Olivia: CEOs estimate it takes a new mid-level leader over six months just to start adding more value than they consume. Six months. Jackson: Whoa, hold on. Six months? That feels like an eternity. In most new jobs, you feel like you have about six days before everyone starts forming an opinion on whether you're a genius or an idiot. Olivia: Exactly! And that intense pressure to perform immediately is what Michael Watkins argues is a recipe for disaster. He tackles this head-on in his classic book, The First 90 Days: Critical Success Strategies for New Leaders at All Levels. Jackson: I’ve definitely heard of this one. It’s got a bit of a legendary status, right? Olivia: It absolutely does. Watkins, who's a Harvard-trained expert on leadership transitions, essentially wrote what The Economist famously called “the onboarding bible.” He did it because he saw so many brilliant, capable people fail in new roles, not because they were incompetent, but because they fundamentally misunderstood the new game they were playing. Jackson: Okay, I’m hooked. Misunderstanding the game is a feeling I think everyone can relate to. It’s that sense of panic when you realize the rules you thought you knew no longer apply. So what’s the biggest mistake people make? Where do they go wrong first? Olivia: It starts with a paradox that is both simple and profound: your greatest strengths from your last job are often the very things that will cause you to fail in your new one.

Jackson: Wait, that sounds completely backward. How can being good at your job be a bad thing? Isn't that why you got the new role in the first place? Olivia: It is, but the context changes everything. What made you a star performer in one role can become a fatal liability in another. Watkins tells this perfect, and frankly, brutal story about a woman named Julia Gould. Jackson: Uh oh, this sounds like a cautionary tale. Lay it on me. Olivia: Julia was a marketing superstar at a big consumer electronics company. For eight years, she was the go-to person. She was known for her incredible attention to detail, her deep knowledge of the products, and her need for control. These traits made her an amazing individual contributor and a great marketing manager. So, she gets a big promotion. She’s asked to lead a major new product launch, coordinating a cross-functional team from R&D, sales, manufacturing—the works. Jackson: The dream promotion. She’s moving up, leading a big, important project. This is the goal. Olivia: It was. But it fell apart in less than two months. She walked into this new leadership role and did exactly what had always made her successful. She tried to control everything. She dove into the technical details of the manufacturing process, a world she knew nothing about. The engineers on the team were immediately put off. They’d say, "Julia, with all due respect, you don't know what you're talking about." Jackson: Ouch. I can feel the cringe from here. That’s a tough start. Olivia: It gets worse. When they challenged her, she got defensive and retreated to what she knew best: marketing. She started micromanaging the marketing plan, alienating the very people who used to be her peers. They felt like she didn't trust them anymore. Within a month and a half, the project was in chaos, the team was demoralized, and leadership had to step in. They pulled her from the project. Jackson: Pulled her completely? After being a star for eight years? That’s rough. Olivia: Sent her right back to a role in the marketing department. It was a massive career setback. And the key insight from Watkins is that Julia didn't fail because she was suddenly bad at her job. She failed because she didn't make the mental break. She was still trying to be the star marketing expert instead of the cross-functional leader. She didn't let go of the old role to embrace the new one. Jackson: Okay, so the principle is that you have to shed your old skin. But that’s terrifying. It feels like you’re being asked to abandon the very skills that give you confidence. What should she have done instead? Just sit on her hands and not do the things she's good at? Olivia: Not exactly. It's about shifting your focus. Instead of being the one with all the answers, her new job was to be the one asking the best questions. Her value was no longer in her personal depth of knowledge, but in her ability to draw out the expertise of her team and align them toward a common goal. She needed to transition from being a "doer" to being an "enabler." Jackson: That makes sense. It’s a change in your value proposition. But it’s a hard switch to flip, especially when you’re feeling insecure in a new role. I’ve seen some readers say this book’s advice can feel a bit overwhelming, like it’s geared more for a CEO than a first-time manager. Does this "letting go" idea apply even in smaller promotions? Olivia: Absolutely. Watkins argues it's universal. Even moving from a team member to a team lead requires a fundamental shift. You're no longer judged on your individual output, but on the output of your team. The temptation to just jump in and "do it yourself" because you can do it faster or better is immense, but every time you do, you're failing at your new job, which is to develop your people. Jackson: Right. You’re still playing the old game. So if the first step is a mental reset, what’s next? How do you figure out what the new game even is? Olivia: That is the perfect question, and it leads directly to what I think is the most powerful tool in the entire book. It’s a diagnostic framework that acts like a GPS for your new role.

