The Lift

Here’s a scorching hot take: modern workplaces make it nearly impossible for employees to forge real connections. But according to third space culture expert Adam Tanaka, it’s not the connections themselves that are impossible – it’s the space where they’re (not) happening in.So we took this episode into a wood-fired Finnish sauna pop-up on the Brooklyn waterfront to test his theory. Topic Highlights:– The power of physical space design to create real human connection – The case for wellness as infrastructure, not luxury– What the "dinner party rule of six" tells us about why most meetings and offsites fail– The analog advantage: why real human experience offers an exponential premium in an AI-saturated worldGuest Bio:Adam Tanaka is the COO of Therme Group, a global wellness infrastructure company. Adam holds a PhD in the sociology of culture, which means he's probably spent more time studying in a bathing suit than anyone you know.Episode Links:Therme GroupCulture of Bathing (Substack)Building a park in the sky (Robbie Hammond’s TED Talk)Connect with Us:theliftpod.comLet’s stay in touchSubscribe to The LiftFind Ben online: LinkedIn | InstagramSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

When was the last time someone on your team told you something you didn't want to hear? If you have to think about it, you have your answer (too long ago).Too many leaders have spent their entire careers avoiding conflict, and now they're running teams where nobody tells them anything useful, nothing real gets decided, and everyone is very, very pleasant about it.According to Amy Gallo, this isn't harmony – it's dysfunction with better manners.Topic Highlights:– Why the cost of staying silent is almost always higher than the cost of speaking up– The "eight-lane highway to harmony" metaphor about conflict avoidance– How AI is quietly making us worse at disagreeing with real humans– The important difference between being liked and being respected– The practice of "conversational receptivity"Guest Bio:Amy Gallo is an expert on workplace conflict and feedback, a contributing editor at Harvard Business Review, and the author of Getting Along: How to Work with Anyone (Even Difficult People).Episode Links:Getting Along: How to Work with Anyone (Even Difficult People)Radical CandorThe Five Dysfunctions of a TeamFull Article Connect with Us:theliftpod.comLet’s stay in touchSubscribe to The LiftFind Ben online: LinkedIn | InstagramSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Roughly 75% of the global workforce has a faith identity that shapes how they work, when they need time off, and whether they feel like they can truly show up.Reverend Mark Fowler isn't asking leaders to get a theology degree. He's simply asking them to be a better host.Topic Highlights:– How religion is already happening at work – usually in quiet corners and over lunch – and what leaders are missing by pretending otherwise– The legal reality: religious accommodations aren't special treatment, they're a protected right– The "hospitality framework" for religious inclusion that can be more useful than DEI training– Why "manage your behavior, not other people's beliefs" might be the most useful leadership principle you’ve heard yetGuest Bio:Reverend Mark Fowler is the CEO of the Tanenbaum Center for Interreligious Understanding, an ordained interfaith minister, and a conflict resolution specialist who has been helping organizations navigate diversity at work for 20 years.Episode Links:Tanenbaum Center for Interreligious UnderstandingHow to Be a Perfect Stranger (multi-faith etiquette guide)Connect with Us:theliftpod.comLet’s stay in touchSubscribe to The LiftFind Ben online: LinkedIn | InstagramSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

One in five Americans has a learning or thinking difference, and 53% of Gen Z identifies as neurodivergent. That means neurodivergent employees are already on your team, whether you know it or not. Nathan Friedman isn't here to make this a DEI checkbox issue. He's here to make it a business case.Topic Highlights:– Why the best neuroinclusive management practices are just...good general management practices – The "design for the margins" principle and the value of closed captions and pre-read agendas– What companies get wrong about job postings, interview questions, and the "great handshake" test – Why 50+% of neurodivergent employees choose not to disclose, and what that means for your systems– The business case for neurodivergent talent and data on top-line growth, turnover, and productivity Guest BioNathan Friedman is the Co-President and CMO of Understood.org, a nonprofit serving 70 million Americans with learning and thinking differences, and the host of the Minds at Work podcast.Episode LinksUnderstood.orgMinds at Work podcastKay Sargent’s Designing Neuroinclusive Spaces guideThe 4A's FoundationFull ArticleConnect with Ustheliftpod.comLet’s stay in touchSubscribe to The LiftFind Ben online: LinkedIn | InstagramSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Most brands don’t fail because they’re ugly. They fail because they’re unclear about the most fundamental question: what is our purpose?