Essential) Solutions

Outsourcing to an MSP can help alleviate most of the challenges and headaches highlighted above. However, it is essential that there is a partnership basis for the outsourcing arrangement, where the MSP is genuinely focused on your pain points and objectives.

A summary of other solutions to common challenges includes:

  • Technology adoption across the organization must align with business goals
  • Getting buy-in from the top on the necessity of a digital transformation strategy and the need to leverage emerging technologies
  • Automating as many repetitive IT processes as possible, with help from your MSP


The day-to-day work of an IT manager is largely technical. However, the root cause of the most common challenges is not technology, but people. People are also the core of the solution.

We are here to help you alleviate these challenges. Feel free to book a call with us so that we can discuss how we can simplify and improve IT for you and your company.


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Since 2001, StepUP IT Services has been helping businesses in Eugene and throughout Oregon with their technology needs. We are your IT partner. We manage and maintain your technology, empowering your organization to reach its goals. Making you happy is what makes us happy.

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