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#555 - Discovery Masterclass: Everything You Need to Run a Perfect Discovery Call

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#555 - Discovery Masterclass: Everything You Need to Run a Perfect Discovery Call

This transcription outlines a structured approach to mastering discovery calls in sales, emphasizing that discovery is the hardest yet most vital skill. The hosts introduce a 60-minute course summary focused on selling without feeling salesy. They break a 30-minute discovery call into three segments: an initial 5 minutes for rapport and agenda-setting using the "90-second rule" to demonstrate business knowledge and respect before personal small talk; a core 20 minutes to uncover meaningful problems while building trust in the product's ability to solve them; and a final 5-minute "drill" to assess if proceeding is worthwhile. The method avoids common pitfalls like excessive pitching or questioning, instead advocating for a balanced dialogue. Key techniques include trigger-based rapport or astute observations to establish credibility, a PPO (Purpose, Plan, Outcome) agenda to set expectations, and a "discovery tree" framework to escalate problems from operational to executive levels and ultimately to business impact. The goal is to position the seller as a trusted peer, ensuring prospects feel understood and motivated to continue the conversation.

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(upbeat music) Good morning everybody and welcome to this playbook episode of 30 Minutes to Presidents Club. My name is Armand Furrowke and I'm here with my co-host, Nick Sigelski and folks in celebration of our first ever codified discovery course called How To Sell in a Way That Doesn't Feel Like Selling. This is a 60 minute summary of everything you can expect to learn inside of that course and by the end of this video, you will know exactly how to structure a discovery call from beginning to end. Nick, why should people listen? So to help you master the hardest skill in sales, which is discovery, we have broken down the discovery call into the sum of its parts. And in this episode, you should expect to get a ton of examples of what to do, what to say, and how to sound in every single situation that you could expect to encounter in a discovery call. Along the way, we're gonna give you a ton of different question asking techniques and frameworks that you can use. And we're also gonna give you some best practices to help you control the interaction as well as steer the conversation in your favor. So let's start by setting the stage a little bit here folks. Discovery is literally the single most important skill to learn in sales. The problem is most people have been taught to run discovery calls like they are used car salesmen. They either spend 90% of their time talking at their prospect, pitching and blabbering on about their features, their NASCAR logos, before they've even found a problem worth solving the first place. So their pitch falls completely flat. Or they realize, oh, you're supposed to ask discovery questions before you start pitching. And so that's literally the only thing that they do. They interrogate the living daylights out of their prospect, asking question after question after question, until their prospects are like, what the hell do you actually do at the end of the call? And along the way they lose all of their prospects trust because they've only taken information without giving anything return. Great discovery actually balances two things at once. First, finding massive problems that are actually worth solving. While also giving your prospect enough trust in you and the product that you sell, that they actually want to spend more time with you because they believe that you and your product can make that problem go away. So let's actually start this thing by zooming out and breaking a 30 minute discovery call into the three distinct parts that make that 30 minutes up. A 30 minute discovery call is gonna have three separate chapters. The first five minutes are for your rapport and your agenda, where your whole goal is to establish some sort of credibility and set expectations for how the rest of the call is gonna go. From there, the next 20ish minutes take you into the meat of the call. And your goal here is to find massive problems that are worth solving while simultaneously giving them enough trust that you and your product can solve those problems. And then the last five minutes are used for what we call the five minute drill. Most folks think about next steps there. We use the five minute drill as a way to validate whether or not it's actually worth setting a next step with the prospect. And if so, setting the next step in a way that actually drives urgency with the deal. So let's start with the first five minutes of a discovery call. Typically, before you set an agenda, there's some amount of building rapport on a sales call where you have some small talk. And the problem is most sellers completely lose their prospects respect in the first three minutes of a discovery call because they start by saying things like, "Oh, where are you calling in from?" Or, "Oh, how's the weather going over in San Francisco?" Or, "It's been really cold over here." Or, "Oh, how many people are on your team?" It seems like you're growing a lot. And whenever you hear these things as a prospect, I would hear these things all the time when I was buying software as a VP of sales. Three things happen. Number one, I categorize this seller in with every other seller who's starting these calls this way. Number two, I immediately get impatient because this person's trying to win me over by smoozing me instead of showing me that they know something about my business. And then number three, I immediately break the multitasking seal because I'm like, "Okay, I know this meeting isn't actually going to start until three minutes in. Let me start checking my slack on the side until this person's actually ready to start talking about business." So don't get me wrong. I'm not saying you shouldn't be personable whatsoever, but the best way to establish respect on a sales cycle is to show me that you respect my time and you know something about my business. You establish business respect first and then personal respect. And that's what we call the 90 second rule. Where in the first 90 seconds of your call, you wanna do something that demonstrates that you know something about their business and you respect their time. And then you can transition to personal rapport. So there's a couple different ways that you can do this. The way that I do it is using what's called trigger based rapport, where I actually prepare a piece of small talk before the call. And what I'll do is I'm not looking for any generic thing of small talk, I'm actually looking for something about them or about their business that's somewhat related to what my product solves. So an example right now I sell all of our 30 MTC advertising or sponsorships. And what I'll do to prepare for a meeting with a CMO is I'll look for, did they launch a new product recently, have they had a big event recently, did they throw a webinar? And when the meeting starts, I'll say, hey, you know I'm really excited for this one. I was prepping for this call and I saw the news about the big parallel dialer launch you all had. That thing looks freaking awesome. And what I'm showing is, hey, I know something about you. I did some prep. And since I'm selling advertising, usually these people are wanting to advertise the new stuff that they're launching. And if they get excited and like, yeah, you know, this is a really big launch for us, I'm able to do a little bit of like predescovery before we even get into the meeting. And we start the call on a business small talk tone rather than me asking them about what the weather's like in Rochester. The second way that you can do this is through what I call the astute observation. I want you to imagine that you're walking into your friends home and they're cooking a nice dinner for you. And today duck breast is on the menu. You could walk in and give a very basic compliment. Like, wow, that duck breast smells great or this duck breast tastes delicious. And they would be like, okay, thanks. Or you could say something like, oh my god, the scoring on the duck breast was perfect. And that made the charge just like, absolutely spot on. You must have been cooking duck for a while. And by saying that, that immediately shows you that I've cooked duck breast before or I at least know that you