Active Listening In Discovery Calls

Goals Of A Discovery Meeting

One of the single most important moments of the lifecycle of an MSP’s customer journey is the discovery call. Not only is it the origin of the relationship (or lack thereof), but it also sets the stage for how the partnership is structured, and whether or not expectations are aligned from the beginning. Even if you are able to convert the customer, a bad discovery call can backfire later on, most of the time as early as the onboarding phase of the journey. This is why it is important to go into these calls with a clear goal in mind and a bag of tools at your disposal. 

Mike Herrington, VP of Sales & Marketing at i.t.NOW has had many of these calls over his 14 year career in selling IT Services. As he describes; “When starting a discovery meeting, there are a few key goals to keep in mind. First, focus on asking, not telling. The objective is to ask questions and actively listen—aiming for 80% listening and only 20% clarifying questions. Second, seek to understand. At this stage, you’re not selling anything yet because you don’t fully understand what the client cares about or needs. Your goal is to learn about their business, the motivations of all parties involved in the purchasing decision, and their problems and pain points. 

Finally, remember that motivations matter. It’s essential to dig deeper than surface-level issues, asking how those problems affect their business and how they make them feel. The most valuable insights and core buying triggers are typically found after asking three or more probing questions.” 

Listen With Your Ears, Not Your Mouth

The fallacy that a lot of MSPs tend to suffer from on these discovery calls is what I would refer to as “Solution Fixation Syndrome (SFS).” This is when you are so eager to fix whatever is broken, that you don’t take the time to fully hear and understand the problem. I thought Dean Trempelas, VP of Operations from Helpt painted a truly accurate picture of this all too common scenario:

“Imagine I’m your MSP, and you call me in a panic, repeatedly saying, ‘I CAN’T PRINT, I CAN’T PRINT!’ My mind immediately starts thinking about potential issues. I know you have that networked Brother printer I installed last year, so it should be working. So I start asking troubleshooting questions, like whether it’s powered on, trying to figure out the solution. 

But you’re still panicking, so I decide to go on-site. When I get there, the printer is working perfectly. Finally, I take a step back, talk to you, and ask some general questions. It turns out that you weren’t just saying ‘I can’t print’—you were trying to print in a specific shade of blue, which that printer can’t reproduce.

Because I wasn’t truly listening, didn’t acknowledge your emotional state, and didn’t take the time to figure out what problem you were actually frustrated with, I ended up solving the wrong issue. No one is happy now. I wasted my time, your time, and you still can’t print in the blue color you needed. Once I learned to shut up, stop trying to solve everything at once, and just listen… boy did things get easier.” 

Enabling Your Discovery Mode

Much like connecting a bluetooth device and clicking that little button with the blue and red lights, MSPs should put themselves in ‘discovery mode’ whenever meeting with a prospect for the first time. Flipping this mental switch ensures you are in a constant state of receptiveness for the entirety of the meeting. It also helps you personally recognize the realities that you face and expectations of what ahead.

I thought Dave Sagraves, Founder of MSP Growth OS did an excellent job of putting these realities into perspective. “You have to set yourself in a frame of mind when you go into this meeting. There are two things at war: a buyer has a way that they think they should engage with you, and then you have what you want, which is to ask all these questions. One of the things I try to do is acknowledge that the buyer isn’t going to tell you everything up front. You can’t assume their first answers are the full truth. You need to keep probing gently, using techniques like paraphrasing, labeling their emotions, and asking open-ended questions. That way, you’re guiding them to be more open, and you’re understanding the bigger picture.” 

Active-Listening Techniques To Apply

The sum of the techniques that Dave described is called “active listening,” which is the practice of fully concentrating, understanding, responding, and remembering what is being said in a conversation. It involves not only hearing the words being spoken but also engaging with your counterpart through verbal and non-verbal cues, like paraphrasing, asking clarifying questions, and showing empathy. The goal of active listening is to ensure both parties in the conversation feel understood, leading to more meaningful and effective communication.

