Why “Do You Have IT?” Is the Wrong Way to Start an MSP Cold Call

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Starting An MSP Cold Call

Most MSPs struggle to find the right words when picking up the phone for a cold call. It’s awkward. It’s adrenaline-fueled. And it’s all too easy to blurt out the first question that comes to mind, such as: “Do you have IT support?” But according to Johnathan Schofield, Founder of Skofi and FindMyITPartner.com  this is not the way you want to start a conversation.

Drawing from years of outbound sales experience, Johnathan offers a refreshingly blunt perspective on why most cold calls fail before they even begin. In this interview, he breaks down why generic IT questions are the wrong entry point and how a more verticalized, problem-first approach is key to making real connections.

The Problem With Generic IT Questions

There’s a common trap MSPs fall into when cold calling: leading with an open-ended question that feels random to the person on the other end of the phone. On the surface, it seems harmless. But to them, it can even feel oddly unwarranted, especially when they don’t know your motivation for asking.

As Johnathan Schofield puts it, “It is difficult to articulate what an MSP really does without becoming vague or overly general. When the first question you ask is about IT, you are starting with something the prospect already assumes is covered. It feels irrelevant and sometimes even intrusive.”

The misstep here isn’t just about topic choice. It’s about the emotional context. Cold calls are inherently delicate. You have just a few seconds to earn trust, and a broad question about IT can make prospects feel like they’re being probed without reason. Johnathan illustrates this clearly: “You cannot open a cold call with something broad like asking how they manage IT today. To a prospect, it is like a stranger suddenly asking about a sensitive part of their life. Their guard goes up immediately.”

Why MSPs Struggle With Outbound Messaging

If asking broad questions about IT is a dead-end, then the next logical step is to get more specific. But that’s exactly where many MSPs may hit a wall as well. Even those with strong service delivery often struggle to clearly articulate who they serve and why it matters. That lack of clarity likely shows up in every cold call, email, and LinkedIn message they send.

Schofield sees this all the time: “Most providers can tell you what they do, but very few can explain why their customers choose them. That lack of clarity changes who they call, how they message, and what triggers they try to pull. Without that foundation, the outreach falls flat.”

It’s not just a messaging problem. It’s a positioning problem. When your offer is too broad, your list becomes too big, and your message becomes too weak. Schofield adds, “When I ask an MSP who their ideal customer is, they say small businesses or professional services. That is too broad to create powerful outcomes in a cold conversation. You cannot talk to everyone at once and expect results.” The solution isn’t to invent a new pitch every time. It’s to zoom in far enough that your offer feels relevant to a real person with a real problem.

The Power of Specific, Vertical Pain Points

When you truly understand the specific problems your target market faces, you don’t have to ask them to explain it to you. Vertical pain points are what make the conversation feel justified, not forced. As Johnathan Schofield explains, “When you know the specific industry and the problem they struggle with, the entire conversation changes. In healthcare, for example, doctors often batch their patient notes until the end of the day. Helping them speed that up is a far better on-ramp than asking about IT support.”

These are the kinds of insights that signal credibility. They give the prospect a reason to stay on the line because you’ve just brought up something painfully familiar. Johnathan expands on this idea by saying, “Targeting a prospect with a problem you know they have creates instant credibility. It shows you understand their world before you have even talked to them. That opens the door to a deeper technology conversation.” The best part? You don’t need a decade of industry experience to apply this. You just need to start with problems instead of services.

Building Better Conversational On-Ramps

MSPs often default to talking about IT because it’s familiar. But familiarity doesn’t always convert. A better approach is to look for entry points that feel grounded in the prospect’s daily experience. Johnathan makes the case: “You must identify the on-ramp to the technology conversation. If you come out swinging from broad categories like cybersecurity or compliance, the odds of missing are high. Start with something specific and highly relevant to their day.”

That shift from “What do you do for IT?” to “Are your doctors spending an hour each night on patient notes?” might feel subtle, but it completely changes the temperature of the conversation. Schofield explains why that matters: “The goal is to demonstrate competence in their world before you ever talk about IT. When you hint that you have real value behind you, the prospect is far more willing to hear more. It becomes a natural transition.” In other words, the more relevant your opening, the less resistance you face.

Identifying the Real Decision-Maker

Getting the pitch right is only half the battle. The other half is making sure you’re saying it to the right person. In MSP outbound, decision-maker dynamics can vary wildly depending on the vertical. That’s why guessing based on job titles often leads you in the wrong direction.

Johnathan gives a clear example: “In healthcare practices, the doctor may own the business, but the office or practice manager often holds the keys. They keep the operation running and are more involved in decisions than people think. Knowing that saves you a lot of wasted effort.”

This changes not just who you target, but how you approach the entire conversation. For instance, Johnathan notes that “In manufacturing or logistics firms, the owner or CEO is usually far more involved. Going through a mid-level manager in those environments can be an uphill battle. It changes who you call and how you frame the first conversation.” Treating every cold call the same ignores the real-world power structure inside different types of businesses.

Reverse-engineering Your Buying Channels

Most MSPs build their go-to-market strategy around the wrong assumptions, especially when it comes to how buyers actually evaluate and select vendors. Schofield suggests a dead-simple fix: just ask. “One of my favorite questions to ask a customer is how they would replace their MSP if the current one disappeared tomorrow. The answers reveal exactly how they search, who they trust, and what their buying process looks like. It is a powerful way to reverse engineer the channel.”

What he’s found in response to that question is just as revealing. “Not once have I heard a customer say they would Google IT support in their area. Yet many MSPs spend money in channels their customers do not use. The easiest way to know where to invest is to ask.” Rather than guessing where attention lives, talk to real customers, understand their path to purchase, and build outreach methods that mirror it.

Why Consistency Is The Main Ingredient

It’s easy to write off cold calling after a few bad reps. The discomfort, the rejection, the awkward silences, it’s enough to make even experienced founders throw in the towel. But Johnathan Schofield argues that many MSPs have a consistency problem above all else. 

“If you are not giving at least an hour a day to business development, you do not have a sales motion. Most founders take a crack at cold outreach and then fall off because it feels uncomfortable. What they really lack is consistency.”

He’s not recommending you become a full-time salesperson. He suggests putting in enough work to build the muscle memory required to get better over time. “Your first cold call will feel unnatural, and you may even walk away thinking you never want to do it again. But every skill feels that way at the beginning. If you say you want to grow, you have to put in the time and effort to make it happen.”

Conclusion

Cold calling will never feel natural if you’re talking to the wrong person with the wrong messaging. But when you lead with relevance, know who you’re talking to, and stay consistent in your approach, the results will slowly compound.

Johnathan Schofield reminds us that outbound is less about magical phrases and more about meaningful structure. Skip the vague IT questions. Skip the spray and pray lists. And skip the channels your buyers don’t even use. Instead, study their workflow, find the real decision-maker, and build a system around habits that scale. The uncomfortable truth is that cold outreach will always feel clunky in the beginning. But that’s not a sign to stop. It’s a sign to increase reps so that you can get better.