Choosing the right IT Managed Service Provider (MSP) is more than just an administrative decision—it’s about forging a partnership that can elevate your business to new levels of efficiency and innovation.

At the current pace of innovation, technology evolves fast, increasingly becoming more sophisticated and valuable at the same time. Despite this ever-growing complexity, modern businesses still need to leverage technology in order to stay competitive and thrive. In a survey by Deloitte, 85 percent of small and medium-sized businesses (SMBs) confirmed tech’s importance in business performance. 

Traditionally, an in-house IT department has always been the go-to solution for supporting enterprise-level digital infrastructures. But nowadays, even that isn’t cutting it.

  • For one, retaining an IT team is becoming way too expensive; that is if you can find qualified candidates to hire in the first place. The average IT specialist annual base salary in Canada is a whopping C$65,777 (as of April 2024), without counting employee welfare expenses.
  • Second, most internal IT departments simply can’t keep up with technical innovations and challenges. Clearly, this is not a sustainable tech support approach for companies with ambitious IT goals. 

Many organizations are now turning to managed services to meet their unique IT requirements. IT outsourcing has evolved to an all-rounded solution where you only need one service provider to cover the entire IT infrastructure. This makes IT partnerships vital in maintaining technical and business performance. The big question is, how to choose a managed service provider (MSP)? 

Hiring the right IT partner for any business is a weighty decision. Here’s everything you need to know when making your pick: 

What is an IT Managed Service Provider?

An IT Managed Service Provider (MSP) is essentially your IT support team externalized. MSPs handle your IT operations externally, providing a breadth of services under a predictable pricing model. Commonly, MSPs offer network, application, system management and more—think of them as your IT guardians.

Core Services Typically Offered by MSPs

  • Network Services: Managing and monitoring VPNs, bandwidth, and firewalls
  • System Management: Handling IT infrastructure such as servers and storage devices
  • Cybersecurity: Protecting data through continuous security monitoring and response
  • Support and Helpdesk: Offering ongoing support and troubleshooting
  • Cloud Services and Management: Facilitating cloud infrastructure management, including migration and maintenance

Benefits of Utilizing an MSP

Here’s why partnering with a reputable MSP is more than just a cost-effective move:

  • Scalability: MSPs can scale services to match your growth.
  • Reduction in Downtime: Proactive maintenance means less unexpected downtime.
  • Expertise on Tap: Gain access to top-notch IT experts without the full-time salary tab.
  • Compliance and Security: Stay up-to-date with the latest in compliance regulations and cybersecurity threats.

Assessing Your IT Needs

Before diving headlong into the sea of MSP options available, you’ve got to start with a comprehensive assessment of what your business currently has and where it aims to be. This phase is crucial as it shapes the criteria that will guide your selection of an MSP. Understanding your IT requirements isn’t just about covering your immediate needs; it’s about paving the way for future innovation and growth.

Identifying Your Business Requirements

First things first, sketch out the blueprint of your business operations. Which processes are dependent on IT? How does technology drive these processes? And most importantly, what are the pain points? Answering these questions will give you a clear picture of what services you require from an MSP.

Example: If real-time data access and collaboration between global teams are vital to your operations, you’ll prioritise MSPs that offer robust cloud solutions and real-time collaboration tools.

Evaluating Your Current IT Infrastructure

Take a hard look at your current setup. This includes your hardware, software, network configurations, and any bespoke systems you might be using. Evaluating your current infrastructure helps in identifying gaps that need to be filled.

  1. Hardware Assessment: List all physical devices and their capacities.
  2. Software Inventory: Catalogue applications, user numbers, and purposes.
  3. Network Efficiency Test: Check for any bottlenecks or security loopholes.
  4. System Compatibility Check: Ensure new solutions will integrate seamlessly.

This stage often reveals whether it’s time for a complete overhaul, an upgrade, or a simple tweak in your IT environment.

Future-Proofing: Planning for Growth and Scalability

Think long-term. How easily can your IT set-up scale to keep pace with your business growth? Here’s where your MSP can play a pivotal role. You need a provider that not only fits your current situation but can also expand swiftly as your business grows.

  • What growth do you anticipate in the next 5-10 years?
  • Can the MSP handle significant increases in demand?
  • Do they offer flexible services that adapt to changing needs?

MSPs should not just respond to changes; they should anticipate and prepare you for them. Selecting a provider that offers scalability ensures that you’re not just working for today, but are set for tomorrow.

Before moving to the criteria on how to choose your MSP, ensuring that your current and future IT needs are well understood and documented is essential. This prepares you for a more informed and focused search for the right MSP partnership.

