The IT Red Flag Report

Introduction

Why IT Partnerships Matter

Importance of reliable IT support

When you're running a business, there's an endless list of priorities that hit your desk daily:

• Cash flow issues
• Leadership decisions
• Growth strategies

The last thing you need to worry about is whether or not your technology will be one of them. That's why having reliable IT support is crucial. Whether it's handling daily operations or aiding your long-term strategic goals, IT systems have become the backbone of modern businesses. When that backbone is weak, your company can face some serious risks:

• Operational disruptions
• Security breaches
• Financial losses
• Reputational damage

It's no wonder tech jobs are expected to grow at nearly twice (2x) the rate of overall employment across the economy by 2034.

Purpose of this Guide

Raise awareness about common issues

Like the rest of your business operations, you want to be prepared. You want a strategy you know will deliver results. Why should your IT solutions be any different?

We want to ensure that you're equipped with the right tools to make the best decision for your organization. Outsourcing IT for your business is no small feat. It's a fundamental part of your business strategy, and we don't take that lightly.

This guide highlights common issues businesses face with poor IT partnerships. After 35 years of serving businesses with IT solutions that protect their assets and help them grow, we know how damaging a poor partnership can be to your company's overall growth and vision.

Some issues you may be aware of, and others may come as a surprise. Either way, use this as a reference to evaluate whether your IT partner is supporting your best interests or their own.

Help businesses identify and address problems

By understanding these issues, you can take proactive steps to improve your IT partnership. This guide will give you practical advice for identifying red flags and offer strategies to address these problems with your current IT partner. Or help you identify what to avoid when looking for a new IT partnership.

Ready? Let's dive in.

01. Poor Communication

Lack of Responsiveness

Slow Reply Times

When was the last time anyone looked forward to being stuck in an endless hold cycle with their IT support? Or worse—a representative tells you someone will reach out shortly, only for hours (or even days) to pass before you receive a follow-up.

It's important to ensure your MSP has created guaranteed service level agreements (SLAs) for all issues. This not only assures you that your needs will be heard and met, but it also holds your IT partner accountable for delivering on those outcomes.

Ignoring Urgent Requests

Ignoring urgent issues is a major red flag. Critical issues need immediate attention, and your IT partner should have processes in place to handle emergencies properly.

If you feel your issues are being ignored, talk to your IT provider. Review your service level agreements and what you can expect regarding response and resolution times.

It's not that you're being nitpicky or aggressive. It's about accountability and ensuring everyone respects the partnership enough to uphold their promises. Because how they handle your issues is a direct reflection of the value your IT provider places on your partnership.

Important: Here's an example of SLA response times based on priority levels:

• Emergency Response: Respond within 1 hour
• Critical Response: Respond within 24 hours
• Standard Response: Respond within 24-48 hours
• Low Response: Respond within 72 hours

Inconsistent Updates

No Regular Status Reports

Just like any part of your business, you need to know what's going on with your IT environment. And that requires proper communication from your IT support.

Your status reports should include information about system performance, security updates, and any ongoing or upcoming maintenance or purchases. Because without this level of transparency, you can't effectively plan or make informed decisions.

Make sure your IT provider is meeting with you quarterly to review your status reports. Better yet, your MSP should pair you with a dedicated client relationship manager (CRM) to handle any questions regarding your technology plan and IT infrastructure.

Surprises and Hidden Issues

Save your surprises for puppies on Christmas morning, not hidden issues. Your IT provider should be upfront about everything that's happening in your IT environment. This means proactively monitoring your network for any anomalies and addressing them quickly before they escalate.

02. Frequent Downtime

Unplanned Outages

Regular System Crashes

Here's why system crashes are more than an "inconvenience":

• They disrupt workflows
• They can result in data loss
• They reduce overall productivity
• They frustrate employees and impact morale

A reliable IT partner should implement proven systems and monitoring tools to prevent frequent crashes. Because downtime is costing you money (on average up to $437 per minute). Curious to see how much downtime is costing you? Talk to one of our IT experts, and they'll be happy to help you uncover the truth with our signature Downtime Calculator.

