How to Speak So Senior Leaders Listen with Ben Pearce
37m 6s
The conversation, hosted by Jack Cochrane and Matthew James, features Ben Pierce, founder of Elevated You, discussing how to effectively communicate with senior leaders in pre-sales. Ben emphasizes that executives, like a CEO he interviewed, prioritize the "what" and "why" of a solution over the "how," seeking confidence that technical aspects are covered without needing deep details. He warns against the "curse of knowledge," where technical experts overwhelm audiences with jargon and irrelevant specifics, which can confuse rather than build trust. Instead, he advises adjusting a mental "graphic equalizer" to slide up relevance and business impact while reducing technical depth.
Preparation is key, structured around three pillars: relevance (understanding the specific stakeholder’s pain points and objectives), compelling content (crafting stories, visuals, or ROI demonstrations), and excellent delivery (rehearsing and maintaining a high-performance mindset). Ben suggests leveraging AI for research to better understand personas and industry challenges, enabling more targeted conversations. Delivery is the most challenging aspect, as it requires confidence from solid preparation, openness to feedback, and managing pressure—like athletes performing under scrutiny. The episode concludes with a teaser for a potential follow-up discussion, emphasizing the importance of these skills for both new and seasoned pre-sales professionals.
[MUSIC] Christopher Nolan released an incredible film and it's called The Prestige. If you haven't seen it, spoilers ahead. The whole thing is a two plus hour Odyssey leading up to an incredible climax. And you're sitting there in the theater, hopefully your home theater with arm chairs and soda, in your favorite popcorn. And you are just taken on this incredible journey. But Jack, how would you feel if you walked into a meeting and someone tried to build this thread by thread conversation for two hours? I don't know about you, but that's not how I want my meetings to go. I mean, I've been in those meetings and I can tell you they're not as fun as a movie where that's the expectation. I remember asking once when someone did it to me, can I pause? I don't know why I'm here nor where this is going. And I'm like, I'm sorry, I have to leave soon. What are we doing here? Why are we here? In the nicest way possible, you were saying to that person and to all of us, you're not Christopher Nolan and I get it. You're right. What we need to be doing, especially as we get up the chain and we're talking to senior leaders is getting the punchline out really soon. And that's what we focused on with Ben Pierce in today's conversation. Yeah, that's absolutely right. Real quick, welcome everyone. This is the pre-sales podcast. I'm Jack Cochrane, General Manager and co-host of the show, and with me, Matthew, giving our wonderful Christopher Nolan analogy, Matthew James, my fantastic co-host. Welcome. If you haven't seen the procedure, you must simply go and watch it. Hugh Jackman's in it. Never heard of that guy. Believe it or not, I haven't seen that one. I guess I'll add that to my weekend watching list coming up very soon. A little bit about Ben just in case, you're not familiar with him. Ben Pierce is the founder of elevated you. He himself was a techie, ran a successful customer facing team for companies like Microsoft for over 10 years. He left Microsoft to start his own coaching company. So coaching teams, basically helping techie people, talk to non techie people is kind of his game. It's what he does. I've known him for quite a while now. I've been on his podcast tech world human skills. He's a contact contributor for our enablement program in our polls newsletter. Really fantastic person with a lot of great perspectives. And it was a really fun conversation that I unfortunately felt like I had to cut off way before we read the end of our conversation today. I guess that means everyone should make sure that they are following Ben on LinkedIn for more of these great tips. Absolutely. You should. Today, we're talking all about talking to senior leaders as Matthew said. And more than likely, they'll be a part two at some point. Not sure when, but I'm sure we'll bring him back to continue the conversation before we hop into it. Matthew, anything else you wanted to highlight. I think that's it. So let's get into it after the break. This episode is sponsored by Storyline. Tired of endless demo requests eating up your calendar. Your prospects want to experience your product instantly, but traditional demos mean more scheduling, more prep time, and more repetitive presentations. Meet Storyline, the leading demo automation platform for pre sales teams, create personalized interactive demos in minutes, not hours, capture your software in a few clicks, customize environments without code, and build a library of demos that just work. Share demos anywhere in bed in your sales sequences, use as conference lead behinds or let Lily our sales AI agent handle initial discovery and qualification calls while you focus on late stage deals. Try Storyline for free at storyline.io. That's STORYLANE.io. Storyline. Build killer demos in two minutes. Then welcome to the pre sales podcast. Very excited to have you here. Thank you so much for inviting me. We were just talking backstage before you've been on my podcast, the tech world human skills podcast. Now I'm here and hopefully I can do half the job that you did when you were guesting on my podcast. So thank you so much for inviting me. Oh, it's going to be great. I've been really looking forward to this, especially coming out of that. You're delighted to talk to enjoy having you. You also contributed to our pulse newsletter as well. I've teased on LinkedIn recently. You were I think the first piece of content we featured on that newsletter. What an honor. So again, thank you for that so much. And that was really exciting. We were talking about how you sort of