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Top 5 Challenges When Hiring a Managed IT Services Provider for Your Small Business

November 18th, 2023 | 5 min. read

By Marissa Olson

Selecting an IT services provider (or Managed IT Services provider, MSP) is a pivotal decision for small businesses. It's not just about finding a vendor but a partner who will support your technological journey.

Let's explore these challenges more deeply to ensure you make the best decision for your business.

Challenge #1: Identifying the Right Level of Service

One of the most challenging parts of hiring a managed IT services partner is understanding the types of services your organization actually needs.

By partnering with the right company and following the steps below, you’ll be more equipped to make the most intelligent technology decisions for your business and employees.

Conducting a Comprehensive Analysis of Business-Specific IT Needs

The first critical step is to conduct an exhaustive analysis of your unique business's current and future IT needs. This includes closely examining factors such as:

  • The current size of your business operations and the number of employees

  • The specific industry vertical you operate within

  • The nature of the business data you collect and handle

  • Future goals for scaling or expanding the business

  • Peak usage times and seasons that may impact IT demand

  • Any existing technologies already in place and how they are utilized

  • Regulatory and compliance requirements in your industry

This thorough analysis provides the foundation for identifying the optimal service level that aligns with your budget while still delivering the necessary IT capabilities.

Implementing an Extensive IT Strategy

Implementing an extensive IT strategy can certainly seem like a challenge. However, there are a couple of great steps to take beforehand to ensure your IT needs are being met now and in the future.

In-Depth IT Audit: IT professionals can conduct a comprehensive audit of your current systems. An in-depth audit aims to uncover strengths and weaknesses and pinpoint priority areas for improvement or upgrade.

Long-Term IT Planning: With audit findings in mind, developing a multi-year IT strategic plan directly linked to your overarching business goals is critical. Remember, revisiting this annually helps adjust for your company's and employees' evolving needs.

Challenge #2: Navigating Budget Constraints

Balancing budget realities with the need for robust and reliable IT services represents a common challenge for small businesses. It's crucial to view IT spending as a long-term investment that enables growth rather than a simple operating expense.New call-to-action

Useful Financial Planning Methods

Many small businesses utilize a couple of different financial planning methods when hiring an IT services company.

Detailed Cost-Benefit Analysis: Break down the specific costs of different IT services and stack them against tangible benefits, calculating hard cost savings as well as softer benefits like mitigating downtime.

Return on Investment (ROI) Analysis: For each IT investment under consideration, carefully estimate the anticipated ROI over a multi-year period, factoring benefits like improved efficiency, lower downtime risk, better data security, and increased agility.

Challenge #3: Ensuring Cybersecurity and Compliance IT Environment

In today's high-risk digital environment, systematically protecting sensitive data and ensuring compliance with evolving regulatory standards is non-negotiable.

This mandates a multilayered approach addressing both technical and organizational factors.

Building Robust Security and Compliance

Multi-level Security Infrastructure: Implement overlapping modern security tools like next-gen firewalls, intrusion detection systems, endpoint protection, and 24/7 monitoring. Conduct regular audits and penetration testing.

Proactive Compliance Planning: Set reminders to review compliance requirements and standards frequently, ensuring your IT systems consistently adhere to the latest industry best practices and regulations.

Challenge #4: Deciphering Complex Technical Jargon

For non-technical stakeholders, navigating complex IT terminology can be an intimidating barrier. Establishing clear communication and a shared understanding between you and potential providers is imperative for making fully informed decisions.

Below are some techniques to improve your understanding:

"Jargon-Busting" Review Sessions: Schedule regular sessions with prospective vendors to demystify the technical language and clarify the exact meaning of unfamiliar terms and acronyms as they relate to your business needs.

Simplified Service Agreements (SLAs): Request service contracts, SLAs, and other documentation using straightforward language that avoids unnecessary technical jargon when possible while still maintaining accuracy.

Challenge #5: Ensuring Long-Term Support and Adaptability

Finding dependable and ongoing support is sometimes the most complex challenge businesses face when looking into outsourcing their IT.

The reliability and adaptability of your provider matters, both for consistent day-to-day support as well as adjusting to inevitable changes in business needs and technological shifts.

Below are some elements of future-ready provider support:

Performance Benchmarking: Establish clear quantitative benchmarks for service and support and continuously monitor provider performance data against these Key Performance Indicators (KPIs).

Proactive Evolution Planning: Seek providers who take a consultative approach to ensure their services and solutions flexibly evolve along with your changing needs. Confirm they proactively advise on emerging technologies that may benefit your business as it scales.

The IT Services Provider Selection Process


Once you have clarified your needs and goals, thoughtfully evaluating and selecting the right provider is critical. Here are proven tips to streamline the selection process:

  • Develop a comprehensive RFP outlining your essential requirements and priorities. Seek tailored responses from potential providers on topics like security, compliance, support models, and technology roadmaps.

  • Thoroughly research provider qualifications, looking beyond marketing content to find candid reviews and testimonials. Request and contact client references with profiles similar to yours.

  • Set up extensive initial interviews with shortlisted candidates to directly evaluate their technical expertise, communication skills, problem-solving approach, experience with clients like you, and so on. Consider including your IT staff.

  • Request free demos, pilots, and trials to experience services firsthand before committing. Assess factors like system usability, response time, feature integration, and overall workflow.

  • Systematically compare proposals based on your defined selection criteria. Involve both IT staff and business stakeholders in the scoring process.

  • Carefully negotiate contract terms that allow the relationship to flexibly evolve as your needs change. Define clear metrics and SLAs to ensure accountability.New call-to-action

The Final Say: Top 5 Challenges When Hiring a Managed IT Services Team

There is one thing we can’t say enough, and that is to do your homework! Dedicated due diligence in selecting your IT services partner pays off with greater innovation, productivity, security, and agility over the long term.

If you need some assistance or expert opinions about managed IT service providers or office technology solutions, make sure to reach out to us. We’re here to give you peace of mind to help you win more business.

Marissa Olson

A true southerner from Atlanta, Georgia, Marissa has always had a strong passion for writing and storytelling. She moved out west in 2018 where she became an expert on all things business technology-related as the Content Producer at AIS. Coupled with her knowledge of SEO best practices, she's been integral in catapulting AIS to the digital forefront of the industry. In her free time, she enjoys sipping wine and hanging out with her rescue-dog, WIllow. Basically, she loves wine and dogs, but not whiny dogs.