The "Questions That Sell" Summit

(upbeat music) - Welcome to the caliber show where revenue professionals come to build the skills, capabilities and standards required to perform at the highest levels. We are on a mission to elevate the standard of the entire revenue profession. In a world obsessed with tools and shortcuts, we focus on what actually drives revenue outcomes, human performance. This show is about mastering the skills and systems behind the highest performing revenue pros on the planet so you can become the highest caliber revenue pro you can, the kind that others measure themselves against. So if you're here to grow your revenue, accelerate your career and increase your income, tune in every Monday and Friday morning, and now here's your host, Chris Orlov, CEO of caliber. - Welcome to the questions that sell some of everyone today. We're gonna master a few things. I would not consider today to be the basics or like foundational stuff. We're gonna talk about advanced techniques on questions that sell. We're gonna learn and master three types of questions that sell, that separate great sales people from everyone else. Now, who saw the data from a couple of weeks ago from the caliber index? Write data in the chat. If you know what I'm talking about, if you saw the research report that we put out, that talked about what we're calling strategic synthesis. Okay, a lot of us. We're gonna start by talking about that data because it's gonna seamlessly flow into the what and why between or behind questions that sell. Okay, there's this unexpected difference between merely good and great sellers. And we're gonna review that by looking at data. Like I said, we analyzed 1,592 account executives in our skill model data set with about 300,000 calls with AI. And we're gonna talk about one of the things we found that separates great people, great sales people. Now, write, bin there in the comments. If you've ever been in a situation even remotely like this before, I wanna tell you about a discovery called that I ran at the beginning of my career as an account executive. I was maybe a year or two into closing deals, right? I was pretty green. And about five minutes into this call after asking a few questions, the COO, he goes, "Just stop." I don't have time for this generic line of questioning. And I thought I was doing everything right, right? Talk less, listen, more asked questions. And here I was on this discovery call trying to do exactly that. And the buyer literally left the meeting a few minutes in. And just kind of a funny side note, after he left his director of operations and I sat there like awkwardly, right? We were on a go-to meeting. And he goes, "I'm as confused as you are." Breaking the silence. He trains our sales team to do exactly what you just did. Now, just, just write yes in the chat if you've ever been there before. Maybe not that intensely, but you've gotten like the discovery pushback, discovery fatigue as I like to talk about it. Okay, so the question is what separates sales people? This is data that I published about 10 years ago, right? We found great sales people have this talk to listen ratio of 43.57. Okay, that's the ideal talk to listen ratio. Seller talks 43% of the caller less, the buyer talks 57 or more. But here's the big gotcha with it. In an attempt to actually do that, sellers everywhere get kicked in the teeth. Just like I did in that story. And here's one of the reasons, right? The valuable part isn't knowing that you need a lower talk to listen ratio. Everyone in this room probably knows that by now or at least most of us do. The value is knowing how you actually do it and away that moves the deal forward. Okay, so how do great sellers earn the trust they need to get their buyers opening up to begin with? It's not such an easy question to answer. And why do some buyers open up to great sellers and almost treat them like trusted advisors while they keep other sellers kind of at arm's length they give very short responses, right? Advisor in the chat, if you've ever gotten the advice that you need to be a trusted advisor with your clients and your prospects, but you're not exactly sure how to actually execute on that. Okay, it's easy to say go be a trusted advisor. It's not so easy to do it. We're gonna talk about how to do it today. So as a seller, doing this is not as easy as it sounds. Getting your buyer to open up at length, not as easy as it sounds. Buyers everywhere are afflicted with what I call discovery fatigue. Okay, discovery fatigue. I'm sure many of you in this room have dealt with that before. It's just obvious that the buyer doesn't want to answer your questions or do the generic discovery dance. Okay, so back to our question, what skills separate sellers who have this elite talk to listen ratio and as a result, advance their deals rapidly compared to everybody else. How do great sellers consistently do that? Well, according to the data that we released, just I think it was two weeks ago, maybe three, now two weeks ago, it's not that they ask a lot of questions. It's not always the quality of their questions, although there's something to be said for that and we're gonna talk about that today, great salespeople get their buyers talking and therefore trusting them because they are strong at one seemingly minor skill, strategic synthesis. That's too much of a mouthful for you, we can just call it synthesis today. Now what does that mean? It is the ability to effectively summarize what the buyer is saying throughout your discovery call in a way that does these three things. Number one, makes the buyer feel deeply understood, which is very rare by the way. Number two, clarifies the buyer's problem in a way that they couldn't. You hand the problem back to them sharper and clearer than how they gave it to you. And number three, by doing it in the way that we're gonna talk about today, it demonstrates your credibility and your expertise in your domain. Just give me another, I just wanna make sure everybody's still with me and engaged, just give me another yes in the chat. If you want to get exceptionally good at this skill and unlock what it can do for your sales performance. Great, now here's what the data says about this. This is not just the typical analysis of sales conversations that stops at statistics like the talk to listen ratio. In this data, we're talking about which skills actually drive certain outcomes. Now that artificial intelligence is smart enough to define skills, identify skills, and measure skills on a scale. So this is how we did it. As you can see, we have the skill maturity curve in the caliber platform when we work with our business clients. And it scores skills on a scale from zero to 100 in terms of what we call overall skill rating or OSR. And it spans five skill maturity levels on every skill that we're scoring. Novice, which means they don't have any skill. Developing, which means there's weak levels of skill. Proficient, which means skill is there, but it's inconsistent, strong, which is consistent skill demonstrated and then expert, total mastery of whatever skill we're talking about in question. So we asked ourselves this question, what skills do sellers that have a consistently exceptional talk to listen ratio have that other sellers do not? And let me talk about what we found in the data. I'm gonna break down what you're looking at here to be really easy to follow. So the first thing we did in this data set, we grouped the sellers in the study into three groups. Okay, those with strong talk to listen ratios, right? This group averaged 43% or less strong. Those with what we would consider to be decent or good talk to listen ratios, not amazing, but good. Okay, this