Executive Sales Masterclass: Close Big Deals At Power (Step-by-Step)

In this masterclass, you're going to learn everything you need to know to master executive level selling. So we're going to start with talking about how you get an executive's attention in prospecting. Then we're going to talk about how you run discovery to get them rethinking the problem that your solution solves. And last but not least, we'll talk about how you run that big, scary team meeting with all of the players that are involved on their side of the business in making that decision. I'm Jen Ellen Knuth, aka Demand Gen with a J, and I've spent 18 years as an AE selling into executives in the enterprise segment. And I'm excited to walk you through a lot of the lessons learned I had today and what I'm doing now instead. Let's get into it. By the way, this is a high level summary of my course Selling to the C Suite. So if you want to get the detailed breakdown of how I handle all of these things, all the questions I ask, all the research that I do, all the scenarios that might go left instead of right, you can access that in the course Selling to the C Suite. Now, before we jump into prospecting, let's talk about all of the stuff I got wrong selling into executives. So. So the mistake I was making is I was trying to reach out to C level executives to talk to them about products and solutions, but I was failing to get them to appreciate why the problem our solution solved even mattered for their time and attention to begin with. And so what would ultimately happen is I would do one call or two calls. The executive would leave that call and say, sure, let me think about it or I'll get back to you or why don't you send me some more information? And then I never hear from them again. So it caused me to step back and say, what, what am I doing inside of my conversations that's making this outcome happen? It's what I'm saying that's causing them to give me a reaction that I don't like. And so I started talking to my head of sales to figure out what are the things I was saying and doing in my conversations that might be leading to these negative outcomes. And one of the things he shared with me was, you're just droning on and on about how great our solution is. If you think about what an executive's job is, it's to mitigate risk in a business. So every executive works for a CEO, a president, someone at the top of the house, and every year that person at the top of the house, well, they set a set of objectives, things that the business must accomplish that year. Once that happens, every functional leader, well, they start making this really long list of all of these things that could potentially go wrong that would be their fault. So that leader is now thinking about of all of these things that could go wrong, what are the things that will actually present the greatest risk? And so they start prioritizing this. So the word or the phrase that I use to describe this is cost of an action. If I let this risk continue, what negative consequence does that create for my team and this business and our ability to achieve those objectives? Now that list then becomes much shorter. Not because the problems on that list are not important, the ones that don't make the cut, they are. But there's trade offs they have to make. We can't solve for every problem. And so now the executive has a much shorter list. And now they're thinking about what are all of our options for solving that. And then they formulate their plan of action. So these are some of the things that we're going to talk about today. This is why I've built the approach that I have for thinking about how I prospect, thinking about how I run discovery, and thinking about how I get that buying group to agree on making any decision whatsoever. So, so let's start with prospecting to an executive level contact. So you've identified an account, you've identified a prospect, and now it's time to write that message. And you're probably looking at a blank email screen. Biggest mistake I see is something I call the wee wee problem. It's where I open up an email, I start writing all about our business, how great we are, our solution, how wonderful it is. Easy way to spot this is by looking at the emails you're sending and seeing how many times do I use the word I? We, our, us, our company name. The more we're talking about ourselves, the more we're just wee weeing all over our prospects. So we're going to prevent that by writing an email that's actually all about the prospect and not at all about us. Now here's how we're going to do it. I'm going to break it down line by line. So line number one, your executive is selfish. Not because they're a bad person, just because they have to be. There's a lot of work they have on their plate. They can't take the time to read every seller's 200 or cold email. So the first line here's something I saw that is happening in your business that points to a larger objective. Let's say I'm selling to a head of manufacturing. They opened up a new shipyard in in a city and what they're trying to do is deliver a bunch of ships on time and it's a really important project for the business. So here's how that first line might sound. I saw the news regarding the new shipyard you opened in Portsmouth. There's no niceties there, there's no warming them up, it's just getting them quickly to the point of here's the thing, the subject matter that I'm going to with you about now. If this is the head of manufacturing, chances