Unexpected Maintenance

Another thorn in your side might be unexpected maintenance. Not only does it disrupt your operations, but it can also lead to surprise costs that weren't outlined within your budget. To give you confidence in your devices, your IT partners should schedule regular maintenance during off-peak hours and communicate these plans in advance to minimize disruptions.

Important: If you're curious whether or not your IT provider is performing at industry standard, here are two questions you can ask:

"What is your approach to keeping our systems up-to-date and optimized? How far in advance are you keeping track of needed replacements?"

Expected Answer: Your provider should outline a proactive maintenance schedule that includes regular software updates, system optimizations, and periodic hardware assessments. They should also share their lifecycle management strategy, showing you how they forecast hardware end-of-life and plan for replacements to avoid disruptions. These should be tracked several years in advance to properly plan your budget.

Slow Recovery Times

Long Periods of Downtime

Extended downtimes can halt business operations, leading to missed deadlines, lost revenue, and dissatisfied customers. Which can severely damage your organization's reputation. As a solution, your IT partner should have efficient disaster recovery plans to minimize downtime and ensure business continuity.

Poor Disaster Recovery Plans

A poor disaster recovery plan can prolong downtime and cause significant damage. Just how much? Studies show that organizations with frequent downtimes face financial losses that are 16 times higher than other companies.

To ensure you're effectively prepared for a disaster, your IT partner should develop comprehensive disaster recovery plans, regularly test them, and ensure all employees are trained on these procedures.

Important: Here is an example of key components that a disaster recovery plan should include:

1. Pre-Disaster Planning — Create policies and procedures for handling various disasters. This includes assessing risks, developing recovery strategies, assigning roles and responsibilities, establishing communication protocols, etc.
2. Disaster Declaration — Identify how your organization will declare an official state of emergency if a disaster occurs. Whether it's a pandemic or cybersecurity incident, make sure to align your team with the current situation, so you can start taking the proper steps toward recovery.
3. Emergency Response — Here, your organization will take immediate action. This may include contacting your MSP, evacuating employees, providing first aid, and taking appropriate steps to ensure the safety of your company and its people.
4. Business Recovery — Once the immediate threat has passed, your company will enter recovery. This may include restarting operations, reviewing backups and storage, repairing damage, and helping your team and customers in any way possible.
5. Post-Disaster Review and Improvement Planning — Make sure to evaluate the recovery process's effectiveness. Identify where you can improve the plan so that your company is better prepared for future disasters.

03. Security Concerns

Outdated Security Measures

Using Old Software and Hardware

Old software and hardware are more than signs of entering senior citizen status. They often lack the latest security features, making them easy targets for cyberattacks. According to recent studies, 24% of companies that have experienced a cyberattack and lost between $50,000 and $99,999.

Lack of Regular Security Updates

64% of Americans have never checked to see if they were affected by a data breach, which is terrifying, and why your business should have regular security updates. Your IT partner should implement automated updates and continuously monitor your systems for vulnerabilities.

That said, make sure to check with your IT partner to verify that your systems are updating. You can't solely rely on the idea that your systems are automatically updating (nor should you). We've spoken to companies who assumed their MSP backed up their data regularly, only to discover it had been months since their most recent backup. As the age-old adage reminds us: "Trust, but verify."

Data Breaches

Incidents of Unauthorized Access

Data breaches can have devastating consequences for your organization.

• Financial losses
• Legal penalties
• Reputational damage

One of the ways this can happen? Unauthorized access. Incidents of unauthorized access can occur due to weak security measures. The problem? Some cyberattacks can go undetected for an average of 146 days. This gets even more harrowing as the Department of Justice reports that only 1 in 7 cybercrimes are actually reported.

Your IT partner should implement strong access controls, encryption, and monitoring to prevent unauthorized access and keep your business running smoothly.