group averaged between 44 to 59% talk ratio. And then finally, we had a group of those who had what we considered to be weak talk ratios on their discovery calls. They averaged talking 60%. In other words, this group talked a lot. And then we ranked their skills on the scoring model that I just walked you through across about 36 standardized skills. Okay, things like question quality, your ability to set agendas, your ability to deliver a compelling point of view, uncovering customer problems, multi-threading objection handling, right? The whole taxonomy and universe of selling skills. And it turns out there is one skill in our model that those with strong talk to listen ratios, those who could really get their buyers talking and talking without friction. And that skill was strategic synthesis. Great sellers, now that you are oriented to the data, great sellers averaged a 71 out of 100 on this skill. Now, for context, that means they are strong. Decent sellers, this middle group here, they averaged only a 42 out of 100. Okay, proficient, not amazing, not bad, proficient. And then weak sellers, as you can see, who frankly just talked a lot, they only averaged 36 out of 100. Okay, we call that category still developing. Now, here's what's interesting. I don't know if you got this immediately, but the difference between a week? and decent is negligible, right? That's not a huge difference between these two groups, this proficient group and this weak group, but then if you look at this, the difference between decent and strong is absolutely massive. And here's the takeaway from this data. Great sellers are not just a little bit better at the skill that we're talking about right now. They are in a totally different league. Okay, according to the data, they are a whopping 69% stronger at this skill than even average sales people. That is almost double the skill level. That tells us something about sales success. That is a profound leap forward in our understanding of what actually drives successful revenue outcomes for individual sales people. Just right, yes, if you took anything away from this data so far, we're going to get to the strategies and the tactics and what have you. I just want to make sure we're with it today. All right, really interesting data, right? So the question is, why does this work? Why does strategic synthesis work or just synthesis for short? Now that you have the data, let's talk about that. Let's talk about what good looks like and then we'll back into what we're here to talk about today, which is the questions that sell summit and how we build on all of this. Now, to appreciate this skill, I want you to imagine something and really do this, right? Imagine that you're a modern buyer, could be the typical persona or ideal customer that you sell to. You've been on a bunch of discovery calls with sales people and most of them are pretty bad. It's basic band qualification, that kind of thing. You get on yet another one and that's seller as usual starts with a few questions to get ball rolling. Okay, so there's nothing unique about that so far. You're probably waiting to be bored. But after you share kind of the overview of your challenges with this seller, this seller does something different. They say something like this. Let me back up and summarize what I'm hearing so far. Your biggest challenge is an inconsistent variance in performance across your sales team. You've got different frontline managers running their teams in different ways, creating kind of a Wild West situation. Now, in addition to that, the sellers themselves have a wide variance of skill gaps. Some struggle with discovery, others struggle with value-based demos, others struggle with pipeline generation or multithreading. And these two factors, right, manage your variation in how they run their teams and then this seller skill gap variation, they're compounding the variation in revenue attainment and performance. Am I hearing you right so far? Now, imagine you're a VP of sales evaluating something like caliber, and you hear that from a seller. You know you have a pro, because I want you to pause and notice something about that very simplified conversation. It doesn't just rightly summarize exactly what the buyer said. It does some of that, but the summary itself actually has insight baked into it. Right, yes, if you see the difference between just a plain vanilla summary and one that actually connects the dots for your buyers. In other words, it's not just a summary, it is a synthesis. Okay, the seller synthesizes what they've heard and condenses an otherwise messy situation into clarity and insight for the buyer. And when a buyer sits back and listens to it, it may give them an epiphany. It often does. And they often respond with something like this. Yes, that's exactly what's happening, and also, and then they expand on it. You earned massive trust. You earned massive credibility, and then they spend the rest of their discovery call, getting you up speed on the depths of their pain, their challenges, their executives' priorities, and so on. No discovery fatigue at all. You don't even have to ask another question if you get this part right. And all the while, while you've done that, you as a seller have demonstrated a couple things about yourself. Number one, I'm intently listening and understanding where you're coming from. And number two, I know what I'm talking about because I see this a lot. When sellers do this right, buyers feel compared to share even more. Right power in the chat, if you're starting to see how powerful getting this right can be. It is so simple. It's almost underwhelming of a sales technique, and yet it's incredibly powerful. So why do buyers respond to this? Because you as a seller just proved that this conversation is time will spent for you as a buyer. And the more the buyer shares, the more productive it's likely to become. So share, they do. They see you as a guide or an advisor. Now, here's what's super interesting. Let me back up. Great sales people, a whopping 69% better than their peers at this skill. Here's the other part of it. Most sales people do not do this at all. Let alone do it well. That's not an opinion. That's also what the data says. Only 17% of sellers score strong or higher on this. And that for everybody on this summit today is a massive opportunity for you. Because if most sellers do this poorly, that is another chance for you to blow past them in terms of the value you provide. So back in 2016, the data around talk to listen ratio, useful, viral, insufficient by itself. It didn't tell us how the best sellers actually get there. And now, after reviewing this data with you all, we're one step closer to knowing. It's not just the volume of questions. It's not just the quality of questions. It is synthesis throughout your discovery conversations. Okay, the ability to hand a buyer their own problem back, sharper and clearer than they gave it to you. I'm gonna say that one more time because I personally think that that is the biggest takeaway. Your ability to hand the buyer their problem back, sharper and clearer than they gave it to you. That's a learnable skill. And most sellers have simply never been told. It's one that matters. Everybody in this room is now up to speed. Okay, so great salespeople don't just ask better questions. They hand buyers their problem back, sharper and clearer than the buyer gave it to them. In other words, they can articulate their buyer's problem better than the buyer can articulate the problem. So the question becomes, how do we do it? How do we synthesize like a pro? Who's ready to start getting into the tactics and strategies, what you all came here for? Just write yes