are that is a big priority for them. They're going to need to set up operations there. They're going to make sure those operations go smoothly. Now the second line is where I'm going to start using something called unsure tonality. Idea being if I am specific and I frame it with an unsure tone, I'm inviting them to correct me where I'm wrong. A correction is a reply. So that might sound like not sure if the US welder shortage is making it harder to hire and retain welders. Do I know that that's probably hard? Yeah. But I'm still not going to frame it that way because we don't want to rub someone the wrong way by showing up to their house and pointing off out of their all of their ugly spots. So this intention here is to take that objective in the first line and connect it to a problem that I think they might have. Now, the third step or the third part of the email is instead of going to, well, we help companies do this, this and this, which is just a pitch, it's an advertisement. We're not going to be the hero. We're going to point to another customer who is up against something similar. So I could say something like another company was up against the same problem and was trying to use higher wages to attract more welders. But it wasn't filling the gap. Now, my intention here is to show to the reader that I have access to other companies, other executives who are up against similar problems. Because that at its core is what executives are into. What are you doing that I'm not? What do you know that I'm not? It's exactly why they go to meetings, why they belong to communities, why they all have phone of friends that they will call when they're up against something hard. It's something I find we sellers continually devalue is the amount of insight we have into how others are solving problems. So that's what I'm going for in that part. In the close of the email, instead of going to, would you be opposed to spending 16 minutes or 27 seconds or 44 minutes on Tuesday or Wednesday or Thursday or Friday, which just reeks of desperation? All I'm going to do here is just make it very easy to get a clear answer as to whether they are interested in this problem or not. So the way I phrase it is simply, are you open to hearing how they avoided costly mega project delays? Instead, all I'm doing there is teasing that they used to use higher wages, then they switched to doing something else. Are you interested in hearing what that something else is? Yes, I'm interested. No, I'm not. That's the easiest reply an executive can give us. Yes or no. And then at the very end, in my opinion, great personalization is best placed at the end. It's not used as a bait in the beginning to say, look, I found out that you went to school at Penn State, will you take my meeting instead? I'm putting at the end to soften it so I'll phrase it as either PS or either way and then drop that personalization line. So it might sound something like if I know they're going to an upcoming conference that I'm going to, it could sound like either way. Looking forward to seeing you at robocon in March. The idea is when you read that email, it doesn't sound like I'm begging, it doesn't sound like I'm pitching. What it does sound like is I'm offering an exchange of an idea. And that is exactly what will draw an executive in to having a conversation. It's a discussion around the problem, not the product to solve it. Okay, so at this point you might be wondering, well, how do I use AI to get these answers to be able to write a message like this? Or how does this translate? If I'm cold calling or using social selling, you might be thinking about what are the do's and don'ts of reaching out to an executive level audience? Or how does this fit into a bigger sequence? We'd love to have the first email make the first meeting happen, but often we need more than that. So those are exactly the types of questions we get into. And in our course, selling to the C Suite. Okay, step two is we've now booked the meeting with the executive and now it's time to have that first discovery conversation. So I'm going to break this section into two parts. Number one is how to prep and number two is how to bring that prep into a discovery conversation, not a presentation. So number one is how I prep. Now, there's four key ingredients that I want to know before going into any discovery call. Whether that's scheduled, outbound or inbound. Those ingredients are, number one, what are the CEO's objectives for this account? What is it that that business is trying to achieve this year? Number two, what might make it hard for my prospect at the prospect functional level to achieve those objectives? Number three, how do they appear to be solving for those problems today? And then number four, what might be the negative consequences of that approach? That's it. Those are the four key things I want to know going into a discovery call. So number two is now how do I bring that content to life in the conversation? So the very first thing that I'm mindful of in a discovery call is a stat I came across a while ago. It said that 82% of B2B decision makers feel that sellers are completely unprepared for their first conversation. So in my mind, what I want to avoid is in that very first, first open, I want them to understand I'm not part of that, that crew. Like I've taken the time, I'm here for a reason. You're not just a call on my calendar today. Like, I have intention behind this conversation. And so the way that I'm typically