need to score duck breast before you cook it. And naturally that gets you to sit up and be like, oh, this person knows a thing or two about cooking and they actually take your compliment more seriously. And so the astute observation involves you pointing out something about their business that is unique and sharing your perspective on why you know it makes them different from other people in the market. So for example, I oftentimes will advise founders on their early stage sales process. And if I notice that a founder is closing 100K deals pretty quickly, I might say something like, holy smokes, you guys are closing 100K deals in three months. It usually takes companies at this stage six months to even land their first one because you're in like a pretty complex enterprise sales motion. And that shows them one, not only did I do my prep, but then two, it shows them that I know what good looks like in the early stages of the company. Now again, you wanna use either of these two approaches in the first 90 seconds of a discovery call. If you wait to give this stuff 10 minutes in, you lose your opportunity to reset the demeanor of the call in the first 90 seconds. But if you drop this at the beginning of the call, they'll oftentimes sit up and categorize you as a respected peer for the remaining 28 minutes of your discovery call. - I literally think about wanting to beat them to the punch in getting to this to show them that I actually understand them. I also wanna beat them to the punch to transitioning off of small talk and into the actual business conversation. And so you don't wanna linger in small talk too long, even if it's this good stuff that we're talking about, you eventually wanna move to setting an agenda, setting expectations for how the call is going to go. What a lot of sellers do is they roll right from small talk into asking their first couple discovery questions. They don't actually set an agenda. And the problem with this is your prospect likely came to this call with a list of questions that they have and things they wanna know. They might wanna see the product, they might have questions about integrations, they might have hit the requested demo button on your website. And when you start asking them questions, the red alert alarm starts going off in their head where they're like, hey, hold on, wait a minute, I thought this was gonna be a demo. Why is this dude asking me questions? Or he's asking me questions and this is fine, but am I gonna learn about what pricing is on this call? And so before you get into the meat of the call, it is imperative that you take a moment to set or reset expectations for how this interaction is gonna go in the first place. And the easiest way to do that is by setting what we call a P-P-O-A-Genda. P-P-O stands for Purpose, Plan, Outcome. So let's actually break that down. For the purpose, you need to let them know that the purpose of this meeting is not for you to pitch, not for you to go through your product, but rather to figure out if there's even any fit here. And the reason that you do this is a lot of prospects have been trained by bad salespeople to expect this to be a pitch fest or expect you to just start going through your product. And if you start asking them questions or trying to explore fit, they're gonna be confused because they might have thought that this meeting was for them to sit back and just consume a lot of information, not have a conversation to even figure out if you can solve their problem. And so what that might sound like when you lay out your P-P-O-A-Genda is, so Mike, really the purpose for today, honestly, is to see like, can we even help you with some of your big goals as it relates to marketing to sales leaders and teams this year? From there, I'm gonna roll into my plan, the way that I'm actually gonna figure out if we can help them. And so here I'm going to let them know the topics we're going to cover, how much time we're going to spend on each topic, and the order in which we're going to go through things. I'm going to set the expectation that, hey, I've got a couple questions for you to even figure out if we can help you, if you have a problem that we can solve. And then in the back half of this thing, I'm happy to talk a little bit about how we might actually solve that problem. So in terms of how we spend our time, I'm thinking it might be helpful to spend the first 10 to 12 minutes, just getting a better understanding of some of the big brand pushes that you have this year, and also understand a bit more about how you're thinking about structuring your demand plan. From there, I'm happy to share a little bit about how we might be able to help support some of those big initiatives, and I can share some examples of things we've done with other customers in the past. And then I'm thinking we might end about five minutes early to talk about, like, based on what we've seen today, we're obviously not going to be able to cover everything, but I think we should learn enough about each other to figure out, like, does it even make sense for us to keep talking after today? So I'd recommend we end about five minutes early to talk through that stuff if that sounds cool with you. What I did there was I actually voiced over the last piece of PPO, which is the outcome. What I need to do up front is let my prospect know that at the end of the meeting, I'm going to ask them to make some sort of decision. If I wait until the end and say, all right, let's talk next steps, they might have been like, whoa, whoa, whoa, this was just an intro call. Like, I got to think about this a little bit. I need to let them know in advance that I'm going to ask them to give me their honest take about should they or should they not keep looking at this thing? So I lay out that PPO and then I ask one more question, which is, does that sound right to you? Is there anything else that you want to cover today? I give them a chance to agree or disagree with that agenda. Once they give me the thumbs up, now I can roll into my first discovery question. And that brings us to the meat of the call, where you actually start to uncover problems and suggest solutions to solve those problems. Now, I know everyone probably wants us to jump right into discovery questions. And this is a really common mistake that sellers make is a lot of time sellers are obsessed with the perfect discovery question. But you don't even know what question to ask until you know what problems you're trying to surface or the problems you're trying to get in the first place. And so what we need to do before we start talking about every discovery question you could ask is we actually need to build out a map of problems. In other words, how do you take prospect from what are they doing today? To what's the operational problem that your champion faces? To what's the executive problem that their boss is freaking out about? To what's the business impact that impacts the entire company? And then once you have those four levels of problems defined, all you have to do is ask yourself, what's the best question that I can use to take this prospect from situation operational problem or from operational problem to executive problem or from executive problem to business impact? So let's actually walk through those four levels of problems using an example from when I sold compensation software at Pave. So if you haven't heard me talk about this before, I used to be the VP of sales over at a company called Pave. And the problem that Pave would solve is oftentimes you'd be running compensation reviews or promotion cycles out of spreadsheets. And that one just took tons and tons and tons of time. But then too, it also led to a lot of compensation mistakes because it's really hard to make sure that managers are making all of the right compensation decisions inside of spreadsheets. So Pave could automate a lot of compensation recommendations and give your manager's guidelines while giving you one place to run all of your compensation reviews and make sure that no compensation increases were being made out of policy. And so folks, if you're not watching this on YouTube right now, I definitely recommend going to YouTube really quickly because we're actually going to pull up a picture of this discovery tree and walk through it live. There's a link in the show notes. There it is. All right, so level one of your discovery tree is the situation, which is literally like how they do the thing. So at Pave, the situation they were in was usually they were planning compensation and spreadsheets. But there's no problem associated with