Ever feel like you’re talking at prospects instead of with them? 

You show up, you pitch, you power through 43 slides... and then? Crickets. 

Sound familiar? 

You’re not alone—and you’re definitely not the problem. 

The problem is your sales process. And more specifically, that it’s stuck in the Stone Age, waving around a flip phone and asking if you’ve “tried turning it off and on again.” 

Most Managed Service Providers still rely on the same tired playbook: 

• Info-dumps disguised as PowerPoint decks 

• Feature-heavy rambling that could sedate a caffeinated squirrel 

• “Tell, tell, tell” instead of “Ask, ask, ask” 

In today’s market, that approach doesn’t just underperform—it actively repels buyers like week-old shrimp at a networking mixer. 

So, let’s hit pause. What if instead of chasing, convincing, and pitch-slapping your way to a maybe, you pulled prospects in with one simple shift? 

Enter: Question-Based Selling. 

Why Most MSP Sales Fail Before They Even Start 

Let’s be honest—your prospect has already Googled five of your competitors, read three Reddit threads, and watched two “Top 10 MSP Horror Stories” TikToks before you even pull up your PowerPoint. 

They’re not looking for another feature-flaunting techno-wizard. They want a real human who actually gets what keeps them up at night—and no, it’s not just compliance. 

When you lead with features, pricing, and “we’ve been in business 17 years,” here’s what your prospect hears: 

“This is about me, not you. Also, please enjoy this unsolicited TED Talk about our backup systems.” 

That’s a losing game. The second they don’t feel heard, they mentally replace you with a Google search bar and a bottle of Advil. 

So, What Is Question-Based Selling? 

Question-Based Selling (QBS) is exactly what it sounds like: Leading the sales conversation with smart, strategic questions that gets your prospect sharing with you, instead of reading your “fun facts about Multi-Factor Authentication” bullet points like bedtime stories. 

But it’s more than a sales trick. It’s a personality upgrade. 

QBS shifts your role from salesperson to Navigator. From persuader to Partner. From vendor to Guide on the heroic quest to rescue their network from spaghetti-cable hell. 

And that shift? It’s the difference between being ignored and being indispensable. 

3 Reasons Question-Based Selling Is a Game-Changer for Managed Services Providers 

1. It Surfaces the Pain They’re Not Telling You 

Most prospects won’t outright say: 

• “I don’t trust my current provider.” 

• “I’m scared of losing my job if this migration fails.” 

• “Our tech stack is one intern click away from digital Armageddon.” 

But ask the right questions, and those skeletons sprint out of the closet like they heard there was cake. 

Example: “What would it mean for your business if this problem went unresolved for another 90 days?” 

Boom. Now we’re not talking about licensing fees—we’re talking about livelihoods. That’s where decisions get made. 

2. It Helps the Prospect Build the Business Case—Not You 

The more they talk about their mess, the more they own the need to clean it up. 

And when that happens, your proposal doesn’t just make sense—it feels like a rescue mission from the heavens. 

Example: “What’s the cost of downtime for your team right now?” 

When they say the number out loud, it hits different. Suddenly, your proposal isn’t expensive—it’s cheaper than the consequences. 

3. It Neutralizes Objections Before They Explode 

Objections don’t come from logic. They come from doubt. Fear. That little voice that says, “Are these folks gonna break more stuff than they fix?” 

Question-Based Selling helps you locate and defuse those doubts early—before they turn into ghosting or last-minute freak-outs. 

“What concerns would you have about making a change like this?” 

It’s like an emotional antivirus. You patch the issues before they take down the deal. 

Question-Based Selling in Action: From Theory to “Holy Crap, This Works” 

Here’s how to start using Question-Based Selling immediately—no AI bot, sales ninja certification, or LinkedIn humblebrag required. 

Step 1: Prep 5–7 Smart, Open-Ended Questions 

Not “How many endpoints do you have?” (yawn). We’re talking: 

• “What’s the biggest tech headache you’ve had this year?” 

• “If your IT was perfect, what would you never have to deal with again?” 

• “How does your current issues make you feel… emotionally?” 

Yes, you can go full Dr. Phil, if it gets results. 

Step 2: Listen Like a Human, Not a Sales-bot

This isn’t a podcast where you’re waiting to talk next. Reflect back. Get curious. Say things like: 

• “It sounds like you’ve been duct-taping things for a while.” 

• “That’s gotta be frustrating—what’s the ripple effect from that?” 

This isn’t empathy theater. It’s connection that converts. 

Step 3: Resist the Siren Song of the Pitch 

You’re going to want to jump in with solutions. Fight that urge. 

Hold it. Like you’re on a tech support call waiting for a reboot. Just sit in the silence until you’ve got the full map of what matters most to them. 

Then? Drop the proposal like a mic. 

Why MSPs Win Big With QBS 

You’re not selling antivirus software. You’re selling peace of mind, reduced chaos, and the chance for a business owner to not get a call at 2AM because someone clicked a sketchy PDF. 

Question-Based Selling frames your services around real outcomes—less stress, more uptime, fewer meetings about “who unplugged the router again.” 

And when you make that the focal point, price becomes a footnote. 

CharTec Academy: The Hogwarts of Selling (Without the Magic Wands) 

We’ve coached thousands of MSPs through Question-Based Selling, and guess what? None of them asked to go back to pitch decks and awkward pauses afterward. 

Academy is where real sales pros get trained: 

• No B.S. No “sales Jedi” nonsense. 

• Just battle-tested frameworks, real talk, and enough role-play to make a theater kid blush. 

You’ll learn to lead sales calls like a boss, handle objections like a therapist, and close deals without sounding like a late-night infomercial. 

If you're ready to close more deals and boost MRR in 2025, Academy is where you need to be. Learn more here.