The 5 Whys: A Method to Win More MSP Clients

At Cloud Services for MSPs, we’ve been in your shoes. We started as an MSP and grew into a cloud provider that serves other MSPs—and along that journey, we learned that success often hinges not on what you say but on what you ask.

Today, I want to introduce you to one of the most deceptively simple (but incredibly powerful) methods we used to win more clients: The Five Whys.

Yes… just asking “Why?” five times can change everything!

The Problem Behind the Problem

We’ve all heard it before…

• “Our network is too slow.”
• “We’re worried about cybersecurity.”
• “Our current IT provider just isn’t responsive.”
• “We don’t have the budget for IT upgrades.”

Sound familiar? Sure they do! These are the surface-level complaints that prospects throw at you. And if you treat them as the final word? You might end up offering the wrong solution.

That’s where the Five Whys come in.

Where It All Began

This method was created by Sakichi Toyoda, the founder of Toyota, to identify the root causes of manufacturing issues. Toyota made it a core part of their production philosophy, using it to eliminate inefficiencies at their source.

So, why should MSPs care?

Because it’s not just for car companies! This technique helped us uncover what was really going on with clients—the stuff they didn’t always know how to explain—and it helped us win more deals with solutions that actually worked.

What It Looks Like in Practice

Let me walk you through a real-world scenario we encountered back when we were still operating as an MSP.

We met with a prospect who said, “We don’t have the budget for IT upgrades.” Most MSPs might stop there. Cut back their proposal. Offer a discount. But we asked…

Why don’t you think you can afford the upgrades?

“Because we’re spending too much on IT already.”

Why are you spending so much on IT?

“Our systems are always breaking, so we’re constantly calling our provider.”

Why are your systems always breaking?

“We don’t know—they just keep having issues.”

Why don’t you know why this keeps happening?

“Because our current IT provider can’t tell us either.”

Why doesn’t your IT provider know?

“They never spent the time to figure it out!”

Boom. There it is! The real issue wasn’t the budget, it was a lack of proactive support. That insight gave us the chance to recommend a comprehensive network audit and present a strategic solution that would reduce reactive costs and fix the root cause!

Real Value, Real Trust

You see, the Five Whys helped us move past vague objections and into meaningful conversations. We started applying this in all our discovery calls. And guess what? It worked!

Clients opened up, we built trust, and we positioned ourselves as the MSP who didn’t just listen, but actually understood.

Sometimes the concern really was the concern. But often, it wasn’t. By digging deeper, we tailored proposals that met clients where they truly were!

Try The Five Whys This Week!

If you’re still in the trenches with your MSP, I challenge you: on your next discovery call or client review, use the Five Whys. You’ll be surprised what you can uncover!

I’ll leave you with one of my favorite quotes from Albert Einstein, “If I had an hour to solve a problem, I’d spend 55 minutes thinking about the problem and five minutes thinking about the solution.”

Have a great week!