Complex Selling: Executive Selling Isn’t Just Suits in a Boardroom
Tea and TimbitsMay 17, 2026
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00:22:0920.28 MB

Complex Selling: Executive Selling Isn’t Just Suits in a Boardroom

This week, we’re recording together in London for a rare in-person episode, which naturally means things go slightly off the rails before we even get to the topic.


We kick things off with a story about hiring event security, where we learned the hard way that ticking qualification boxes doesn’t always mean someone can actually do the job. Turns out “having the badge” and “being able to climb stairs without needing a lie down” are apparently separate competencies.


From there, we dive into the world of complex selling and executive selling — and why most big deals are won (or lost) long before the final proposal lands.


We explore:

  • Why executive selling is more than just presenting to senior leadership
  • How to use your own executives as part of the sales strategy
  • The importance of coaching leadership teams before customer meetings
  • Why one uninformed stakeholder can derail an entire deal
  • How to tactfully expand conversations to include hidden decision-makers
  • The role of context, repetition, and preparation in complex sales
  • Why executives need exposure to real customer conversations


Along the way, we also accidentally turn the conversation into relationship advice and realise that executive communication skills might be just as useful at home as they are in the boardroom.


It’s a practical, slightly chaotic conversation about influence, credibility, preparation, and the human side of complex deals.

[00:00:16] Hey everybody, I am one of your hosts Scott Snowden coming to you today from London, UK. Andy Baqone Baqone And I'm Andy, also here in London with Scott. So thank you for joining me here today Scott. Andy Baqone A rare in-person episode. It's really fun to be over here. So this is the Tea and Timbits Podcast, Global Perspectives on Business Development to Help You Prosper. We're in the month of May and we are going to be talking about things related to complex deals.

[00:00:47] And we're going to get specifically into talking about what it takes to sort of sell to the executive level. There's a certain nuance there and some deals you find yourself there pretty quickly if not exclusively. Anyway, before we do that I think it's still your turn to tell a story Andy. Andy Baqone It is. Thank you very much. So this weekend just gone I've been putting on a number of live shows, live music shows.

[00:01:12] And obviously part of that, having a lot of people, ticketed events, you need security for that. Yes. And what became very apparent very quickly. This could go on in many ways. What became apparent to me very quickly, because of course I have a military background. Ah.

[00:01:29] And so I was able to see very quickly that something we've talked about before is the skill and the competencies and the personal attributes. Yes. And a lot of these people, they have the skills because they have to have a certain qualification in order to be able to be security personnel and manage doors and do all these sort of things.

[00:01:55] However, they were not actually personable in any way and they had no social or human skills. They got a little excited doing the job that they were hired to do? Well, almost the opposite of that actually. Yeah. So, you know, if you're a security company you kind of expect that you've got to maintain a certain level of fitness. You've got to maintain a certain level of ability to do something.

[00:02:18] The guys that we got sent for the first show, one of them was so heavily overweight he couldn't even make it up the first flight of stairs to the landing without getting out of breath. Well, what are you doing here? So I fired him and sent him home and told the company to send a new one who was actually able to do the job. It's no good if someone's doing something and they can't even get up the stairs to the venue.

[00:02:38] But my point is, if you're hiring someone to do a job, it's true that they may have the skills, the qualifications and the overall capabilities to do it. But if they don't have the personal attributes to actually deliver it or the energy to actually put it out there. The message needs a medium. Correct. So I just wanted to bring that up because it is something we've talked about before.

[00:03:02] And it became very apparent in that scenario where you're very reliant on these people's skills to be delivered in a way that actually still brings some value to the event. You need the wrapping, you need the package, you need it. Yeah. And you need those personal attributes as well. Yeah. And if you can't, you don't just check those three boxes and say, great, right? Correct. Yeah. So what had happened there is clearly a hiring process had taken place where this person ticked a load of boxes, but those certain boxes were not included in there and that was their personal skills.

[00:03:30] Well, I would imagine there's a lot of businesses who just need to check that box themselves and say, yes, we have security. Yeah. You know, um, insurance wants to make sure you've got 24 hour monitored security. Okay, great. Well, that's very different from, you know, needing to do crowd control at a music venue. Exactly. Yeah. Anyway, uh, I like the, uh, I like the analogy and the segue into, uh, uh, what we talked about as well. Uh, so like I said, we're in the month of May and, um, I was kind of excited when we put this in the calendar.