in the chat. I just wanna make sure you're all engaged with me as we go today. The real reason is I just need a sip of water every few minutes. Okay, let's talk about a framework and then we're gonna talk about questions that sell. Now, when you're having a discovery conversation with a buyer, a value-based business conversation and they voice their problems, there are typically four categories of information that they share with you, that matter. And I'm gonna walk you through them because it'll help you synthesize. Number one is surface level symptoms. Most buyers start discovery conversations with this. Surface level versions of the problem. Number two is what I call the need behind the need. The real, deep underlying problem that's actually driving them to even talk about the surface level system. Number three is consequences of the problems. Okay, not the problems themselves, but what issues are they causing across the business or organization? And then number four, the root causes of the problems. This isn't the problem itself, it's the culprit. The thing that's actually causing the problem. Okay, so your first step in becoming exceptionally good at synthesis is just starting to recognize these four categories as you're having conversations with buyers. Are we talking about symptoms? Are we talking about underlying problems? Consequences or root causes? When you start getting good at identifying those as buyers speak to you, and it may take you some time, give yourself some patience, you will be able to synthesize far better than sellers that do not have a mental model like this. So train yourself to identify those problems or those categories of information, I should say, and then you synthesize in that order. So let's say I'm 10 minutes into a discovery call, and a buyer shares a variety of pieces of information with me, all of which span these four categories. My synthesis might sound something like this. Here's what I'm hearing from you so far. At first, you told me you were struggling with X and X is the symptom. But after we got to talking underneath that, it seems like there was, it was leading to a much bigger issue. Why, why being the underlying problem? Now, when you think about how this is impacting other areas of the business, now you talk about the consequences they shared, and finally, what's causing all of this, the culprit that's making all of this true is, and then you insert your root cause. Okay, I know this is a lot easier for me to talk about today than it is to actually do. I don't imagine anybody is going to be able to walk away from today and immediately be able to implement this. Perfect. Unfortunately, it's going to take some practice and some repetition. But just give me one more yes in the chat. If you can see how this framework can help you start acting on this insight you've been talking about today, around synthesizing. This is the mental model. So if that's how to synthesize, well, what do you need to actually start doing that? You need to surface this information to begin with. And to be able to do that, you need to learn to ask questions that sell. You have to ask great questions for you to even have a seat at the table to synthesize your buyer's problem. And that's what we're going to talk about now. What you're looking at here is a typical funnel, a typical buyer's journey of how a buyer progresses through the journey of pain resolution, from latent pain to active pain to prioritized pain, to urgent pain all the way to signing a contract with you. And you're going to learn to ask questions that align with different stages of this pain journey. And they're designed to pull buyers down this funnel in a way that progresses toward a deal with you. The first one is insight lead questions. We're going to talk about that first. These are designed to activate latent pain. Pain that buyers are just dealing with in the background, but not acting on and to activate them, to turn it into active pain. Then we're going to talk about how to crystallize active pain into a priority, a priority that actually gets funded. Then we're going to talk about consequence mapping, right, negative impact, but an advanced version of it that heightens urgency. And at that point, the deal is yours to win or lose. So let's talk about the first one context lead questions. This is, I made a promise at the beginning of today, we're going to talk about three types of questions that sell. This is the first one context lead questions. This is how to convert latent buyers into active buyers using insight lead questioning techniques. Right. Yes, in the chat, if you intuitively understand what I mean by latent pain, latent buyers versus active buyers, typically a good way to think about it is buyers you went out found to that might not have pain. Okay, everybody seems to be getting this good. We're going to make it even more clear for those that don't you remember this story? I would have been better served if I asked this guy a context lead question, right? Three questions in this guy goes just stop. I don't have time for this generic line of questioning. We're going to talk about a question type that counter acts this, that prevents this from ever happening to you. Now here's another piece of data that we found. It turns out when you're in the room with a senior executive, the number of questions you ask actually has a negative correlation with win rates. In other words, the more questions you ask when you are in the room with a person that matters, the less likely you are to win that deal. That is so counter to what we are trained to believe as salespeople. You can see that after about four questions here, our win rate starts to drop off. It goes up, up until we hit about four questions, and then it starts to dissipate. Who finds that counter intuitive, right? Yes or me in the chat or something like that if you find that counter intuitive, okay? Now, does that mean questions don't matter when you're selling to an executive? No. It means two things matter, synthesis and highly effective insight-led questions, okay? Question quality matters a lot more when you get into the room with the C suite exact. So what is a context-led question? It is a question that starts with a relevant observation or insight or data point followed by a related, insightful question. When you get this right, you get a few things. You establish trust and authority. You convert passive buyers into an active conversation that they want to have. You thought out, quote unquote, "cold buyers," and you warm them up and get them talking. And typically, when you do this right, you generate long, rich responses that lead to rich business conversations. Right, Tim in the chat, if you've ever heard of Tim Ferris, I'm going to show you an example of how he does this in his podcast interviews. He's the podcast host of this show called The Tim Ferris Show, and he interviews top performers from different walks of life. A few years ago, he interviewed LeBron James and LeBron James personal trainer, Mike Mancias. I actually don't know if I'm pronouncing that right, but hopefully that was the ballpark. And I want to take kind of a snippet of his interview with those two. And this is what it looks like. He goes, "Hey, Mike, I'd love to dig into recovery and injury prevention with you." So LeBron, as I understand it, you're a bit of a unicorn in the sense that you've played more than 50,000 minutes in your career. Most players hit a wall in deteriorate after 40,000 minutes. So you're defying all the predictions of player decline. So Mike, maybe you could give us a window into some of that because you walk us through some of the tools of the trade and the approaches that you use to