bring content to life using some stories and some anecdotes. And perhaps if you're not a natural storyteller, you're not the bloke down the pub that's got everybody giggling and laughing for the entire evening, how you can do some really simple things to bring some of your anecdotes to life. So yeah, that's what we were talking about on that. Such an important thing in pre-sales. Also, if I could just kind of like make this so meta, if we're talking about making techies able to talk to non-techies, I think that is the job really. That is the summary of what I usually tell people when they say what in the world is pre-sales. So we're really excited to be chatting today. Excellent. Why not today we want to focus on a specific slice of that, which is specifically senior leaders. When maybe you're in front of a C-suite or a senior executive that, especially if you're relatively new to free sales, you may not have ever spoken to an executive at this level before. So love to get back in your perspective. Check it off for us. Why is speaking to that level of executive? Why is it differ from speaking with anyone else? Not only can I say that there's maybe people that haven't done it before because they're new to pre-sales. I speak to a lot of leaders that are maybe stuck in the tech department. They're selling a product and they're stuck in IT and need to get to the business. And that comes up a lot even for the season pros. So I'm seeing it a lot both from people new in pre-sales but also people that are those season pros. And I think it's very different because you have to talk to a different type of person about very different things, things that are out of your comfort zone, things that perhaps you don't know as much about. Things that you might not be as interested in. So actually, it is quite different to kind of elevate your conversation so you're speaking to different people about those different things. And there's loads of things that we'll talk about, I guess, over the coming half an hour or so, as detectically how you can do that and amp up your game a bit. So what if I go in there and I'm speaking to a senior leader and I start hitting them with a bunch of in-depth technical jargon? And that's what I'm comfortable with. That's usually what I'm used to, especially if I'm coming from maybe deep in-depth discussions with their tech team. They've gone into the specifications. What's going to happen if I bring that to a senior leader? Well, I think America's got talent or Britain's got talent. It crosses the international border well. Three red crosses, you know. You know, basically what it is. The very first podcast I did two years ago was when I started with my podcast and I had a chat that came on it called Tony Whitehall. And his job was he was the CEO of Hyundai UK. So not in the tech world at all in the automotive industry. And the episode I did with him is how to talk to the C-suite. And so I said this exact thing to him, you know, what's your experience of people from the tech sector coming and speaking to you? And basically he said to me, they keep wanting to talk to me about the how. And I don't care. I care about the why. I want to tell me one of these and why it's important. They need to give me a bit of confidence that they've got the how covered. But I don't care. I just want to know what and why. And they keep talking to me about how and versions and migration paths and things like, don't care. I just want to know why it's good for my business, for example. So there was somebody like maybe a CEO type level saying that's what I care about. And do you know what? I think he's probably a good fit for many senior leaders. Now I'm not saying that all senior leaders don't care about that none of them care about how, that none of them have got technical backgrounds, that none of them will ask you those maybe some of those questions. But typically if they do, that's because of their past, not because of what they need to do now. So really it's about talking about the what and the why and a lot less about the how. You mentioned something that he wants to know a little bit about the confidence. And I love to dig into that a little bit because I feel like that's maybe where we as technical sellers sometimes get too much into the how do I build confidence? Why build confidence by showing the features, showing my expertise. I've seen a lot of people maybe tell me if you've seen this as well. Use that well. How else do you believe that I know what I'm talking about? If I don't spew all the facts, I know technically. Or so often our worth in the tech sector has been tied to our expertise. So how much do we know about this thing? And that we've spent so long invested in that expertise and care about it so passionately that we almost get to what is often called the curse of knowledge where now somebody asks you a question and they say, well, this work, unless you've got version X, and unless you've got this thing, oh, and unless you've got that because those are really valuable things when you're actually deploying a solution that's going to work, right? All of that expertise is going to be really valuable. And that's going to be important in the deployment in the later, but it's not important when you're talking to that senior leader. So you've almost got a wipe out all that expertise you go and right, we're talking in much simpler terms in much higher level. And all of that stuff that you're really confident with that you've invested in is actually a bit of a curse now. And you've got an hour go, right? We're just at the very high level. We're talking about the what and the why and a tiny, tiny little bit about the how I have a story from my past that I feel like pull illusory kind of what you're talking about perfectly when I was moving into my house, the person showing me around kind of showing me how things work because there were some systems in the house that was specifically a sprinkler system for if there's a fire, there's some sprinkles are dropped down.
