
The Helpful Saboteur
11 minA Tactical Playbook for Managers and Executives
Golden Hook & Introduction
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Olivia: A Gallup poll found only 20% of employees feel their strengths are used every day. Jackson: Wow. Only 20 percent? That’s… depressingly low. Olivia: It means most companies are running at one-fifth of their potential. And what if the reason isn't the employees, but the very managers who are trying to 'help' them? Jackson: Okay, now you’ve got my attention. That’s a bold claim. You’re saying the managers are the problem? Olivia: That’s the provocative argument at the heart of the book we’re diving into today: Coaching Salespeople into Sales Champions by Keith Rosen. Jackson: I feel like I’ve heard that name. Olivia: You probably have. Rosen is a giant in the sales coaching world, a real pioneer. This book is his magnum opus—it’s won five international book awards and is basically a playbook that distills over 35 years of his experience. He argues that traditional sales training is a waste of money if you don't fix the management layer first. Jackson: A five-time award winner. No pressure then. But honestly, Olivia, ‘coaching’ is such a corporate buzzword. Every manager wants to be a ‘coach.’ What makes Rosen’s take any different? Olivia: That’s the perfect question. Because for Rosen, coaching isn't about giving better pep talks or just being more supportive. It’s a fundamental, and sometimes painful, shift in your entire mindset as a leader.
The Mindset Revolution: Why Your Best Intentions as a Manager Are Sabotaging Your Team
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Jackson: A painful shift? That doesn't sound like a great selling point. What do you mean? Olivia: Well, let’s start with a type of manager we all know. The Problem-Solver. This is the person whose door is always open. They thrive on fixing things. An employee has an issue, they have the answer. They’re the hero, the one who keeps the machine running. Jackson: That sounds like a great boss! That’s the person who gets promoted. They’re reliable, they’re helpful. What’s the problem? Olivia: The problem is that in solving every problem, you inadvertently teach your team one thing: "You are not capable of solving this yourself. Come to me." You create a culture of dependency, not accountability. Jackson: Okay, but someone has to solve the problems. You can't just let things burn. Olivia: And that’s the exact trap. Rosen tells this fantastic story about a client of his named Michele. She owned a marketing firm called DesignWorks. She was passionate, brilliant, and deeply cared for her 10-person sales team. She was the definition of a caring boss. Jackson: I’m sensing a ‘but’ coming. Olivia: A huge one. She had a new salesperson, Jennifer, who just wasn't hitting her goals. And Michele was agonizing over it. She’d lie awake at night thinking, "Should I invest more time in Jennifer? She has so much potential! Or should I let her go? But what if she just needs a little more support? What if I fail her?" She was completely stuck. Jackson: I mean, that sounds like a conscientious manager to me. She’s wrestling with a tough decision and trying to do right by her employee. Olivia: She was. But her coach, Keith Rosen, pointed out something that stopped her in her tracks. He said her thinking was consumed by fear and "what-ifs." He told her, "You can’t coach what you fear." Jackson: "You can't coach what you fear." That’s a heavy line. What does it even mean in this context? Olivia: It means Michele was so attached to the outcome—either Jennifer succeeding or the company not failing—that she couldn't have a clear, objective conversation. Her fear was clouding everything. Rosen introduced her to a core principle of masterful coaching: detachment. Jackson: Hold on. Detachment? That sounds cold. How can you be a good leader and be detached from whether your team succeeds or fails? That feels like the opposite of leadership. Olivia: It’s a common reaction, and some critics of the book find this part a bit jarring. But Rosen’s definition of detachment isn't about not caring. It’s about detaching from your ego's need for a specific result to happen in a specific way. It’s about shifting your focus from the result to the process. Jackson: So it’s like a surgeon. They have to be detached from the overwhelming emotion of the life-or-death situation to focus entirely on the precision of the procedure. The process is the result. Olivia: Exactly! That’s a perfect analogy. For Michele, it meant detaching from the need for Jennifer to become a star overnight and instead focusing on creating a clear, repeatable process for performance evaluation and support. A process that would work for Jennifer, or the next person, or the person after that. The outcome—whether Jennifer improved or was let go—would be a natural byproduct of a well-executed, unemotional process. Jackson: So the caring manager, Michele, was actually the bottleneck. Her intense desire to help was preventing her from building a system that could actually help. Olivia: Precisely. She had to stop being the hero who swoops in and start being the architect who builds the stadium where the players can win on their own. It’s a massive identity shift for most managers. Jackson: No kidding. You’re asking them to give up the very thing that probably got them recognized in the first place: being the go-to problem-solver. Olivia: And that fear of letting go, of not being the hero? It’s often fueled by a story the manager is telling themself. Which brings us to one of Rosen's most powerful, if slightly dramatic, concepts.
