Why the Best Boss You Ever Had Made You Uncomfortable

Stop Fixing Yourself. Find the Right Room

Stop Fixing Yourself. Find the Right Room. | Liza Adams, Part 1 Liza Adams spent her whole career being the person who shares. Ideas, connections, credit. In the right rooms, that made her invaluable. In the wrong ones, people assumed she had an angle. "What does she want? What is she positioning for?" As if generosity at work always has to be a move. She didn't figure this out from a book. She figured it out by living through both versions. CMO role, acquired out from under her. Job market that wasn't hiring. And a quiet realization that the thing she kept trying to fix about herself was never the problem. This is Part 1 of my conversation with Liza. She's an AI advisor and GTM strategist now, but this episode isn't about AI. It's about what happens when your best instinct keeps getting punished, and what shifts when you stop asking "what's wrong with me?" and start asking "am I in the right room?" Liza also reframes something I think a lot of leaders carry quietly. She stopped saying "they ignored me" and started saying "I allowed that." That's a small shift in language. It changes a lot about what you do next. * Your natural style isn't the problem. The environment that punishes it is. Knowing the difference changes every decision after it. * "I allowed myself to be snuffed" is a different sentence than "they snuffed me." One keeps you stuck. The other gives you something to work with. * Liza picked her entire career from a magazine list at 16, pivoted out of engineering in 18 months, and made it to CMO. The throughline wasn't a plan. It was knowing when to walk toward the crack that opened.

He Asked 9 Executives to Name the Company's Goals. He Got 74 Answers. | Jeff Miller

A CEO rattled off three company goals without hesitation. Then Jeff Miller interviewed nine executives on the same team and collected 74 different answers. That gap between what leaders assume and what teams actually understand is the throughline of this conversation. Jeff Miller is a leadership coach and organizational advisor who works inside executive teams to surface misalignment before it becomes dysfunction. In Part 3 of his conversation with Ken, he breaks down why collaboration fails at work (and traces it back to how conflict was handled in elementary school), shares the framework he uses to move teams from chaos to commitment, and gets personal about risk, regret, and the advice he gives at every career stage. He also shares the story behind the Jester and Farley Fund, a nonprofit founded in memory of his childhood best friend, David Saltzman, who wrote and illustrated a children's book while battling Hodgkin's disease at Yale. 3 Specific Realizations: * The reason most executive teams can't align isn't strategic disagreement. It's that no one verified whether they were even talking about the same goals. * Jeff traces workplace collaboration failure to a specific pattern: when kids fought in group work, teachers separated them instead of teaching them to resolve it. That gap never gets closed. * He went eight years without a day off and doesn't call it a regret. He calls it a wish, which says something different about how high performers process cost. This is Part 3 of a multi-part series with Jeff Miller. Link to the Jester and Farley Fund in the show notes.

Why the Best Boss You Ever Had Made You Uncomfortable

Most people have had a boss they didn't fully appreciate while they were there. The one who said the thing everyone else was too careful to say. Jeff Miller has spent a career trying to understand why that kind of feedback is so rare, and what it costs people when they never get it. Jeff is a partner at Door2 and a longtime coach to leaders navigating the gap between how work looks and how it actually feels. This is Part 2 of our conversation. Part 1 is worth going back for, but this one stands on its own. We talk about how to ask for feedback without sounding like you want reassurance, why "soft skills" is a name that undersells the hardest work in most organizations, and what it means to define success when the marker keeps moving and you're a few years from 60. Near the end, Jeff got a Facebook message from a sixth-grade student he taught in 1995. Thirty years later. What that person said is worth staying for. Three things from this conversation: * Asking "how am I doing?" is too big a question for someone with 80,000 things going on. Asking for feedback on three specific things changes the whole transaction. * "Soft" doesn't mean weak. It means the skill changes depending on who's in front of you. That's what makes it hard. * The best boss most people ever had was someone they didn't fully appreciate at the time, because that person said the thing everyone else was too careful to say.

Jeff Miller: Most People Say You Did Your Career Backwards

Jeff Miller built his career in the wrong order, at least by conventional standards. He was teaching in one of the most dangerous schools in Los Angeles before he ever managed a corporate team. He violated a university contract to take a director role he didn't fully understand yet. And he didn't get his first real corporate job until his late 30s. Jeff is a partner at Door Two, but the path there ran through gang-violence schools in South Los Angeles, English teaching in Japan, a contract violation he made knowingly, and a stretch where he was working a corporate training job by day and teaching graduate school until 10pm three nights a week. This is Part 1 of a two-part conversation. Jeff and I talk about what it actually cost to build a career "backwards," why imposter syndrome doesn't go away (and what it means when someone tells you it does), and why 30 students in a classroom aren't that different from 30 people on a corporate team. This episode is for anyone who has ever looked around the room and wondered how they got there and whether they belong. Three Specific Realizations from This Conversation * The moment Jeff realized he had authority wasn't a meeting or a title announcement. It was someone snapping to attention in a retail store, and he had to recalibrate on the spot. * Imposter syndrome isn't a phase you graduate from. Jeff's framing: "the greatest deception is self-deception," and most people who claim to be past it aren't being honest with themselves. * Managing a classroom of children in a high-violence school was better preparation for corporate leadership than most formal management training. Not metaphorically. Literally the same skills.

Amy Bray (Google): You Have Permission to Say It's Not Working

Someone told Amy Bray something she had never heard in her career: it's okay to tell your boss you're unhappy. That sounds simple. It wasn't. She was in a big job on an interim basis, working through something she describes as toxic, pulled away from her kids, grinding through it because nobody had ever told her she could stop and say it wasn't working. When she finally did, her career didn't fall apart. Her boss heard her. She moved into a role she loved. But the thing that stayed with her wasn't the outcome. It was that she needed permission from someone else to say something true about her own experience. Amy Bray is a senior marketing leader at Google. This is Part 3 of our conversation. We also get into how she actually uses gut instinct on a team that runs on data, what she tells people who are overwhelmed by AI, and the pattern she has noticed across every role where something eventually stopped working. Three things from this conversation: * She didn't need a new strategy. She needed someone to tell her she was allowed to speak. That gap between what's true and what feels permissible is something a lot of people carry quietly for years. * On gut vs. data: she doesn't treat them as opposites. She uses gut to form the hypothesis, then data to validate or challenge it. That framing is specific and repeatable. * The marker she uses to assess a role isn't about title or comp. It's the feeling at the end of the week: did I show up well or did I lose myself in it? Part 3 of a 3-part series.