going to open the call is I'm going to say, before we get too far into the conversation, do you mind if I just share a little bit about what I learned about your company and what I seem to gather about your role before we start talking about us at all? I don't want to assume I have all the correct information simply because I did some research. What I'm doing there is a couple things. Number one, I'm saving my from them going on a 10 or 12 minute tirade about like, here's what we did, here's when our company founded and here's all the offices we have around the world. Like stuff that you probably already know because you've done the research. So it's maximizing my call time. But the second thing is I'm showing them that I understand that their time matters. And so I'm going to, I'm going to respect it and I'm going to be very clear that I've done research for this conversation. So once we align on what their business does, they fix anything that I've Kind of screwed up there and what their role is now I'm going to say, okay, great, that's super helpful. I don't work at your company, but when I was doing my research, it seemed like the business was focused on this objective. And I'm thinking maybe it's because of this reason, but what did I get wrong? Again, I'm getting them to correct, but I'm also getting them talking. Maybe I picked an objective that the business is thinking about, but there's another big one coming that I didn't know. I would much rather give them something to react to than start with some open ended question of like what are you working on or what are your priorities? Because again, that's a take motion. It's a high effort motion for them. Correcting me is a much easier motion once we align on what the big objectives are. Now I'm going to shift to what might be hard about their job. So I'm going to say, well, one of the things when I'm talking to other CFOs that seems to make achieving that objective hard even is this problem. But how's that different from what you're seeing today? Again, seeking to be corrected, but also showing I'm having conversations with other CFOs and I'm bringing that perspective to that conversation. Very different motion than and what's hard about that, Where I'm asking the buyer to do all of the heavy lifting, number four is when I get into status quo. I might be off here, but it seemed like the way the business might be solving that problem today is by doing A, B and C. And I bet that's probably a pretty good approach for it for these redeeming reasons. Let me pause here. The reason I'm doing that, the reason I'm actually touting status quo is good versus attacking. It is because what I do not want to create here is an offense defense dynamic. One where I am attacking how the prospect is solving the problem and then they're getting defensive and trying to protect same. So when I illuminate what might make that a great way to solve that problem, what I'm doing is I'm softening sales breath. Like I'm not. I'm not in their face trying to pitch them or convince them or change them. And so instead of making it about us, the way I'll position this is, I'll say, okay, now that I understand what they're trying to achieve, what makes it hard, what they're doing now it's, you know what this other company we worked with was doing something similar. But one of the things they were surprised by is this. And the reason we're using that language around they were surprised by is because again, we're not being, we're not here to judge or attack. We're not saying everybody else knows this and you're the only idiot in town that doesn't. We're saying, like, this status quo approach to solving the problem made a lot of sense until they saw this negative consequence. And that's what we're trying to raise to the surface. The negative consequence is essentially the problem that warrants them changing. The change is our solution. Last but not least, this is where I'm going to dive deeper into just really tailored questions about how they're solving the problem today with the goal of illuminating what some of those things might be. So my approach here is to try to get them by the end of the call to say, you know what this negative consequence threatens, this objective that we're trying to achieve and it's worth looking into, or the opposite. It's just not. It's not worth my time. It's not a big enough problem to solve. Both of those outcomes are a win. So the way I close that conversation sounds like this, you know, Mr. Mrs. Prospect, I'm going to ask you two questions. I'm going to ask them separately and I would just ask that you be completely and utterly transparent with me. My first question, based on what we've discussed so far today, does this feel like a problem worth solving? I shut up. I do not try to convince them that it is. I just listen and let them think. You will probably have a little bit of awkward silence. Sit in it. It's a good thing. It shows they're thinking and reflecting. Then the second question I will ask is, is this a problem worth solving now? Same idea. Shut up. Don't try to convince them that it is. What I'm looking for here is to avoid the mistake I used to make, which is getting happy ears because we have a fun conversation about this problem. But in the back of their mind they're like, yeah, this is so minor compared to all the other stuff I need to get done. So I will walk out of this call either with one, yes, it's a problem worth solving and it's worth solving now, or no, it's not a