Éva Goicochea has built a category-defining company, maude, in one of the most taboo industries in business: sexual wellness. She did that by stripping the “brand” down to one thing: clarity. Simply put, if you can’t say what you are in one sentence, you don’t have a brand. You have noise.Topic Highlights– Why aiming for “cool” is a trap, and what offers the real competitive edge in branding instead– The difference between a brand, a product, and a commodity– What maude did right to make sexual wellness feel…ordinary– The right (and wrong) way to partner with a celebrity– Why saying “no” might be your most valuable growth leverGuest BioÉva Goicochea is the founder and CEO of Maude, the modern intimacy brand that brought sexual wellness into mainstream retail, including Sephora.Episode LinksmaudeOur Bodies, OurselvesForever and Everlane, Amen A Century of Flight (Delta documentary)Full ArticleConnect with Ustheliftpod.comLet’s stay in touchSubscribe to The LiftFind Ben online: LinkedIn | InstagramSee Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of The Lift, Ben is joined by Robbie Hammond – Co-Founder of The High Line, a beloved elevated park and greenway in NYC – and the global president of Therme Group, a company centered on urban wellbeing.Key takeaways: Break big, long-term visions into small, self-contained projects that show progress and keep you motivatedTenacity matters more than perfect conditions, especially when politics and timing are outside your controlKnowing your own strengths (and limits) makes it easier to find partners who complement your skillsExternal success doesn’t automatically create internal well-being; therapy, meditation, and sometimes medication can be part of the leadership toolkitPhilanthropy and nonprofit structures can “hold the vision” while you wait for the right political and economic climateThis week on The Lift, Ben chats with Robbie about what it really takes to stick with a big idea for decades and actually make it happen.Robbie never set out to be “the High Line Guy.” In fact, he describes himself as someone with a short attention span who came from dot-com startups, not urban planning. He was working in tech when he read a 1999 article about an old elevated freight rail line that the city planned to demolish. Curious, he went to a community board meeting, sat down next to a stranger (who turned out to be his future High Line Co-Founder, Joshua David), and realized they were the only two people in the room who didn’t want the structure torn down.Neither of them had money, power, or relevant credentials. The mayor wanted it gone. Nearby property owners wanted it gone. Most neighbors wanted it gone. Robbie estimates the odds of success at the time were maybe one in a hundred. So why bother?Robbie’s answer: It was a passion project. He still had a day job, but the High Line gave him a chance to work with architects, designers, and community members he never would’ve met otherwise. Even if the park never got built, he felt like the smaller projects along the way – a design competition, an education program, a street fair, early branding – were all meaningful in their own right.That’s the core concept behind Robbie’s approach is “micro-dosing the vision.” When a project might take 10–20 years, you can’t wait for the grand opening to feel like you’re making progress. Instead, he advises, you break the journey into bite-sized, shippable milestones: a brochure here, a website there, a new partnership, a public event, a feasibility study. Each micro-project becomes proof that the idea is moving, even if the finish line is far away.Ben and Robbie also explore the invisible emotional cost behind high-profile success. Robbie shares candidly that, even as the High Line became one of the most famous parks in the world and helped dramatically reshape Manhattan’s West Side and neighboring Hudson Yards, he didn’t actually enjoy his life for a long time. Like many founders, he was driven by fear of failure and chronic self-doubt.What finally shifted? A mix of therapy, years of experimenting with different kinds of meditation, and eventually medication in his mid-40s. Those tools helped him regulate anxiety, sustain a healthy relationship, and build a family. They also gave him the internal stability to appreciate what he had already created instead of immediately chasing the next big thing.On the strategy side, Robbie talks about the value of selling different versions of the same vision to very different audiences. For