Here are a few of the most notable techniques and how to apply them to your discovery calls: 

Paraphrasing 

Paraphrasing is one of the most important techniques to learn when it comes to active listening. Having ready-to-use starter phrases can make paraphrasing a seamless part of your conversation. Some helpful transitions include: “So, what I’m hearing is…,” “It sounds like you’re saying…,” or “Let me make sure I understand this correctly….” You can also try phrases like “If I’m following you, you mean…,” or “Just to clarify, are you saying…?“

The goal is to take the prospect’s complex explanations and simplify them to confirm you’ve understood the key point. For example, if the prospect says, “Our current network infrastructure is slow and unreliable, and it’s making it difficult for everyone to get their work done,” you might paraphrase with, “So, your team is facing productivity issues because of IT downtime?” You can also paraphrase in the form of a question. Dave Sagraves shared with me one of his favorites, which is; “When you say that, do you mean…?’ This reframe often prompts the prospect to clarify further. Before you know it, I have them really telling me what’s actually going on in the business.”

Open-Ended Questions

I thought Mike Herrington perfectly described the practice of structuring your discovery questions in an open-ended way. As he explains,“Many people in IT have a natural troubleshooting mindset, and these skills can be leveraged to ask questions that help uncover the root of the issue— without rushing to solve it immediately. By asking clarifying questions such as, Tell me more about X?, When X happens, how does that impact your team?, or How severe is the problem?, you can start to unravel the client’s true needs. Other helpful questions include What solutions have you explored so far?, Can you give me some background on X?, How long has this been an issue?, and How much longer can you afford to have the problem go unresolved?

The key here is to ask open-ended questions that encourage the client to speak freely, rather than providing answers they can quickly confirm with a simple ‘yes’ or ‘no.’ By allowing the conversation to flow in this way, you’ll reach a deeper level of understanding much faster. You’ll be surprised at just how much you can learn through this approach.” If you are an MSP Owner or Salesperson, I highly suggest keeping a list of such questions nearby or memorizing them for use in these calls. If you already have these queued up, you may be less likely to fill the conversation with unnecessary commentary that could distract as you navigate through. 

Emotional Labeling

Emotional labeling is the technique of identifying and verbally acknowledging the emotions the other person is experiencing during a conversation. When a prospect expresses frustration, excitement, or concern, instead of just focusing on the technical issue, it’s important to acknowledge the emotion behind the words. For example, if a prospect seems dissatisfied with the state of their operations and their current IT provider, you might say, “It sounds like you’re feeling really frustrated with the constant downtime and problems you’ve been experiencing.” If the prospect is excited about the potential for growth and wants to make sure their IT can support it, then you might respond, “It sounds like you’re really excited about expanding your business and want your IT infrastructure to support that growth.”

Robert Gillette, Owner of MSP Dojo is one of the most emotionally in-tune sales experts I know. When talking to him about this technique, he suggests; “If you feel it, say it. Too often, we pick up on emotions or impressions from our prospects that we overlook or ignore. As subject-matter experts, it’s our responsibility to recognize and label these emotions during conversations. This helps guide our prospects and clients through their own discovery process. We need to be so confident in our expertise and approach that we can also afford to be vulnerable, acknowledging what our clients feel and addressing it openly.”  

Silence & Pauses

One of the most difficult but most powerful tools in active listening is simply silence. Pausing after a question creates a space for your prospect to think and give a more genuine answer. As MSP Owners or Sales Professionals, there’s often a temptation to fill every silence with commentary or the next question on your list, but this can sometimes stifle deeper insights.

“Silence is one of the most powerful tools in active listening. When you’re asking a question and then pause, it gives them space to really reflect and answer truthfully. In discovery calls, sometimes it’s the quiet moments that bring out the most valuable insights because people tend to fill that silence with what’s actually on their mind.”  explains Sagraves. The best approach is to take a moment of silence after each significant question you ask. These moments encourage the prospect to share additional thoughts or concerns they might have otherwise held back. And, often, those insights are where the true business needs reside.

Non-Verbal Queues 

Non-verbal cues play a critical role in every conversation we have. Your body language, facial expressions, and tone of voice can either reinforce or undermine the message you’re trying to convey. On the flip side, picking up on your prospect’s non-verbal cues can help you gauge their level of engagement, interest, and honesty. While this can be easier in-person, it’s a little more difficult to capture over a Zoom or Teams call. 

As Robert Gillette, pointed out, “Most people don’t have a particularly professional audio/visual set up, so the brightest light source on their desk is often their monitor. One of the ways I can tell that I’ve lost someone’s attention is if I can see the color or brightness of their face changing from time to time. It’s an easy way to spot if they’re opening and closing windows (like their email, or browsing Reddit) while you’re giving your presentation or trying to draw out information.” Monitoring for these subtle clues can help you adjust the pace and energy of the conversation or change your approach entirely. 