[00:04:00] um, cause I don't think I've really ever not done a complex sale, right? Like it's, it happens. It happens. And you're kind of delighted. You're right. You're like, Oh, that was, that was a quick one. That was great. Um, but that's few and far between. Right. Um, and so, um, often you are needing to interface with the executive level. And, um, and so that's what we wanted to talk about today.

[00:04:26] We've spent a whole episode on executive selling, um, communicating with that, that top, top leadership, senior, uh, management. Um, and I do think that there are nuances and difference that you, that you have to accommodate for. You have to think about, you have to be aware of, you have to work into the way that you're doing the deal. Um, how would you start it? Well, I would, uh, frame executive selling slightly differently. Awesome.

[00:04:54] So for me, executive selling is everything that you said, but there's another layer to it. And that other layer is that you, within your business, you use the executive level. Ah, and you coach them and train them to sell what you're doing. To sell. Got it. To their peers within the counterpart business. Right.

[00:05:17] And so it's a very different type of selling because they're not looking at, they're not looking at going in there and, uh, you know, and trying to uncover problems and opportunities. They're looking at going in and understanding the corporate level impact of the, the established and known problems within the business. Interesting. The job of the salesperson is to uncover the root cause of the problems. Right.

[00:05:42] Not to find what the problem is because that's where the problem, that's where very basic sales happens and also where it's very difficult to overtake your competitors or also jump in. But if you're doing a complex sale, then you need to involve all levels of your business. And as we talked about, uh, previously as well, other departments as well should be understanding what they're supposed to be doing, how they're supposed to be doing things and, uh, and have some sort of skills when it comes to, uh, to selling.

[00:06:08] So for me, executive selling is a, is a crucial part of that whole sales process in a complex sale, because you need to have a, uh, a person who has, uh, the executive level credibility to be able to speak to their peer. Yeah. And then they will after those, you know, it should be part of a process that ultimately leads to the salesperson being introduced to that level as well.

[00:06:37] But the, the counterpart executive in the potential customer business, they feel confident that they have an executive sponsor within their business as well. And so that, that to me is what is where executive selling really adds value in a complex. Interesting. Because I, I, I, I see where you're coming from. And as soon as you sort of shifted the perspective of how I was interpreting it, I went, Oh good God, no way. Interesting.

[00:07:05] I, I've only been in two situations when it comes to sort of leveraging the executive. I mean, first of all, like, I would guess you could consider that I am the executive in a lot of the selling that I do. Small agency, that's what you get. Yeah. Um, and so there's that founder sales, uh, kind of mentality and that's, I think where I come at it from. Um, there's, there's two kinds of executives that you want. Uh, sorry. There's two kinds of executives.

[00:07:30] One, the one you want in the room because they came up through it and they want to see their organization grow and they don't even need any coaching there. So you get out of their way, not the other way around. And then there's the ones you're like, Oh good God, don't put them anywhere near that. I thought we wanted to sell something here, not, not turn it into something that was unrecognizable.

[00:07:50] Um, so, um, uh, I, I guess, are you describing a scenario where you've got somebody in the middle there and you are sort of coaching them and leveraging them? Or do you have to recognize, um, or do you have to learn how to recognize what you have at your leadership level on the selling side to make the determination of whether to bring them into the process or to leave them on the other side of the planet?

[00:08:15] I think in a complex sale, it's important that you do bring them in regardless of their ability. Uh, and that's why the executive selling framework needs to be established within a business. You need to have a structure and a kind of training program in a way for the executive, right? So that they understand what the purpose of the meeting is, what their role in the meeting is, and then coach them and even potentially role play with them.

[00:08:45] Yeah. On what they're supposed to be doing, why they're doing it and what the benefit is of them doing it. But I guess in your situation though, it's also a mapping exercise. It's like, okay, well, what kind of executive do I have on my team? Yeah. And then where can I envision inserting them into the process effectively so that I'm not going to be able to spend a heck of a lot of time training my executive. And let's be honest, a lot of them are not, you know, comfortable. Trainable. Yeah, they're not trainable. Thank you.

[00:09:13] And so it really is more about identification of possibility and opportunity, and then figuring out sort of how you can shape the engagement around leveraging that resource appropriately. The other advantage of introducing executive selling in a large organization and a complex sale process is that it breaks down a lot of those silos that often establish in a larger organization.

[00:09:38] And you have, you know, an operations team and a finance team and a sales team that only ever talk to each other when they absolutely have to. Right. And by bringing those departments that are very unlikely sales departments into the sales process, not telling them that they have to do sales.