help with recovery in between games. I want you to take away something from that. Look at the insight and the context Tim teed this question up with. Much more powerful than what the typical interviewer or salesperson would do. They would have just asked him, "So Mike, tell us about injury prevention and your recovery process." Compare those two questions mentally, do you see how the one is significantly more powerful than the other? Just write "yes" in the chat. If you can see how much more powerful that first question is, then this basic, almost soft-mork second question. So let me break this down with a real sales example. So this is one that might be more applicable to me, but I just gave you an interview example. Let's talk about a sales example, so the seller starts with, "Do you mind if we start with an observation I have based on research I did with about the company?" And the seller says, "It looks like you stepped into the COO role three months ago, and from what I can tell your top initiative after talking to some people in your company, is to consolidate your go-to-market team under one umbrella." You have five products with five specialized sales orgs you plan to decilo them and have all sellers represent all five products. Returning your AES into generalists, what typically comes with that change is sellers have to learn a variety of new skills that they didn't need before, like multi-threading, or selling to new personas, or more complex discovery, to what extent are you anticipating that being the case. Now full disclosure, I think this could be simplified, this is pretty wordy, but imagine walking into a discovery call with an executive buyer like that, on the one hand most sellers are like, "So what's your top initiative?" And then they get smacked in the face verbally. And another seller comes in with an insight like this, they earn their buy-in, they state a relative observation, or a relevant observation, and then they ask a perceptive, insightful question, totally different response. Okay, these kind of questions help you earn the right to discovery with otherwise discovery fatigue buyers. Okay, context-led questions, in other words, are particularly effective for selling to power. Okay, write the word "power" in the chat if you're looking to sell to power more effectively. It could be a C-suite exec, if you sell to different parts of an organ, or not businesses, like K-12, higher ed, that kind of thing, could be somebody very senior, okay? This is the type of question that works in the room with senior executives. Now, a little later today, I'm going to talk to you about something that you can use to boost your win rates, and this is not a typo, by 130 when you're selling to power. Okay, so stick around, we're going to cover this toward the end, but I wanted to kind of tease that, because we're already talking about questions that sell. We're already talking about selling to power, a little bit later we're going to go deeper on this. Okay, so that's the first type of question that sell. Next right, yes in the chat, if you took something away from context-led questions, and you want to give those a try. Great. Leigh, I just saw your name, it's good to see you here. Great, great, great. Okay, the next one is now that we get buyers talking with insight-led questions, and we start to get their pain on the table, we're going to talk about a type of question that crystallizes their pain into a priority. Okay, many sellers get confused when they surface pain, they think there's an ROI there, they have a problem, and then the buyer ends up either going dark or saying circle back in six months. The difference between sellers who close the deal, and sellers who hear circle back in six months, is crystallization. Saving pain into a priority. Okay, there's this book called the Qualified Sales Leader, and he's interviewing a buyer in the book, CIO of a Fortune 500 company, and that buyer says most people think my job is to be a firefighter, and to put out any fire that looks like this. I ignore these kinds of fires. Now, translation fire means problem, and buyers ignore these because they're focused on this. So as a seller, your job is to unearth the raging forest fire, okay? Because what the buyer says in that story is he says, "My job is not to be a firefighter, firefighter at all. My job is to be a forest ranger, okay? I go attack the big fires and I let the small fires burn. I let the small fires burn." Many of you in the room right now probably have deals in your pipeline that you think you're going to close, and you don't realize that the problem you're talking about with your buyer is a small fire that somebody is just going to let burn, that the economic buyer is going to say, "That sounds okay, but let's tackle that in six months," right? Yes in the chat if you've dealt with that situation before. You think you've got a problem, you think you've got ROI, circle back in six months, or just goes dark entirely because the problem was not urgent enough. What we're talking about in this section of today is about turning little problems into big problems, which turns little commission checks into big commission checks. Now, I want to give you an example of what these conversations can sound like, and then I'll give you the question itself. Years ago, me and a rep on my team back at GONG, we're having a discovery call where we have these two people in the room, a low-level sales enable manager, and an SVP of sales. And these buyers came to us, right? They asked for a sales call. And so naturally, we kicked off the discovery call saying, "What made you reach out?" And of course, it's never power that starts these conversations for some reason. Of course, the low-level enable manager takes over the conversation and he says, "Well, we need visibility into our sales conversations." OK, so we continued peeling the onion back and we said, "Well, why do you need that?" And he says, "Our reps are struggling to sell to power." So we need to coach him up on that. Now, most sales people would stop here. If they have a solution that helps a buyer sell to power more effectively, got it. That's all I need to hear. I'm going to show you a demo. Instead, we said, "Well, tell us more about what's making you prioritize selling to power as an initiative." And he said, "Well, because we're so bad at this, we have a long sales cycle." It's nine months. And in our annual operating plan, it should be six months. OK, so we've gotten three layers deep. Do you think we're going to stop there, though? First of all, this is actually a pretty good problem to sell to, but we can keep going. And so instead, we asked another question. We said, "I understand why you would want to shrink your sales cycle, but you also brought two people to a call to a vendor you haven't met with." It tells me that this probably has some priority behind it. So why are you focused on decreasing your sales cycle so much compared to anything else you could be focused on right now? And that's when power took over the conversation. The closer you get to the center of the onion, the more likely you are to be speaking the language of power. And here's what she said. Nine-month sales cycles mean we have an 11-month cash cycle. OK, that means we don't get paid for 60 days until after we close a deal. So from the time we open an opportunity to the time cash hits our bank account, 11 months go by. That is putting a strain on our cash position over the long term. And if we don't solve that, we're going to have to raise dilutive financing that disintegrates some of our company's valuation. This is what I mean by taking a problem, like we don't have visibility into calls, we're not that good