problem worth solving at all. Okay. Or yes, it's a problem worth solving, but no, it's not worth solving now. Any of those outcomes are good if it's the final one. Yes, it's a problem worth solving, but not worth solving. Now that's a timing issue. My goal here now is just to understand, okay, can you help me understand why what has to come before this? Often there's an order, events that has to happen for someone to solve a problem. That's okay, that's out of my control, but it allows me to forecast accurately if it's a yes and a yes. Great. Now I can shift to what we're going to do in the next call. So at this point you might be wondering, well, how do I actually find all of this stuff in prep and know it's right and what does this actually sound like in a real scenario? Like how does the discovery conversation flow or how does this change if it's an inbound scenario or an outbound scenario, or rip and replace or rfp? And then probably the biggest question is like, when do I even get to talk about our solution and how we can help? So that's all the stuff we dive deeper into in the course. Selling to the C Suite. Last but not least, now we have an activated champion. They're interested in solving the problem and solving the problem now. But it's rare that a company would make a decision to change with just one person's input. And so what we're going to do now is think about how do I work with that activated champion to get access to all the other people that go into making that decision for the business, AKA the buying group. What I'm going to take you through is a high level overview of the seven steps. What happens from I've got a champion. They're excited, they want to push go all the way to how do I get this group to say yes, this is a problem worth solving and solving now. So step number one is I'm going to align with my champion on the problem statement, not the solution. So the don't here is I don't want to just send them a bunch of solution collateral and ask them to share it around. The do here is I want to get the definition of the problem and its urgency down to a super short succinct statement, something I can put on one page, which I will later use in that buying group meeting to start activating discussion. And so the problem statement simply takes what's the objective for the business? What's the problem that threatens our success on that objective? How are we solving it today and what are the negative consequences of that? That's it. It's the same stuff we just talked about in discovery So I am taking one person's opinion of that. My champion. I'm putting that on a page and I'm sending it to them. And the way I'm framing it is to say, I want to make sure before we get in front of the buying group, you feel comfortable with the way that we're characterizing this problem. This prevents something that would happen to me from time to time where the champion shows up and all of a sudden they're like, well, I didn't really mean it like that. And then that's a terrible start to that meeting with the buying group. So step number one is aligning with your champion. And here's how we're going to position the problem and its urgency to the rest of the team. Now, step number two is something I used to totally gloss over. So I would be like, okay, great, now we're aligned on that problem statement. Can you go get that meeting scheduled with the rest of the buying group? That's a big fat ask. Not to mention when I hang up with that executive, they're probably going into seven more back to back meetings. So when they get to the end of the day, it's one of those things that they often look at and say, I know I should do this, but I'll wait till tomorrow. And then tomorrow becomes next week and then next month, and then these deals die on the vine. So it's very simple. But the step two that I'm going to take here is I'm going to offer to ghost write the meeting ask. Now, there's a very intentional way that I write it and I share that with my prospect. I say, I'm going to write a note for you to send out to the team. Now, you can put your own touch to it, obviously, but I'm writing in a specific way where I'm talking about the problem and I'm not talking about the solution. The reason for that is when people hear solutions, they think dollar signs, they think change. They think. And so we don't want to reference that. We want this to be a discussion of the problem. And so the note sounds simply like this team as we consider this problem. I've asked Jen Allen Knuth to spend 30 minutes with our team. I met with her this week to share some of the roadblocks we've encountered as we're working to achieve this objective. And she had some really interesting insight from other companies she've worked with, like A, B and C. Any concerns with us spending 30 minutes on this together? And then the executive's name. Notice it is not a pitch. I'm not selling. I'm not talking about our solution. I'm simply trying to get the group to understand that by coming together. The point of this is to get the holistic groups to input on the problem, not just one person. Because again, most deals don't get done with one person. There's almost always friction involved. So that's step two. It's just ghostwriting it for them, making it easy for them to do. Step three is before I get to that meeting, I've got to identify all of the threats that could potentially derail it. I do not want to show up to the meeting and realize, wow, there is someone who is so skeptical of us