The Lift: Executive Leadership for Organizational Change

In this episode of The Lift, Ben is joined by Margaret Andrews, Harvard professor of executive education programs on leadership, emotional intelligence, and self-management, founder of The MYLO Center, and author of Managing Yourself to Lead Others.

Key takeaways: 

• Self-awareness is the foundation of great leadership
• Emotional intelligence matters more than many leaders realize, particularly when it comes to communication, trust, and feedback
• The best bosses stand out for their interpersonal skills, not just IQ or technical expertise
• Feedback and emotions are data, and leaders who learn to interpret both can make better decisions and build stronger relationships at work
• If you want to change how people think, you have to change how they feel
• Leadership growth starts with self-reflection: understanding your values, your definition of success, and the people and experiences that shaped you 

What makes someone a truly effective leader? According to Margaret Andrews, it starts with a skill that many business schools and workplaces still undervalue: self-awareness.

The core idea of this conversation is simple but powerful: before you can lead other people well, you have to understand how you think, feel, behave, and impact others. That sounds obvious, but in practice, many leaders skip this step. They focus on strategy, process, execution, and technical skill while overlooking the emotional and interpersonal habits that shape every meeting, every relationship, and every decision.

Margaret’s own path into this work started with difficult feedback. Early in her career, a boss told her she lacked self-awareness. It was painful to hear, but it became a turning point. Instead of dismissing the comment, she began asking deeper questions about why she showed up the way she did, how others experienced her, and what she needed to change in order to become a more effective leader. That journey led her to develop a framework for managing yourself before leading others.

In the conversation, Margaret shares six essential questions leaders can use to better understand themselves:

1. Who and what ideas shaped you?
2. What life events changed you?
3. How do you define success?
4. What are your core values?
5. How well do you understand your emotions?
6. What feedback have you received over the course of your life?

These questions get at the heart of leadership development because they force people to examine the beliefs, experiences, and emotional patterns they bring into the workplace every day. Margaret makes the case that leadership is not just about getting results through others. It is also about understanding the forces inside yourself that affect how you listen, react, communicate, and influence.

Margaret asserts that people are not nearly as rational as we like to think. If you want to change the way people think, she says, you first have to change the way they feel. That insight has huge implications for managers, executives, and founders. You can have the smartest strategy in the room, but if you do not understand the emotional reality of the people around you, your message may never land.

Margaret also shares a practical exercise she uses in executive programs: think about the best boss you ever had, then identify the top reasons they were effective. Across years of teaching, she has found that most people’s answers do not focus on IQ or technical brilliance. Rather, they focus on interpersonal skills: things like listening, trust, empathy, communication, calm under pressure, and the ability to make others better. In other words, the qualities that make someone memorable as a leader are often the very ones organizations treat as secondary.

This episode is especially valuable for leaders who have relied on competence, speed, achievement, or hard-driving standards to succeed and are now realizing those strengths may not be enough. Margaret offers a more sustainable model – one rooted in emotional intelligence, reflection, and behavioral change. She also draws an important distinction between personality and behavior. You do not have to become a different person to grow as a leader, but you may need to change how you behave.

For anyone trying to become a better manager, a more grounded executive, or a more thoughtful human being at work, this conversation is both practical and deeply personal. It is about more than leadership theory. It is about how your inner life shapes your outer impact.

If you want to lead others more effectively, start here: know yourself better, manage yourself more honestly, and build from there.

Links: 

• Margaret Andrews
• The MYLO Center 
• Managing Yourself to Lead Others
• Harvard Executive Education programs
• International House at UC Berkeley 

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.

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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 motivated
• Tenacity matters more than perfect conditions, especially when politics and timing are outside your control
• Knowing your own strengths (and limits) makes it easier to find partners who complement your skills
• External success doesn’t automatically create internal well-being; therapy, meditation, and sometimes medication can be part of the leadership toolkit
• Philanthropy and nonprofit structures can “hold the vision” while you wait for the right political and economic climate

This 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 Hammond
• The High Line
• Little Island
• Therme 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” documentary

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.

In this episode of The Lift, Ben is joined by Kut Akdogan – entrepreneur, strategist, and Managing Partner at Gaussian Holdings – to explore how leaders can build strategy in a world defined by uncertainty, rapid change, and AI disruption.

