If you’re in MSP sales, you know that uncovering a prospect’s pain points is critical to closing the deal. But what are the best ways to do that? How do you dig deep enough to not only understand what’s going wrong for them now but also position your services as the perfect solution?
Subscribe to the TMT YouTube channel here
I’ve been in countless sales conversations where I’ve seen how effective the right questions can be. Here’s how you can use strategic questioning to uncover pain points and open the door to a successful sale.
The Power Of Questions
When it comes to identifying pain points, the right questions can make all the difference. You’re not just looking for surface-level issues; you need to get to the core of what’s driving their dissatisfaction. Think of it like a doctor diagnosing a patient. They don’t just ask, “Are you in pain?” They ask where it hurts, how it started, how long it’s been going on, and what it’s preventing you from doing.
For example, if a prospect reaches out to you, already looking for new IT support, it’s a clear signal they’re dissatisfied. Here’s where your job gets interesting. You don’t just take the surface issue and run with it. You dig deeper with questions like:
- “What’s going on with your current IT support?”
- “Where are they falling short?”
- “What specifically are you dissatisfied with?”
Most people in pain will happily tell you what’s bothering them. When they’ve had bad experiences with an IT provider, they’re usually more than willing to vent about it. This is where you take notes, listen intently, and then offer up your solutions as the fix they’re looking for.
Different Situations Call For Different Approaches
Now, let’s say you’re cold calling someone or following up on a lead you generated from a free network assessment offer. The approach is different, but the goal is the same: uncover their pain.
The key is to ask questions that open the door for them to reveal their problems. You might start with something as simple as:
- “Who do you currently use for IT support?”
- “Are you outsourcing your IT, or do you have someone in-house?”
- “How satisfied are you with your current provider?”
Once you start getting answers, you can ask more targeted questions to really get to the heart of their issues, like:
- “Do you feel like your current provider is responsive enough?”
- “Do they proactively talk to you about cybersecurity or compliance?”
Notice how these questions are designed to make them think about the quality of service they’re receiving now—and where it’s lacking. You’re gently leading them to the conclusion that they deserve better, and you’re the one who can provide it.
Tailor Your Questions To Your Value Proposition
Remember, your questioning strategy needs to be aligned with what you offer. If compliance isn’t a service you provide, then there’s no point in asking about it. Instead, focus on the areas where your company excels. If you’re known for fast response times or proactive cybersecurity, lead with those strengths and ask questions that uncover whether the prospect is missing those things with their current provider.
The goal is to get them to say, “No, I don’t have that,” or “Yes, that’s been a big problem for us.” Once you hear that, you can move into how your MSP can fill those gaps.
Use Wedge Questions To Open the Door
Sometimes, prospects won’t readily admit there’s a problem. This is where “wedge questions” come in. Wedge questions are designed to create doubt in their mind about their current provider by highlighting potential problems they may not have even realized were there.
For instance, asking, “Do you feel like your current IT support is keeping up with the latest cybersecurity threats?” or “Are they proactively communicating with you about upcoming compliance regulations?” can introduce the idea that their current provider might not be as on top of things as they thought. Even if they haven’t had issues, these types of questions can sow doubt and get them thinking.
Don’t Forget To Listen
One of the biggest mistakes I see MSPs make is not truly listening during sales conversations. You might be eager to pitch your services, but if you don’t fully understand the prospect’s pain, you’re not going to be able to position your MSP as the best solution.
When you ask these pain-point questions, don’t rush to the solution. Let them talk, vent, and explain. The more they share, the more ammunition you have to close the deal. Once you’ve gotten a clear picture of their pain points, only then do you pivot to how your services address those issues.
The Bottom Line: Strategic Questioning Closes Deals
The next time you’re in a sales conversation, whether it’s a cold call or a meeting with a hot lead, focus on asking the right questions. Don’t settle for surface-level answers—dig deeper. Uncover what’s really going on with their current IT situation and position yourself as the answer to their problems.