Time & Pace

Understanding the natural flow of a conversation, and how time influences openness, is crucial during discovery calls. Conversations evolve, and the longer the call goes, the more authentic the answers tend to become. Dave Sagraves offered a valuable insight on this topic as he suggested: “At the 30-minute mark and the 50-minute mark in a meeting, there’s a human thing that happens. At 30 minutes, we start to get a little more real. At 50 minutes, literally, the bullsh*t cannot stand any longer. They actually have to start telling what they think as truth versus what they’re programmed to communicate. So, the time spent in a meeting begins to lower the barrier for this wall they’ve put up, allowing you to get to the real issues.”

By managing time effectively and giving your prospect enough room to open up naturally, you gain access to the most honest and valuable information. When scheduling such calls, make sure you allow time for this to actually happen. If you are only allotting 20-30 minutes for the meeting, it is not likely that you are going to build enough rapport to get to the actual truth. In that case, a follow up (or several) are probably necessary to completely flesh out the opportunity.

Attentiveness

Given the time required to really establish trust in the conversation, it can be difficult to stay focused for the entirety of the call. This can be especially true if the individual you are meeting with is not overly personable or easy to talk to. Nevertheless, attentiveness and your ability to focus on the task at hand is crucial. If the meeting is virtual, be sure to minimize your browser windows and silence desktop notifications while on the call. You may also want to put your phone on silent mode, with the screen side down. 

Another technique for ensuring that you are fully focused on your prospect is good old-fashioned note taking. Sure, I realize there are transcription tools and AI summaries that make this unnecessary and a bit old-fashioned, but think of it as a way to check your focus throughout the meeting. The physical gesture of this also acts as a non-verbal signal to your prospect that you are there to listen and you understand what it is they are trying to say. 

What A Good Discovery Looks Like

Unless you’ve been a fly on the wall, or have had the privilege of shadowing an elite salesperson in our industry, it’s difficult to know what a good discovery call actually looks like. Fortunately, Mike Herrington walked me through the play-by-play of one of his most memorable calls, which I think encapsulates the exact result MSPs should be looking for: 

“One of the largest managed services deals I ever sold was to a chain of assisted living facilities. The conversation started like most discovery meetings. I asked, ‘Tell me about what you’ve been doing to handle your IT needs so far?’ They explained that they were working with an outsourced IT provider but were unhappy with the service. I dug deeper, asking about the specific areas where the provider had fallen short, and they shared several instances of poorly executed projects. As I probed further, I discovered that their organization frequently grew through acquisitions and often needed to act quickly to meet deal terms. The people responsible for IT decisions were also in charge of acquisitions, meaning speed was critical.

I continued by asking, ‘Were there other challenges?’ They revealed that they often had multiple projects happening simultaneously, but their current provider didn’t seem to have the resources to handle them. This led to another key point—the provider lacked a dedicated account manager to own these projects, and with no one managing the workload, things were frequently dropped. I asked, ‘What do you think the ideal solution to this would be?’ They admitted that they needed someone to manage these projects full-time.

Curious if they were considering an internal hire, I asked, ‘Are you looking into hiring someone?’ They explained they had considered hiring an IT director who would build a team, but the requested budget was six times what they were currently paying their provider. They were also hesitant about overseeing an internal IT department, which didn’t align with their core competencies. I followed up, ‘So it sounds like, in addition to resolving your current issues, you also need a dedicated project manager from your IT provider rather than hiring internally?’ They agreed, and there it was—the key buying trigger was buried nine questions deep. I proposed a solution that addressed all their pain points, including a full-time project manager dedicated to their account. Unlike the other proposals, ours solved the complete set of needs, and as a result, we won the contract.” 

Conclusion

Discovery calls aren’t just about hearing the words your prospect is saying—they’re about digging deeper, understanding the true motivations behind those words, and fostering a sense of trust. Active listening is your best tool to uncover the real pain points, especially the ones not immediately visible.

As Dave Sagraves wisely concludes, “If you don’t go into every meeting with the mindset that you’re unraveling layers of guarded information, you’re going to miss critical details. Active listening is not just hearing—it’s about reading between the lines, understanding what isn’t said, and keeping the conversation flowing so that they eventually feel safe enough to share the real problems.”

Your expertise is valuable, but your ability to listen and align your services with what really matters to your clients is priceless. In the MSP world, listening is the most important service you can offer.