[00:09:58] But it's a kind of, you know, we refer to it as executive selling because they're out of their normal role and they're integrated into the sales process in order to build confidence and credibility within the customer organization. So, I mean, I'm warming up to this idea. And as we continue to talk about it, I'm thinking now from the executive's perspective.

[00:10:23] So, if you're an executive listening to this and you do not get involved in the business development process, at least the way we're describing here, I think that the challenge, the task, the ask is, hey, how can you do that? You need, there are some of those executives, which I would want to keep very far from the boardroom table, the business development table, are the ones that need that exposure the most. Yes.

[00:10:49] They are the ones that you're like, oh my God, can we just get them to understand the customer instead of, you know, this idealized perspective that they have or get them out of the spreadsheets because, you know, the way that our product or service is used or purchased is completely different. They're so naive. So, there's a ton of value to the selling business.

[00:11:10] So, there's a ton of value to the business, maybe not as productive to the conversion of the deal, but definitely in advancing the maturity of the organization as well. And it also helps as well building that credibility with the customer organization in that they appreciate, the executives within the customer organization appreciate that they are being brought into a buying process that they would not normally be part of.

[00:11:36] And they may not actually have a decision ultimately in the end, but to have been involved in that process is unusual for a selling organization to do. And therefore it differentiates you and you end up with an executive sponsor, if it's managed correctly, within the customer's organization.

[00:11:54] I go, oh, but why are we not using that company? They came in, they made an effort, you know, the CFO to CFO conversation is incredibly effective because those people are not usually involved in the sales process or not usually involved until much, much longer afterwards. And then they start to question it because they don't understand why certain costs have been changed because the impact and everything else and all of the benefits are not necessarily clear to them because they've not been involved in that process.

[00:12:22] If, however, you involve them early on and you involve them in that executive selling part, both the customer organization and the selling organization will learn and benefit in a way that builds that credibility and confidence in the solution. Yeah, absolutely. So let's flip the coin over and come back to the way that I was interpreting the scenario at the top of the episode here. Which is still a very important part of it. Well, thank you. It is, 100%. Yeah.

[00:12:51] It is being able to recognize who those decision makers and it's never one person. I think of it more as a, you've got a collective, you've got this buying group on the other side and you've definitely got a collective of people you need to try and influence to make a joint decision. We talked about team selling last month. We didn't talk about how you can have one single detractor in that buying group that scuttles the entire thing. Really can, yeah.

[00:13:19] So although it's rare to have one person whose job it is to make the final decision, you can absolutely rely on one person to screw it all up. Yeah, that's very true. And so it's really important to make sure that in those kinds of team selling complex deal situations, you ask who's not in the room. Who else is going to be privy to some of the information? Who are you taking this back to and sharing?

[00:13:43] And I don't, my advice, my thought on this is when that is revealed to you, don't immediately jump on it. Say, well, we'd love to talk to them too. No, exactly. That's where we're going. That's what we need to see happen. But you do that diplomatically. What way would you suggest doing that? Because I have a way that I would typically advise. Oh, I don't have a necessarily way.

[00:14:07] I just think it needs to be done with tact and you need to on the next conversation say, you know, last time you mentioned that your CFO was somebody that, you know, did you get a chance to talk to them? How did you communicate that? Would there be an opportunity for us to meet with them directly together? And you just sort of make it seem a little bit, you know, more coincidental than directly, direct expectations. So how would you do it?

[00:14:32] Typically, when you're having the conversation, exactly the same conversation that you were having there where you are discussing, you know, the other departments that need to be involved or need to make the decision or impacted by the challenge or the goal that is being looked to achieve. Yeah. Is to start asking questions about that. And to typically say, OK, oh, yeah. So, you know, Johnny from operations, he's your operations director. He needs to be involved as well. Yeah.

[00:15:02] Or he will be involved as well in the decision making process. So tell us a little bit about, you know, some of the impact of this challenge we'll have on his department. Oh, I'm not too sure. Yeah. Maybe, maybe it's a little bit of this. I think he told us it was this. OK. Well, what about this? And then you ask, you know, certain questions and then suddenly the people in the room realize they don't have the answers. They don't have an issue. And then they invite them into meeting the next one.