that. Who cares if they're planning compensation on spreadsheets? If literally everything is going perfectly and no comp mistakes are being made, that brings us down to the next level, which is the operational problem. And this usually sounds like something that literally no one would want to do, where it's the thing that your champion will usually complain about. So at Pave, for example, there were two common operational problems that would happen if you were planning compensation on spreadsheets. It either meant you were spending way too much time in spreadsheets or you couldn't oversee manager decisions in spreadsheets because it was super easy for a manager just like sort of punch in whatever they wanted or you had so many spreadsheets that you couldn't possibly keep tab and make sure that every composition was correct. So those were the two operational problems. Now the issue is that who cares if you're spending all of these hours in spreadsheets, if you as the compensation analysts are getting paid 90K a year, and that's maybe 25% of your job, and we're trying to charge you 75 grand for the solution. The CFO is going to look at you and they're going to be like, well, yeah, that's your job. And that's why we need to turn this operational problem into an executive problem. And an executive problem sounds like bad news that a VP would deliver to their CEO. So for example, if we follow the left side of the tree, if the operational problem was I spend too much time in spreadsheets, the executive problem would oftentimes be that when you spend so much time in spreadsheets, oftentimes you literally have 70 different spreadsheets that you need to constantly reconcile every single time there's a compensation change. And you start to make compensation mistakes. And compensation mistakes are the type of thing that blow up not only to the CHRO but to the CEO, and they oftentimes lead to massive PR risk. So that is an executive level problem. The executive problem is that if you can't oversee manager compensation decisions, oftentimes that leads to managers making biased, comp decisions, which leads to compensation inequities, and compensation inequities freak out, achieve people officer or achieve HR officer. And so these are the executive problems. Now the final piece is turning executive problems into business impact. And business impact usually sounds like something that is either a sea level metric, an existential business risk, or a key executive level initiative that gets thrown off because of this executive problem. Compensation mistakes can usually lead to either massive employee retention issues, which is obviously a board level metric or massive PR risk, which will definitely blow up on the CEO or on the board radar. And the same thing goes for compensation inequities. If people feel like you have inequitable compensation practices, that is either going to leave to tons of employees leaving cultural issues, which leads to massive business PR risk. And so both of those can lead to the same business impact all the way at the bottom. And so to recap the four different levels that we talked to. This is literally how they are getting the job done today, how they're doing the thing. Operational problem, which is something that no human being would ever want to do. This is something that people most often complain about. Executive problem. This is usually something related to that operational problem that is keeping them from making more money. This is costing them money that they shouldn't be spending or is leading to risk. And then that last layer, the business impact is something like a sea level metric, a existential business risk, or a big sea suite priority that those problems that layer into it are keeping them from being able to accomplish. Now two quick tips while you're navigating your own trees is one, you don't need to get all of this stuff on the very first call with a prospect. It's pretty unrealistic to be able to quantify the business impact problem in a 30 minute discovery call. And so your goal on a first call shouldn't be to build out a full business case where you quantify the business impact, but you should be able to get down to an executive problem and at least point at the business impact that may be affected by this exact problem. The other key to success here is you're not just going to have one discovery tree. You'll likely have multiple trees if you have multiple products that you sell, multiple personas or ICTs that you sell to, or multiple different prospect situations. So don't feel like you have to have just one master tree. You're likely going to build out a couple of these. So as you start to build out your own trees, there are three steps that you can follow that will make this a little bit easier. So number one, try to start with the problem that your product solves. So don't start at the situational level because there are literally a million situations that don't matter relative to the problem you solve. But you can either one, listen for the problem that your champions complain about the most. So for example, people would always complain about planning compensation and spreadsheets. Or you can go on your website and oftentimes you can just invert the feature benefit. So for example, on Pave's website, at some point it says like, get better visibility in a manager compensation decisions to make sure that they're making fair decisions. Well, if I invert that feature benefit, that means, oh, you can't oversee manager compensation decisions and make sure that they're actually being made fairly. So that's number one. Number two is then you can work your way up and think, okay, if those are the two problems that I solve, what are the situations under which those problems exist? And both of those problems exist if you're planning compensation and spreadsheets. But if you have an existing compensation planning tool, that was actually another discovery tree entirely because those problems were not relevant. And then lastly, number three, once you have the problem and the situation identified, you can just ask yourself, so what to work your way down the tree. So if someone is spending a ton of time in spreadsheets, well, that usually leads to compensation mistakes. Ah, that's the executive problem. Well, compensation mistakes, I guess that's bad. But so what? Oh, if I make compensation mistakes, my employees are gonna start leaving. Ah, that's the business impact. And so you can sew what your way down to get to the bottom of the tree. And then again, make a couple different trees for different products or different use cases that you have. So now that you have your trees built out, now we can talk about how you use questions to navigate your way from situation to operational problem to executive problem to business impact, all right? So there are four keys that we're gonna cover when you're asking good discovery questions. Number one, your goal is to get them talking. And I know that sounds really obvious, but Gangda da Shoe is that the best sellers get their prospects talking for 57% of the call. And that is rarely the case if you look at most sellers' calls. Number two is again, you wanna think about what am I trying to get instead of what's the discovery question that I wanna ask? You wanna look at where you are in the tree. Am I at my prospect just told me that I'm spending a ton of time in spreadsheets. And then just ask yourself, what do I need to get next? Oh, I need to turn that into compensation mistakes. Ah, so I just need to figure out the best way to ask the question. And in the worst case, I could literally just ask, oh, oftentimes when people are spending so much time in spreadsheets, it usually leads to the compensation. Has that happened? It doesn't have to be the perfect question as long as you're trying to get the right thing. Another key to success with asking questions is thinking about the difference between how questions and why questions. How questions typically keep you at the same layer that you're at, which actually isn't a bad thing. A common misconception people have when they see these trees is they think they're only allowed to ask one question per layer, which is preposterous and would make you sound like a total buffoon. Sometimes you need to explore more at the current layer to understand where to take the call from there and which branch of the tree to go down. And so how questions help you explore the current later? Whereas why questions help you then go deeper into the tree? The last thing is you wanna make it as easy as possible for your prospect to answer