Unmasking the S.C.A.M.M.: The Self-Sabotaging Stories That Derail Performance
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Jackson: Okay, I’m ready. Lay it on me. Olivia: He calls it the S.C.A.M.M. Jackson: The S.C.A.M.M.? That sounds like something out of a spy movie. Is this where we learn the secret handshake? Olivia: (laughing) Not quite. It's an acronym. It stands for the Stories, Cons, Assumptions, Meaning, and Mindset that we use to justify our circumstances and our performance. Jackson: So a S.C.A.M.M. is like the personal PR campaign for my own failures? Olivia: That is a brilliant way to put it. It’s the narrative we construct to avoid accountability. For a salesperson, it might be, "The economy is bad," "These leads are terrible," or "My territory is the worst." For a manager, it might be, "I inherited a weak team," or "I don't have the resources to succeed." Jackson: I’ve heard all of those. I’ve probably said some of those. Olivia: We all have! And Rosen's point is that a bad manager either believes the S.C.A.M.M. or argues with it. A great coach does neither. A great coach helps the person see the S.C.A.M.M. for what it is: a story. He tells another great case study about a team leader named Lauren. Jackson: Let’s hear it. Olivia: Lauren was incredibly stressed. Her company was growing, but her team wasn't, so her workload was ballooning. She was working insane hours, totally overwhelmed. Her manager, Joan, noticed and asked what was wrong. Lauren explained the situation and said she was terrified that the quality of her work would suffer. Jackson: That seems like a legitimate fear. Olivia: It does. But Joan, using a coaching approach, dug a little deeper. She pointed out that Lauren had an underutilized account manager on her team. She asked, "Why not delegate some of this work to them?" And that's when the real story came out. Lauren confessed she was terrified of delegating. Jackson: Why? Fear of losing control? Olivia: Even deeper than that. When Joan kept asking questions, Lauren’s S.C.A.M.M. unraveled. It went like this: "If I delegate a task, my team member might make a mistake. If they make a mistake, we could lose a client. If we lose a client, my reputation will be ruined. If my reputation is ruined, I'll get fired. If I get fired, I won't be able to provide for my family." Jackson: Whoa. From delegating a report to her family being on the streets. That escalated quickly. Olivia: That's the anatomy of a S.C.A.M.M.! It’s an irrational chain of logic fueled by fear. Lauren wasn't drowning in work; she was drowning in a story she was telling herself. The coach’s job wasn't to tell her, "Don't worry, you won't get fired." It was to hold up a mirror so Lauren could see the irrationality of her own story. Jackson: And that’s what he means by coaching the person’s relationship with the story, not the story itself. You’re not debating the facts of the story; you’re exploring why the person has chosen to believe it. Olivia: You’ve got it. You’re helping them become the editor of their own story, not just a character trapped in it. You ask questions like, "What's the evidence for that belief?" or "What would be a more empowering story to tell here?" You’re not providing solutions; you’re providing a new perspective. Jackson: This feels like the core of the whole book. It’s less about sales tactics and more about becoming a sort of corporate therapist. And I can see why some readers find the book dense or jargon-heavy. Concepts like 'S.C.A.M.M.' and 'detachment' require you to slow down and really think. Olivia: They absolutely do. It’s not a light beach read. It’s a book that demands you examine your own leadership style, your own fears, and your own S.C.A.M.M.s first. You can't help your team rewrite their stories if you're still a prisoner of your own.
Synthesis & Takeaways
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Jackson: It’s fascinating. The whole philosophy seems to be built on an internal revolution. First, as a manager, you have to completely change your own operating system—from being the heroic problem-solver to a detached, process-driver. Olivia: A shift from being the main actor to being the director. Jackson: Right. And then, once you’ve done that, you have to become a sort of psychologist, helping each person on your team de-bug their own faulty code—to see and dismantle their own S.C.A.M.M.s. Olivia: It’s a profound shift from managing activities to coaching mindsets. And Rosen provides hundreds of questions in the book to help managers do just that. The ultimate takeaway is that you cannot change your team's results until you change the questions you ask them. Jackson: So it’s not about having all the answers anymore. It’s about having all the right questions. Olivia: That’s the heart of it. And it’s a skill. It takes practice. So, here’s a simple, practical step for our listeners, straight from the playbook. The next time an employee brings you a problem, resist every instinct to give them the answer. Jackson: Bite your tongue, basically. Olivia: Bite your tongue, and instead, just ask one simple question: "That’s a tough one. What have you tried so far?" And then just be quiet and listen. Jackson: I can already feel how uncomfortable that would be for a lot of managers. But I can also see how it could be a complete game-changer. I would genuinely love to hear how that goes for people. Olivia: Me too. If you try it, let us know. Share your experiences with the Aibrary community on social media. Did you get a blank stare, or did you witness a breakthrough? Jackson: The answers might be surprising. This was a fantastic deep dive, Olivia. It challenges a lot of conventional wisdom about what it means to lead. Olivia: It really does. It’s about building champions, not just managing a sales force.