The Undercover Boss: Lessons for MSP Leaders!

When Was the Last Time You Sat on the Support Desk?

The other day, I caught a bit of Undercover Boss during my lunch break. If you haven’t seen it, the premise is simple: CEOs and business owners go undercover in their own organisations to experience life on the frontlines. What often follows is an eye-opening journey, as these leaders discover challenges, frustrations, and, sometimes, incredible stories of dedication from their employees.

It got me thinking: When was the last time MSP leaders actually sat on the support desk and took calls?

The Beating Heart of Any MSP

There’s a case to be made that the support team is the beating heart of an MSP. Why? Because everything flows through them:

1. They’re the First Line of Defence: When a client has an issue, the support desk is the first port of call. They’re not just solving technical problems—they’re calming frustrations, managing expectations, and protecting your reputation.
2. They Represent Your Brand: For many clients, the support team is your MSP. It doesn’t matter how great your tech stack is or how innovative your solutions are—if a client’s interaction with the support desk is poor, their perception of your business suffers.
3. They Keep the Wheels Turning: From troubleshooting to escalating complex issues, the support desk ensures that your clients’ businesses can keep running smoothly. Without them, everything grinds to a halt.
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So yes, the support team is the heart of an MSP. And like any heart, it needs care, attention, and understanding to keep performing at its best.

Why Leaders Need to Stay Connected

It’s easy for leaders to lose touch with the day-to-day realities of their teams and clients. As MSPs grow, the demands on leadership shift toward strategy, sales, and operations. But here’s the problem: when you lose sight of what’s happening on the ground, you also lose sight of your people and your clients.

Relying solely on performance metrics can still fail to tell the whole story. Of course, they're a valuable tool, but they only provide a snapshot of what’s happening, not why it’s happening or how it feels to the people experiencing it. Sometimes, the numbers look great on paper, but the reality on the ground is very different. A support team might be hitting SLAs, but are they stretched too thin? Are they cutting corners to meet deadlines? Are clients being told their issues are resolved when, in truth, the underlying problem isn't?

This is why staying connected to the frontline is so important. Metrics are a starting point, but they need to be balanced with qualitative insights to truly understand how your MSP is performing—not just in terms of numbers, but in terms of people, culture, and client experience.

At the end of the day, great service isn’t just about what the reports say—it’s about what your clients feel and what your team experiences. That’s the real story, and it’s one every MSP leader needs to hear.

The Lessons from Undercover Boss

As part of my daily activities running the UK’s only recruitment agency dedicated purely to MSPs, I speak to a lot of MSP leaders. Whenever I evaluate a potential new client, the first thing I do is call their support line. It’s my way of getting a feel for how they operate at the coalface—where their culture and approach to customer service are most visible.

Unfortunately, a surprising number of my calls either go straight to an answering service or, worse, go unanswered altogether. For me, that’s a concern.

Why? Because your support desk is often the first true reflection of your business—for both clients and employees. It’s where the promises you make to clients meet the reality of day-to-day operations. If that first interaction doesn’t inspire confidence, what does that say about your business?

This is why it’s so important for leaders to stay connected to the frontline. Sitting on the support desk—even for a day—offers valuable insights that metrics alone can’t provide:

• Understanding Your Team’s Challenges: Are the tools they’re using effective? Are they overloaded with tickets? What are the pain points that make their job harder than it needs to be?
• Seeing the Client Experience Firsthand: How long are clients waiting for support? Are their issues resolved quickly? Are they happy—or are they frustrated?
• Building Empathy and Trust: When leaders take the time to understand what their teams and clients go through, it fosters trust and demonstrates that they care.
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Practical Ways to Stay Connected

You don’t need to go “undercover” to stay in touch with your support team and clients. Here are a few ideas:

1. Shadow the Support Desk: Spend a few hours a month sitting with your support team. Listen in on calls, observe ticket handling, and ask questions. Hey, even make the coffees as a sign of appreciation!
2. Hold Regular Team Check-Ins: Create opportunities for your support team to share feedback, challenges, and ideas directly with leadership.
3. Engage with Clients: Join client review meetings or check in directly with key accounts to understand their experience and expectations.
4. Test the Support Line: Call your own support line as if you were a client. See what the experience feels like from the other side.
5. Celebrate the Support Team’s Wins: Highlight their successes in company meetings or newsletters. Recognising their hard work boosts morale and reinforces their value to the business.
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The Bottom Line

MSPs thrive when their support teams are empowered, appreciated, and equipped to deliver exceptional service. And MSP leaders are at their best when they stay connected to the people and clients who make their business tick.

So, when was the last time you sat on the support desk? If it’s been a while, maybe it’s time to grab a headset and reconnect with the beating heart of your MSP. Because at the end of the day, your clients—and your people—deserve a leader who walks the talk.

Let's Talk

As an MSP leader, staying connected to your support desk and clients is crucial—but so is building the right team to uphold your standards. We help MSPs hire people who not only solve problems but also strengthen your culture and client relationships. Let’s talk.