Key takeaways: 

• Why humans are wired to resist uncertainty – and how leaders can work with that wiring instead of against it
• How to define a clear “North Star” so uncertainty feels like crossing the Atlantic rather than drifting aimlessly at sea
• Why traditional 3–5 year planning often breaks down in volatile environments
• How to treat AI as a powerful tool, not a god or a gimmick
• How to earn complexity by starting small, solving real problems, and scaling what actually works
• How agile, incremental strategy creates stronger outcomes than rigid long-range plans

Why this episode matters:

Uncertainty has become the water leaders swim in.

Markets shift overnight. Technology evolves faster than the planning cycle. And AI seems to promise everything while threatening everyone at the same time.

In this conversation, Ben and Kut unpack what uncertainty really is, why it feels so destabilizing, and how leaders can navigate it with more clarity, better judgment, and stronger strategy.

In this episode, Kut explains:

• Why uncertainty has a “brand problem” in business
• Why saying “I feel uncertain” is often treated like admitting weakness
• How human beings are wired to crave both comfort and progress
• How a clear long-term objective can make uncertainty more manageable – and even productive

Kut uses a powerful metaphor to underscore his main idea:

• If you get in a boat with no destination, every wave feels existential
• If your goal is to cross the Atlantic, storms are still stressful, but they make sense in context

For leaders, that means the first job is to define a North Star: a clear objective that stays steady even when conditions change.

A better approach to long-term strategy:

Kut argues that too many organizations still build strategy as if the world will remain mostly stable.

He says that approach no longer works.

Instead, he advocates for “incremental moonshots”: pairing a bold long-term ambition with smaller, testable steps that allow you to learn, adapt, and course-correct over time.

Rather than pretending uncertainty is just a downside risk, leaders should build strategy that assumes change is coming.

That means:

• setting a long-range direction
• making smaller bets
• creating room for adjustment
• treating learning as part of execution

AI, strategy, and the danger of magical thinking:

Ben and Kut also dig into the biggest source of modern strategic anxiety: Artificial Intelligence.

Kut is deeply optimistic about AI’s potential, but he is equally clear that leaders need to strip away its sci-fi mythology.

His view is simple: AI is a tool. A very powerful tool. But still a tool.

They explore:

• why flashy AI demos often create unrealistic expectations
• why “weekend experiments” rarely translate into real enterprise value
• what the “95% of AI projects fail” statistic reveals about poor implementation
• why leaders should stop using AI hype to justify eliminating roles they do not fully understand
• how successful AI adoption starts with specific problems, not broad promises

Kut’s principle here is earning complexity:

Start with a real problem.

Run a contained experiment.

Create actual value.

Then scale.

What leaders should watch for next:

In his “heat check” on the future of work, Kut predicts:

• a more grounded correction in AI expectations
• a new generation of entrepreneurs and intrapreneurs emerging from today’s uncertainty
• winning organizations will be the ones that combine clear anchors with enough flexibility to experiment

He also shares a Moby-Dick quote that captures the restless, creative energy many founders and leaders feel when they are drawn toward difficult, uncertain work:

“It is not down on any map; true places never are.”

What leaders should remember:

If you are trying to lead through AI hype, market volatility, or constant ambiguity, this episode offers a useful reframing:

You do not need to eliminate uncertainty. You need to anchor it.

Set the destination.

Take smaller steps.

Solve real problems.

And keep moving.

Links:

• Kut Akdogan
• Gaussian Holdings
• Moby-Dick by Herman Melville
• “Pale Blue Dot” by Carl Sagan
• The Oregon Trail
• Home Assistant

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.

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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 week
• The 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 companies
• The three chief of staff archetypes (Operator, Strategist, Proxy) and how to match them to your stage and funding model
• How Chiefs of Staff can quantify their impact and avoid becoming a “catch-all” role
• The #1 skills gap Keziah sees in Chiefs of Staff and why financial and business acumen are non-negotiable for the role

When 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 executive
• Chiefs of Staff own cross-functional, non-transactional projects, planning cycles, and change initiatives where no single function “owns” the work
• COOs 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 accountability
• The Strategist: a thought partner who can translate board or investor expectations into messaging, plans, and decisions
• The Proxy: a highly trusted stand-in who can represent the CEO in key meetings and contexts

Ben 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 Wonstolen
• Vannin Chief of Staff
• Why Chiefs of Staff Need an Effective Framework

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.