and supposedly put out the fire which is great. I'd never been in a house with that system before. And he was showing me all the things. He went to the area where all the levers are and he goes, okay, so here's all the things you need to know about him. For seats to tell me some specific things. And then he starts to mention things that I would need to know if I had certain systems installed that I don't. And he said, now if you had this installed, you need to make sure you flipped that out before this one, but you don't have that. They said, why are you telling me this? Well, you would need to know it if you had that. And I'm going, but I don't have that. So why are you confusing me? He's like, well, I just want to make sure you know. Oh, and also if your house was built before this year, like when is my house built after that? I don't need to know that you know all these facts. I just need to know what I need to do so that the water doesn't start spewing out of the ceilings when it's not supposed to. Absolutely. And he'd probably already forgotten the important things he told you because there was so much that he was telling you. So you've already forgotten the important bits and now the irrelevant stuff you just swamped. I remember the vagaries of the things I'm not even supposed to know about and not the specifics of what I need to know. It's exactly right. It just turned into an anecdote for a podcast rather than actually teaching you about your house. It's exactly. It's been a great life lesson for me in sales, but unfortunately, I feel less safe because of this. So then Ben, how do we actually get this message right for our senior leaders? What do they care about? The first thing is you can't say senior leaders and go, well, here's the answer, right? This is what all senior leaders care about. So probably what I'd say is firstly, let's get in this mindset of more what, more why, less how. And I like to think about it like a graphic equalizer, like a boom box. I'm old enough to have used to have physical sliders on a high fire at home where I could slide up the base and slide down the middle and slide up the treble. But perhaps in a digital world now on our thumbs, you can slide up the base. So in that regard, slide up a bit of what? Slide up a bit of why and a lot less how. So then it's then thinking about, okay, so in that what and why, what is relevant to that stakeholder that I'm talking to? Well, if I'm talking to a CEO, that's gonna be different to if I was talking to a chief data officer. Now that's gonna be different to if I was talking to a CISO, which will be different to a CTO, which will be different to somebody from the business department. So I guess the point I'm making is there's not one answer. The framework or the practice is to think about what are the questions that I need to be able to answer in order to be relevant? 'Cause this is what the name of the game is, is being relevant. Because if you can be relevant, then you can be valuable. And that's how you're gonna make the sale. So it's about what questions do you ask? What research can you have done beforehand to make sure that you're able to talk to them in some language that works for them? Other than the goal of being relevant is a very different feeling from being an expert. If I were to go somewhere and just think about research, if I'm researching something to be an expert on something, I'm going to get very deep. I'm just thinking this through in real time. But if I'm searching on one of your relevant, I'm probably sticking at much higher level. I want to be able to understand what's going on, not try to be the person who's trying to solve all of your problems. It's almost like just helps with a lot with the positioning of how we go about preparing for these conversations. And this is where we can start to use a lot of the modern AI tools. A lot of people come to me and say, all the time, Ben, how can we use the AI to be better presenters and better communicators? And one of the first thing I can say is you can use it for all of your desk research. You can use it to understand the personas that you're gonna be talking to. Because if you can understand them, and at least be close, right? 'Cause every individual's an individual, and they're gonna have a very individual agenda. But you can be a lot closer if you've used maybe AI to say, right, I am talking to a chief data officer in a retail company. What is the pain that that industry is going through and what will that repay me going through? So if you can understand their pain, and then right, what are they trying to achieve as that type of persona? And we can use AI to get some pretty cool stuff. Right, so now we've got some pain, now we've got some objectives. So already, any presentation material that you might need to create for them or pitch material, you've already pitched it a lot closer than you would have before. And also, you might go, I don't understand this. So maybe that invites you to do a lot more discovery, exercise a lot more curiosity. 