city government, the pitch was an economic-development story: invest public dollars to generate future tax revenue through higher property values and new development. For neighbors, it was about public space and quality of life. For partners and donors, it was about civic legacy and design innovation.He describes how he and Joshua deliberately hired the kinds of experts developers usually use against community groups, like seasoned land-use lawyers, consultants, and lobbyists,so they could meet powerful stakeholders on equal footing.Robbie also reflects on his work with Little Island and its founder, media executive Barry Diller. Initially, he was skeptical of the project and worried about yet another billionaire-backed park in an already amenity-rich neighborhood. But he’s come to respect Barry’s sheer tenacity and willingness to keep funding both its construction and ongoing maintenance, which is something many wealthy patrons don’t stick around for.Today, Robbie is channeling his long-game muscles into Therme Group, which builds massive, urban wellbeing campuses inspired by ancient Roman baths. For him, Therme is a way to democratize wellness: not luxury spas for the few, but a social infrastructure for the many.Because those projects move slowly, he’s still micro-dosing the vision through smaller, related creative experiments: hosting pop-up sauna villages, writing his “Culture of Bathe-ing” Substack, and collaborating with a Japanese creator who built a traveling onsen in the back of a truck. These side projects may not directly build a future Therme campus, but they keep the idea culturally alive and keep Robbie energized to keep going.Ben and Robbie return to a few core leadership lessons throughout their conversation:You don’t need perfect credentials to start; you can learn in public and hire for the skills you don’t have.Long-term civic projects almost always require waiting out multiple political cycles. Nonprofits and philanthropy can act as the “memory” that holds the vision until the timing is right.Success is not a substitute for well-being. Tools like therapy, meditation, and medication aren’t weaknesses; they’re often what make brave, sustained work possible.Ultimately, this episode serves as a necessary reminder that while trends come and go, the real work is figuring out what keeps you going over the long haul.Links:Robbie HammondThe High LineLittle IslandTherme Group“The Culture of Bathe-ing” (Robbie’s Substack)The QueensWay rail-to-park initiative Jane Jacobs“Citizen Jane: Battle for the City” documentary“Valentino: The Last Emperor” documentaryThe Lift is hosted by Ben Brooks. Find out more about Ben Brooks and his company, PILOT, here. The show is made by editaudio. Follow Ben on LinkedIn and Instagram.For even more fun, follow along on Ben’s adventures with his puppy, Jetson.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

In this episode of The Lift, Ben is joined by Keziah Wonstolen, founder and CEO of Vannin Chief of Staff. A former management consultant and Chief of Staff (CoS) herself, Keziah is passionate about transforming how modern leaders work through optimizing the role of the CoS. Key takeaways: Why so many CEOs feel like they’re “drowning” and how a Chief of Staff can give them back hours each weekThe real difference between a Chief of Staff, Executive Assistant, and COO (and when you actually need each role)Vannin’s three-part Chief of Staff framework: Align, Execute, Amplify — and how it works inside high-growth companiesThe three chief of staff archetypes (Operator, Strategist, Proxy) and how to match them to your stage and funding modelHow Chiefs of Staff can quantify their impact and avoid becoming a “catch-all” roleThe #1 skills gap Keziah sees in Chiefs of Staff and why financial and business acumen are non-negotiable for the roleWhen you’re a CEO or founder, “drowning” can start to feel like a permanent state of being. You’re responsible for strategy, culture, fundraising, customers, the board, and your team (and you’re still the person everyone pings when something goes sideways). In today’s episode, Keziah Wonstolen draws on her own experience as a management consultant and Chief of Staff at a global firm to break down what a great Chief of Staff actually does – and just as importantly, what they don’t do. She explains why the role has exploded in demand over the last five years, especially in a world of post-pandemic hybrid work, constant change, and AI reshaping every function.Vannin uses a simple but powerful framework for the Chief of Staff role: Align, Execute, Amplify. According to the framework, the best Chiefs of Staff start by aligning tightly to the CEO’s vision, then building the operating cadence and cross-functional projects that actually deliver on that strategy, and finally amplifying the CEO’s impact through sharper