I’ve had a lot of conversations with leaders who know their Managed Service Provider (MSP) relationship isn’t where it needs to be. They’re frustrated with slow response times, constant recurring issues, or a lack of real strategy. But even with all of that, the idea of switching MSPs still makes them nervous.
And I get it. Switching MSPs can feel like replacing the engine of a plane while you’re still flying it.
But here’s the truth I’ve seen over and over: staying with the wrong MSP is usually far riskier than switching to the right one.
You feel the pain every day—lost productivity, old problems resurfacing, delayed projects, and security concerns that never seem to get addressed. Those problems don’t magically get better on their own.
The good news? A managed service transition done right doesn’t have to be chaotic or stressful. In fact, it should feel calm, deliberate, and predictable.
Let me walk you through how to get there—and what I’ve learned makes the biggest difference.
Most MSP Switches Go Wrong for One Simple Reason
Let’s start with the blunt truth:
Most MSP transitions go sideways because the right questions never get asked—and the right information never gets collected.
Everyone is eager to jump in, “fix things," and make an impression. But without the right context, that enthusiasm just creates messes.
When I talk with customers, I tell them plainly:
“We have to take our time and make sure we ask all the right questions. That’s what lets us support your business efficiently. The homework matters.”
This part of the process isn’t glamorous, but it’s absolutely essential. If we rush discovery, we pay for it three times later—through confusion, surprises, and problems that could have been avoided.
The goal isn’t to transition fast. It’s to transition correctly.
Start With Listening
You’ve probably had a provider claim they “listen," and then immediately open with a list of tools they want to install. That’s not listening.
When I sit down with a client, my first job is understanding:
- Why you want to make a change now
- What's working today that we shouldn't disrupt
- What's been frustrating you
- Where you're feeling risk
- What "better" looks like in six months
- How your business actually operates day-to-day
This isn’t an audit—it’s context. The kind of context that saves us from pulling the wrong lever too quickly.
The more we understand your business, the smoother everything else goes.
And yes, sometimes I do ask a lot of questions. But that’s because I’d rather measure twice and cut once, instead of the reverse.
It’s O.K. if The Process is Boring! That’s the Goal.
There’s this idea that MSP transitions should be fast, exciting, or dramatic.
Honestly? If a transition feels dramatic, something is wrong.
The most successful transitions I’ve led have been—and I mean this in the best way possible—boring.
Boring means:
- No surprises
- No scrambling
- No “emergency” meetings
- No guessing
- And no wondering who owns what
A good MSP transition is predictable, clean, and organized. A few principles make that possible:
1. Clear, written plan
Milestones, owners, dates. Everyone knows what’s happening and why.
2. Smooth credential and documentation transfer
No mystery passwords. No “tribal knowledge.” No hoping someone remembers how something was configured five years ago.
3. Defined roles
During the cutover, everyone has a job. No overlapping responsibilities or decisions made on the fly.
4. Realistic pacing
Push when it’s smart, slow down where it’s risky. When an MSP transition is done right, it honestly shouldn’t feel like a big event. That’s the whole point.
You Can’t Treat Security as a “Later” Problem
Every MSP transition creates a moment where things are shifting—access rights, administrative roles, monitoring, backups. That movement can either increase your security or expose you.
Security can’t be something we “deal with later.” It has to be part of the transition from day one.
Here’s what I want visibility into immediately:
- Who has privileged access today
- How backups work and whether they’ve been tested
- What endpoint protection looks like
- Identity and MFA posture
- Any obvious vulnerabilities in public‑facing systems
- What monitoring is—or isn’t—catching
Handled well, a transition is actually a great opportunity to strengthen security quickly. Handled poorly? You inherit a problem you may not even know you have.
The Customer Success Hand-Off: Where the Long-Term Value Happens
Once the transition is complete and the environment is stable, the ownership of the relationship shifts—intentionally and for good reason.
This is where your Customer Success Manager (CSM) becomes the heartbeat of the partnership.
After onboarding, the CSM steps in to:
- Meet with you quarterly
- Track performance and satisfaction
- Review what’s working and what’s not
- Ensure the service experience stays strong
- Keep you on a meaningful technology roadmap
- Align decisions with long-term business goals
This shift isn’t about “passing you off.” It’s about giving you someone whose entire role is making sure you’re supported, heard, and progressing.
It also ensures the relationship becomes exactly what it should be: a partnership, not a vendor contract.
Your sales rep, your solutions architect, and your onboarding team set the stage. The CSM builds the long-term relationship and helps your business grow with the technology.
Communicate Like You’re Managing Change (Because You Are)
Even if most employees don’t care which MSP you use, they definitely care whether their systems work. A little communication goes a long way.
I like keeping it simple:
- What’s happening
- When it’s happening
- What they should expect
- How to get help
Employees don’t need a novel. Just clarity.
What Should Happen in the First 90 Days
If a transition is healthy, it will follow a predictable rhythm.
Days 1–30: Get control and stabilize
- Transfer access and documentation
- Validate backups, MFA, endpoint protection
- Review high‑risk items
- Establish predictable support response
Days 31–60: Remove friction and reduce noise
- Fix recurring issues
- Tighten security gaps
- Create consistent communication rhythms
- Deliver a few “quick wins”
Days 61–90: Plan the next 12–18 months
- Strategic roadmap
- Budget alignment
- Clear success measures
- Governance and communication plan
By this point, you should feel like things are running better and heading in the right direction.
Staying With the Wrong MSP Is Often the Bigger Risk
Leaders sometimes tolerate poor support because “switching seems harder.” But the cost of staying adds up:
- Operational slowdowns
- Security exposure
- Burned-out IT staff
- Projects that never happen
- Business goals that get delayed
Doing nothing is still a decision—it just rarely leads somewhere good.
The Bottom Line
Switching MSPs shouldn’t be scary. It shouldn’t cause chaos. And it shouldn’t keep you up at night.
When the process is handled with discipline, communication, and a clear focus on your business goals, a transition can feel surprisingly smooth—and even energizing.
For more than 20 years, Matt VanderPlas has helped organizations bring clarity and confidence to their technology environments—especially when they’re navigating big transitions or projects. As a Regional ITSG Sales Specialist at Loffler Companies, he supports clients across Minnesota, Iowa, Wisconsin, Nebraska, and the Dakotas, working with leaders who want an IT partner that brings stability, transparency, and long‑term alignment. Much of Matt’s work centers on strengthening the core elements of an organization’s IT foundation. From improving Microsoft 365 hygiene to addressing essentials like MFA, patching, backups, and endpoint protection, he focuses on identifying risks early, simplifying the complex, and helping teams move from reactive chaos to proactive confidence. These conversations often become the starting point for building a more resilient IT strategy—especially for organizations evaluating or transitioning to a new Managed IT partner. His work also extends into Loffler‑managed Unified Communications and Physical Security solutions, areas that complement a strong IT foundation by supporting better communication, safer workplaces, and consistent operational performance. These pieces fit together to give organizations a fuller, more dependable technology environment. Away from work, Matt’s happiest around family—BBQing on the weekends, cheering on his kids as they dive into the activities they love, and finding time with his wife to enjoy a great dinner together. Those moments keep him grounded and remind him why strong, worry‑free technology matters: it lets people focus on what matters most.