'Cause if you just jump in with your big feet, talking about irrelevant things is gonna do more damage than if you spent a bit more time exercising curiosity. - So we're equipped now with a bit of research. We've gone to our AI tool. We've probably come through some of their public documents. We have some good discovery questions. - Let's keep walking down this path. What does effective preparation look like, maybe in terms of content, what we put together and prepare before we walk into that meeting? - So I would like to think that in three things, I'm a simple man. So three is probably all I can make. The first thing is relevance. So whenever I'm gonna be talking to anybody, either this could be an important meeting or this could be getting on a stage at a big conference, relevance. Am I gonna be relevant? So that's the first thing. So invest a load of time in that. The next bit then is, do I have some compelling content? And that compelling content has been created on all the research from my relevance. So am I relevant? Have I got some really compelling content? That might be great stories. That might be great slides. That might be great diagrams that explain things. That might be great graphs that show return on investment. That might be great demos, depending on what it is, but you know, if you got that great content. And then finally, can you deliver it with excellence? Can you not choke? (laughs) Have you got that high performance mindset? Can you read the room and listen? And then when it's your turn to speak, do it justice. So I tend to think of it in those three parts. I am relevant. Have you got great content? And then are you able to deliver it really effectively? When you think of effective delivery, how do you go about getting that rate? That is the hardest one I would say. Because research, anyone can do it at the desk on their own under no pressure. Create content. Anyone can do that at desk at home on their own in the office, whatever with a group, no pressure. You probably got a great marketing team to help you out with that one. Exactly. Delivery, that's where the rubber hits the road. So to my mind, the first thing is all about that preparation. If you've done well with those first two things, you can go in with some confidence, you know, that are not going to be called out here, because I'm going to be talking about firewall ports and they want to talk about return on investment, right? So you can go in with some confidence. I would say that preparation, also that kind of rehearsal. And maybe what I mean by that is, can you talk to other people maybe from a similar persona or maybe people inside your own company that are more maybe business oriented, maybe senior leaders inside your own company or account executives, whoever it might be that's a little bit more perhaps business oriented and used to those personas. So can you prep, can you rehearse, get some feedback and take that feedback on board? So a bit of humility, a bit of vulnerability. Say, oh, I'm not the world's best at everything here. There are things that I can learn. So I think those are all really important things that you can do. And then I would say, there's something about high performance mindset. So in the UK at the moment, as we record this today, it is the women's European football. Or soccer is a quality that I'm going to call it like a way round bar. Yeah, exactly. So it is the women's European football championships and England are playing tonight in the semi-final. They are playing Italy. They went through the last round by beating Sweden on penalties. So it got right to the end. We had the full game. We had extra time. We got to penalties. It was one of the worst set of penalties I've ever seen in my life. Why was that? They would put the ball down and they need to kick it. Is it 12 yards? I think they need to kick a ball 12 yards into a massive goal in front of them. And I think it's something ridiculous, like they missed seven out of nine, something like that, ridiculous. I put it to you that on an average Wednesday, each of those players could cook a ball 12 yards into the goal in front of them. But the pressure of 30,000 people watching in the stadium, millions of people watching on television, a goalie staring you down in the eyes, that was what caused the stress that meant they missed and didn't even hit the target. And that comes down to high performance mindset. And that same sort of thing, I think, affects people in pre-sales and people that get in those really important presentations, those really important meetings. They get there and they're so stressed that they're too overactivated. They're not thinking properly. And perhaps then revert back to their comfort zone. I'm going to talk back to the things that I know about. Whereas actually, if you've done a bit of work on sort of high performance mindset, how to deal with stress, how to perform under pressure, that's going to really help you as well. So I think it's taking your great relevant content that's really well created and having the mindset that you can deliver under pressure. Speaking of sports, there's one thing that I think athletes do that pre-sales doesn't do as well. And you kind of mentioned it is that most Wednesdays, the average footballer is going to be able to go out and kick that penalty into the goal, no problem because they're practicing. And what do pre-sales people typically not do? We go from preparing to performing. And you can work on your high performance mindset all the time, but if you've never practiced, you're going to be practicing in front of your customer. That's the piece that I feel like we have to start doing more confidently as well. That's what leads to high performance mindset. I feel like if you spend time, go.