in this meeting. Or here's someone who's so protective of Status quo. And because then I'm going to be scrambling in the meeting to try to overcome that stuff. So before the meeting, I'm going to have a transparent, direct conversation with my champion to ask them deeper level questions. Now I'll give you some of the questions that I might be asking them. So one would be, who is most likely to be skeptical of solving this problem? Why? And what else would they prioritize above it? The intent of this question is to surface what are competing priorities internally that might take precedence over solving this one? Second question I might ask is around, like, who actually just would really die hard for Status Quo? An example of this would be when I was selling a sales methodology, if someone internally had just built a sales training program. It doesn't matter how good my training program is. They just want to protect what they build because by changing it means they've just done all this hard work for nothing. So some of the other questions I might ask are around the political dynamics. So I used to sell into sales and marketing. We all know there's an unhealthy relationship between the two of those functions often. So I might just lay that on the table. Like, often one thing I find is sales and marketing kind of go head to head at each other. Has there been a recent disagreement in this group? And what that is intended to do is when I get to the meeting, I don't know if this has ever happened to you. Sometimes you just pick up on these, like, extremely weird vibes and you assume that it's because they don't like you. Often it's because they don't like each other. And so if I know that I could be really intentional with how I'm positioning the problem, how I'm inviting their opinion And I can just be mindful of those dynamics and the political stuff that's happening before assuming it's just, like, lack of interest in me. And then, last but not least, you know, we think a lot about our competitors. We don't think as much about competing projects. So one question I'll ask my champion to try to surface those competing priorities would be, what are the other organizational priorities or projects that might take precedence over this one and would be in competition for time, budget, and attention? Again, the whole goal here is just to, like, figure out that stuff in advance, because being caught in the moment in a group meeting is a really tough place to be, and I'm just trying to avoid that. So a great champion will be able to give you honest answers to all of those things. A great champion will talk about friction, problems, challenges. A bad champion will be like, no, there are no competing priorities. Nobody's skeptical. Nobody wants status quo. If you start hearing that stuff, that's a red flag. You do not have a champion. You've got someone living on a different planet. Step four is prepping my champion. So the last thing I'm trying to protect against before the meeting. I get to the meeting, and all of a sudden, the champion is nowhere near as talkative as they were with me, nowhere near as vocal about the problem. So I'm going to send an email that sounds like this. We're not going to march through slides, but there are a couple slides that I put together that I think will help serve a purpose of getting the group talking. I've placed in the speaker notes a few questions that I'd like for you to ask in the meeting. Any opposition to that, and what I'm wanting them to do is to take on some of those potentially uncomfortable questions that are going to sound a little bit weird coming from me. So, like, back to that last section. If there's weird political dynamics, I might plant one of those questions for them. What I want to do is make sure that it's not me versus the group. It's me and the champion together engaging that group. On step five, opening the meeting. We are salespeople. They're going to expect that we're there to pitch. So we want to change the tonality of that meeting right from the get. So I will say the purpose of today's conversation, as Mary laid out, is to talk about this objective that we're trying to get, and this problem that sits seems to be threatening that objective. Our goal today is to arrive at a shared understanding of the problem. Mary And I have had some conversations, but I recognize that everybody in this room brings a unique perspective because of your roles and responsibilities. Now, if we get to the end of the meeting, we decide that this is not a problem worth solving right now. That's okay. It's a perfectly acceptable answer. Now, the reason I'm doing that is because I want to lower their defenses. I want them to understand this is not going to be a pitch. This feels more like a consultative conversation and than a sales pitch. And then lastly, I'll just explain, like, here's why I'm here. I work with these other companies. They were also trying to achieve something similar. So I'm going to weigh in from time to time with what I'm seeing from other organizations to help frame that conversation when I'm running the meeting. Remember that one page problem statement we talked about in step one? That thing's going right up on the screen. And what I'm going to do here is say, is frame it as, this is what Mary and I have discussed in our conversations. But again, I recognize there's different roles, responsibilities in the room. And I want everybody to take like a minute to read it and then we're going to