at selling to power or sales cycles too long, into a crystallized priority. Right? Yes, in the chat if some light bulb went off as I was going through this kind of sanitized conversation, OK? In other words, we're going from symptoms to problems to very high priority problem that gets funded and closes. When you uncover the need behind the need, as I call it, you have a better chance of crystallizing fleeting pain into a stabilized priority that sticks. That's what you need as a salesperson. Symptoms get ghosted, priorities get funded. It's almost rhythmic. You should be able to remember that, but it's also worth writing down. Symptoms get ghosted, problems get funded. And the thing you need to crystallize priority is to peel back the union, to uncover the need behind the need. And the question that I like to ask that works in almost every situation. I haven't found a situation where this doesn't work yet. As your buyer starts voicing surface-level problems and fleeting pain, you hit them with this. That challenge is going on in your world, that's driving that to be a priority. And that is where the deep, strategic priority lives. Right? Yes, in the chat, if you are looking forward to giving this question a spin on your next discovery call, I'd highly encourage you to do it. OK. We are two of three questions on the way. We're going to talk about negative impact questions now. And we're going to do this in a lot more of a sophisticated way than how most people teach this skill. This is how to intensify and expand a sense of urgency with what I call consequence mapping and negative impact. OK. So we're going further down the funnel. We've activated latent pain. We've crystallized it into a priority. And now we're going to fan the flame with urgency. OK. So what exactly are negative impact questions? These are questions that ask about the negative consequences or the implications or the second order of facts of a customer's business problem. Just right. Yes, in the chat, if you've ever been trained on some version of this, my guess is at least 50% of us have, right, impact questions. Nothing new. I didn't invent this. What we're going to do is talk about how to do this in a far more sophisticated way that actually creates urgency and helps you do this with powerful people in a way that doesn't make them cringe. What I'm not going to teach you to do today is something basic like, how is this affecting you personally? You get into a room with a C-suite executive and you ask that question. You will get laughed at. That is not what works when you're selling to a seasoned executive. We're going to talk about a different way to do it. But before we do, I'm going to show you the power of this. I've already mentioned this book once before today. The qualified sales leader. I'm going to walk you through an example he talks about in this book when he, the author John McMahon, is at his office and he picks up a cold call from a life insurance sales person. And instead of hanging up, he entertains it because he's the student or a student of the sale. Now that's how it started. That's how it ended. John buys life insurance and we're going to talk about how this conversation happened. Here's how it went. So as they got into the call, the rep asks, "John, do you have children?" And John says, "Yes, too." A boy who's five and a girl who's seven. The rep says, "Are you planning to put the kids through college?" He says, "Yes." The rep says, "How much do you think it's going to cost for each child to attend college?" And John says 250 grand each probably. Okay, so nothing crazy here yet, but we're starting to quantify a few things that the rep is going to use later. So at this point, Dan, the rep, have John thinking about his kids. It's a good start. Here's how it continued to go. The rep says, "Do you own a home?" "Yes, how much is your mortgage?" "I owe a ton on my mortgage." And in the book, he says, "I said that with a chuckle, my house was a gamble. I leveraged my finances, counting on working hard and making enough money in the future to pay for it, but things could always get bleak fast." Right? Yes, in the chat, if you can feel your stomach just starting to churn a little bit with where you can see this going. Now the conversation continues, and the rep says, "Does your wife work?" John says, "No. If she did work, how much money could she earn?" Not enough to pay the bills. Enough to pay the mortgage? No. The rep says, "Do you spend a lot of money every month?" Okay. Now, so at this point, John comments, "He's quantifying the major costs in my life. We've talked about 250 grand a pop for school, an expensive mortgage, and the fact that his wife is a homemaker." Right? She's not a careerist. So she doesn't have, at the time anyway, income earning capacity. Conversation doesn't stop there, though. The rep says, "Do you have any parents in the area?" He says, "No, I married a Dutch woman, all of her families in the Netherlands and my parents passed away." And now here's where things get interesting. The rep says, "Now, John, if you box up tomorrow, which means pass away," right? It's like slaying term, "John, if you box up tomorrow, what would happen?" Think of it this way. Would your wife have to go back to work? Yes, I guess so. Is it possible your wife would have to sell the house because she can't pay the mortgage? Yes, that's most likely what would happen. Would your wife have to put your kids in a daycare center since she has to work? Yes, since you have no relatives in the area, who would drop off and pick up the kids from daycare every day if your wife is working? Now, we're going to do this in a different way than this rep did, but you're going to you can see. Now, according to John, thinking about the future of my kids was uncomfortable. Just write yes in the chat if you can sense the discomfort. In that conversation, he says, "Now I couldn't think about anything but this conversation." And finally, the rep says, "And if you did box up, have you considered that your kids wouldn't be able to attend college?" And John says, "Now I wonder how I could be so stupid not to have life insurance." He picked up the cold call because he's a student of the sale and that's the only thing he intended to talk about. It's just I want to see this rep spit some game at me. And boy, did the rep do that. And he says, "At this point, Dan changed my priority on life insurance from never considering it to a must-have top priority purchase." Right? Yes in the chat, if you want to figure out how to take your buyers from not really considering what you sell, you must have top priority purchase. Okay? Dan created urgency. You can create urgency. Not every single time I don't want to oversell it. But if you're talking to your ideal customer profile and you're not doing something like this, I can only imagine how much money you're leaving on the table. Okay? So let's talk about how to do this. We are going to talk about this in the business way. Okay? I'm guessing nobody here sells life insurance. I don't either, nor have I ever. And we're going to talk about this concept called negative impact market fit. Right? Yes. In the chat, you've ever heard of the concept of product market fit. Okay? Or message market fit or anything like that. Okay? If you work in tech particularly, you've probably heard of product market fit. It's basically finding the right feature set of your product that gets buyers to buy and stay. Message market fit is finding the right narrative and marketing message and sales message that resonates with your buyers. Now, the commonality these two things have is they're based on patterns in your market. The same thing is true of impact market fit. Instead