your question the right way. You want to steer the conversation in the direction of problems that you can actually help solve. And so the tools that you can use to do that are one include context in your question and two use multiple choice to steer them. And what that might sound like is, so Armani, I know we've talked a bit about your billing practices and one thing I wanted to ask you about is I know you also just opened an insurance defense practice group. And in my experience, insurance billing can be really, really complex relative to some of your other practice areas. Typically when I'm talking to someone billing insurers, there's one of two major problems coming up. Problem one would be the insurers are pushing back and asking for like deductions and rejections when your bills aren't sent in the right format. One other common thing that I see is oftentimes attorneys get super bogged down in like, they have to use the right language on their bills. Otherwise the insurers get upset. And so I guess I'm curious are either of those things that you're running into. And that's a far more nuanced and strategic question than me just saying, so Armani, could you tell me a little bit about your billing practices? The prospect could answer in any number of directions, some of which we actually don't help solve. So I want to steer in the direction of places our product actually helps. - All right, so let's actually go through some example discovery questions that you can use at each layer of the tree. And for this example, we're gonna get off of pave and we're actually gonna use a different company that most people are familiar with, Gong. And Gong does a lot of different things, but in the case of this, why don't we just focus on their call recording tool? Okay, for now, all right. So step number one is you wanna drop into a problem. Ideally you wanna drop your ways deep as possible into the tree and not start at the situational level. 90% of your calls, if you just ask them why they took the call, it'll drop you into the right tree. And ideally it'll drop you into a problem. So the way you ask that is you might say like, so the way I usually like to start this is, honestly I have a bunch of reasons why I think you might have joined us today, but I'm curious if you just be willing to share like, what prompt did you take this call with me in the first place? Couple of things might happen. Number one, they might give you a problem right away, which is I really struggle with coaching all my reps because I don't have enough managers anymore and I've got to teamvate. Great, now you're at the operational problem level. Other times they might give you a situation, which is well, the reason that I'm jumping on those calls is because I'm planning conversation and spreadsheets or I'm currently recording my calls on Zoom. If that happens, I'm just gonna ask why again. So I might say like, awesome, well, we talked to a lot of people who are recording calls on Zoom. I'm curious like, what's prompting you to wanna get off of Zoom? And that will oftentimes lead them to turn the situation into a problem or they might ask, you know, I really want a better way to coach all these different calls across all my reps. And in this case, you're just gonna do what we did when we were building out the trees, which is invert the feature benefit or turn a want into a why. Which is like, awesome, like, I'm really glad that you wanna go and make sure that you can cover all these different calls. I'm curious like, what's prompting that in the first place is that you can't de-risk every deal, you can't coach every single rep, or you're like struggling to figure out exactly what's going on in the market because you can't cover all your different calls. All right, so you can make sure to turn that want into a why. And then the last thing that will happen is sometimes they'll give you like a lead source. It sounds like, well, you called me and I'm like, yeah. And so I'm just gonna ask why again. I'm gonna be like, okay, well, look, I appreciate you calling out the fact that I called you, probably cut you out there at the right time. My guess is you don't take calls with every single person that gives you a ring. So I'm curious like, what was it whether it was something in my email or something that I said that particularly resonated with you just 'cause I wanna make sure that I start in the right place. And then at that point they'll usually tell you what problem resonated with them the most. The last thing that will happen is they'll give you an answer that just sounds somewhat confused. So for example, at Pave, they'd be like, we're really looking for someone to help us build our compensation philosophy. And I'm like, ah, God, I think they think we're compensation consultants. And at that point I would do what we call the 90 second approach. And what that would sound like is this. I'd be like, hey, Nick, is it okay if I take like a quick minute to give you a sense of like the three different problems that we solve for customers? It goes, sure. And then I would pull up a very brief slide. And it would just show them the three operational problems we solve. Well, Pave is a platform that allows you to run compensation reviews more efficiently. And the reason for that is number one, like it tends to be really hard to find compensation data. That's accurate. Number two, it tends to be really cumbersome to run compensation reviews when you're doing it all on spreadsheets and make sure everything's going right. Or number three, it gets really hard to like retain your employees when a lot of them really don't understand the value of equity and benefits. And so I'm curious like for those three problems there are anyone that really jumps off the page for you. I'm basically suggesting the three operational problems or the three trees for each of the products. And then having them pick one, and then I drop into the operational problem. One other pro tip here is you should actually have that approach prepared for every single call that you have with every other stakeholder at the business. I can't tell you the number of times where I'm on like a fifth call with a company and there's a new stakeholder. And it is obvious they have no clue what we do. So you should get that approach on autopilot. Now we've gotten the operational problem, Armand, knowing that we might explore it a little bit. We might talk about it a little bit. When we're ready to, how do we transition down to the executive level problem? So oftentimes stories are the bridge between the operational problem and the executive problem. Because a story is when the operational problem happened or manifested in real life, and usually when an operational problem occurs into a real event, that's something that gets on the executive radar. So I'll give you an example. Let's say that the situation that the prospect is in is that they're manually recording all of their calls via Zoom, for instance, right? Well, the three operational problems we could solve are, well, you can't coach every single rep. You can't de-risk every single deal, or you don't know what's happening in the market. Again, what's the so-what behind each of those? Well, if I miss out on coaching opportunities, that usually would mean that I have performance issues on the horizon. And that's an executive problem. Well, how would I know that that executive problem actually came into existence? I would see a rep that was underperforming. And so I'm going to ask what's called a magic moment question. So if Nick says, I'm really finding that we're missing out on opportunities to coach all of our reps, I'm just going to be like, hey, Nick, I totally get that. My guess is you didn't wake up yesterday and think, oh, shoot, I'm missing out on opportunities to coach my reps. I guess when was the moment that you realized that was a problem? Was it you caught one call that went totally off the rails with one of your reps? Were you seeing some performance issues across both of our ups? I'm curious, like, what actually caught you to want to solve this problem in the first place? The moment they admit that they have a problem, just ask them when was the moment that you realized you had that problem? Nine times out of 10, Nick is going to answer it with a story about the rep who blew up a call or had a performance issue or something like that. And that gets you to the executive problem. One other way that you can go from the operational problem down to the executive problem is just to like, directly ask about that next layer. That said, you need to be