communication, stakeholder management, and better use of time.Ben and Keziah also get into one of the most common points of confusion: what’s the difference between a Chief of Staff, an Executive Assistant, and a Chief Operating Officer? Keziah lays it out clearly:Executive Assistants handle repeatable, transactional work (calendars, travel, logistics) and are essential leverage for any executiveChiefs of Staff own cross-functional, non-transactional projects, planning cycles, and change initiatives where no single function “owns” the workCOOs sit in the C-suite, own operational metrics and teams, and are often the next step for seasoned Chiefs of Staff in larger organizations.She also shares the three archetypes she sees most often:The Operator: a junior COO who builds operating cadences, OKR systems, and drives accountabilityThe Strategist: a thought partner who can translate board or investor expectations into messaging, plans, and decisionsThe Proxy: a highly trusted stand-in who can represent the CEO in key meetings and contextsBen and Keziah talk about why role clarity is the make-or-break factor and why vague job descriptions with phrases like “ninja,” “rockstar,” or “24/7 support” are red flags. Instead, Keziah walks through how she helps CEOs start with a brutally honest time audit: What should you be doing at this stage as CEO? What are you actually doing? And which gaps call for an EA, a Chief of Staff, a CFO…or even a therapist?For leaders who already have a Chief of Staff or EA, Keziah shares practical ways to get more value from those partnerships: regular one-on-ones, co-designing the “office of the CEO” rhythm, and being explicit about what success looks like quarter by quarter.And if you are a Chief of Staff, there’s plenty here for you, too. Keziah highlights the biggest skills gap she sees across Chiefs: financial and business acumen. She explains why being able to read a P&L, understand value‐creation plans, and speak the language of EBITDA, margins, and runway is essential if you want a real seat at the table and a long-term career beyond the CoS role.Whether you’re a founder thinking about hiring your first Chief of Staff, a CEO wondering if you’re using yours effectively, or a Chief of Staff looking to uplevel your own practice, this episode will help you see the role – and your own time – in a whole new way.Links: Keziah WonstolenVannin Chief of StaffWhy Chiefs of Staff Need an Effective FrameworkThe Lift is hosted by Ben Brooks. Find out more about Ben Brooks and his company, PILOT, here. The show is made by editaudio. Follow Ben on LinkedIn and Instagram.For even more fun, follow along on Ben’s adventures with his puppy, Jetson.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on The Lift, Ben is joined by meditation expert and teacher Michael Miller, founder of New York Meditation Center and London Meditation Center (and the first person to teach Ben to meditate 15 years ago). Key takeaways: Why practicing real meditation over simply going for a run is more powerful for stress relief and anxiety managementThere are three main types of meditation, with Vedic meditation being ideal for busy, high-performing leadersHow a twice-daily 20-minute practice can improve sleep, reduce anxiety, and actually create more time in your dayWhy most meditation apps and monk-style techniques don’t stick for people with jobs, families, and real-world responsibilitiesHow meditation helps executives show up as more present, creative, and emotionally regulated leaders at work and at homeWhy becoming a “net giver” (not a “net taker”) starts with stabilizing your own nervous system firstThis week, Michael Miller unpacks a big claim: the right kind of meditation doesn’t just help leaders feel calmer – it can actually give them more time back in their day.When Ben met Michael, he was leaving a demanding corporate job and needed something that would help him manage anxiety, stay focused, and show up more powerfully for his next chapter. The practice Michael taught him – Vedic meditation – has been a daily anchor ever since.Michael starts by debunking a line most leaders have heard (or said) at some point: “Running is my meditation.” Yes, intense exercise can quiet the mind temporarily as your nervous system finally gets to complete its fight-or-flight loop and you get a brief sense of relief. But that’s not the same as accessing a deep, restorative state that rewires your baseline for stress, focus, and emotional regulation.From there, Michael breaks down the three main categories of meditation in clear, practical terms:Concentration/focused attention: Trying not to think, staring at a candle flame, forcing the mind to stay on one object. It “works,” but it’s hard work and often leaves people feeling like they “can’t meditate.”Open monitoring/mindfulness: Classic app-guided practices (watching the breath, feeling your feet on the floor, noticing thoughts like clouds in the sky). Helpful, but highly dependent on external guidance and often difficult to sustain in a stress-heavy life.Automatic self-transcendence (Vedic meditation): The technique Michael teaches. You use a personalized mantra that gently attracts the mind inward. The mantra becomes subtler, thoughts quiet down, and you naturally “transcend” thinking into a state of pure awareness. No forcing, no concentration.Vedic meditation, he explains, was designed for householders: people with jobs, families, and responsibilities, not monks living in caves. Instead of needing hours of practice or multiple 10-day retreats, this technique is done 20 minutes twice a day, eyes closed, anywhere you can sit. It’s meant to fit into a busy schedule and deliver a clear ROI on time and energy.Michael shares his own before-and-after story. While working at Variety magazine in a relentless, deadline-driven environment, he was constantly wired and anxious. After learning Vedic meditation, he noticed he was sleeping better, feeling less anxious, and thinking more clearly – all without changing jobs or moving to a monastery. The anxiety “vibration” that used to run in the background started to quiet down.Ben echoes this with his own experience as a CEO and executive coach. His morning meditation helps him start the day grounded and intentional. The afternoon or early evening meditation is often the difference between “I just need to go home and shut down” and actually enjoying a client dinner, a date, or a walk with his dog. Instead of reaching for extra alcohol or scrolling to numb out, he finds he has the capacity to be present.Michael also addresses why most meditation apps don’t stick. Research he cites shows that 95% of users stop using an app within a month, and that most people complete only a handful of sessions. It’s not that apps are bad; it’s that techniques designed for renunciates (or for short-term relaxation) don’t translate well into the lives of overstretched leaders trying to juggle real-world constraints. In contrast, people who learn Vedic meditation in person quickly see the benefits, which makes it much easier to keep going.The conversation then zooms out into leadership. Meditation isn’t just about feeling calmer for your own sake; it changes how you show up for others:You have more space between stimulus and response, so you’re less likely to snap, shut down, or overreactYou’re more present and creative, which makes you better at complex problem-solving and decision-making under pressureYou can be a more consistent and emotionally regulated leader for your team, your family, and your broader communityMichael frames it as a question of impact: In a stressed, reactive world, are you a net giver or a net taker? If you’re constantly depleted, your presence drains others, even if your intentions are good. When you regularly reset your nervous system and reconnect with your deeper self, you’re able to give more attention, clarity, patience, and creativity – all without burning out.The episode closes with practical pointers. Michael shares how listeners can learn more through his and Jillian Lavender’s work at the New York Meditation Center and the London Meditation Center, and why “well begun is half done” when it comes to choosing a technique and a teacher. Ben concurs: if you’re serious about leadership growth, mental health, and sustainable performance, meditation isn’t a luxury. It’s a core tool in your leadership toolkit.If you’ve ever thought “I’m too busy to meditate,” this conversation might flip that script – and help you see how the right practice can give you back more time, presence, and capacity than it takes.Links: Michael MillerLondon Meditation Centre New York Meditation Centre Do Reset: Meditate. Move beyond thinking. Find clarity.Why Meditate? Because it Works. Speaking of Meditation See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on The Lift, Ben is joined by Sir Andrew Likierman, professor of Management Practice in Accounting at London Business School and the author of Judgement at Work: Making Better Choices. Key takeaways: Good judgment is a learnable leadership skill, not intuition or instinctApplying judgment principles requires context and flexibility, not rigid rule-followingAwareness of personal biases and emotions strengthens decision-makingIn the age of AI, judgment is a critical human advantage, helping leaders assess nuance, break patterns, and adapt when situations don’t fit the dataStrong leadership judgment depends on execution, not just analysis — a decision isn’t “good” if it can’t be carried out in the real worldIn today’s episode, Ben sits down with Professor Sir Andrew Likierman to unpack a deceptively simple idea: judgment isn’t a feeling. It’s a process.Andrew