Olivia: Alright Jackson, what’s the first image that pops into your head when I say the words 'sales book'? Jackson: Oh, easy. A guy in a shiny suit, slicked-back hair, holding a book with a title like 'Crush, Kill, and Close!' and a giant, toothy grin. It probably smells of desperation and cheap cologne. Olivia: That is a painfully accurate and widespread image. And it's exactly the stereotype Nancy Bleeke is trying to dismantle in her gold medal-winning book, Conversations That Sell: Collaborate with Buyers and Make Every Conversation Count. Jackson: A gold medal-winning sales book? That’s a new one on me. Usually, they just have glowing blurbs from other guys in shiny suits. Olivia: Well, this one is different. What's fascinating is that Bleeke herself resisted a sales career for years because of that exact image. She saw herself as a helper, a problem-solver, and the whole idea of being a 'salesperson' felt manipulative and inauthentic to her. Jackson: Okay, now I'm interested. A sales book written by a reluctant salesperson. That feels like getting a cookbook from someone who used to hate food. There has to be a good story there. So what's her big idea? How do you sell without becoming that 'sales weasel'?

Olivia: Her core idea is that in today's transparent world, the 'sales weasel' is not just unpleasant, he's obsolete. Buyers have access to nearly infinite information. They can research products, compare prices, and read reviews before they ever speak to a salesperson. The old model of hoarding information and using it to pressure someone is completely broken. Jackson: Right, you can’t trick someone into buying something they can Google in ten seconds. So if the salesperson isn't the gatekeeper of information anymore, what is their job? Olivia: Their job is to be a sense-maker. A collaborator. Bleeke shares a powerful story from her childhood about this. After a storm destroyed her family's garage, they called their insurance agent, a man named Louie. Louie didn't just process a claim; he showed up, eased her mom's worries, and had a crew of carpenters rebuilding the garage within a week. To her, he was a hero. Jackson: That’s a great story. He solved a real, painful problem. Olivia: Exactly. But here's the twist. Her dad, a union man, had a different name for him: 'Louie, the thief.' He embodied that deep-seated cultural distrust of anyone in a sales role, even when they were providing immense value. Bleeke's entire philosophy is about closing that gap—how to be the hero in the story, not the villain. Jackson: I love that framing. But 'collaborative selling' still sounds a little like corporate jargon. What does that actually look like in practice? Is it just about being nicer? Olivia: It’s more than just being nice. It’s a structural shift in the goal of the conversation. The old goal was a win-lose. I win the sale, you lose your money. A slightly better version was a win-win: the buyer gets a solution, the seller's company gets a sale. Jackson: That sounds pretty good. What’s wrong with win-win? Olivia: Bleeke argues for what she calls a 'Win-Win-Win' or 'Win3' scenario. The buyer wins, the seller's company wins, and crucially, you, the salesperson, also win. Your goals, your commission, your sense of professional satisfaction—they all matter. It’s not about sacrificing yourself for the client; it’s about creating a system where everyone benefits from the transaction. It’s a partnership, not a service. Jackson: Huh. I’ve never heard it put that way. It reframes the salesperson from a simple conduit for the company into an actual stakeholder in the outcome. I can see how that would change your approach. The philosophy makes sense. But it still sounds... abstract. How do you actually do it? Is there a system?

Olivia: There is. And this is the heart of the book. She calls it the WIIFT™ system, which stands for 'What's In It For Them?' It’s a five-step framework that acts like a GPS for your conversations. The steps are: Wait, Initiate, Investigate, Facilitate, and Then Consolidate. Jackson: A GPS for conversations. I like that. It sounds like a pre-flight checklist. You don't just jump in the cockpit and hope for the best. But 'Wait' is a surprising first step. I thought sales was all about taking action and being proactive. Olivia: And that’s the most counter-intuitive and brilliant part of the whole system. The 'Wait' step is all about preparation. It’s the idea that the most important part of a successful conversation happens before you ever open your mouth. It’s about eliminating distractions, researching the person you’re talking to, and most importantly, getting crystal clear on your objective and what’s in it for them. Jackson: So the most important part of talking is... not talking? It's the prep work? Olivia: Precisely. She tells this incredible story about a sales team in India that was preparing for a massive meeting. They were trying to close a $4.6 million deal. Instead of just winging it, they spent significant time in the 'Wait' phase. They researched the buyer's personality type—which we'll get to later—and completely re-tailored their presentation to fit his style. They practiced their responses, anticipated his questions. Jackson: And what happened? Olivia: They closed the entire $4.6 million deal in a single visit. A sale that they said would normally have taken at least four visits. That’s the power of the 'Wait' step. It’s not wasted time; it’s an investment that pays off massively in efficiency and effectiveness. Jackson: Wow. Okay, that’s a concrete result. So after you've done your homework in the 'Wait' step, you 'Initiate' the conversation. I assume that's the 'hello.' What comes next? 'Investigate'? That sounds a bit like I'm putting on a trench coat and shining a lamp in their face. Olivia: That’s the exact trap she warns against. It’s 'Investigation,' not 'Interrogation.' The goal isn't to fire off a list of questions to qualify them. It's to have a genuine discovery conversation to understand their POWNs—that's her acronym for Problems, Opportunities, Wants, and Needs. Jackson: POWNs. Another acronym. But it makes sense. Can you give me an example of a good 'Investigate' question versus a bad, interrogation-style one? Olivia: A bad question is, "What's your budget for this?" It's transactional and puts the person on the defensive. A good, collaborative investigation uses what she calls a 'Four-Point' framework. You ask about 'Today'—their current situation. 'Tomorrow'—where they want to be. 'Risk'—what happens if they do nothing. And 'Reward'—what are the benefits of success. Jackson: Ah, I see. It's a narrative approach. Olivia: Exactly. So a better question might be, "Looking out six months from now, if this problem were completely solved, what would that ideally look like for you and your team?" You’re not asking for a number; you’re inviting them to paint a picture of their desired future. You’re co-creating a vision, and that’s a fundamentally different dynamic. And that investigation gets even more powerful when you realize you're not talking to a generic 'buyer,' but to a specific type of person.