going through and doing a full out loud, full pressure as much as you can practice to realize, oh, I don't have it when the nerves are there. Now you know what to work on. But so many pre-sales professionals, sales professionals, we don't do the practice. We don't put in the real time to test things out. Yeah. And when you throw in the extra complexity, there's, let's say, an account team. So maybe you've got an AE or technical commercial specialist or whatever. So you're already making it more complicated because maybe you've got different parts that you're presenting. And then you've got maybe all the different personas that are in the meeting that you're in. So you've got different people that you're trying to present with to these different people that have all got their own agenda. And you've not done any of that. It can lead to some pretty difficult situation. Some car crashes, shall we say? It's always something to skip the dry run, right? Everyone's calendar is busy. There are so many deals coming through in any given moment. But you're so right, especially for those strategic deals that we know we want to get it right for. Yeah. So often I speak to people and you go, right, okay, how did you prepare for this presentation that you're giving? Oh, well, I grabbed some slides from marketing. I didn't like one. So I added a few in from another deck. And that's it. But then if I can then counter that, right? Because then the challenge that people will then say to me, but then I'm really busy, right? There's no way in the world that I can prepare like you're telling me to prepare for all of these different meetings. I've got how I respond to that is how many personas realistically are you going to be talking to? And it might be, let's say four. Okay. So let's say there's four different personas you're talking to. How many different industries? Oh, well, I've got retail and I've got manufacturing and I've got finance. Okay. So you go, right. So three industries, four personas. So let's say that 12 pieces of content. There are only to be tweaked and bespoke. But what about if you made just those 12 things brilliant and you spent some time to make those brilliant and I tell you what, how about you do that amongst your team? So you and your team just come up with the shared content that is brilliant, the content punchy, the stories we've got are excellent. The demos full of data. It's full of really compelling visualizations for a senior leader, whatever it might be. And we share that around and we make that better between us and we curate that and make that better. So every time we go to it, we know there's going to be something great. You create this reusable content and then you practice with it and then you tweak it. That's a great way to elevate the quality of what you're doing and it not take ages and ages and ages for every single meeting that you got. Let me throw in one little tidbit here because I know there's not the main focus of the conversation. I think this is a huge place where pre-sales can show up because if you find that every single conversation you're having is with a different persona, that is something that is worth your leader knowing and your sales leader knowing because that's pretty challenging to build a business that way. And it just has to become very generic then, doesn't it? You know, if you've got no time and loads of personas, everything becomes vanilla, everything becomes generic and it goes back to that relevance point. But if you really solve that problem for that specific people, that's going to be really valuable for them. So the less generic you can be and then you've got to manage that with time. So I think mapping out your personas, mapping out your industries and working together to create that high quality stuff is a great way to do it. I think there's a difference between practice and the specifics of the prep that you're doing for a specific account. We can continue to use force analogies on this one. If you think about a team going through practice, they're doing the fundamentals of specific plays and things that become wrote memory of how we pass the ball from one person to another, how we move where you can expect people to be at different points of a play, what someone's intent is going to be, how we're trying to advance, all those things become part of just how we operate. And that's what you're talking about with those personas, right? We're preparing for no matter what situation we're in, these are the types of stories we know we can go to. This is how we move from one section to another. The preparation becomes okay and now we're going up against this specific opponent. Some things we need to know about them to specifically tailor this for them, but it has to begin with, you have to have that fundamental piece worked out between you and your kind of executives that you can practice generically, so to speak, so that your prep becomes a lot more tactical. But most of the time all we're doing is the prep without the practice and a lot of times even the prep doesn't get that strategic. Completely great. I want to take this up to that senior leader again, kind of refocus us on, how do we get that message right? So let's say we've gone and we've found our relevant message, we have built our content, we have done some dry runs, and we're in, let's say the last dry run before we walk into the big meeting. We've got our C-so in the meeting in that moment. What