discuss it. Give them the silence to read it. No references to solution, just problem language. And then once that minute is up, I'm going to do the opposite of what most of us do. Instead of seeking agreement, like, does everybody agree this is the right way to solve the problem so I can get to talking about our solution? I'm going to say, who has a different opinion on this? And then shut up. Now, the key here, where we can break this is if we hear a different opinion and then we try to overcome it, we treat it like an objection to be handled. Our goal is to surface that friction in the deal. There will be different points of view. There will be things that Mary didn't see that others in the group see. That is a good thing. We have to learn to be comfortable with not hearing that everything is roses and pretty. And so when I do hear that kind of thing, then I'll use a facilitator technique called prompting, where I'll say, you know, Joe, it sounds like you think this is a bigger issue. Debbie, given your role, I'm not sure where you sit on the side of the fence, but how would you suggest the group weigh these two problems? So getting the group to think out loud is a great way to, quote, unquote, overcome objections. Because it's not me doing it, it's asking them to share their logic so that the rest of the group can take that apart. Now, step seven, closing the meeting. This is going to sound very similar to the discovery call, but instead of saying, is this a problem worth exploring? When I've got about five minutes left, I'm going to say something to the effect of listen, we're in the thick of a discussion. I could keep going all day long, but I know we got meetings to get to. I'm going to ask the group to pause. I'm asking two questions, one based on what we've discussed so far. Does this feel like a problem worth solving? Same thing. Shut up, get your answers. And second question, does this feel like a problem we're solving right now? Now, I would love to say that everybody says, yes, it's a problem we're solving and yes, it's worth solving right now. That rarely happens, right, because we've just had probably one 30 minute or one hour conversation with the group. If it does not happen, our job as the facilitator is to identify what's the stall point. Now, the most common thing I see is it's an argument of opinions. So I think we should do this and I think the problem happens because of this and I think it happens because of that. So what I will often end up doing is I'll label the stall. I'll look for who might provide data that grounds us all in an objective point of view on the problem. So I might say, like Mary, you sit over sales ops. We're having this debate around whether we should be solving for a new logo problem or a customer renewal problem. Would you be able to pull both loss sizes? So we can kind of bring that to next week and compare the two and figure out which one takes precedence over the other. So you're giving the group a reason to come together again and you're creating sort of curiosity around like we're going to learn something together and it's learning about our business, not the vendor's business. If you do get consensus, congratulations, that's awesome. Jackpot. Ask the question. Now that we've had this discussion, who should have been here that wasn't not, Is there someone who should have. It is extremely rare that I will get nobody. Usually. It's. Well, now that I know more about what we're talking about, so and so should have been involved. Now my next step is before the group reconvenes next week. I'm going to get someone to introduce me to that person. I'm going to share that summary statement And I'm going to meet with them to make sure that they're not going to drag the group back in the next meeting. So all of this ends up forcing a really natural timeline. I'm not saying like I want to meet with you on Wednesday. I'm giving them a reason to want to reconvene and I'm making sure that the group as a whole is weighing in on the problem. So that's how I manage that group meeting. And by this point, what we end up with is consensus that this is a problem worth solving or, or this is not a problem worth solving. And just like we talked about in discovery, both are great outcomes because both give me an idea of how I should spend my time on this deal versus others. So that's a high level overview of how I think about getting the group to problem consensus. Now in the course Selling to the C Suite, we go much deeper into how do I even identify if I'm working with the right champion. What are more of the questions I can ask to understand the group dynamics? What are the things that might blow up in a group meeting? Let's say everybody has their cameras off or there's an executive dominating the meeting. How do I handle that? And then last but not least, now what we've got problem and agreement. But now we need to get solution agreement. So how do I build a business case? How do I share that back with the executive and how do I move that deal forward to a close? So in this masterclass, we covered three of the steps to sell to the C Suite. In the course Selling to the C Suite, we cover every step you need to close a deal with a C Suite executive. I'll show you exactly how to apply it to your your sales motion, whether you're selling software, hardware, services, education or something else. And you'll know it actually work because it's backed by Gong Data. So thanks for tuning in and you can check it out down below.