Olivia: The biggest lie in business isn't about the numbers. It's the one we tell ourselves after a big, exciting strategy kickoff: "This time, it's going to work." But it almost never does, and the reason why has almost nothing to do with the strategy itself. Jackson: Okay, that's a pretty cynical start, Olivia. Are you saying all corporate planning is just an elaborate, expensive form of team-building theater? Because I've definitely been to a few of those. Olivia: Not at all! But it points to a massive blind spot in leadership, a kind of Bermuda Triangle where great ideas go to disappear. It’s a problem that Patty Azzarello tackles head-on in her book, MOVE: How Decisive Leaders Execute Strategy Despite Obstacles, Setbacks, & Stalls. Jackson: Patty Azzarello. The name sounds familiar. Olivia: It should. What's fascinating is that Azzarello isn't an academic theorist. She's a Silicon Valley veteran. She became a general manager at HP at 33, was running a billion-dollar software business by 35, and was a CEO at 38. She wrote this book from the trenches, not an ivory tower. Jackson: Wow, okay. So she’s seen a few of these strategies vanish into the Bermuda Triangle herself. Olivia: Exactly. And she argues the failure happens in a place we rarely talk about, a place she calls "The Middle." It’s where the initial momentum from the kickoff meets the gravitational pull of reality. Jackson: The Middle. That sounds ominous. It sounds like a place I’ve been many, many times without knowing its name. Olivia: We all have. And that’s our first stop today: exploring this treacherous middle ground where all great plans seem to die a quiet, slow death.

Jackson: So, this idea of "The Middle"... it feels incredibly familiar. It’s that project that everyone was fired up about in January, but by April, no one even mentions it in meetings. It’s just… gone. What’s the dynamic there? Olivia: Azzarello illustrates this perfectly with a story from a corporate executive leadership program. Picture this: a room full of senior executives at an off-site retreat. They're playing a business simulation game. Jackson: I’m already getting hives. Lots of trust falls and jargon? Olivia: A little less trust fall, a little more strategy. In the simulation, they could invest in initiatives like 'manager training' or 'supply chain cost reduction.' They’d click a button, allocate the virtual budget, and boom—instant results. Their costs would go down, their time-to-market would speed up. The initiatives worked perfectly, every time. Jackson: That sounds like a fantasy world. That is not how reality works. Olivia: Precisely. And that’s what one of the executives said. He joked to the group, "The great thing about these initiatives is that they actually work! In our world, we just spend the money on the initiative, and then it doesn’t help. I wish our initiatives worked this well." Jackson: Oh, that hits hard. That’s the sound of a thousand failed projects laughing from the grave. It’s the gap between the PowerPoint slide and the quarterly results. Olivia: That’s the exact gap Azzarello is targeting. The simulation gives you the outcome without the work. The real world gives you the work, and the outcome is… optional. The space between those two is "The Middle." It’s the long, hard, unglamorous slog after the kickoff party ends and the posters are taken down. Jackson: It’s like the February of New Year's resolutions. The gym is packed on January 2nd, but by mid-February, it’s empty again, and you’re back to eating pizza on the couch. The initial motivation is gone. Olivia: That’s a perfect analogy. And Azzarello would add that the problem isn't just that motivation fades. The bigger issue is that the initial phase of change is often fueled by three things: Dissatisfaction with the way things are, a Vision for the future, and some clear First Steps. It's an actual formula called the Change Equation. But that formula only gets you started. It doesn't get you through the marathon. Jackson: So what does get you through it? If motivation and a clear vision aren't enough, what is? Olivia: Defined work. The Middle isn't a phase of inspiration; it's a phase of construction. It requires breaking down the grand vision into concrete, tangible, and sometimes boring tasks. It’s about building the new habits, processes, and systems brick by brick, while the "gravitational pull" of the old way of doing things is constantly trying to drag you back. Jackson: The gravitational pull of old habits. I like that. It’s the force that makes you open the same spreadsheet you were supposed to replace, just because it’s familiar. Olivia: Exactly. And this is where most leaders fail. They are great at the vision part—the big speech, the exciting kickoff. But they don't architect the Middle. They don't define the concrete outcomes, the mid-term checkpoints, or the metrics that will keep the team moving when the initial excitement is a distant memory. As Azzarello puts it, "Strategy without execution = talking." Jackson: And we’ve all been in a lot of talking-shops. So the first step to escaping this corporate ghost story is just acknowledging that The Middle exists and that it’s going to be hard. Olivia: It’s acknowledging that it’s the hardest part. It’s easy to get excited at the beginning and to define the long-term goal at the end. The virtue, as the old proverb goes, is in the middle. And to navigate it, you need the right vehicle. Jackson: What’s the vehicle? Olivia: That brings us to the next letter in her MOVE model—the 'O' for Organization. And her take on this is brutally direct and something many leaders don't want to hear.