really, really careful about your tonality here, because when you're going to that executive level problem, that's typically where there's some touchy sensitive stuff. So if we look at this gong example, we have the operational problem of missed coaching opportunities. But the executive level problem is literally people having performance issues, missing their quota, and maybe losing their job. And so I can't just be like, so Arma, and you mentioned these coaching issues are people missing quota and getting fired? I'm gonna look like a total ass if I ask that way. Instead, I've got to find ways to soften those hard and direct questions. And one of my favorite ways to do this is using something that I learned from Charles Mulbauer, which is called a humbling disclaimer, which is simply a preface to that direct question to help soften it. And so common phrases that you can use to humbling disclaim your direct questions are things like, I'm not totally sure how to ask this, or I recognize this might be a really direct question, or this might feel out of bounds for me to ask. or I know this can be a sensitive area. Anytime you preface your direct question with the humbling disclaimer, it makes it way easier for the prospect to open up. So now the final step is to go from executive problem to business impact. So folks as a reminder, you don't have to get all the way down the tree and you do not have to quantify the entire business impact on the call. However, if you can at least point to the metric, point to the initiative or point to the risk in the discovery call, that is in the money zone. And then later on in a business case or in a future meeting, you can quantify how much the executive problem is costing the business. So there are two ways you can get this. Number one, you could use another humbling disclaimer to soften the direct question. Or number two, you could use what I call push pull question. So for example, if I wanted to turn performance issues into missed revenue targets, that's a really uncomfortable question for me to ask an executive. And so I'm actually going to give them the right to say it's not impacting their ability to hit revenue targets or it is. So that might sound like this. And so I really appreciate you sharing the fact that there are performance issues and like look, we've helped tons of teams solve this. And I think it's awesome that you're even like focused on this problem at all. I want to make sure that we're solving the right problem here. And you've mentioned this Q2 revenue goal a couple of times throughout our call. I'm curious to what extent is solving the rep performance issues, going to impact hitting that Q2 revenue goal. Is this like number one most important thing that you've got to solve for the team? Or is it like even if we solve the rep performance issues, we don't have enough pipeline for marketing. We don't have enough SDRs on the team. Our forecasting is totally messed up. Or is it like something else? I want to make sure that this is the right problem to be solved in the first place. And by telling them that I'm OK if they say that this isn't that important or this isn't blowing up their business, they're more likely to give me the truth in their answer. So one other approach that you might consider taking when you're meeting with an executive is instead of starting the call by asking why did you take the call, make your first question around the big priorities that they might have, but help them taper their response in the direction of the areas that you help. So when I'm sitting down to meet with a CMO to sell one of our sponsorships, I might say something like, look, I know you probably have a lot of different focuses over the next couple quarters. Usually folks bring us in when they're looking for help amplifying really important brand campaigns, or they're looking for help around things like extremely targeted demand-gen campaigns in place. But honestly, we can help with pretty much anything as it relates to marketing to sales leaders and sales teams. And so I'm actually thinking it might be helpful to start the conversation with just getting a sense of what some of your really big rocks are over the next two to three quarters, and then I can share a little bit about how we might help fit in with some of those things. Does that sound fair to you? And so I'll kick this call off by just getting a sense of the big meaty things that they care about, which helps me figure out which tree I might explore with this executive in the first place. So regardless of which approach you take, asking why they took the call or leading with the priority conversation, folks will give you a response that is either at that executive problem tier or the business impact tier. Either way, what I'm going to do is I'm going to reverse tree climb to fully map the problem from situation all the way down to business impact, even though I'm starting at the bottom. And so if they talk to me about, hey, we have a business impact goal, I'm going to now ask about the executive level priority that is making them focused on that thing. So an example was I recently met with a VP of marketing who literally kicked off the call saying, yep, pipeline's down, and that's why we're looking at a sponsorship. And I've responded, and I said, OK, we can probably help with something like that. I guess I'm curious. Typically, when somebody tells me pipeline is down, it's because of one of two things. Thing number one would be there's an awareness or brand perception problem where folks either don't know you exist or they feel like you're dated and not really like a modern tool. The other reason that pipe might be down is because your demand plan is not functioning in a healthy way, and you need to find a way to up those lead sources that feed into that. I guess I'm curious, from your perspective, do you feel like it's one over the other? What I did here was I offered multiple choice of the two things that the layer above that might be impacting pipeline. What I heard in response was an executive level problem, where the VP told me, yeah, it's actually a brand perception problem where we've been around for a really long time, and folks are honestly feeling like we're kind of an antiquated tool. But in reality, we've released like six or seven pretty cutting edge things over the last couple years, and we know those just don't have enough awareness. And so at that point, I understood that pipeline was down because of a brand perception problem because of an antiquated view people had of the product. And I was able to pitch our sponsorships and how we could help with that in a much more nuanced way than if I just said, okay, pipeline's down. Let me show you how we generate some pipeline. You've got to map the problem bottom to top or top to bottom to have a really nuanced pitch. - Already folks, so we covered all of the questions you can use to navigate your trees from situation all the way down to business impact. But as we mentioned at the beginning, if you're only asking questions and not giving anything in return, you're only accomplishing one of the goals of the discovery call, which is finding a problem that matters. We need to also accomplish the second goal of the call, which is giving them enough trust or proof that we have the solution, and we can actually solve those problems. The way you do that is you balance give and take throughout the call. When you give prospects information as you're asking discovery questions, number one, they're actually more likely to give you more answers or let you ask more questions, which helps you uncover more problems. But then number two, you also start to interweave your solution as they share the problems. So there are five ways that we're gonna give you ways to give as you take so that your discovery feels like a conversation, not an interrogation. So way number one is actually called vertical questions. It's the only one of these five tactics that is not giving. It's the structure in which you ask questions. So discovery fatigue at pave would happen when I would hear sellers ask things like, how do you run compensation reviews? How do you communicate to rewards? Tell me about your benefits program. What HR system are you on? How many employees do you have? They basically just jump tree to tree horizontally or they stay at the situational level way too long and they go across. And this makes your discovery calls feel like survey checklist questions, where you're not actually doing anything with the previous answer to build depth in the conversation. So vertical questions