#515 - 21 PERFECT Sales Discovery Questions to Ask Your Prospect (Part 1)

So I've interviewed over 300 presidents, club-winning sellers and I've been at the top of the leaderboard myself. And in this video, I'm going to teach you the best discovery questions that I've learned to get prospects to open up and spill their guts from the very first time that you meet with them through the rest of your deal. Now, this is part of a three-part series where I'm going to give you my favorite discovery questions for early-stage conversations, mid-stage when you actually have a deal sort of in the works and late-stage when you're trying to get it over the line. And if you want to make sure that you don't miss part two and part three, make sure to hit the like and subscribe button so you are notified when those come out. Alright, so question number one is a really basic but extremely powerful question. And the question is, why'd you take this call with me? This is a broad open-ended question that is designed to one figure out their motivation for meeting with you and to hand them the mic so that they have an opportunity to share all of the context and background detail. The way you're going to ask the question inbound deals, you're going to say, well, look, I know you requested a demo on our site. I guess, what prompted you to reach out to us in the first place? For outbound deals, I know I emailed you last week and you agreed to meet. I can't imagine you take meetings with every single person that emails you. What prompted you to want to meet with me today? This is the best first question because it is intentionally broad. I'm not boxing them in to be like, alright, well, tell me about your current billing process or tell me about your business. I'm figuring out their motivation for being there, which is going to dictate where I take the rest of the call. Question number two, speaking of motivation is called the motivation behind the need. What you're going to hear from a lot of prospects at the beginning of discovery calls is what they want or what they're looking for. They're going to say things like, yeah, you know, we're looking for a more efficient billing system. Or yeah, I responded to your email because we're actually thinking of getting more comprehensive healthcare plans and I wanted to see what you all had. Great, that's helpful to know, but looking for a more efficient billing system or wanting more comprehensive healthcare plans, those aren't problems. Those are desires. Those are wants. And I think if you've worked in sales for more than a minute, you know that paying out sales gain. So we need to figure out what is prompting them, what is motivating them to make a change in the first place. So you're going to ask that. You're going to say something like, okay, today's show is brought to you by Insightly. The CRM helps you spot deal risk early. So pipe reviews actually drive your number. One question I ask in nearly every deal review is, what do we need to get in our next interaction with the customer? If my rep can't answer that question, the deal has risk and I have something I can coach to. Now we built a guide with our friends at Insightly CRM on how to run pipe reviews that surface real risk and get deals moving again. And you can get it for free at the link in the show notes. You're looking for a more efficient billing system. I guess what's motivating you to look in the first place. Now we flipped it from, oh, we want more efficiency to now they're going to be complaining about what their problems are today. What can't they do? What do they want to do? What's stopping them from getting there? Question number three is what I call the big menu. This is an awesome question if you sell a big solution that helps with a lot of different things. I used to sell ERP software to law firms and we literally helped with like 47 different things. And so I need to figure out where to zoom in the call. Now if you sell a point solution, you can just skip to question number four, which I will get to in a second. But for those of you who sell big things, you are going to ask the big menu question, which sounds like, well, look Dave, I mean, we work with law firms on everything from new client intake to billing to collections to how attorneys are going to set up fee structures on their really complex cases. I guess as you think about some of the main focus areas for you in your firm, are there any that are like top priority for you? Their response to this question is going to dictate now where I take the rest of the call. And you might still sell something it helps with a lot of different things. And you're probably going to talk about all those things, but you want to put first things first. Talk about the burning problems before you talk about the, I don't know, smoldering problems. Get to the hot stuff first. So question number four is what I call multiple choice questions. And these are simply questions you're going to ask where you are going to give them the multiple choice of the main problems that you can solve. This is designed to steer the discussion towards pain that you can make go away, not just any pain because there's nothing worse than somebody talking about all the problems that they have. And you sit in there being like, shit, our product actually can't help with this stuff. So the way that I would ask this question is I would say, okay, Dave, typically when I'm talking to a law firm, CFO about billing, there's like three main themes that I hear from folks. Place number one is that billing insurance companies can have a ton of friction associated with it. Place number two, I hear people focused on is that like they want to speed the collection cycle, so actually collecting that cash faster. And then place number three is more about like how the attorneys interface with billing. I know there's like a lot of back and forth of them actually setting up the bills, writing the narratives, tracking their time. I guess as you think about the main focus areas or frustrations with billing, what are some of the places you're looking to solve for? Now I figure out they told me billing is a problem, but now I figure out the subproblems there. Now that takes us to question number five, which is called second level multiple choice questions. All I'm going to do is whatever they tell me was the main focus area on the first multiple choice question, I'm going to now give the three problems underneath that. So if in response to the previous question, they say yeah, insurer billing is a major pain point. Like there's a lot of frustration there and we need to make that easier. I'd say, okay, I hear that a lot. Typically what I'm talking with firms about insurer billing, there's three big places. Place number one is there's all these like deductions where they won't pay your bill if you like put it in the wrong format and you might want to be reducing that. Place number two is I feel like I hear from a lot of firms that the attorneys get pulled into almost litigating the bill to be like no, you do need to pay for that because I accidentally coded it under the wrong thing and it should have been fixed. And that's frankly a waste of their time. And then place number three with insurer billing is just like they can be really, really slow to pay and following up on bills is actually a huge drag on billing departments. When you think about insurer billing, what are some of the main focus areas for you? Now, there's a sneaky bonus to this question which is even if they don't have one of those problems and they have something else, you've signaled to them that you have helped people like them before because you've shown that you know problems other firms who bill insurer carriers are looking to solve. And this sets you at a higher status than other salespeople out there who