This post follows on from last week's entitled: "In-House vs Outsourced IT: A Strategic Choice for Midsize Businesses"
So, you’ve decided to outsource your IT. The next challenge is choosing the right Managed Service Provider (MSP). It sounds straightforward—until you realise the market is crowded, the service levels vary dramatically, and glossy brochures rarely reveal the full picture. For directors of mid-sized businesses, selecting the wrong partner can mean wasted investment, constant headaches, or even security risks.
This article explores the key things to look for when selecting a Managed Service Provider, balancing technical requirements with the less tangible qualities that ultimately define whether the partnership will succeed.
Understanding the Technical Fit
The first thing any business considers is whether the MSP has the right technical capability. At a basic level, this includes the technology stack they support. If your systems run heavily on Microsoft 365, Azure, or AWS, the provider needs proven expertise in those platforms. Similarly, if your business uses specialist software—finance systems, ERP platforms, or industry-specific tools—the MSP must demonstrate competence in maintaining, securing, and integrating those systems.
It is also worth looking at the provider’s client base and typical company size. An MSP focused on small businesses may not be prepared for the complexity of a 400-employee organisation with multiple sites. Conversely, one serving only very large enterprises might lack the agility and personal attention that mid-sized businesses often value. The sweet spot is usually an MSP experienced in companies like yours—large enough to offer full capability, but small enough to care about each client.
And then there’s scale. Your business may be growing. A good Managed Service Provider should handle not just your current needs but also what the next three to five years might bring.
Service Levels and Responsiveness
Beyond technology, the way an MSP structures its service delivery is critical. Directors need clarity on response times, escalation procedures, and service availability. Around-the-clock monitoring and support are increasingly standard, but the devil is in the detail: how quickly will someone respond to a critical outage? How often will they proactively check for security risks? Will you have a named account manager who understands your business, or are you just another ticket number in a support queue?
A reliable MSP sets out clear expectations through Service Level Agreements (SLAs). These agreements provide measurable standards for uptime, response times, and issue resolution. But more importantly, a professional provider treats those SLAs as a baseline—not the limit—of what good service looks like.
Security and Compliance Confidence
IT outsourcing naturally raises questions about data protection and security. A strong Managed Service Provider should hold recognised security certifications (such as ISO27001) and comply with relevant regulations such as GDPR. Beyond certifications, though, directors should ask how security is embedded in their day-to-day operations. Do they carry out regular security audits? How do they handle data breaches if they occur?
Equally, the MSP’s approach to backup and disaster recovery matters. Many companies discover too late that their backups were incomplete, out of date, or slow to restore. A competent provider will offer clarity here, with recovery times and testing schedules clearly defined.
The Intangibles: Trust, Integrity, and Culture Fit
While technical capability is non-negotiable, the softer qualities often decide whether the relationship thrives. Trust sits at the top of that list. This is not simply about handing over your systems; it’s about relying on the MSP to be transparent when problems arise, to own mistakes rather than deflect them, and to give honest advice even when it doesn’t lead to a bigger contract.
Directors should look for signs of integrity during the selection process. Does the MSP oversell its capabilities, or are they upfront about what falls outside their scope? Do they provide clear pricing, or does every extra service come with hidden fees? A provider that communicates openly, sets realistic expectations, and takes responsibility when things go wrong will save you more headaches than the flashiest proposal ever could.
Culture fit also plays a role. The best MSP relationships feel like an extension of your internal team rather than a distant supplier. They take time to understand your business goals, not just your IT systems. They collaborate with your staff rather than treating them as obstacles. If the working relationship feels adversarial during onboarding, it rarely improves over time.
Many companies lean towards local MSPs. Whilst not essential, as a good MSP can provide excellent service from anywhere in the world, this may be a factor to consider. Does the MSP have a location or field engineers in your region? Do they understand your region?
Financial Stability and Longevity
It may feel obvious, but many businesses skip over the financial health of the provider. A Managed Service Provider in financial difficulty brings risk—staff turnover, service disruption, or even sudden closure. Directors should check the MSP’s track record, years in business, and client retention rates. A partner who has served companies for a decade or more, growing steadily along the way, offers reassurance that they will still be around when you need them most.
References and Reputation
Speaking to existing clients often reveals more than any sales presentation. Ask for references from companies of similar size or industry. How responsive is the MSP day-to-day? Do they deliver on their promises? What happens when things go wrong? A provider with a loyal, long-standing client base usually delivers consistently behind the scenes.
Online reviews and case studies also help, though direct conversations carry more weight. A reputable MSP will happily connect you with current clients for a candid discussion.
entrustIT have a variety of case studies - take a look here
Final Thoughts
Selecting the right Managed Service Provider is as much about trust and culture as it is about technology and cost. A partner who understands your business, communicates openly, and delivers on their promises will free your leadership team to focus on growth and strategy rather than IT firefighting.
The goal is a long-term relationship built on expertise, transparency, and shared commitment to your success. Get that right, and outsourcing IT stops being a risk to manage and becomes a genuine competitive advantage.
Discover why so many mid-sized businesses have chosen entrustIT for their IT outsourcing - view our case studies