Jackson: Okay, here we go. This is where the personality types come in, right? Olivia: It is. She calls them 'Tribal Types.' The idea came to her on a trip to Brazil, where a guide pointed out how different 'tribes' of people—families, singles, teenagers—all had their own customs and congregated in different spots on the beach. She applied that idea to business. The four types are: the Achiever, who is fast-paced and results-focused; the Commander, who is analytical and detail-oriented; the Reflector, who is cooperative and process-driven; and the Expresser, who is social and people-focused. Jackson: Hold on, this sounds a lot like those personality tests that some people find a bit simplistic. Some reviewers have pointed out it's very similar to the DISC model. Does it really work, or is it just putting people in boxes? Olivia: That's a fair and common criticism. Bleeke's defense would be that it's not about putting people in boxes. It's about getting out of your own box. It’s a tool for empathy. The goal is to adapt your communication style to make the other person feel comfortable and understood. If you're talking to a detail-oriented Commander, you come prepared with data and a logical plan. If you're talking to a big-picture Expresser, you focus on the story and the relationship. Jackson: So it’s less about diagnosing them and more about adjusting yourself. Olivia: Exactly. She tells a great story about a software salesperson named Mark trying to sell to a construction firm. He identified the project manager, Sarah, as an Achiever—she just wanted to know how the software would help her hit deadlines. But the CFO, Tom, was a Reflector—he needed to see detailed data, analytics, and a clear ROI. Mark tailored his presentations for each of them. He didn't give them the same pitch. Jackson: And he closed the deal. Olivia: He closed the deal. Because he didn't treat them like a monolithic 'buyer.' He treated them like individuals with different ways of processing the world. And this ability to adapt, to have that emotional intelligence, connects directly to her final, and perhaps most profound, point. Jackson: Which is? Olivia: The difference between 'Skill' and 'Will.' You can learn all the skills—the WIIFT system, the Tribal Types, how to ask perfect questions. That's the 'Skill.' But none of it matters without the 'Will'—the internal drive, the confidence, the resilience to actually go out and apply it, especially when things get tough. Jackson: The motivation. Olivia: Yes. She uses a fantastic sports analogy. She talks about watching a Green Bay Packers playoff game. They had all the skill in the world, a team full of superstars. But from the moment they walked onto the field, she could see their 'Will' was missing. They were flat, tentative. They had the skills, but not the drive. And they lost. Sales is the same. You can have the perfect script, but if you don't believe in yourself or your product, the buyer will feel it. Jackson: That belief in the value of what you're offering seems to be the engine for everything else. If you don't have that, you're just the guy in the shiny suit going through the motions. Olivia: That’s the whole game. It’s the difference between knowing the path and walking the path.

Jackson: So when you boil it all down, this isn't just about learning a new set of sales tactics. It's a fundamental shift in mindset—from conquest to collaboration. From a monologue to a dialogue. And you need both the map—the skills and frameworks like WIIFT—and the engine—the will and the genuine belief that you're there to help. Olivia: Exactly. The big takeaway for me is that in a world of infinite information and automated everything, the human element is the ultimate differentiator. Your ability to listen, to adapt, to connect, and to genuinely help someone solve a problem is the most valuable thing you can bring to any conversation, whether you're selling software or just trying to get your project approved at work. Jackson: It makes the idea of 'selling' feel less intimidating and more... human. It's just a structured way of helping. Olivia: It is. And if there's one simple action listeners could take away from this, it's to embrace that first step of the system. The next time you have an important conversation, just take five minutes to 'Wait.' Pause, and think about one thing: What's in it for them? That single question can change the entire dynamic. Jackson: That's a great, simple starting point. I can already think of a few conversations this week where that would have helped. We'd love to hear from our listeners. What are some of your 'sales weasel' horror stories, or maybe even some moments where a conversation created a genuine, collaborative win? Share them with us on our social channels. Olivia: We'd love to read them. It's a reminder that at the end of the day, business is always about people. Jackson: This is Aibrary, signing off.