This article was written by guest contributors Sitima Fowler and Ray Green. After growing and selling her own MSP, Fowler now teaches TMT members how to close big, profitable managed services agreements with ease. Green has helped some of the world’s most successful business coaches execute world-class sales and marketing strategies.


You look great in your sharp outfit, you showed up on time, and you did your research in preparation for the discovery meeting. Unfortunately, that isn’t enough to convince potential clients that you can be trusted with their technology—and more importantly, the business outcomes they seek. That’s why the discovery meeting is more than just gathering crucial information about the prospect’s systems. It’s the time to position yourself as a trusted advisor who can help them align their technology with their business needs.
In their previous column, Sitima Fowler and Ray Green, MSP sales experts who teach the 5-Step Process to Closing an MSP Sale, discussed how to prepare for the discovery meeting. Here, they take a deeper dive into how to open the meeting and build rapport—what questions to ask, how to build trust, and how to cut the crap. If you missed how to prepare for the discovery meeting, see Transform Your Sales Strategy With These Proven Discovery Meeting Tips.
Don’t Shove A Sales Pitch Down Their Throat
Your goal is to differentiate your business from every other MSP that your prospect has spoken to by positioning yourself as a trusted advisor. This means building trust with the prospect and finding their pain before ever offering a solution.
He Said: One key difference between a traditional salesperson and a trusted advisor is that when you think of a consultant, their role is to first help determine what you need, and then offer a solution. When somebody takes the time to do a real discovery and diagnosis, you trust the prescription more.
You’re there to help the prospect solve their biggest issue, but to do that, they have to trust the process and you. Sometimes we hear people say, “Well, I asked them about what they’re spending today, and they didn’t answer my question.” That’s because they haven’t built that trust with you yet. They still see you as that salesperson who’s going to shove a solution down their throat. That’s what we want to change—that perception.
She Said: Exactly! Your job during this process is to ask questions and find the pain, not solve the problem. I see a lot of MSP salespeople and business owners jump to saying, “This is what we do! You’re never going to have issues if you work with us.” They don’t ask questions, but you have to. Your problem is to find the pain. If you can’t find a ton of pain, the likelihood of closing that sale is very low.
In The Discovery Meeting, Think Credibility Over Likability
When it comes to building trust, expressing interest in their unique business is far more effective than small talk.
He Said: You’re selling solutions, which means credibility is more important than likability. Some people like to get chummy with their prospects; they’ll look at the pictures in their prospect’s office and make small talk about their pets or family. At the end of the day, that may increase your likability with the prospect, but it won’t increase your credibility—and likability rarely sells solutions.
She Said: Right! You don’t have time to waste. You’re going to come in, look the part, and be no-nonsense. If you start by asking about their business and listening empathetically, they’ll start telling you more and more, because they’re excited to talk about their business!
Make The Initial Question Count
It’s important to open up the meeting with an open-ended question that makes the prospect feel part of this discovery process. For a role-playing example, check out the above video.
She Said: The initial question to ask is, “I was on your website, and I know you do [insert business here]. Can you tell me a little bit more about the business?” That’s it! Keep it very open-ended.
You want your prospect to feel like they’re part of this process. When you present your solution to their problem, they should feel like you both arrived at the right decision together.
He Said: It’s the same approach a good doctor uses—the patient has already filled out the paperwork explaining what’s wrong, but the doctor still wants to hear it directly from them. If the doctor prescribes some expensive treatment without asking questions, you’re going to doubt if that’s even correct. As a service provider, you don’t want the prospect second guessing your “prescription.” You want them to trust the solution.
Discovery Meeting Goal: Learn How They Use Tech
The following questions should dig into how your prospect uses technology as a business. Avoid getting too much into the weeds. The purpose is to continue building trust while getting a general sense of how technology impacts their day-to-day life.
She Said: From that initial question, follow up with, “So I can get a better understanding of how your business uses technology, let me ask you a few more questions.”
You want to ask them guided questions about each part of their business. Most businesses are going to have these business functions: marketing, service delivery/production, sales, HR, and finance. Here are a few questions to start with:
- What are the most critical applications you rely on to run your business?
- Are they in the cloud, or located here on a server?
- Do they work well for you? Are you having any issues with them?
- How do you generate new sales? What technology does your sales team rely on?
- What software do you use when providing your services to clients? Do you have any frustrations with that process?
Asking these questions will elevate you as a trusted advisor. You want to know the critical things that are going to shut their business down if they fail.
He Said: When you run this type of discovery, you start exposing some latent pains. A lot of times, the quality of a consultant is based on the quality of the questions they ask. So be very methodical and strategic.
Get Out Of The IT Closet
Asking the right questions will allow you to position yourself as a strategic advisor and get out of the IT closet. Remember, you only have 60 minutes for this discovery meeting, so make every question count.



