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.

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 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.

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.

Amy Bray was crushing it. She had the right people, the momentum, the wins. Then her manager left, and the VP asked her to step in on an interim basis. She said yes. And some of it worked. But some of it didn't.

This is Part 2 of my conversation with Amy, who leads teams at Google. We talk about what happens when you take a stretch role before you're ready, how to experiment with your career without jeopardizing your current job, and why a little humility in high-stakes rooms can actually work in your favor.

Amy also gets into the difference between "I deserve this" and "help me grow into this," and why demonstrating competency beats demanding recognition every time.

3 Specific Realizations:

• Taking an interim leadership role revealed gaps Amy didn't know she had, specifically in relationships and understanding business mechanisms, and she had full self-awareness about it in the moment
• Saying "I'm a little nervous" before presenting to executives sometimes gets people rooting for you instead of evaluating you
• The shift from "I've been here X years, I deserve the promo" to "my goal is to grow into this, can you help me get there" changes how managers advocate for you

A stranger walked up to Amy Bray at a little league game and asked, "Are you Owen's mom? I've never seen you before." That sentence stopped her.

Amy is the Global Head of Partner Demand Center at Google Cloud. Before that, she moved from the art world into tech through sheer will, an MBA, and some difficult conversations she still remembers clearly. In episode 1 of 3, she talks about two specific career pivots where she had to do what she calls "the cringey thing": tell the people around her that something wasn't working, even when the timing was inconvenient and the outcome was uncertain.

One conversation was about wanting more. The other was about wanting less. Both required her to say something out loud that felt dangerous to say.

This is the first episode of What We Don't Say, a show about the real version of leadership careers. Not the LinkedIn summary. Not the keynote origin story. The actual cost and the actual doubt.

Three things from this conversation that stayed with me:

• She used the phrase "out ahead of my skis" to describe a role she was struggling to hold. That's not failure. That's what happens when you take a big swing and the support isn't there.
• The MBA decision came down to one real thing: not credentials, not curriculum. She got the next job through people she met in the program. The degree was the entry ticket; the network was the door.
• Choosing to step back from a high-visibility role felt like a regression from the outside. From the inside, it was the only way to stop bleeding into the parts of her life she couldn't replace.

What happens when a 10-year-old uses ChatGPT to plan an entire family vacation—and stays within budget? Andrea Margolin, SVP and Partner at Fleishman-Hillard, is living the AI question from both sides: deploying it at a global communications firm while catching her son using it for Harlem Renaissance homework.

This isn't AI panic or AI hype. This is someone with 20+ years managing teams and client strategy getting real about what she's seeing. Andrea explains why she's not worried about AI taking her job, why she IS concerned about what it's doing to Gen Alpha's critical thinking, and the career advice she gives at three pivotal life stages—whether AI changes everything or not.

💡 What You'll Discover:

✅ Why Andrea's learning to build AI agents (even though her first one is "horrendous")✅ The difference between AI making you more efficient vs. AI replacing your thinking✅ Her exact advice for recent grads, people turning 30, and those in career transition

⏱️ Episode Breakdown:

3:57 - "Am I going to lose my job because of AI?" (Her honest answer)6:41 - The Gen Alpha problem: AI is interfering with deep thinking8:05 - Advice for someone who just graduated9:30 - Advice for someone turning 3010:40 - Advice for someone in career transition

Guest: Andrea Margolin, SVP & Partner at Fleishman-Hillard (20+ years in PR/communications leadership)Host: Ken Roden

Supporting: Let Grow (https://letgrow.org/)—promoting childhood independence, resilience, and common sense. (Now you know why we've been supporting them this series!)

🎧 Subscribe to "What We Don't Say" for honest conversations with real executives navigating the questions nobody has answers for yet.