Criteria for Choosing an MSP

Selecting the right IT Managed Service Provider (MSP) involves more than just understanding your own needs. It’s crucial to evaluate potential providers based on several key criteria that align with your business objectives and operational requirements.

Here’s a detailed breakdown of the essential factors you should consider when choosing your MSP.

Expertise and Specializations

To start with, assess the technical proficiency and industry expertise of potential MSPs. It’s vital that they have a proven track record in handling businesses similar to yours or that possess specializations that resonate with your specific IT demands.

  • Industry Experience: Look for MSPs that have worked with other companies in your sector and understand your industry’s regulatory and compliance requirements.
  • Technical Certifications: Check if the MSP holds any relevant certifications from reputable institutions or technology vendors, which serve as a testament to their skill level.
Specialty Area Description Ideal for
Cloud Services Management and support of cloud platforms, migration, and integration. Enterprises looking to scale or transition to cloud.
Cybersecurity Comprehensive security measures including monitoring, response, and prevention. Businesses handling sensitive data.
Networking Setup, maintenance, and optimization of business networks. Companies needing robust connectivity solutions.
Data Management and Analytics Management, storage, and analysis of large data sets. Data-driven companies seeking insights from big data.
Communications and Collaboration Solutions for improving internal and external communications. Organizations with remote or hybrid workforces.
Infrastructure Management Overseeing and maintaining physical and virtual infrastructure components. Firms with heavy reliance on IT infrastructure.
Support and Helpdesk Ongoing support for IT-related issues, providing helpdesk services. Businesses requiring constant IT maintenance.
Regulatory Compliance Ensuring that IT practices adhere to governmental and industry-specific regulations. Highly-regulated sectors like finance and healthcare.

Compliance and Security Standards

Given the airtight regulations governing data in many industries, ensuring that your MSP adheres to the highest compliance and security standards is non-negotiable.

  • Data Protection: Your MSP must offer robust data security measures in line with industry standards and possibly beyond.
  • Regulatory Compliance: Make sure they have a solid understanding of the specific compliance requirements affecting your industry and how to address them.

Support and Availability

The availability of your MSP for resolving technical issues is paramount. Their level of support can significantly affect your business efficiency and downtime.

  • Service Level Agreements (SLAs): Evaluate their SLAs to ensure they match your expectations regarding response times and issue resolution.
  • 24/7 Support: Consider whether the MSP provides round-the-clock support, which is especially crucial if your operations are global or online continuously.

Customization Capabilities

The ability of an MSP to tailor services to fit your unique needs is another critical criterion. A one-size-fits-all approach rarely works in the nuanced terrain of business IT.

  • Flexibility: Does the MSP offer flexible service options, such as scalable solutions that grow with your company?
  • Custom Solutions: Investigate whether they are willing to develop custom solutions that specifically address your business challenges.

Choosing the right MSP involves a careful balance of these criteria aligned with your specific business needs. It requires due diligence and a strategic approach but selecting the correct MSP partner can result in a robust IT foundation that propels your business forward efficiently and securely.

Remember, the goal is to build a partnership that supports not only your current operations but also anticipates and facilitates future growth and innovation.

Comparing Potential MSPs

Once you’ve assessed your needs and understand what to look for, the next step involves comparing potential IT Managed Service Providers (MSPs). This stage is critical in ensuring that you select an MSP that best fits your business objectives and requirements. Here’s a structured approach to effectively compare your options and make an informed decision.

Gathering a Shortlist of Providers

Start by creating a shortlist of potential MSPs that align with your defined criteria. This can involve:

  • Asking for Recommendations: Reach out to industry peers or consult professional networks for trusted recommendations.
  • Researching Online: Utilize search engines and visit official websites to gather information about services offered, company reputation, client testimonials, and case studies.

Key Factors to Compare

Once you have a list of potential MSPs, compare them based on several key aspects to narrow down your choices:

  1. Experience and Expertise: How long has the MSP been in business? What expertise do they bring specifically to your industry?
  2. Services Offered: Do they provide all the services you need? Are there any additional services that could benefit your business not initially considered?
  3. Cost Structure: Understand their fee structure. Is it flexible? Does it fit within your budget constraints?
  4. Technology and Tools: What kind of technology do they use? Is their infrastructure modern and capable of handling your needs?
  5. Security Measures and Compliance: Verify their compliance with relevant regulations and their cybersecurity measures.
  6. Customer Reviews and Feedback: Look at feedback from current and previous clients to gauge satisfaction and service quality.