Poor Response to Security Incidents

On top of weak security measures, a poor response can increase the damage. While no one wants a data breach, it happens. The important thing is that your IT partner should have clear incident response plans, conduct regular drills, and ensure quick action to mitigate risks.

"In the current threat environment, slow or ineffective incident response isn't just a security gap—it's a business risk. Executives must recognize that prolonged breaches not only drain resources but also erode customer trust and market value. The longer the exposure, the higher the financial and reputational cost, making it critical to partner with an IT provider that can detect and contain threats swiftly to safeguard both operations and brand integrity."

— Eric Langendorfer, Director of Security Management, JMARK

04. Hidden Costs

Unexpected Charges

Imagine you've already planned your budget, crunched the numbers, and made sure your I's are dotted and your T's are crossed. Suddenly, you get a surprise bill.

Unexpected charges can strain your budget and, ultimately, break trust in your IT partnership. To avoid surprise bills and disputes over charges, your IT partner should provide transparent pricing and clear explanations of all charges and services within your contract to prevent misunderstandings.

Underpriced Services

Underpriced services may seem attractive initially. But they can lead to higher costs in the long run due to poor quality or hidden fees.

Paying for unnecessary services can waste your resources. You want your business to operate at a high level—your operations and resources should reflect that. Make sure your IT partner is giving you a personalized solution, not a generic one. Your provider's solutions should meet your specific needs and provide clear value to your business. IT is an investment and should be treated like one.

05. Lack of Proactive Management

No Ongoing Assessments

Not Conducting Regular IT Audits

Like a doctor's physical exam, you should perform regular checkups on your IT infrastructure. Regular IT audits help identify:

• Vulnerabilities
• Inefficiencies
• Areas for improvement

Your IT partner should perform these audits periodically to ensure your systems are optimized.

Failing to Plan for Future Needs

This can wreck your business. Technology is evolving at unprecedented rates, and failing to plan for future IT needs can leave your organization unprepared for the growth and changes that come with it. Make sure your IT partner is working with you to develop long-term IT strategies. Not only will this save you headaches, but it will also keep your budget intact and ready for what's to come. Your technology is fundamental to your continued growth, and your business plans should reflect that.

Don't Require an Approved Tech Stack

Not using an approved technology stack for your IT is like building a Ferrari with junkyard parts. It just doesn't make sense.

When your IT partner requires an approved tech stack, it does 3 things:

1. Ensures your devices come from trusted vendors
2. Makes hardware/software updates smoother across devices
3. Technicians can troubleshoot and solve problems quicker

Failing to do so can lead to a lot of unnecessary frustration—for your employees and your IT partner. Save the stress and make sure your IT provider gives you an approved technology stack for all current and future devices your business will need.

Reactive Approach

Only Fixing Issues After They Occur

Waiting for issues to occur before addressing them isn't a plan. It only leads to frequent disruptions and exposes you to dangerous threats. Your IT partner should proactively monitor your systems and perform preventive maintenance.

Important: Here are some services your IT partner should be including:

• Backup, Disaster Recovery (BDR) and/or Business Continuity
• Cyber Resilience (blended cybersecurity and business continuity)
• EDR (endpoint detection and response)
• Email security
• Endpoint monitoring and protection
• Firewall management
• Identity and access management (IAM)
• MDR (managed detection and response)
• Patch management
• XDR (extended detection and response)

No Long-Term IT Strategy

A lack of a long-term IT strategy can block your business growth. Now, while most IT providers offer long-term strategies, here's the question you need to ask yourself to measure its true effectiveness:

"How flexible is this plan?"

Growth is crucial for any kind of longevity in your industry. To grow, you have to be able to adapt to the current situation. The same goes for your IT.

Support is not a one-size-fits-all solution. Unfortunately, it's what many MSPs, especially larger ones, try to offer. With so many clients to address, it's hard to tailor solutions to their specific needs. While the intention merits understanding, it's also not the best way.

A strong IT partnership should give you the flexibility to pivot as new situations arise in your organization. Because as your business grows, your IT should, too.