Jackson: A GPS for my job? Okay, I'm listening. I get lost in my own building sometimes, so this sounds useful. Olivia: It’s called the STARS model. It's an acronym that stands for five common business situations you might be walking into: Start-up, Turnaround, Accelerated Growth, Realignment, and Sustaining Success. Watkins argues that you cannot succeed until you correctly diagnose which of these situations you're in, because each one requires a completely different strategy. Jackson: Okay, break those down for me. They sound a bit like corporate jargon. Olivia: They’re actually very intuitive. A Start-up is building something from scratch. A Turnaround is saving something that's broken—the classic "burning platform" scenario. Accelerated Growth is about scaling something that's already working. Realignment is about revitalizing a unit that has become complacent or is drifting off course. And Sustaining Success is about preserving the vitality of a successful organization and taking it to the next level. Jackson: It’s like a doctor diagnosing a patient. You wouldn't prescribe aggressive surgery for a common cold, and you wouldn't suggest bed rest for a heart attack. Olivia: That’s a perfect analogy! And just like with Julia Gould, using the wrong approach can be catastrophic. Watkins tells another great story about an executive named Karl Lewin. Karl was a German executive, a hard-driving, decisive guy who was a hero in his company. He had just engineered a massive, successful Turnaround of their European manufacturing operations. He shut down inefficient plants, centralized functions—he was the tough guy who made the tough calls, and it worked brilliantly. Jackson: So he’s the company’s fixer. The guy you call when things are on fire. Olivia: Exactly. So for his next act, they send him to run the supply chain for their core North American operations. He walks in with his hammer, ready to find some nails. He expects another Turnaround. But what he finds is different. The North American unit isn't on fire. It's not broken, it's just... drifting. It's a bit complacent, performance is slightly below average, and the culture is addicted to fighting small fires instead of thinking strategically. Jackson: So it’s not a Turnaround. In the STARS model, what would that be? Olivia: It's a classic Realignment. It doesn't need a hero with an axe; it needs a diplomat with a vision. It needs someone to build consensus, upgrade systems, and slowly change the culture. But Karl came in ready for war. He started criticizing everything, just like he did in Europe. The team, which didn't see a crisis, just saw him as an arrogant outsider. He almost failed. Jackson: Wow. So his strength in a Turnaround—being decisive and aggressive—became his weakness in a Realignment. It’s the Julia Gould story all over again, but at a strategic level. Olivia: Precisely. Luckily, Karl was smart enough to realize his mistake. He had to completely change his approach. He had to slow down, build alliances, and persuade people that a change was needed, rather than just ordering it. He had to shift from being a wartime general to a peacetime statesman. Jackson: This is fascinating. But how do you know which situation you're in? Does your boss just tell you, "Welcome to the Realignment, Karl"? I doubt it. Olivia: You have to be a detective. Watkins provides a whole set of diagnostic questions. You have to ask: Is this business financially viable? Are the right people in the right roles? Is the strategy clear? Is the culture healthy? By answering these questions through conversations and research in your first few weeks, a picture emerges. You diagnose the situation yourself. You can't wait for someone to hand you the map; you have to draw it. Jackson: Okay, so you’ve done your mental reset, you’ve diagnosed the situation with the STARS model. You know what kind of game you're playing. But there’s still that one huge, unpredictable variable you have to deal with: your new boss. Olivia: And that, Jackson, is where Watkins says you move from diagnosis to action. You have to proactively negotiate your own success.