Evaluating Customer Reviews and Testimonials

Customer reviews can provide invaluable insights into the reliability and effectiveness of an MSP. They offer a glimpse into how the MSP handles real-world problems and client relationships. Consider the following:

  • Consistency in Positive Feedback: Are there recurring themes of praise or concern?
  • Response to Criticism: How does the MSP handle criticism or complaints?
  • Long-term Client Relationships: Longevity in client relationships can be a strong indicator of reliable and satisfactory service.

By carefully evaluating each potential MSP against these detailed factors, you can better understand which provider will best align with your business strategies, culture, and technological needs.

This comparative analysis is key to choosing not just a service provider but a partner who will contribute to your business’s growth and adaptability in the rapidly evolving tech landscape.

Making the Decision

After in-depth research and comparing various MSPs, the decision-making stage arrives. This phase is about synthesizing the data collected, aligning it with your business goals, and finally selecting an MSP that stands out as the best match for your needs. Here’s how to seal the deal with confidence and ensure your chosen MSP can deliver on your expectations.

Conducting Trials or Pilot Programs

Before committing to a long-term contract, consider requesting a trial period or pilot program with the MSP. This allows you to:

  • Assess Compatibility: Test how well the MSP’s services integrate with your operations.
  • Evaluate Performance: Monitor the MSP’s effectiveness in handling real scenarios and challenges your business faces.
  • Review Support and Responsiveness: Get a feel for their customer support and responsiveness to issues.

Pilot programs are pivotal in verifying that the MSP can deliver not just in theory but in actual practice.

Reviewing Contracts and Service Level Agreements (SLAs)

Carefully review any contracts or SLAs presented by the MSP. Key areas to focus on include:

  • Service Details: Ensure the services promised are clearly outlined.
  • Performance Metrics: Check that there are measurable performance indicators and they align with your expectations.
  • Cancellation and Renewal Terms: Understand the terms concerning contract termination and renewal options.
  • Pricing and Extra Fees: Examine the pricing structure and any potential fees for additional services or overages.

It’s often wise to have legal counsel review the details to avoid any unfavourable terms that could impact your business in the long run.

Negotiating Terms and Pricing

Negotiation is an essential step in the MSP selection process. Don’t hesitate to:

  • Discuss Custom Needs: Talk about any specific requirements you have that could modify the standard offerings.
  • Request Flexibility: Seek flexible terms that can adapt to your business’s changing needs.
  • Seek Competitive Pricing: Ensure the pricing is competitive and provides value considering the quality and breadth of services offered.

Negotiating transparently can lead to better service conditions and a stronger partnership foundation.

Final Selection and Partnership Initiation

After the evaluations and negotiations, make your final selection based on comprehensive analysis and intuition about the partnership potential. Upon deciding on your MSP:

  • Communicate Clearly: Let them know why you chose them and discuss any immediate priorities and expectations.
  • Initiate Onboarding: Begin the onboarding process to integrate the MSP’s services with your operations.
  • Set Milestones: Establish early milestones to assess service effectiveness and make adjustments as needed.

Selecting the right MSP is about more than securing IT services; it’s about choosing a partner that will drive technological innovation and operational efficiency, propelling your business toward its strategic objectives. W

ith a thoughtful approach and careful considerations at each step—from piloting to final negotiations—you can align with an MSP that truly complements and enhances your business dynamics.

Implementing Your Chosen MSP

After diligently selecting an IT Managed Service Provider (MSP) that aligns with your business’s needs and goals, the implementation phase commences. This crucial step involves integrating the MSP’s services into your existing operations, establishing effective communication channels, and setting the stage for a successful long-term partnership.

Here’s how to ensure a smooth transition and implementation of your chosen MSP.

Transitioning to Your New MSP

Transitioning IT services to a new provider is a delicate task that requires meticulous planning and coordination. Here’s a roadmap to ensure a smooth transition:

  1. Develop a Detailed Transition Plan: Collaborate with your MSP to create a comprehensive plan that outlines every step of the process, including timelines, responsibilities, and expected hurdles.
  2. Set Up a Transition Team: Assign a dedicated team comprised of members from both your staff and the MSP’s staff. This team will oversee the transition operations to ensure that objectives and timelines are met.
  3. Data and Asset Transfer: Securely transfer all necessary data and assets to the MSP. This process should be carefully managed to protect sensitive information and ensure no data loss.
  4. Infrastructure Integration: Integrate your existing systems and infrastructure with the MSP’s technologies. Ensuring compatibility and functionality during this phase is critical for smooth operations.