of asking generic impact questions like how is this affecting you or how is this affecting the business, you can actually identify in advance what consequence you think that buyer is dealing with based on their problem. Ask about it and magnify urgency and builds your credibility all at the same time. So here's what I mean by negative impact market fit. It is finding the specific negative consequences that predictably resonate with your target buyers and individual personas. Think of that life insurance guy. He called John probably knowing who he was calling, right? A high income sales leader with a stay at home wife. He knew exactly what questions to ask because he knows his buyer. We're going to talk about the same thing for you. Now I'm going to give you an example that's more B2B oriented. When I'm selling to a company that's trying to close more enterprise deals, go up market, close higher deal sizes. This is what typically works for me. A VP of enterprise, my potential buyer might say something like this. We have an average selling price problem, a deal size problem. We're selling $75,000 deals with single use cases and we're struggling with the skills we need to close bigger deals. We want to go up market. Okay, that's the problem. Now I know because I know my market well that if that's their problem, they're also probably dealing with a predictable consequence. Turn. If you're selling small deals into large accounts, most of the time you're dealing with a churn issue because it's not transformative, you're selling a tactical use case. And so that's how I phrase my question. When I usually hear this issue in other companies trying to go up market, it has an impact on net retention rate. To what extent is that an issue being discussed? Buyers often feel like I'm reading their mind or at the very least I demonstrate. I know exactly what I'm talking about. And they start to expand on that consequence. They say, yeah, we only have 75% net dollar retention on deals that have that profile. We're churning them like crazy. Do you see how the specificity here is more powerful than a generic? How is this affecting you problem? Or a question? Just write yes in the chat if you can start to glimpse that. Okay, so there's a few things I'm going to give you an exercise to do kind of in your own time to like really nail this. I want you to be patient with yourself. It's going to take you a couple rounds of getting this right. You're not going to nail it your first time. You'll start to nail it on your fifth or sixth attempt. This is one of the highest ROI things you can do as a sales professional though is getting these right. So the first thing I want you to do and you can take screenshots of this in case you need, you know, these directions later. First, step one. Identify the top few most common problems that you solve in your market. For me, just some examples. That's low wind rates, small deal sizes, long sale cycles. Okay, right a few of those down. You can come back to it later. You don't have to do the exercise full blown right now. The second step is underneath each one of those problems, right, two to three predictable negative consequences of those challenges. And then the third step is turn each one into a question that you can start testing. So this is what mine looks like. Right, this is the map you should put together. I call this the consequence map. Up here at the top we've got our problems, right? Low wind rates, small deal sizes, long sale cycle. The black boxes underneath each one of them are negative consequences that I'm going to ask when I hear that particular problem. So if I hear somebody talking about low wind rates, I'm going to ask, how is that affecting your customer acquisition costs? Or how is low wind rates affecting morale? And is that leading to attrition? If your sellers are losing too many deals? Or to what extent is that stifling cash flow? Right, if they're a private equity business or something like that? Okay, so I'm not going to go through all these. You can see these faster than I can read all of them. You can take a screenshot. This is my world though. You should create your own map. Three problems at the top, predictable consequences underneath them. And I just want to make sure you guys are with me and I didn't go too fast. Just right. Yes, if you're with me on this, if you understand what to do, if you understand the value, and you're committed to actually doing it, right, I can't do your pushups for you, unfortunately. Great. So this is the exercise. Now we've covered a few things today. We've actually covered a lot. We spent our first 20 minutes talking about synthesis, the data behind it, how to do it, how to earn credibility. Okay, why great sales people are 69% better at strategic synthesis and how to do it. We talked about the four keys to synthesizing complex customer conversations for trust and credibility. And by the way, as you think about what we've covered today, just write the words worth it in the chat, if you took at least one thing away that made today worth it for you. You also learned how and why to ask context-led questions, especially when selling to senior executives. We talked about the Tim Ferris example. We gave you a business example. We showed you the framework. We talked about how to crystallize fleeting paint into an executive priority that commands budget. Okay, with the need behind the need question, I hope all of you go out and test that question on your very next discovery call. We talked about the killer question. What I just talked about designed to uncover the need behind the need. And we talked about the urgency creating power of consequence mapping and negative impact questions. And you now have an exercise you can do that will help you implement this into your sales motion. So I just want to make sure this was time well spent so far. We still have a little bit more to cover, but just write worth it in the chat. If today has been valuable enough for you to have spent the time on this. Great. Okay, let's keep going. So there is a pattern to everything I just taught you. Before we wrap up, I want you to notice something about everything we covered today. All of it. There's one commonality. Context-led questions, strategic synthesis, getting underneath the surface problem, connecting problems to consequences. Think about where these skills become disproportionately valuable. And it's when you're sitting across the table from a senior executive or a senior buyer or power. These aren't just good questioning skills. They're the kind of executive grade selling skills you need to better sell to power. So speaking of power, just right in the chat one more time, the word power. If you can see the upside of being able to sell to power more effectively, then you did when you started today. And I just want to see what you guys say. Okay, you guys have been an awesome group. Thank you so much for engaging with me in the chat. Right, the word power in the chat if that's you. I talked about this earlier today. Earlier I promised I'd come back to this. Sellers who successfully engage the economic buyer. That's what what EB stands for, hopefully we all know what that term means, it means power, person with the economic authority to sign off on your deal, sellers who successfully engage the economic buyer can see dramatically higher win rates up to 130 according to GONG. The person with the most authority over the deal is the person you most need to know how to sell to in today's AI era. I'm going to say that again and tell you a story behind it. The person with the most authority over the deal is the person you most need to know how to sell to. That is the most AI proof skill that