is just a way to say you should be asking questions down the tree. So if you ask, how do you run compensation reviews today? And they say, oh, we're running them on spreadsheets. I might say awesome. Well, typically when people are running compensation reviews on spreadsheets, it either leads to they're spending too much time in spreadsheets or they struggle to oversee manager compositions. I'm curious which one of those two is the case for you. So not only did I go from situation operational problem, I use their previous answer to build the next question. That's number one. The next approach you can use is called a playback where you literally summarize, recap playback, what you've heard from the prospect thus far. And the reason that you do this is if you ever went to a therapist and spilled your guts and all they said back was, hmm, interesting. Tell me more, you'd wonder what the heck are they actually doing with the information that you're sharing with them? The same applies to our prospects. So anytime a prospect shares a decent chunk of information and goes on a long riff, pause, summarize what you've heard and then use that summary to steer the conversation in the direction of the problems that you solve. And so what that might sound like is, prospect goes on a long riff and I might say, cool. So just to playback what I'm hearing so far, it sounds like there's three big things that you're focused on. Thing number one is it sounds like attorney time tracking is a major pain. Your attorneys are complaining because they can't do their time sheets on their cell phones and they're looking for a way to do that. You also mentioned some problems with new client intake and you're looking to make that a little bit smoother over process. And then you also shared a little bit about this billing issue that you're having with some of your insurance carrier clients. It sounds like they're rejecting a lot of your bills because they're not sent in the right format. And I guess if it's okay with you, I'm wondering if we can talk a little bit more about that billing issue if that sounds fair. What I'm doing is I'm recapping what I've heard. I'm tapering. I'm not recapping all the extraneous detail that frankly we might actually help with or need to waste time on. And I'm pointing the conversation in the direction of my best tree branch. Another technique that I really like to use is what is called the pylon. And what you're doing with the pylon is anytime a prospect shares some information about a problem that they have, I like to add to that problem based upon my knowledge of what that problem actually is. And when you do this properly, it accomplishes a couple things. One, it shows that you're an expert because you know the full extent of the problem without them having to explicitly tell you. But then two, it shows that you have some degree of empathy and you're not just saying, oh yeah, awesome, awesome. Oh yeah, great, cool, perfect when they tell you about their problems. And so what that might sound like is prospect says to me, yeah, we're dealing with this billing issue. We send these bills to our insurers and they're writing them down. They're asking for deductions because we're not sending things in the right format. And I'm gonna respond and I might say something like, yeah, it's ridiculous what these insurance companies do. I feel like for a lot of the law firms I talk to, it's basically like the insurance companies are trying to delay paying your bill to turn you into giving them an interest-free loan. And the prospect might say, yeah, that's totally right. We've literally waited months to get our bills paid sometimes. What I've done is I've shown I knew the problem and I actually added to the problem because now it's not just bill write downs, it's bill delays. - So once you've gotten them to admit to a problem, eventually there's gonna be a point where prospects are like, yeah, I want to solve this problem. And that's when you wanna start to use praise. to reinforce the behavior. So when I was selling life insurance, oftentimes someone would come in and they'd be like, "You know, I really want to make sure that I have my kids covered just in case anything happens." I really want to make sure that like, my spouse doesn't have to move out of the home in case something happens to me got for a bit. And if that's the case, I don't want to just keep ringing them for more pain. I actually want to give them praise. And so what that might sound like is I might say, "Look, Nick, I gotta say that it's really hard to find folks who are proactive in realizing that, like, look just because I'm the main breadwinner today doesn't mean that that's always going to be the case. And they're doing the right things to protect their kids and their family. God forbid something happened." So it's just refreshing to talk to someone who's actually like thinking about the stuff the right way. What that does to Nick is it puts him in a position of higher status because he wants to solve this problem. And he can further lean into that higher status by moving forward and buying some life insurance to protect his kids, protect his family, etc. And he's also far less likely to back off of that path because backing off of that path would mean that he's actually stepping out of that form of steps and taking an action that would say, "Oh, wait, no, I actually don't care about protecting family and kids as much." So whenever someone acknowledges that they want to solve the problem in the first place, always reinforce that with praise. And then the final piece is, once you get them to acknowledge that they want to take on the solution, the final piece is you get to the bottom of your tree and it's time to quote, "pitch." Now, you can pitch by saying, "Well, the way that Pave helps you is we have these features that lead to this benefits that solve that problem." And that's okay. But the best way to pitch is to actually use a parallel story. So for example, at Pave, if I was talking to a company that just went public, I knew that the problem that they would have is that when a company goes public, all their employees are on a ticking time bomb to leave the company because they've cashed out. And so if I'm talking to an HR leader about that, I might say, "Hey, look, we see this all the time and it's really good on you for wanting to handle this and get ahead on it." I was talking to the team over at Slack a while back when they first went public. And one of the things that they struggled with is a lot of their employees were like, "Shoot, should I leave Slack now that I've been here and I've got my million dollar check?" And one of the things that we did is we rolled out these total reward statements that showed employees not only the fact that their equity had a ton of growth in the past, but also that there was even more upside post IPO if their next two or three earnings went correctly and that they would be leaving a lot of money on the table if they left today. And so that's one of those things that I'll actually show you later on in the demo. So notice a couple things. Number one, I used a peer customer in the similar situation as them. And the number two, I basically told them that that's what I'm going to cover later on. And so at this point, you've gotten to the bottom of one discovery tree and you can make a decision. You can say like, "Hey, I've gotten enough in this tree where I could say they would probably buy based on the problems in this tree alone." But realistically, you usually want to cover two or three problem trees and so you'd pivot to the next problem. You might say like, "Hey, oftentimes the other thing that impacts employee retention is how these comp decisions are being made in the first place. I'm curious how are you running these compensation reviews?" And that would be my trigger to jump to the next tree. And so then at the end of your call, you go down a tree, you tell a parallel story, you move to the next tree, you go down the tree, you tell a parallel story, and then you recap it all at the end. You say, "These are the three problems you shared. These are the three stories or the three ways we can help." And that's when you move towards setting next steps. So at this point, you've led with that 90-second rule to establish from credibility and respect. You set expectations upfront with your PPO agenda. You've navigated the problem trees by first mapping out your problem tree, but then also asking all of these different questions that we've shared with you. And you've balanced, given take, with the five different approaches