Setting Expectations and Communication Channels

Clear expectations and open lines of communication are foundational to any successful MSP relationship.

  • Establish Clear Performance Metrics: Define and agree on performance metrics and regular reporting structures. These should align with the goals set out during the MSP selection phase.
  • Regular Meetings and Updates: Schedule regular meetings and updates to review performance, discuss issues, and align on future initiatives. This helps in maintaining transparency and fosters a collaborative environment.
  • Feedback Mechanisms: Implement effective mechanisms for feedback, allowing both parties to express concerns and suggestions openly.

Regular Review and Feedback Mechanisms

To adapt and evolve with the changing dynamics of your business and technology landscapes, establish ongoing review and feedback mechanisms:

  • Periodic Performance Reviews: Conduct regular assessments based on the agreed performance metrics to evaluate the MSP’s impact on your business.
  • Adaptation to Changes: Ensure there is flexibility in the service agreement to adapt to both technological advancements and shifts in business strategy.
  • Continual Improvement Process: Encourage a culture of continual improvement by regularly soliciting feedback from end-users and stakeholders, and discussing these insights with your MSP.

Final Thoughts

The implementation of your chosen MSP is not a set-it-and-forget-it affair. It requires active management and engagement to harness the full potential of your partnership. As you progress:

  • Monitor and Measure: Keep a keen eye on the service delivery and its impact on your business operations. Are the services meeting the agreed-upon KPIs? Is there a noticeable improvement in efficiency or productivity?
  • Stay Engaged: Maintain a proactive engagement with your MSP. Participate in strategy sessions and be open to adopting new solutions or technologies recommended by your MSP that may enhance your business capabilities.

Implementing an MSP is a strategic move designed to stabilize and grow your business’s technological backbone.

By following these outlined steps, you are setting the foundation for a robust partnership that can evolve with your business, supporting and propelling your growth strategies in today’s competitive landscape.


How long should I trial an MSP before fully committing?

Typically, a trial period of 3 to 6 months allows sufficient time to evaluate an MSP’s effectiveness in meeting your specific business needs. This period should provide insights into their responsiveness, quality of service, and operational compatibility with your systems.

What are some red flags to watch out for with potential MSPs?

Beware of MSPs that offer vague service details, lack transparent pricing structures, or show inflexibility in accommodating your business needs. Additionally, insufficient communication or delayed responses during the initial interactions can indicate potential service issues down the line.

How often should I re-evaluate my MSP choices?

It’s wise to conduct a formal review of your MSP’s performance annually, though more frequent reviews might be necessary if your business is undergoing significant changes or expansion. These evaluations ensure that your MSP continually aligns with your evolving business needs and maintains high service standards.

What are the typical pitfalls in MSP contracts I should avoid?

Look out for long-term contracts with rigid terms, hidden fees, or clauses that limit your ability to switch providers if you’re dissatisfied with the services. Always have legal experts review the agreements to ensure they favor mutual growth and flexibility.

Can small businesses benefit from MSPs the same way large enterprises do?

Absolutely, small businesses stand to gain significantly from MSPs, often even more so than larger corporations. MSPs can provide small businesses with access to expertise, technology, and infrastructure that would typically be cost-prohibitive to manage in-house, allowing them to stay competitive and agile in the marketplace.

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Your business is in capable hands with Softlanding’s managed IT services team.

We’ve been in the IT business for over two decades, during which time we’ve earned Microsoft-certified Gold Partner status along with other appreciation awards and achievements.

Get in touch and end your MSP search with Softlanding today.

Helpful Resources

To further aid in your journey of selecting and integrating an IT Managed Service Provider (MSP), here are some helpful resources. These links and tools will provide additional insights and support to ensure you make the best possible decision tailored to your business needs.

  1. MSP Comparison Tools

  2. Guides on IT Infrastructure Assessment

  3. Directories of Certified IT Managed Service Providers
    • Microsoft Partner Directory: A directory where you can search for Microsoft-certified IT service providers, ensuring they meet high standards of service and support.
  4. Forums and Community Discussions
    • Spiceworks: A dynamic community forum for IT pros, offering user-generated reviews, advice, and shared experiences on various MSPs.
Written By:


Softlanding is a long-established IT services provider of transformation, professional services and managed IT services that helps organizations boost innovation and drive business value. We are a multi-award-winning Microsoft Gold Partner with 13 Gold Competencies and we use our experience and expertise to be a trusted advisor to our clients. Headquartered in Vancouver, BC, we have staff and offices in Toronto, Montreal and Calgary to serve clients across Canada.

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