MSP To The Future
MSP To The Future
Jeanne DeWitt
The Top 10 Prospecting Mistakes MSPs Make
11 minutes Posted Jun 22, 2026 at 10:15 am.
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Show notes

Most MSPs think prospecting is the hard part.


It’s not.


The hard part is realizing that sometimes the reason prospecting isn’t working… has nothing to do with the market, the economy, or the people you’re calling.


It has everything to do with small mistakes happening inside the conversation that most salespeople don’t even realize they’re making.


And here’s the interesting part…


These mistakes show up everywhere — in emails, in cold calls, in networking conversations, and even in follow-ups.


They quietly shut down opportunities before the prospect ever has a chance to say yes.


In this episode of MSP To The Future, I’m breaking down the 10 biggest prospecting mistakes, inspired by the work of Wendy Weiss — often called The Queen of Cold Calling.


And I’ll show you how these mistakes show up specifically in the MSP world… and how fixing just one or two of them can completely change your sales conversations.


Because prospecting isn’t about pressure.


It’s about starting better conversations.


Hit play… and let’s take your MSP to the future.