Important: Make sure your IT partner checks in with you quarterly to review your plan and whether it still aligns with your current goals. Priorities change, and it's important to support them with the proper IT strategy and infrastructure.

06. Limited Expertise

Inadequate Skills

Unable to Handle Complex Issues

Complex IT issues require specialized expertise. That means your IT provider should have a diverse team that can handle various challenges. This is important to minimize downtime and ensure that if a technician leaves, someone else can effectively fill their place.

Lack of Necessary Teams to Handle IT

IT has many moving parts. And the challenges are too great for 1 person or team to handle. You need a set of specialized teams to handle every aspect of IT. Because settling for a jack-of-all-trades won't allow them to hyper-focus on a specific part of your business to ensure it operates at the highest level possible. Otherwise, you'll spend more time putting out fires than you can dedicate to tackling the business challenges needed to grow.

Here are some examples of the teams you need for IT success:

• Onboarding team
• Service team
• Projects team
• Cybersecurity team
• Product Development team
• Client Relationship Management team

Technicians Lack the Necessary Knowledge

The whole point of outsourcing your IT is so that you can trust your partner to handle it effectively. But when your MSP's technicians have inadequate skills, it can result in unresolved issues and poor service quality.

Your IT partner should invest in training and hiring skilled professionals. Additionally, your technicians should continually educate themselves and pursue certifications relevant to their roles and professional development.

Willing to Bring on Any New Client

Serving everyone seems great at the beginning, but failing to narrow down who you serve will only limit your ability to refine your products/services and grow. An IT partner who serves everyone is worrisome for 2 reasons:

1. May not offer personalized solutions
2. May not have expert staff in your industry

Additionally, ask your IT partner when the last time they turned down a potential client was. If they're saying "yes" to everyone without vetting, that's cause for concern. The ability to refuse business will not only demonstrate stability in their business model but also show you the maturity of their services and operations.

If you want custom services specifically for your business, partner with an IT partner who knows the clients they want to work with. Like dating, you want a partner who knows what they want and isn't afraid to state it. Because clearly defining the expectations upfront eliminates confusion down the line and makes it easier to walk away when it isn't a good fit.

07. Poor Customer Service

Unfriendly Support

Rude or Unhelpful Interactions

We've all heard the customer service horror stories. Some of us may have even experienced those calls firsthand. Regardless, knowing the frustrations of poor customer service interactions should make it a no-brainer when providing high-quality service on every issue.

If your experience left much to be desired, your feedback should go further than a phone call with management. Your IT partner should take the feedback and work with their team member to correct the action and discuss what to do next time. From there, you should expect an update from the manager on how your feedback has been implemented.

Rude or unhelpful interactions erode trust and satisfaction. Your IT partner should train their staff to provide what we like to call "Grandma Service." Because who would ever feel good about treating their grandmother poorly?

Low Retention/High Turnover

One of the clearest signs of a poor company culture is high employee turnover. Your IT partner's employees should enjoy the work they do and where they do it. How else can you expect that same love and care to be transferred to your business?

Ask your IT partner about their turnover rate and what initiatives they have implemented to support and strengthen their company culture.

• Do they have a committee that lets employees voice concerns, address issues, and develop solutions to build a better culture?
• Do they have a wellness program that prioritizes and incentivizes their employees' physical and mental health?
• Does their recognition for outstanding achievements go beyond "Good job. We appreciate what you're doing"?

A good company culture is more than ping-pong tables and pizza parties. It's about putting people over profits. It's about standing by your team through adversity. It's about creating a space where everyone feels that they matter.

Unclear Support Processes

Confusing Ticketing Systems

IT issues can be confusing, but keeping you in the loop shouldn't be. Confusing ticketing systems can delay issue resolution and leave you in the dark.

Your IT partner should clearly outline the issues being addressed in your ticket, as well as update you when changes are made. Additionally, your IT provider should implement user-friendly systems that streamline the support process.