has spent decades studying what separates leaders who consistently make sound calls from those who get stuck in overconfidence, analysis paralysis, or “rule-following” that collapses the moment the context shifts. His core distinction lands fast: decision-making is an action – it’s something you do. But judgment is a capability – something you bring. We don’t usually praise someone for “good decision-making” as a personality trait; we say they have good judgment. That’s because judgment includes the human element: what you notice, the factors you weigh, who (and what) you trust, and how your beliefs and biases sneak into the room with you.To make judgment practical (and teachable), Andrew offers a six-part framework leaders can use no matter the situation, especially in moments when you’re tired, stressed, or under pressure to move fast. He breaks judgment down into components you can actually improve:Relevant knowledge and experience. What do you truly know that applies here – and what are you assuming?Awareness of context. Every decision happens inside a specific moment: politics, timing, incentives, constraints, hidden agendas.Trust. Are the people, data and inputs reliable? Are you over-trusting a “confident” source?Feelings, beliefs and biases. You’re not a machine. Your emotions and worldview shape what you see as “obvious.”How you make the choice. Slow down or speed up? Consider alternatives or commit? Who stress-tests the decision?Deliverability. The best call on paper is not “good judgment” if it can’t be executed in the real world.Throughout the conversation, Andrew makes a point to push back on rigid principles. Leaders often cling to rules (personal or organizational) as a shield, because saying “it was my judgment” can feel risky in bureaucratic or highly regulated environments. Andrew agrees that while blanket rules can be comforting, context is everything. Principles matter, but how you apply them in a given situation is judgment – mechanically applying a rule of thumb can be dangerous when the scenario doesn’t match the pattern.That’s where ethics enters the chat. Andrew frames ethics not as a compliance checkbox, but as part of how beliefs shape judgment in real life, especially in ambiguous environments where “normal” practices differ across cultures. It’s not just what you believe; it’s how you apply your ethical framework when the pressure is on.And consequently, there’s AI, the looming accelerant behind nearly every leadership conversation right now. Andrew’s take is bracing and oddly empowering: Yes, AI will dominate pattern recognition – the repeatable, rule-based, “if X then Y” stuff. But the differentiator for humans will be the next layer: deciding whether the current situation truly fits the pattern, noticing what’s different, and adapting accordingly. In other words, judgment is what keeps leaders valuable in an AI-shaped world.Finally, Andrew shares a personal example of poor judgment that’s painfully relatable: Not starting a risky project, but staying in it too long and ignoring what the evidence was telling him because sunk cost (and pride) can be louder than clarity. It’s a sharp reminder that judgment isn’t about always being right. It’s about improving your odds and being willing to update your course when reality changes.If you lead people, manage risk, build strategy, or simply want a clearer way to make hard calls, this episode gives you something rare: not what to decide, but how to think while deciding.Links: Sir Andrew Likierman Judgement at Work: Making Better Decisions The Lift is hosted by Ben Brooks. Find out more about Ben Brooks and his company, PILOT, here. The show is made by editaudio. Follow Ben on LinkedIn and Instagram.For even more fun, follow along on Ben’s adventures with his puppy, Jetson.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

This week on The Lift, Ben is joined by Helen Tupper, the CEO and co-founder of Amazing If and the author of Squiggly Careers and Learn Like a Lobster. Key takeaways: Learning is a core leadership skill, not a side projectVulnerability accelerates learning and leadership growthPersonalized, “squiggly” career paths drive engagement and adaptabilityTurning off autopilot improves learning at work – small changes like reflection loops and varied routines increase learning agility without adding time“Mistake moments” – openly reviewing errors – are powerful learning toolsDiversifying how and where you learn leads to longer-lasting growthIn this premiere episode of The Lift, Helen Tupper makes a bold case for modern leadership: learning isn’t a nice-to-have anymore. Learning is the job.In a world where roles, tools, and expectations evolve faster than most org charts, the leaders who thrive aren’t the ones who “already know.” They’re the ones who stay curious, adaptable, and willing to be a