7 Deadly Sins of Managed IT Services: Tips to Avoid the wrong MSP

Tips to avoid choosing the wrong managed IT Services Provider

When you start any new relationship—personal or professional—people often ask: “Are there any red flags?” Choosing an IT provider is no different. But unlike dating, spotting those red flags in IT requires experience and knowledge of what “good” looks like today.

If you’ve been with the same IT company for several years, you may not realize how much the industry has evolved. What passed as “good enough” back then may now be holding your business back.

And make no mistake—choosing the wrong Managed IT Services Provider (MSP) isn’t just an inconvenience. It can cost you dearly in downtime, data breaches, compliance failures, lost revenue, and even reputational damage.

At Proper Sky, we call our approach IT the Proper Way—and it’s about more than keeping the lights on. It means aligning technology with your business goals, securing your systems, and ensuring IT drives productivity instead of problems.

So how do you know when it’s time to reevaluate your MSP?

Here are the key red flags every business leader should watch out for:

1. Reactive Support and Unresolved Issues:

   Do the same IT issues keep coming back? If your provider only fixes symptoms instead of root causes, your business will always be stuck in firefighting mode. A strong MSP proactively monitors your systems, prevents issues before they happen, and resolves problems quickly when they do arise.

2. Lagging in Technology:

   Technology evolves fast. If your provider isn’t talking to you about the cloud solutions, modern collaboration tools, or when to move off on-premises servers, that’s a red flag. Sticking with outdated solutions because your current IT provider fails to stay abreast of the latest advancements slows growth, reduces efficiency, weakens security and ultimately puts your business at a competitive disadvantage. A proactive MSP who is a true strategic partner will continuously evaluate emerging technologies and recommend relevant upgrades to help your business stay ahead of the curve. 

3. Cybersecurity Neglect:

   Cyber threats aren’t slowing down—and neither should your IT defenses. An MSP that treats cybersecurity as an afterthought is leaving your business exposed to ransomware, breaches, and regulatory penalties.

   Cybersecurity must be one of the main service pillars of an MSP today and take the steps to assess your cybersecurity posture, implement comprehensive security protocols, and provide ongoing monitoring and maintenance to safeguard your sensitive data and protect your business from cyberattacks.

4. Lack of Strategic Guidance:

   If your current MSP focuses solely on technical support without engaging in strategic IT discussions about your business goals and challenges, it’s a clear indicator of a mismatch. A valuable MSP should act as a trusted advisor, understanding your unique business objectives and offering tailored IT solutions to support them. Strategic alignment between your technology infrastructure and business objectives is essential for driving long-term success.

5. High Turnover Rates:

   A high turnover rate for a managed IT services provider can be a red flag because it indicates instability within the company, leading to potential disruptions in service delivery and inconsistent support for clients. Additionally, it may suggest underlying issues such as poor management, lack of employee satisfaction, or inadequate training, which could negatively impact the quality and reliability of the IT services provided. This instability could ultimately result in decreased efficiency, increased downtime, and compromised cybersecurity for clients, undermining their trust and confidence in the provider’s ability to meet their needs effectively.

6. Billing Confusion and Transparency concerns:

   If deciphering your MSP’s billing statements feels like solving a puzzle, it’s a red flag. Transparent and straightforward billing practices are essential for maintaining trust and accountability in your business relationship. Your MSP should provide detailed invoices that clearly outline the services rendered, associated costs, and any additional fees, ensuring transparency and facilitating budget planning.

7. Project Backlogs:

   If your business consistently struggles to get on your MSP’s schedule due to project backlogs or a perceived lack of priority, it’s a sign of inadequate resource management. Your MSP should prioritize your business’ needs and allocate resources efficiently to ensure timely delivery of services and projects. A responsive MSP understands the importance of addressing your concerns promptly and making your business a priority.

As a business leader, recognizing these red flags can help you assess whether your current MSP is effectively supporting your needs or if it’s time to explore alternative options. Don’t wait until it’s too late.

At Proper Sky, we’re focused on doing IT The Proper Way. This means we set you up for success from the very beginning and delivering exceptional IT support at every stage of your business. If you’re unhappy with the level of service you’re getting from your current MSP or would like to discuss what a partnership would look like with our Philadelphia-based MSP,  let’s set up a quick call to get the conversation going today.