[00:15:31] So then I think in terms of that's sort of how you make sure you're capturing the right audience and you're getting the right people into the conversation. But I also think that there is a different way that you need to be communicating with somebody who's not direct. Sometimes you've got that executive involved in the process and they're in the weeds and they're in every meeting. They're part of that collective and they come at it and filter it a little bit differently. So be sensitive and aware of that, too.

[00:16:01] But sometimes you've got them kind of coming in, stepping out, coming in, stepping out. You need to calibrate for that. There is a different way to show up, to communicate in those situations. Is it more than just practicing that sort of curiosity that you just described? I would say it's not just about practice, though. It's very much about experience and research. Yeah, yeah.

[00:16:30] Because I think that's often forgotten. It's the preparation ahead of meetings, ahead of entering into a complex sale. Because very often salespeople are already aware of and familiar with the complex sale within their organization, they enter each one in the same way, with the same mindset, with the same process.

[00:16:48] And therefore they don't necessarily tailor it and their approach and the team to a particular customer scenario or problems or challenges or goals that the company is trying to support them with. And that then results in either delays or yellow flags coming up throughout that could have easily been avoided had that preparation been done.

[00:17:12] Also important in a complex sale is to make sure that, coming back to the topic of the executive selling, is that the executives themselves are also sharing valuable information with their counterparts on a regular basis. That is not necessarily related but just keeps them front of mind, keeps them reminding them, oh yeah, well actually this organization has already provided value because they're sharing this information about these type of things without any expectation. Yes.

[00:17:41] I think it's important when you get an executive involved who's sort of coming in or tangential to it that I think that the instinct is to just kind of carry on the conversation or to speak as if you know what they're going to expect you to say.

[00:18:07] And I guess maybe if you have a good instinct or insight for that kind of thing that might be helpful. But I was going to say always reestablish context. So that executive has been given information that you could not control and they probably came in already expecting to drive the outcome and to direct the meeting.

[00:18:32] And you're going to get some big personalities some of those times and I don't think it matters. I think you have to make sure you don't get thrown off or intimidated by somebody who shows up like that. You've got to say, listen, thanks for your input or setting that stage. Bear with me for a minute. This is the way we do it and I just want to make sure I bring you along to where we are right now. So indulge me for five minutes. I'm going to just roll back a bit. We're going to establish some context.

[00:19:01] I want to make sure that you're hearing this the way that we need to be communicated. And you do your thing and you can you and you and you replay some of the key points and how you got to where you are and how you do what you do. And then and then you get into the present moment with with that executive because it's about managing them in their time as well. And just to say, I mean, this isn't a lifestyle and personal development podcast, but don't forget this at home as well. Oh, God. It's so important.

[00:19:30] Sometimes you can deliver a little bit of information. Does my wife text you? But sometimes you can deliver a little bit of information at home. Yes. But you're delivering it to the other person when they're distracted. Something else is going on in their life. And they are not necessarily in the right space or right frame of mind to receive that information when you give it to them. Absolutely. The advantage of having business meetings is that people are coming into those.

[00:19:56] Yes, they may have other distractions, but when they're in that room, they are focused on that topic and that agenda. But in a lifestyle and in the lifetime or human life, external, personal life. Any personal life. That's the word I was looking for. You don't have that. Right. So you are always interrupting someone else's life with anything that you want to give. And this is the case when you're starting Complex House and this is the case when you're going into those meetings.

[00:20:24] At the very beginning of those meetings, you are currently interrupting someone's brain space because they're still dealing with the thing that they were dealing with outside or what's going on at home or what they've just seen on social media. You have to interrupt that, reframe everything and remind them what's going on and give that full information. And repetition is the only way of doing it. Yeah. No, you're absolutely right. I'm just playing back all these scenarios where maybe I should have been more contextual at home.

[00:20:53] Well, I shall save a story for next week which is related to this. Before I get more distracted on that topic, I think we can wrap there. That's been a great conversation about selling at the executive level, executive selling in complex deals. I just love the variations that we came at it today. So, Andy, as always, it's a pleasure. Thanks for the conversation today. Thank you everybody for tuning in. If you would like to get more information, please go to tntimbits.com.

[00:21:22] You can get back episodes and whatnot. You can find us on LinkedIn. And one of those ways, please get in touch. Let us know what you think. And if there's a particular topic that's kind of stumping or puzzling you that you'd love to get our perspective on, we'd love to help you out with that. And if you want us to fly out and come and do the episode in your town, then we'll do that. We will. That's amazing. I didn't get the new budget for the show. This is great. All right. Thanks, Andy. Thanks, everybody. Thanks, Scott.