that we just shared. At this point, you're in the last five minutes of the call. And this is where a lot of salespeople screw things up because pretty much every salesperson has had hammered into their brain. You always got to set a next step. Never leave a call without getting a next step on the books. And that is true, but only for prospects who actually have intent to buy your product and buy it within a reasonable timeframe. You should not be indiscriminately forcing next steps on the books. And frankly, when you get good enough at sales, you can pretty much always pressure any prospect into agreeing to a next step. But a lot of folks are going to ghost you, disappear on you, and then end up wasting your time because they never had intent to buy. So we're going to teach you how to figure out if it's worth setting a next step. And then the best way to actually set that next step in a way that drives urgency in your sale. So you always want to leave at least five minutes at the end of every single discovery call to run what we call the five minute drill. And in your five minute drill, you are going to ask three questions at the end of every single call. The three questions are, do you want to buy? When do you want to buy? And how do you buy? Question number one, do you want to buy? You don't literally ask, do you want to buy? The goal of this first question is to validate that they even agree that this problem is worth solving in the first place. If it's not, there's no point in going into a next demo. And so I might ask Nick the first question like this. Like, hey, before we talk about next steps, like obviously I'm biased. And I think there are a lot of different ways that we can support your team over at Acme Co. But I'm curious from your perspective, based on the problems that we talked about, the things that we said that we could solve for, it's going to take a lot of work in terms of more demos. We're going to bring in people from your team. We're also going to have to go and secure budget and stuff like that at some point in the call. Based on all that stuff, do you feel like this is something that you could realistically see yourself investing time and resources in? Or is it sort of a nice to have? And so notice we're also using that push pull question again. We're saying like, hey, is this something you want to invest in? Or do you want to drop it? And we're moving the pressure of the sale. If they say yes, at that point, I can move to the second question. And the second question is, when do you want to buy? And so I need to make sure that not only do they want to buy it all, but they're going to buy it some point within my reasonable deal cycle length. And for this one, you always want to suggest a timeline based on what you learn in discovery and then ask. And so that sounds like this. Awesome. So Nick, you mentioned that you have a merit cycle coming up in May. And so my guess is you'd probably want to have this thing live by like April time frame just so you're not like configuring last second beforehand. That probably means we would want to get the evaluation done by like March. Give or take. Is that directionally how that lines up in your mind? Or when's the latest you'd want to have something like this in place? So notice that I use something that I learned in the discovery, the fact that they had a merit cycle in May to drive timeline and then validated on their side pro tip here. You oftentimes have multiple discovery trees. And they're going to be certain discovery trees that have more urgency built into them. So at pave, if someone was running a compensation cycle, that was always the tree that I would use to drive deal velocity. When I was selling equity management software at Carter, if a company was doing a valuation, I knew there was a specific time where they had to time that valuation. And so try to have at least one discovery tree that you can use to drive timeline more quickly because that's going to increase your deal velocity. The last question is how do you buy? And this is not actually a question. This is a statement. You have sold your software far more than your prospect has bought your software. And so when you start asking your prospect, oh, what do you think a next step should be? Or who do you think we should loop in from your side? They're going to start bringing you into all these unnecessary demos and they're going to start bringing you below the line in front of all these stakeholders who don't need to weigh in on a decision. And so what you want to do is you want to suggest the next step and the next next step they should take based on how you know they need to buy. And so that might sound like this. Great. So knowing that we're going for an April go live here. Now that it's February, the next step would usually be we should loop in your head of demand gen for like a deeper dive where we really talk through a couple of content concepts here and we talk about a few campaigns we could run together. And then from there if that call goes well, usually we would roll this all up into one big presentation for your CMO Kurt. Does that sound about right in terms of like how you've worked with folks like us in the past? So what you want to do is you want to think about one, what are the things that I want to get out of my prospect? I want to get them on board with the upcoming content launches and then I want to get power on board with this overall plan. And then who are the people that need to be involved? Okay, can I name drop their director of demand gen and can I name drop the CMO that needs to be involved? And now that we know the exact next step and the next next step we're going to take it's literally just a matter of scheduling that time while you are on the discovery call. And even if they don't have their calendar in front of them, send a place holder invite and you can move it around later. Do not leave a call without a next step on the right prospects that you want to set next steps with. Woohoo! We did it Armand! You did it folks! You made it through the discovery playbook to recap. We talked about the three distinct phases of your 30-minute discovery call. Those up front five minutes where you are establishing credibility with some degree of business-related rapport building and then you're setting clear expectations to avoid discovery tug of war by setting your purpose plan outcome PTO agenda. From there we talked about the middle 20 minutes of the call, the meat of the call where you're using your discovery trees and some of the question asking techniques that we talked about to navigate through the situation, the operational problem, the executive problem and the business impact while also balancing give and take using things like praise, pylons, playbacks, etc. And then we talked about at the end those last five minutes using the five-minute drill to validate whether or not it's even worth you setting a next step with this prospect. And if it is recommending what that next step should be and when it should happen to drive timeline in your deals. And lastly, if you need to drive timeline in your deals, the number one thing you should do is give people a discount. And so we're giving you a discount that expires at the end of this week, folks, in celebration of the launch of our upcoming discovery course. There is a link in the show notes. We'd love to hear your feedback on what we put together inside of this course and we will see you on the next episode of 30 Minutes. This episode is going to be a long one. Today's show was brought to you by 11X. You're all in one digital GTM team handling, creating, qualifying and converting pipeline across every channel. If you are still using stale triggers like congrats on the funding, you're getting blended in with everybody else. The best use unique signals, exact linked in posts, negative product reviews, podcast appearances and use those as their trigger. And we built a growth playbook with our friends at 11X breaking this stuff down. You can get it for free at 11X.ai/30MPC or grab it in the show notes. Hey, folks, if you keep getting grilled in your pipeline reviews, try this. Show up with your deal risks already flagged, so gaps in pain, timeline or power and your next move ready to dock. What's kind of where Clary helps is they will show you live signals and risks on your deals in one clean view so you can run your business, not have your manager do it for you in poke bunch holes. So we put together a free guide on three plays to get your sales manager off your back. The link is in the show notes. Go check it out.