are the red flags that we should be watching out for to make sure that we're actually getting this right? One of the hardest bits I think, which is that reading the room. So all of that stuff before is all prepped and it's not real time. Now we've got real time, what's the body language? And so I think this probably comes down to a little bit of empathy in the moment, being able to read people's body language, being able to read the questions that they're asking you, are they yawning? Is your AE kicking you under the table? Things like that. But they are really important. And so I think there's a few things you can do. The first thing is how often are you really in just a presentation, which is let's say like a broadcast, where it's just me spirting. Maybe that happens on a stage. Maybe that happens if you're doing a piece video, a piece to camera. But if you're a real meeting, I think there's a lot more interaction. So I think it comes down to a lot more of the interaction. And I would say my preference is, unless a customer has specifically asked me to come in and present to an audience on some pre-agreed content, which is a bit rare, I would say. I always start off with the exercising curiosity, even if you know, you could call it a mini discovery, a mini setting of the meeting by asking them some questions. And if you can ask them some questions, that is going to give you all kinds of direction. What that will give you is firstly, what are the first things they say to you because they're probably some of the most important things that they might say to you. What language might they use? So it might be, for example, that they come up with a load of sports metaphors, right? We've been talking about sports metaphors. In which case, you're like, right, brilliant, I can use some analogies and metaphors from sport to help bring this alive because that's the language that they're using with me. Whereas if they aren't, you know, it becomes very clear, you know, they hate sport, the worst thing is about a million sports analogies to try and bring it to life. So I think the more that you can exercise that curiosity and then respond to that, mirror the language, understand what the most important bits are and perhaps change the thrust. You know, maybe you were going to thrust a point A, but it's clear that point B is what they're all going to be talking about. Let's talk less about point A and let's talk more about point B. So I think asking questions, listening, internalizing and course correcting are really important things to do. The senior leaders you're talking to, they're going to have who knows how many things running through their mind and they're going to be interpreting your meeting in probably a way that you haven't quite been able to anticipate because they've got whatever set of circumstances going on. So they're walking in either thinking, all right, this is kind of a shoe in like, let's just focus on two things we can get this done or they're thinking, I really prefer someone else in this space. Like this is very challenging for me to get on board with somewhere in between being able to listen to them and just like get them talking is going to help so much. And I think there's also a psychological thing there too. People are so much more likely to be engaged if you get them talking within the first five minutes of a meeting. I think you have to be very careful of the types of questions, the types of questions that will often work for the person that you met with first when you're doing your initial discovery often won't work for an executive who's been pulled. Hey, I need you to come to this meeting. I know you're busy. It's just a half hour. I need to give you this overview. If you come in and start asking those, oh, so what keeps you up at night questions? It's not going to be the right place to start. Do you need to be very targeted with a question that you know is engaging the specifics of why they agreed to take the meeting versus generic questions? And maybe don't so often right, we just think the customer, the customer, we keep talking about the customer, but actually the customer is about 20 different people that are going to make a decision and they're in a committee and they're going to say, and actually maybe we've done all of this pre work. We've met with individual contributors. We've met with architects. They've coached us. They've told us what this person is like. And the higher you go, it seems to me the less time you get. So now I've got two minutes. I've got three minutes. I've got five minutes. I also remember very well some senior leaders that I reckon I could keep control maximum 90 seconds. And then they would button and now it's their meeting. And we've done all this work. We know the message. We've crafted the message nail it in that 90 seconds. The amount of times I've been in meetings where they take what I call the punch line approach. We build up. We build up. We build up. We build up. We build up. We build up. And now's the twist. The punch line. The thing that's going to ah-ha, the ah-ha moment. But the problem is you lose control of the meeting before you get to the punch line. So you do the build up. The build up. The build up and you've lost it. And you know, why haven't said the thing? Why haven't said the thing? If you just sit there for 10 more minutes, you're going to really love the payoff. Just wait for it. Exactly. I would say, hit between the eyes like this.