are just asking, oh, okay, insurer billing, what are your biggest problems with that? When you can suggest problems, you fast track the conversation and you show that you are more of a consultant or expert than you are salesperson, which obviously sets you apart from your competition. So question number six. So at this point, we've talked a lot about like the focus areas, the problems that they might have. I now really want to dig that knife and I'm going to do that with question number six, which is called the magic moment question. This is a question that you can use to get your prospect to tell you a story. You might have heard that story sell and thought that that is meant to be you telling stories, which is true. But if you can get your prospect to tell you a story about the moment they realize this thing was actually a problem, you are going to get so much more context and detail of this pain. So the way that you would ask this is you might say, okay, well, you know, Dave, I'm thinking about this like, I can't imagine that you woke up earlier this week and you were like, we've got to fix this insurer billing issue. I guess when was the moment that you realized this thing was something you had to fix? You are almost always going to get a story in response of like a huge $200,000 bill that an insurance company wouldn't pay or a report that they looked at in the executive meeting where they got torn apart by the managing partner or whatever made them be like, oh, I've got to fix this problem. And this is how you get to that visceral detail of that pain, which is going to help you sell how you solve that pain in the demo so much better. So that's the magic moment question. Now, if the magic moment question takes that pain deep, the next question here, which is the who else is getting driven crazy by this question takes it wide. So I kind of gave it away. Question number seven is who else is getting driven crazy by this? This is designed to figure out, is this a problem that just lives with the CFO or is it also affecting her whole billing team? Is it also affecting the COO and that person's part of the org? Is this something that the managing partner is pissed off about? We want to figure out who else is affected by this problem? I like to say driven crazy because affected is just like a little bit bland. I'd be like, who else is getting driven crazy by this? Because now in the demo or in future conversations, I know who else I need to get in front of. Bonus points here, if you can suggest by name, the people who might be getting driven crazy by this. I guess who else is getting driven crazy by this? Do you feel like Mark over in the ops department is also dealing with this? Now when I share someone by name, they don't have to go through their full role at X of everybody at the firm or at the company and they can be like, yeah, you know what, he is. And that's how I get access to Mark because I show, oh, I'm already thinking about how his part of the org might be struggling with this. So question number eight is one of the most important questions to ask on a sales call, which is, what are the business outcomes you are looking to accomplish by solving this problem? The reason this question is so damn important is in order to sell your product, you need to understand three things. You need to understand where are they today? Where are they looking to go? The outcomes they want to accomplish? And what's stopping them from getting there? The previous seven questions I gave you were all focused on the pain, the annoyance, the frustration, the things they couldn't do, which is important to note. But we need to, when we show them the demo, be able to position, hey, here's how we make these problems go away. And here's how we also get you to the destination that you want. When I sold Billings Software to law firms, they might have any different type of destination. Some law firms wanted to cut down on deductions and just collect the full bill amount. Other law firms were like, hey, we need to speed our collection cycle and going back and forth with these insurance companies is slowing down collections. And so while those outcomes are related, they're also pretty different. And the way I position the demo is going to change based upon where I know they're looking to go. The other really important part about this question is I'm asking about business outcomes as opposed to personal outcomes. I've never seen a company sign a six figure contract to make one person's problems go away. In order to sell big deals, you have to solve problems for businesses, not just individual human beings. So I'm asking about business outcomes to figure out what should I be anchoring this sale to in the first place. Number nine is what I call the priority push away. And this question is used to figure out like, how much do they actually care about solving this problem and getting to where they want to go? Because if it's like a man, you probably don't have a real deal. But if it's like, this is priority number one, you've got a hot one. And we want to figure that out. And honestly, we want them to verbally say out loud that this is top priority because it's really, really hard once you've told another person that something is top priority to deprioritize that thing. So the way that you're going to ask this question is you're going to say, all right, as we think about like this billing problem, I guess I'm curious where this sits on your priority list. Is this like a, we've got to solve this this quarter sort of thing? Or is this a, yeah, it'd be nice to make this thing easier. And so they're answered or this question is going to help you figure out a how real this deal actually is. So you don't waste time on it if it's not real. And be how fast you should be pushing. If they're like, we've got to get this done not this quarter, but this month, you know you should be going full steam ahead on this deal. If they're like, yeah, this is a 2027 initiative, you know, to back off a little bit. And that brings us to the last question of this video. Question number 10, the wish list question, which is designed to get them to tell you exactly what you need to show in the demo to get your deal closed. The way that you ask it is you're going to say, well, look, I have to imagine that you've given some thought to how you'd like your new billing system to work. And frankly, like there's a lot I could show you in the demo. As you think about your wish list items, are there certain things that you're really hoping to be able to see or do? I want to make sure I show you those when I show you the product. Now you know exactly what to show in the demo. And you've been given a cheat code. There you have it. Those are my 10 favorite discovery questions to ask on a first discovery call. Big caveat here that gosh, I probably should have given up front. You are going to look like a total drone AI asshole. If you just ask these 10 questions in sequential order, you're going to need to have a conversation, not an interrogation. And so if you ask all of these questions on a call and it doesn't work, it is your fault. Pick your favorite three or four from this video and find a way to naturally weave them into your conversations. These are tools not meant to be a checklist of questions that you should be asking. If you liked this video, the next one I'm going to do in this series is questions that you should be asking in the mid stage of your deal. This is when you've shown a demo. Maybe you've started to multi-thread and the quality of the questions that you ask in the mid stage are going to dictate how fast you close, how big you close, and they're also going to help you beat out your competitors. So so that you don't miss that video, make sure to hit like and subscribe, and I will see you on that next one.