Podcast Summary

Key Points:

  1. Discovery is the most critical sales skill, requiring a balance between identifying significant problems and building prospect trust.
  2. A 30-minute discovery call should be structured into three parts
  3. Effective discovery avoids extremes—neither pitching prematurely nor interrogating prospects—and uses frameworks like the "discovery tree" to map problems from situational to business-impact levels.
  4. Setting a clear agenda with Purpose, Plan, and Outcome (PPO) aligns expectations and controls the conversation flow.

Summary:

This transcription outlines a structured approach to mastering discovery calls in sales, emphasizing that discovery is the hardest yet most vital skill. The hosts introduce a 60-minute course summary focused on selling without feeling salesy. They break a 30-minute discovery call into three segments: an initial 5 minutes for rapport and agenda-setting using the "90-second rule" to demonstrate business knowledge and respect before personal small talk; a core 20 minutes to uncover meaningful problems while building trust in the product's ability to solve them; and a final 5-minute "drill" to assess if proceeding is worthwhile.

The method avoids common pitfalls like excessive pitching or questioning, instead advocating for a balanced dialogue. Key techniques include trigger-based rapport or astute observations to establish credibility, a PPO (Purpose, Plan, Outcome) agenda to set expectations, and a "discovery tree" framework to escalate problems from operational to executive levels and ultimately to business impact. The goal is to position the seller as a trusted peer, ensuring prospects feel understood and motivated to continue the conversation.

FAQs

The main goal is to find significant problems worth solving while building enough trust so the prospect believes you and your product can solve them.

A 30-minute discovery call consists of the first five minutes for rapport and agenda, the next 20 minutes for problem-finding and trust-building, and the last five minutes for the 'five-minute drill' to validate next steps.

The '90-second rule' means establishing business respect first by demonstrating knowledge of the prospect's business and respect for their time within the first 90 seconds, before transitioning to personal rapport.

A P-P-O agenda stands for Purpose, Plan, Outcome. It sets clear expectations for the call, ensuring the prospect understands it's about exploring fit rather than a pitch, which helps avoid confusion and builds alignment.

The four levels are: Situation (how they do things today), Operational Problem (what they complain about), Executive Problem (cost or risk issues), and Business Impact (C-level metrics or existential risks).

Use trigger-based rapport or astute observations by preparing specific, business-related small talk that shows you've researched their company, demonstrating respect and knowledge quickly.

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