like literally bang right, get in there, right? I've got in front of the senior leader. I've got a few minutes. I think I know what's relevant. Now I'm going to take a punt and I'm going to say something that I think is really impactful. We will do this thing that is causing you massive pain. Let's talk about that. I've got that out there. That's not coming out in 10 minutes. We are going to do this thing that is solving you loads of pain. We're going to help you meet this objective that's really important and we're going to do it with this solution. Now I'm happy to talk to you about the detail of that because if you start to show some interest in how, then that's brilliant. That's brilliant buying signals, right? Because we're solving your pain. But if they're not interested, well, there may be that's a different thing. But if you can get in there and hit in between the eyes, that really helps. I think confidence can be a really big challenge when it comes to that because you're kind of staking a flag in the ground. You're saying, "All right, based on all of my research, here's what I think we can do for you." And that can be a very big thing. The room can kind of like drop silent after that. And you don't know whether they're about to say, "Great." Or, "You've got it all wrong." I've seen sometimes that actually, even if you do miss the mark by a little bit, if you've done the right research and you've hit on the right things that they are thinking about, they'll be very happy to correct you. And actually, sometimes that can come with even more thoughts behind it because then suddenly they're saying, "What you've forgotten about is that we have its other business that is also maybe we're buying or something like that." Yeah, completely agreed. And then it's that, "Listen again, that active listening, isn't it?" So you're actively listening, taking that in, course correcting, thinking what you've got in your knowledge bank from all the prep that you've done before, that you can show them that might be really useful or excite them. Yeah, completely great. Keeping one thing in mind, maybe this is worth touching on a little bit here from an executive's perspective. We're thinking about them walking into the room, which we've been talking about a little bit here. When they're exploring bringing in a new partner, someone they're going to have to pay money to, someone who's going to be directing something happening within their organization and their business, we're always talking about a little bit around risk. Yes, you're coming in with a problem, or solution to a problem. Hopefully, you're not coming in with years of problem. And no solution to it. But one thing you have to keep in mind is that executive is looking at you and your team going, "Me deciding to move forward with this team is this presenting an organizational risk. Is this something that I will later be asked why we chose to go with them versus maybe someone we know, maybe someone with a bigger name, maybe kind of the standard company, that whole, what's the old adage you'll never get fired for buying IBM? That's been around for years, right?" And so from an executive perspective, you represent risk. And so I think Matthew, you're 100% right. And I'd love to get your take on this as well, Ben. You can present them the reasons why and get them to start asking how this probably not necessarily coming from at how does this work, but how can I be assured that this risk is worth taking as well? Ben, do you see that as well in the executive conversations you've been a part of? Absolutely. And people buy from people. And I think as we're going on this massive AI journey, the bar of standard content is getting higher for everybody. So how do you differentiate yourself now? And everybody's written everything in chat, GPT or Claude or whatever it is. Everybody's written everything in like that. Everybody's got the same internet that's being scouted. And so now the differentiation is the people. And this is where I worry for people in tech that their entire career is around the expertise they have because that can be replicated pretty quickly by AI. If you've just got a heuristic system, those jobs, I think, will be gone. What is AI really bad at doing? It's really bad at holding a room, making people smile, engaging, giving tough messaging, right? Anything where it needs to really interact with the human world. That is where AI is not so good. So I think it's about, and I think presale's function a really great position here to be able to build on the shoulders of that expertise, but now to be able to fuse that with the ability to communicate effectively, to listen effectively, to under pressure come up with the right solution or the right answer to the question. Those human skills coupled with all of that kind of tech expertise, which can probably be replicated by AI, it's going to be really powerful. And so to your point of de-risking, it comes down to how well you listen to people, understand their problem, solve it, give them confidence that you've got that how dialed, going right back to Tony Whitehorn that we talked about. That is going to be the differentiator. You understand their pain, you've got a solution and they trust that you're the person to do it. That is not by boilerplate chat, GPT. That by humans convincing people. I think. I think absolutely right. Time just has flown with this conversation. I want to make sure to give you a couple of moments to let people know where they can find you if they want to maybe continue this conversation with you. Maybe you strike a chord with