exists. I was talking to the VP of sales at one of the top three hottest AI companies on the planet. They closed Cisco for 5 million dollars on a sign-up link to procurement with a rep that was three months into the job and you would think that that's all they need. Now here's what ended up happening though. Cisco expanded their usage of the product from 5 million bucks to 10 million bucks. What do procurement teams like to do when that happens? They put it out for bid. They want to keep their vendor honest and they put it out for bid and make it competitive. That's exactly what they did. Even though this company closed a 5 million dollar deal, lightning fast with a sign-up link, guess who took the deal away from them after they were already a customer? The number one hottest AI company in the planet. I'm not going to tell you the name of the company, but they stole the deal. Why? It's not because they were cheaper. It's because while the original company closed the deal on a sign-up link with procurement, the other company that eventually stole the deal had direct access to the economic buyer and a multi-threaded league of champions. And so by the time procurement went out to bid, it was easy for them to steal that company or that customer. Because asking great questions once your front in front of an executive is one thing, but how do you get access to them in the first place? How do you activate them? How do you align them around decision criteria and an evaluation process? How do you prevent your champion from blocking you in getting the power? How do you use power's political capital to win the deal when it counts at the end? How do you get them to use their authority to actually get the deal across the finish line? I want to take the last few minutes to show you exactly what this is, how it works, and who it's for. I want to introduce to you a flagship certification program we have here at Caliber called the Economic Buyer Selling System. This is the flagship executive selling system and live program for serious revenue professionals brought to you by us at Caliber, the global leader in revenue skill development. Now this is a four week live certification in what we're calling the economic buyer system. This is a framework for activating your champions, engineering access to power, and closing the deal with the person who controls the budget, the economic buyer, and it's taught by me personally, live, four sessions, one real deal from your pipeline, and one performance based exam that only 58% of people actually pass and earn a credential behind. What you learned today during the questions that sell summer helps you once you're in a serious conversation with an executive. It's useful. But selling power is a much bigger motion than just asking a few great questions. You have to know how to activate the economic buyer, how to gain access to them, how to align them around the decision, how to influence the decision criteria in your favor, how to enroll them in how you want to run an evaluation, and like I mentioned, how to use their authority to get the deal approved. You want economic buyers expending political capital. Okay, that's the system. I've spent years figuring out why some sellers consistently get senior executives involved in their deals while other sellers struggle to do it at all. And eventually, I realized the entire motion can be broken up into these four stages. This is the whole system. Great executive level sellers know how to do four things. They activate their champions and economic buyer into a genuine pursuit, not a casual exploration, a genuine evaluation. They engineer access to power instead of hoping for it. They align the economic buyer around how the deal should be evaluated and they do that early in the sales process, not at the end, like most sales people do. And then they use the economic buyer's authority to get the deal across the finish line, even against headwinds like procurement issues. Activate, access, align, approve. It is the four A system for selling to economic buyers. That is the economic buyer system. Now this isn't some optional advanced skill. Buying decisions, and I'm sure you can feel this, have moved up the organization. If you sell meaningful deals, eventually somebody senior, typically a C suite executive is going to decide whether your deal lives or dies. And that's only going to become more and more true. So the question isn't whether the economic buyer matters. It's whether you have a repeatable system for selling to them. And fortunately, you can learn this. You can move yourself into the elite tier of sales people who can do this. The sellers who are respected by economic buyers and the sellers that economic buyers buy from. It's a learnable skill. It's a framework that you can follow. And people have used this skill on very real deals. $1.7 million total contract value. This isn't theoretical material. And this is the part I want to emphasize with you before we close out here in just a few minutes. You do not need another bag of tricks for selling to senior executives. You need a system for selling to the economic buyer. That's three things. A framework you can follow. Strategies for each stage. And tactics underneath those strategies. That's what this certification program teaches. In this program, it's four weeks. One single two-hour session every week hosted by me with 30 other like-minded peers where we are going to install the 4A economic buyer selling framework into how you sell. Like one, you're going to learn how to activate your deals into pursuit. And how to activate your champion to get you access. Week two, you're going to learn a system for getting access to power. Not hope. Not staying boxed in with your champion. Nothing like that. An easy to follow repeatable system that gets you access to power most of the time. Week three, we're going to talk about how to align with the economic buyer. How to enroll them. In how to evaluate your deal. How to influence the buying criteria in your favor. And the non-negotiables you need. There are seven of them. To successfully align with the economic buyer. If you don't do this in the first half of your sales cycle, by the way, you're really signing up for two sales cycles. One with your champion. And one at the end when the economic buyer finally learns that what you're talking about even exists. Then week four is the approval stage. How to get your economic buyer to spend political capital on your deal so that it closes with minimal friction. Okay, it's four weeks. It's eight total hours of learning. Okay, it's not a video course. It's live Tuesdays, that 9 p.m. Pacific. You work live for two hours with me and your peers. Wednesday through Friday, you're going to be doing hands-on excerpt sizes with the deals that are actually in your pipeline. So that you actually start to see ROI from this program, not six months, not six months from now, but immediately. Okay, within that, you're going to walk away with this framework, the economic buyer alignment spectrum where you take economic buyers from unaware of what you do to aware, to supportive, to aligned, all the way to making the economic buyer a champion in their own right and becoming extremely engaged. Now, what comes with this at the end is a credential. And I want to talk about why this certification matters because most sellers never build the skill that decides these kinds of deals, getting in the room with the person who controls the budget and being worth their time once you're there. Okay, this is a real credential that only 58% of people pass. This is not a participation trophy. This is something that increases This is your value in the marketplace, whether it's at your