The Four Biggest Roadblocks To Selling More

Let me tell you something most MSPs don’t want to hear. The biggest thing standing between you and more sales is not your competitor. It’s not the economy. It’s not pricing. It’s your status quo.

I’m saying that with love because I’ve been there. When I was helping build our seven figure MSP, I experienced it firsthand. Something would work beautifully and I’d think: this is it, I’ve cracked the code! Then it just stopped working. And when it stopped, I had two choices: defend it or change it.

This episode is inspired by someone I respect deeply in the world of sales: Wendy Weiss, known as the Queen of Cold Calling. She’s trained thousands of sales professionals, and one of her core beliefs is that the biggest enemy to sales is the status quo. Most people think that refers to prospects who don’t want to change. And that’s true. But the same rule applies to us.

1. Repeating the Same Actions and Expecting Different Results

MSPs love to complain that prospects resist change. They don’t want to switch providers. They don’t want to move to the cloud. They’re comfortable where they are. But here’s the irony: you’re doing the exact same thing.

You’re sending the same proposals. You’re saying the same lines. You’re posting the same content. You’re going to the same networking groups. You’re following up the same way. And when it doesn’t produce consistent appointments, you say: “Well, it should be working.”

Sales doesn’t care about what should work. Sales cares about what does work. If what you’re doing isn’t producing appointments, it’s not working. Period. I had to learn that lesson myself. Instead of defending what used to work, I adjusted. Most MSPs defend their habits because they’re comfortable with them. But comfort does not grow revenue.

So here’s the question: are you protecting your comfort or are you protecting your growth?

2. Not Doing the Homework

Some prospects are better than others. Period. Yet I watch MSPs spend months courting businesses that were never going to buy. Instead of qualifying them, they just sit back and hope.

What specifically makes a prospect qualified for you? Do you even know? Is it their revenue range? Their industry? Compliance requirements? Cloud readiness? Geography?

When I helped build our MSP, we learned very clearly who fit our model and who didn’t. We focused on disaster prone businesses because we were cloud focused. We focused on businesses that needed and valued uptime; businesses that understood risk. When we aimed at the right targets, sales became so much easier.

A lot of MSPs out there are exhausted. Not because selling is hard, but because they’re chasing the wrong people. If a prospect doesn’t meet your parameters, disqualify them and move on!

3. Expecting Instant Results

Selling is your number one priority, but buying is not your prospect’s number one priority. Let that sink in.

You’re thinking about your pipeline. Your prospect is thinking about payroll, operations, hiring, supply chain issues, family stress. Switching MSPs feels risky and disruptive to them. You can’t expect a yes after one meeting.

Selling is a process. Some cycles might be 30 days. Some might be six months. Some might even stretch past a year. Too many MSPs follow up once or twice, decide the prospect isn’t interested, and stop. But they weren’t uninterested; they just weren’t ready. There’s a big difference between those two.

When I used telemarketing in my MSP, we had a structured follow up. Multiple touches. Multiple conversations. Persistence without aggression. You don’t need to be aggressive; you need to be steady. Silence does not mean no. It often means not now.

4. Letting Fear and Preconceived Ideas Stop You

“I don’t want to be pushy.” I hear that from MSPs constantly. But what does pushy even mean? The only definition that matters is your prospect’s definition. And you can’t read their mind.

So what happens? Fear wins. You don’t ask for budget. You don’t address objections. You don’t follow up. And then you wonder why you’re not closing. Without action, you are not going to sell!

Here’s the cycle: you repeat ineffective habits, you aim at the wrong prospects, you quit too early, you let fear justify all of it, and then you blame the competition. Revenue doesn’t lie. If revenue is flat, something has to change.

Your Challenge This Week

Which roadblock are you stuck on? What are you defending? Are you defending a habit that isn’t producing results? Are you chasing someone who isn’t qualified? Did you quit too soon?

“If you always do what you’ve always done, you’ll always get what you’ve always got.” – Henry Ford

If your sales haven’t moved, don’t blame the market: change your status quo!

Have a great week and weekend