them as well. So you have any final thoughts or any heartics or anything else like that before we end the episode. Thank you so much, Jack. So I would say if you go to www.elevatedu.live/psc for pre-salescollective, that is my landing page where you can find all the things. So you can find all the things there. You can find out how to connect with me on LinkedIn about my newsletter or about my course. What I spend most of my time doing is working with tech companies on how we build those skills, learning stuff, but also giving them chance to practice and for me to give them some really honest feedback on how they can build those skills and get better. So that's what I spend most of my time doing. And so links to all of that www.elevatedu.live/psc and get in touch with me there. Excellent. Any final thoughts from here on the topic of speaking to senior leaders? I genuinely think that the human skills of people in tech have been under invested in for years and I am still talking to big up and coming companies. Their entire readiness enablement is tech, tech, tech, tech. And I think AI is just going to eat that and you need to invest in that fusion of the tech with the human skills. So to me, I think this is such an important topic. Maybe on bias, I'm probably on bias, but I can only see this being so important. So if you're thinking people only need tech skills to thrive, I would say have a rethink because I think it's going to be those other bits that are going to be the difference on whether people take a risk with your company. Absolutely. Thank you so much. Ben, have enjoyed having you on the show and Matthew, thank you as well for being a fantastic host and everyone here. We'll see you next time. Thank you. Thank you for listening to the pre-sales podcast by pre-sales collective. The pre-sales podcast is recorded on our live show pre-sales live with a live Q&A at the end of each episode. For more information on the pre-sales podcast, to listen to past episodes and to know how to join an upcoming recording, visit pre-salesflective.com/podcast.
Podcast Summary
Key Points:
Speaking to senior leaders requires focusing on the "what" and "why" rather than the "how," as executives care about business impact, not technical details.
Overloading conversations with technical jargon or irrelevant expertise can confuse and alienate listeners, as illustrated by a story about a house tour with unnecessary sprinkler system details.
Preparation involves three key elements
Using AI tools for desk research can help understand industry pain points and persona objectives, making conversations more relevant and valuable.
Effective delivery is the hardest part, requiring confidence from thorough preparation, feedback from others, and managing pressure, similar to athletes performing under stress.
Summary:
The conversation, hosted by Jack Cochrane and Matthew James, features Ben Pierce, founder of Elevated You, discussing how to effectively communicate with senior leaders in pre-sales. Ben emphasizes that executives, like a CEO he interviewed, prioritize the "what" and "why" of a solution over the "how," seeking confidence that technical aspects are covered without needing deep details. He warns against the "curse of knowledge," where technical experts overwhelm audiences with jargon and irrelevant specifics, which can confuse rather than build trust. Instead, he advises adjusting a mental "graphic equalizer" to slide up relevance and business impact while reducing technical depth.
Preparation is key, structured around three pillars: relevance (understanding the specific stakeholder’s pain points and objectives), compelling content (crafting stories, visuals, or ROI demonstrations), and excellent delivery (rehearsing and maintaining a high-performance mindset). Ben suggests leveraging AI for research to better understand personas and industry challenges, enabling more targeted conversations. Delivery is the most challenging aspect, as it requires confidence from solid preparation, openness to feedback, and managing pressure—like athletes performing under scrutiny. The episode concludes with a teaser for a potential follow-up discussion, emphasizing the importance of these skills for both new and seasoned pre-sales professionals.
FAQs
The episode focuses on how to effectively communicate with senior leaders, especially for pre-sales professionals, by shifting from technical details to business relevance.
Ben Pierce is the founder of Elevated You, a former tech professional who led customer-facing teams at Microsoft for over 10 years. He now coaches teams on helping technical people talk to non-technical people.
Senior leaders typically care about the 'what' and 'why' rather than the 'how.' They want to know how a solution benefits their business, not technical details like versions or migration paths, which are more relevant for technical teams.
Using too much jargon can confuse and disengage senior leaders, as they may not care about the technical 'how.' It can also cause you to miss the key business points, similar to overwhelming someone with irrelevant details.
Ben suggests using a 'graphic equalizer' approach: slide up the 'what' and 'why' while sliding down the 'how.' This helps you focus on business outcomes and relevance rather than technical implementation.
Preparation involves three key areas: ensuring relevance by researching the leader's pain points and objectives, creating compelling content like stories or ROI graphs, and delivering with excellence through rehearsal and a high-performance mindset.
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