current job or whether it's you're looking for your next role. Now like I mentioned, I'm going to be teaching this one personally. If you're in this room with me, I assume you know who I am. My name is Chris Orlov. I'm the CEO of this company called Caliber. Previous to that, I helped grow gong from about 200 grand in revenue to a little over 200 million in revenue, and we got really good at this motion while we did it. Now, I'm about to invite you into it, tell you a little bit more about it, and then we're going to close out. This is limited to 30 people, because I'm teaching this live, and we need to keep the classroom, the virtual classroom, over Zoom, manageable. It starts on October 6th, that's three weeks from today. It is the executive selling system that turns unfunded problems into budgeted priorities, unfunded, fleeting, pinging into a budgeted priority that an economic buyer acts on with you. It's a four week live certification where we install the framework into how you sell. Here's everything you get. Number one is four live, two hour intensive sessions with me, where you master, activate, access, align, and approve, live with 30 other people. Number two, you will earn your economic buyer selling certification. Like I said, this isn't a participation trophy. You'll demonstrate actual proficiency and earn this credential. And then the other thing we're including with this is 12 months of the caliber platform. So that after this program is done, you continue building elite selling skills for the next 12 months, not just during the certification. Now the unfortunate part of this is I can only open this to 30 people until we do this again next year. So here's how to sign up right now if you're interested. Your investment in all of this is 1295, 30 total seats available, first come first served, and you can sign up right now by going over to that link, caliber.io/october. And I'm going to put that link in the chat just so it's a little bit easier to click it and go sign up. So I want to give you a little bit of context on the price. There are gurus out there that literally charge $25,000 per year for their training programs. There are reputable companies that charge $25,000 for certification programs like this one. Next year this certification program is going to be $1,995 today for this cohort in October, as long as you're one of the people that grab one of these 30 seats. It's only $1,295 and that comes with one year of the caliber platform. Now if you don't know anything about the caliber platform, I'm going to give you a quick overview. It is a SaaS platform where you have access to expert lead training programs and courses that are taught by the top 1% of revenue experts on the planet. Every skill topic you can imagine, from enterprise grade discovery, to building champions, to multithreading, to business cases that sell, to pipeline generation, to crafting points of view, to advance negotiation techniques, how to run closing motions. There's expert lead courses and content taught by people who have been there, done that. When you sign up, now one of the things that's worth mentioning is if you go to our website right now, you can sign up for $995 for the platform. The certification, like I mentioned next year, is going to be $1,995. You are getting the bundle of both of these to accelerate your skills over the next 12 months for only $1,295. Now if you're not aware, this isn't just access to content. Within the platform, you can actually go practice your skills with AI simulations that are based on the content. So imagine taking Nate Nisrella's course on champion development and he teaches you a specific way of testing your champions live on a call. Well, before you go actually use that skill in real life, you can step into our practice simulation, practice it, get the marbles out of your mouth, build muscle memory, so by the time you actually use the skill for the first time with a real buyer, you're already pretty good at it. A few minutes ago, I told you to start using the killer question that we talked about with the questions that sell, right? The thing that uncovers the need behind the need. Well, instead of practicing on your buyers and possibly screwing up the deal because you flubbed it for the first time, now you can go get the marbles out of your mouth, practice, refresh on the content if you need to, practice some more and by the time you show up, you can already perform under pressure. Most of you are probably familiar with our success stories because they're pretty incredible. This isn't an untested learning model, sellers across Calibur and our platform are using this approach to close bigger deals to move faster and to improve their performance. So there's upside and downside for this, right? The upside is if you get exceptionally good at selling to the economic buyer, you are likely to boost your win rates up to 130. I would argue that selling to the economic buyer is the highest paid skill sales professionals can learn. It's the highest leverage skill that exists. The downside is according to Forester, only 7% of sellers are any good at this, according to their survey, 93% of C-suite executives name the interactions they have with vendor salespeople as a waste of time. That means there are 7% of salespeople, that the executives actually respect and to follow and allow themselves to be guided by. This framework is how you get there. I'm going to put the link in the chat one more time for you to enroll and then I'm going to take some live questions if anybody has any. But this is the economic buyer system. So if you want to become genuinely dangerous at selling to power, this is the program I'd recommend. We have 30 total seats because I'm teaching it live myself. The October cohort starts October 6, that's in three weeks from today. If you can't make some of the sessions because it's one two hour session per week followed by office hours, that's okay. Most people miss one session or going to record all of them, you'll have access to them. In fact, one guy in our last cohort that we did in July didn't attend a single one. I wouldn't recommend that. I think you should attend it, but he chose to learn it on demand by the recordings. But that's what it looks like, so click the link in the chat right now if this is interesting for you. Caliber.io/October, secure your seat, and I'm going to hang here for a few minutes and answer any questions while people enroll. So if you have any questions, go ahead and voice those right now. Bradford, you said I'm already a Caliber member, is this information available within? No, the economic buyer system is not a course in the Caliber platform right now. This is specifically a live certification program. It may be a course at some point in 2027, that's not in the plans right now for 2026 or anytime soon, so no, this is not something you can learn in your typical Caliber membership. Okay. Any other questions? I'm going to hang around for just a couple of minutes in case there are any, and I'll make sure this link is just at the top of the chat. Next says Katie is a champ, absolutely he is. Okay, Bill, how much do you probably ask that before we talked about the price? 1,295 bucks, Kylie, thank you. I hope you got something of value from this. All right. It doesn't look like there are any other questions, so I'm going to close out now. Thank you, everybody, for joining today. Fill up. Yes, we're going to have the recording. We'll send that out probably later today. Thank you so much for joining. I'd encourage you to join the economic buyer selling system, and until next time, thanks y'all. Thanks for listening to the Caliber podcast and make sure you tune in next time. [MUSIC]