Olivia: So, you've accepted you're in The Middle. The journey is long, the work is hard. Now you look around at your team. Azzarello’s argument is that if you don't have the right people on the bus, you're not going anywhere. Jackson: Okay, that makes sense on the surface. But what does "the right people" actually mean? Is it just about skills? Olivia: It’s more than that. It’s about being ready, able, and motivated for the specific transformation you're undertaking. And she delivers one of the most chilling lines in the book on this topic: "There is no effective antidote for the wrong team." Jackson: Hold on. That feels… harsh. Isn't it a leader's job to coach and develop the team they have? It sounds a bit like an excuse to just say, "Oh, the team was wrong," and wash your hands of it. Olivia: I see why it sounds that way, and it’s a really common and empathetic reaction. But Azzarello’s point is rooted in pragmatism, not cruelty. It’s about recognizing that a major strategic change isn't just business as usual. It's a different sport. Jackson: A different sport? What do you mean? Olivia: Think about it this way. You could have a team of world-class marathon runners. They are elite, dedicated, and highly skilled athletes. But if your new strategy is to win a weightlifting competition, are they the right team? Jackson: No, of course not. Their entire physiology and training are for endurance, not explosive strength. Olivia: Exactly. They are a great team, but they are the wrong team for that specific goal. A leader's job isn't to try and teach marathon runners how to powerlift overnight. It's to build a team of powerlifters. Azzarello argues that in a transformation, you are fundamentally changing the game. The skills, mindset, and even the temperament required to succeed in the new reality are often completely different from what made the team successful in the past. Jackson: Okay, that analogy helps. It’s not about good people vs. bad people. It’s about fit for purpose. But how do you even identify that? In the real world, it’s not as clear-cut as marathon runners and weightlifters. Olivia: She says you have to be ruthlessly honest. You need to design your ideal organization on a blank sheet of paper. Forget the people you have for a moment. What roles, skills, and structures do you need to achieve the new strategy? Then, and only then, do you see who from your current team fits into that new structure. Jackson: That sounds like a terrifying exercise for a manager to do. You’re essentially creating a blueprint that might not have a place for people you’ve worked with for years. Olivia: It is terrifying. This is the "Valor" part of her MOVE model—the courage to face the hard stuff. But the alternative is worse. The alternative is keeping someone in a role they are not equipped to succeed in, which is not only bad for the strategy but also deeply unfair to that person. It sets them up for failure. Jackson: That’s a really important reframe. The "nice" thing to do, which is to leave everyone in their comfortable roles, might actually be the cruelest thing in the long run. Olivia: It is. And it’s a guaranteed way to stall in The Middle. You can’t afford to have anyone on the team who isn't fully on board—ready, able, and motivated. A single person who is dragging their feet, actively resisting, or simply incapable of performing in the new context can sabotage the momentum of the entire group. Jackson: So the message is, first, diagnose that you're in The Middle. Second, be brutally honest about whether you have the right Organization to get through it. It’s a one-two punch of realism. Olivia: It is. And it’s why the book is so highly praised by leaders at major tech companies. It’s not feel-good theory. It’s a practical, and sometimes painful, playbook for what actually works when you need to make a change stick. It’s about moving from just talking about the strategy to actually building the engine that will drive it forward.

Jackson: So, as we wrap this up, what’s the core insight we should be taking away from this? It feels like a pretty tough, no-nonsense message for anyone in a leadership role. Olivia: I think the biggest insight from MOVE is that strategy execution isn't a "soft skill." It's a hard-nosed engineering problem. You have to diagnose the real point of failure, which is almost always The Middle, and you have to use the right tools for the job, which starts with having the right Organization. Jackson: The right people in the right seats on the bus. Olivia: Exactly. But it’s more than that. It’s about realizing the bus is heading to a completely new destination, and you might need a different kind of bus and a different kind of driver. The book forces you to confront the gap between your aspirations and your capabilities. As Azzarello says, "You can lead a transformation from the top, but you can’t do a transformation from the top." It requires everyone. Jackson: And if you have the wrong "everyone," you're stuck. Olivia: You're stuck. So the actionable takeaway for anyone listening isn't to go and dream up another grand five-year plan. It’s to look at the most important initiative you have on your plate right now and ask two brutally honest questions. Jackson: I’m ready. A little scared, but ready. Olivia: First: Are we still coasting on the fumes of the exciting kickoff, or are we lost somewhere deep in The Middle? Be honest. And second: Looking at my team, do I have the organization I need for this journey, or just the organization I happen to have today? Jackson: Wow. That is a powerful and slightly terrifying pair of questions to take back to the office tomorrow. It forces you to stop admiring the problem and actually look at the machinery. Olivia: That's the whole point. Stop admiring the problem and start the real work of moving forward. Jackson: We’d love to hear from our listeners on this. Have you ever seen a project die a slow death in "The Middle"? Or have you been on a team that just wasn't built for the mission? Share your war stories with us on our social channels. Olivia: This is Aibrary, signing off.