If relationships are the currency of a career, but the systems for building them are broken, what do you actually do? Andrea Margolin, SVP and Partner at Fleishman-Hillard with over 20 years leading teams and managing multimillion-dollar accounts, gets honest about something most people at her level won't say out loud: she still battles imposter syndrome.

This isn't theory from a leadership coach. This is someone with actual decision-making power over teams, budgets, and client relationships sharing what really happens behind closed doors. Andrea breaks down why "working hard" is the wrong metric, how she builds trust instead of just checking networking boxes, and why her #1 strength (responsibility) is also her most toxic trait.

💡 What You'll Discover:

✅ Why a 20-year partner still has to remind herself she's earned her seat at the table

✅ The "return on impact" framework that changed how she evaluates her work

✅ Her actual advice to recent grads: how to leverage relationships without being transactional

⏱️ Episode Breakdown:

4:53 - Being authentically you vs. being professional

7:38 - "Nobody knows what they're doing" (even at the SVP level)8:48 - Why working hard isn't the point—impact is

10:33 - What she tells every intern and recent grad about building relationships

Guest: Andrea Margolin, SVP & Partner at Fleishman-Hillard (20+ years in PR/communications leadership)

Host: Ken Roden

Supporting: Let Grow (https://letgrow.org/)—promoting childhood independence, resilience, and common sense.

🎧 Subscribe to "What We Don't Say" for honest conversations with real executives, not the polished LinkedIn versions.

What if the career moves you're taught to make are costing you the wrong things? Andrea Margolin, SVP and Partner at Fleishman-Hillard, moved across the country multiple times to build her career—but she carried the weight of leaving her sick mother 3,000 miles behind.

In this raw conversation, Andrea opens up about the guilt that followed her from DC to San Francisco, the moment she stopped apologizing for being a working parent, and why the pandemic forced her to bring her whole self to work—Legos in the Zoom background and all.

💡 What You'll Discover:

✅ The internal struggle of "am I being selfish?" when you choose career over proximity to family
✅ Why Andrea leads with "I'm a mom" before her professional title—and refuses to apologize for it
✅ How living 3,000 miles from her sick mother shaped her leadership philosophy

⏱️ Episode Breakdown:

2:32 - The guilt of leaving responsibilities behind
4:33 - How family gives her strength to do everything else
7:15 - Three moments that fundamentally changed her trajectory

Guest: Andrea Margolin, SVP & Partner at Fleishman-Hillard
Host: Ken Roden

Supporting: Let Grow (https://letgrow.org/)—promoting childhood independence, resilience, and common sense.

🎧 Subscribe to "What We Don't Say" for honest conversations about the career convos nobody posts on LinkedIn.

Should you stay or quit your job? A Chief Revenue Officer who's navigated this decision multiple times shares the exact framework that could save you years of pain and regret.

CRO Carl Oliveri opens up with host Ken Roden about the "perfect job" that nearly broke him—and the hard-won lessons that changed how he thinks about career moves. This isn't generic advice from someone who's never been there. This is battle-tested wisdom from the trenches of toxic boards, misaligned cultures, and the moments when you realize you're breaking yourself for the wrong reasons.

💡 What You'll Discover: ✅ The "running away vs. running towards" framework—and why this distinction changes everything
✅ How to recognize when you're being picked apart (before your health suffers)
✅ The questions you should be asking when interviewing YOUR next boss
✅ Specific career advice for new grads, 30-somethings & people in transition
✅ Why "just push through" isn't always the answer (and when it is)

⏱️ Episode Breakdown: 0:00 The perfect job that turned into a nightmare
1:58 When you can't see you're being picked apart
3:06 Toxic boards and exits that don't feel like wins
5:23 Running away vs. running towards: the critical difference
8:37 How to flip the script and interview your boss
10:13 Career advice by life stage: grads, 30s, transitions

Guest: Carl Oliveri, CRO with 20+ years navigating leadership roles
Host: Ken Roden

Supporting: FaceIT Foundation—providing peer support that makes recovery possible.

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