No Clear Escalation Path

The worst feeling when dealing with an IT issue is not knowing who to contact. Your IT partner should have a clear escalation path that outlines your first point of contact and who you should speak to if the issue worsens.

This not only helps you when you need it, but it also shows that your IT partner has a clear process in place to deal with these issues. The last thing you need to do is worry if your IT partner is just as confused as you are about who to contact.

10 Questions You Should Ask to Identify IT Red Flags

Recognizing red flags early can help you avoid long-term issues with your IT partner. Regularly evaluate your IT partnership to ensure it meets your business needs.

1. "How do you practice and uphold transparency and accountability within your partnerships?"

Expected Answer: Look for a commitment to open communication, regular updates, and transparent reporting. The provider should discuss their policy for admitting and correcting mistakes, as well as how they handle project assessments and feedback.

2. "What proactive measures do you take to prevent downtime and data breaches?"

Expected Answer: Expect to hear about proactive monitoring, the use of advanced cybersecurity tools, and regular risk assessments. Your provider should also mention their strategy for keeping systems up-to-date against the latest vulnerabilities.

3. "How do you ensure my company's data remains secure and compliant (if applicable)?"

Expected Answer: The provider should discuss their comprehensive security measures, including data encryption, secure data storage, and regular security audits. For compliance, they should describe how they adapt their practices to meet industry-specific regulations when applicable, ensuring that your business meets all legal obligations efficiently if needed.

4. "Can you provide examples of how you've helped businesses like mine achieve their goals?"

Expected Answer: Expect specific case studies or references that demonstrate the provider's ability to deliver solutions that drive growth, improve efficiency, or enhance security for businesses similar to yours.

5. "What are your response times, and how do you ensure prompt resolution?"

Expected Answer: The provider should offer clear response time commitments and explain their process for resolving issues efficiently, including the availability of support teams.

6. "How do you support scalability for growing businesses or changing business needs?"

Expected Answer: The provider should explain their approach to scalability, including how they plan for increasing data volumes, user load, and new technology integration, ensuring that IT infrastructure can grow seamlessly with your business.

7. "How do you stay ahead of emerging technologies and trends?"

Expected Answer: Look for an answer that includes continuous learning, partnerships with technology leaders, and a commitment to innovation that ensures they provide the most current and effective solutions.

8. "How do you handle the integration of new technologies with our existing systems?"

Expected Answer: Expect a detailed strategy for technology integration that minimizes disruption and leverages your current assets, including how they assess compatibility and test integrations before full deployment.

9. "What is your protocol for handling IT incidents?"

Expected Answer: The provider should outline their incident response protocol, which includes immediate assessment, containment, and mitigation strategies to minimize impact. They should detail their communication process during incidents, how they document and learn from incidents, and the steps they take to prevent future occurrences.

10. "What role do you play in strategic IT planning?"

Expected Answer: Your IT provider should demonstrate how they align IT strategy with your business goals. They should discuss their process for conducting technology assessments, identifying IT solutions that support your strategic objectives, and planning for technology adoption that anticipates future industry trends.

Steps to Take If You Spot Red Flags

When issues arise, communicate them clearly with your managed service provider (MSP). Provide specific examples, discuss expectations, and work together to find solutions. If problems persist despite efforts to resolve them, it may be time to consider finding a new IT partner. Evaluate potential partners carefully to ensure they meet your business needs.

Template: How to Communicate Concerns with your MSP

To: <Your MSP>

Subject Line: Addressing IT Infrastructure Concerns

Hello <Name>,

I wanted to discuss a few concerns regarding our IT infrastructure. I believe addressing these will help us avoid potential issues and improve our overall efficiency.

• Frequent downtime affecting our operations
• Slow response times for support requests
• Data security measures and compliance
• System updates and maintenance schedules

Could we schedule a meeting to go over these points?

Your expertise has always been invaluable, and I'm confident we can work together to find effective solutions.

Thank you for your attention to this matter.

Best,
<Your Name>
<Your Contact Information>