beginner, even (especially) when it feels uncomfortable. Helen opens with a line that frames the entire conversation: Vulnerability is a normal part of the learning process – it’s not something to fight against; it’s something to grow through.Her work challenges the idea that career progress should look like a straight climb upward. The “career ladder” model is limiting for individuals (because “up” isn’t everyone’s goal) and limiting for organizations (because it stalls talent mobility, cross-pollination, and resilience). Instead, Helen advocates for squiggly careers: development that can move sideways, diagonally, in loops, or into brand-new lanes. This is a career driven by learning, not just promotion.Senior leaders often feel anchored by responsibilities to teams, reputation, family, and the pressure to appear “certain.” But Helen says it’s more about age than career stage. People often become open to pivots during moments of change: restructures, new mandates, burnout, or opportunity windows. The question shouldn’t be, “What if I lose?” but rather, “What if I learn?”Helen introduces the earned dogmatism effect: When someone sees themselves as an expert, curiosity can quietly shut down. They begin to protect the identity of “knowing,” which makes learning feel like a threat. For senior leaders, this can be especially sticky because executive culture often rewards confidence and punishes uncertainty.But when leaders act like they don’t need to learn, teams learn less, too. The cutlure becomes one where success is aligned with certainty. That undermines psychological safety and makes it harder for anyone to ask for help, admit mistakes, or experiment.A major myth Helen dismantles is that learning must be time-consuming. Leaders often push learning to the bottom of the list because they picture courses, certifications, or big formal programs. Instead, Helen argues for “learning in the flow of work” by engaging in small practices with outsized payoff.One of her simplest tools is asking a series of questions that serves as a quick reflection loop after a meeting, conversation, or decision: “What? So what? Now what?”What happened / what did I notice?So what does it mean (patterns, feelings, implications)?Now what will I do differently?This kind of micro-reflection turns everyday work into a learning engine without adding hours to the week.Ben and Helen explore curiosity as “collecting and connecting dots.” Your brain will connect the dots naturally, but you have to collect them by varying inputs and breaking routine. Helen shares the “backwards bike” idea (a simple left/right reversal that forces your brain out of autopilot) as a metaphor for leadership learning: small rewires like shorter meetings, walk-and-talks, and different question prompts create conscious attention, which creates learning.And when the emotions show up – frustration, fear, failure – Helen normalizes them as part of the process, not proof you’re doing it wrong.Helen’s upcoming book Learn Like a Lobster uses the lobster as a powerful metaphor: To grow, a lobster must shed its shell, a process that takes energy and leaves it temporarily vulnerable before it grows back stronger. That’s the leadership invitation: If you want to keep growing, you can’t cling to the shell of “competence at all costs.”For perfectionists and high-achievers, Helen shares two practices that make learning safer and more consistent:“Mistake Moments”: Instead of rushing past errors, Helen’s team shares and unpacks them (what happened, why it happened, and what they’ll do differently). It releases shame, banks learning, and role models healthy vulnerability.Ask for feedback first: Feedback is less threatening when leaders initiate it. Helen uses “What worked well? Even better if…” because it keeps you in the driver’s seat and builds a habit of continuous improvement.Helen shares her own current “shell-shedding” experiment: evolving her podcast format in public by learning openly rather than staying comfortable on autopilot.If you’re a senior leader feeling pressure to have the answers, this episode offers a liberating alternative: lead like a learner, because your adaptability is now your advantage.Links: Helen Tupper Amazing If Learn Like a LobsterThe Squiggly CareerAmy Edmondson on Psychological SafetyEmployee Coaching and Development for the Hybrid/Remote Workforce 3 ways to measure your adaptability - and how to improve it | Natalie FrattoBookTrustHarvard Business Review article on impact managers have Values InstituteHow to cage your confidence gremlins The Lift is hosted by Ben Brooks. Find out more about Ben Brooks and his company, PILOT, here. The show is made by editaudio. Follow Ben on LinkedIn and Instagram.For even more fun, follow along on Ben’s adventures with his puppy, Jetson.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.