Jackson: "Negotiate success." I like the sound of that. It feels active and empowering. But it also sounds a little… confrontational? Like you’re going to war with your new manager. Olivia: It’s the opposite, actually. It’s about building a productive alliance from day one. Most people passively wait for their boss to tell them what to do. Watkins says you need to flip that script. You need to manage your boss by establishing expectations, securing resources, and aligning on working styles before any problems arise. Jackson: That sounds great in a book, but what if your boss is just… difficult? Or has a reputation for being a shark? Walking in and trying to "manage" them seems incredibly risky. You could come off as arrogant or naive. Olivia: It’s a huge risk, which is why the story of Michael Chen is so brilliant. Michael was promoted to be the CIO of a business unit. His new boss was a woman named Vaughan Cates, and her reputation preceded her. Colleagues literally warned him, "Vaughan will eat you alive." She was known for being incredibly tough, results-driven, and had already pushed out several people she inherited. Jackson: Okay, this is the ultimate test case. If it works for Michael, it can work for anyone. What did he do? Olivia: He didn't hide. He went to Vaughan on his first day and laid out a plan for his first 90 days. But it wasn't a list of things he was going to do. It was a plan for how he was going to learn. He said, "For the first 30 days, my goal is to meet with these key people and understand the business. At the end of that month, I will come back to you with a diagnosis of the situation and a proposed plan of action. Does that work for you?" Jackson: That is a bold move. He’s not asking for permission; he’s proposing a contract. How did she react? Olivia: She was a bottom-line person, and this sounded structured and professional. She agreed. So Michael bought himself 30 days of breathing room. During that time, he kept her updated, but when she tried to pressure him into making a quick decision on a big software purchase after just three weeks, he held firm. He said, "I'm not ready to make that call. It's in my 90-day plan to evaluate this properly, and I need to stick to the process we agreed on." Jackson: Wow. He used the plan he got her to agree to as a shield. That's smart. Olivia: Incredibly smart. At the 30-day mark, he delivered a fantastic plan. She was impressed. A month later, he came back with some early wins and used that credibility to ask for more resources. She grilled him, but he had done his homework and successfully defended his case. He was building momentum. Jackson: But what about the "eating him alive" part? The personality clash? Olivia: That was the final, and most masterful, move. Once he had established his competence, he proactively raised the issue of their different styles. He said something like, "Vaughan, I know we have different approaches. You're very direct, and I'm more of a planner and team-builder. I want to assure you that even though my style is different, I am just as committed to delivering results." Jackson: He just put it on the table! He named the elephant in the room. Olivia: He did. And because he had already proven he could deliver, she respected it. He wasn't making excuses; he was building a bridge. He turned a potential conflict into a point of mutual understanding. He didn't just survive; he thrived by proactively shaping the terms of his engagement with her.

Jackson: That’s an incredible story. It reframes the whole idea of starting a new job. It’s not about just showing up and working hard. It’s a strategic campaign. Olivia: It really is. When you pull it all together, Watkins is giving you a three-step dance for any transition. First, you have to mentally break from your past self and your old strengths, like Julia Gould failed to do. Second, you diagnose the new reality with a clear framework like the STARS model, so you don't apply the wrong strategy, like Karl Lewin almost did. Jackson: And third, you proactively build the most critical alliance you have—the one with your boss—to get the support and resources you need to execute your plan, just like Michael Chen did with Vaughan. Olivia: Exactly. It’s a sequence: Prepare Yourself, Diagnose the Situation, and Negotiate Success. Jackson: So for someone listening who is literally starting a new job next Monday, what is the absolute first, most important thing they should do, based on all this? Olivia: Don't try to do anything. Your only job for the first week, maybe even the first month, is to learn. Watkins calls it "Accelerating Your Learning." Schedule conversations with your boss, your team, your peers, and even customers if you can. Ask them questions like: "What are the biggest challenges you see for this team?" "What would a quick win look like in your opinion?" "What's the one thing I should avoid doing that could get me into trouble here?" Jackson: So your initial credibility comes from your desire to understand, not your desire to act. Olivia: That's the secret. Simply displaying a genuine desire to learn and listen builds more trust and influence than trying to impress everyone with how much you already know. Your early wins will come from the insights you gather in that learning phase. Jackson: That’s such a powerful reframe. It takes the pressure off of having to be a hero on day one. We’d love to hear from our listeners about this. What are your new job horror stories, or your biggest success stories? What's the one piece of advice you'd give someone walking into a new role? Find us on our socials and share your wisdom. Olivia: This is Aibrary, signing off.