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In this episode of The Lift, Ben is joined by Sachin Shivaram, the first non-family CEO of the nearly 110-year-old Wisconsin Aluminum Foundry. Sachin is also an adjunct faculty member at the Schneider School of Business at St. Norbert College and serves on the boards of half a dozen companies and organizations, including the Green Bay Packers.

Key takeaways: 

• Community leadership isn’t a distraction, it’s a growth strategy – serving on boards and civic committees provides strategic insight, policy influence, and access to funding
• Board service can directly benefit your company 
• Democratizing engagement builds trust with employees. Think: Facebook groups instead of forcing them into “corporate” channels
• Technology + relationships = real-time leadership. Use calendars, communication tools, and short, focused check-ins aggressively
• Childcare is both a business and a moral issue; employers must play a role in better childcare access
• Old-school rituals – weekly family dinners, long conversations, small-town community life – still matter 

What happens when a manufacturing CEO decides that his job doesn’t end at the factory gates? In today’s episode, Sachin and Ben dig into community leadership, board service, and childcare advocacy as tools to actively grow a business (rather than distract from it).

Sachin runs a 100+ year-old, family-founded aluminum foundry in Wisconsin that pours molten metal into sand molds to create mission-critical parts for medical equipment, trucks, cookware, and more. It’s classic American manufacturing in a sector that’s been under pressure for decades, from globalization to talent shortages to policy whiplash. 

Yet instead of hunkering down and only focusing on on-time delivery and scrap rates, Sachin’s calendar is full of board meetings, economic development councils, university trustee roles, and even a directorship with the Green Bay Packers.

So…why would a CEO in a turbulent industry say yes to more responsibility?

According to Sachin, strategic board work actually makes him a better, more effective CEO. Sitting on the board of companies like Lodge Cast Iron, he sees different markets, capital structures, and approaches to strategy and risk. Those patterns feed directly back into his decision-making at Wisconsin Aluminum Foundry. In one example, he describes how seeing another company use the U.S. New Markets Tax Credit program helped him recognize that WAF was eligible, too, resulting in roughly 25% of a major capital project being offset through the program. That’s real money, and a powerful argument for why board service can be ROI-positive for your day job.

We also get a behind-the-scenes look at how Sachin manages optics and bandwidth. He knows that to his board, his employees, and his customers, the perception of a distracted CEO could be a risk. His antidote? Radical transparency and relentless follow-through: 

• Every morning at 8:05 am, he and his leadership team run a detailed standup
• Employees can reach him directly via text or on plant-specific Facebook pages 
• He continually shows up with specifics about defects, staffing, and shipments that prove he’s deep in the details

That same “meet people where they are” philosophy drives how he communicates with a politically diverse workforce. In a rare move for a CEO, Sachin openly shares who he votes for, writes politically biased opinion pieces, and posts them in employee Facebook groups where people comment freely, including the occasional “Sachin, don’t play ignorant.” Instead of hiding his beliefs or banning politics from the workplace, he leans on a simple principle: if you’re going to say something, say something. That candor helps build trust across very different political views while keeping the focus on how national policy actually hits the shop floor.

Outside the plant, Sachin’s home life is intense but intentional. He and his wife (a McKinsey partner) are raising two boys while navigating demanding careers, and a very full calendar. The infrastructure that makes it possible includes aggressive use of shared calendars and old-school rituals like Friday night family dinners at their favorite Wisconsin supper club.

One of the most powerful moments of the episode comes when Sachin talks about childcare and early childhood brain development; he is often invited to share his POV that childcare is a workforce issue – how employers need it so parents (especially mothers) can work. What really moves him here is the neuroscience behind this framing: the permanent impact of what happens from ages 0–5 on a child’s brain, and how inconsistent, low-quality care can shape their entire life. After hearing stories from his own employees about patchwork childcare arrangements, he became a vocal advocate for better systems and started offering stipends and structural support through the company.

Throughout the episode, Ben and Sachin return to one big theme: being a great leader in your company often requires stepping outside it. Whether it’s lobbying for policy that impacts your industry, serving on boards that sharpen your strategic thinking, or investing in childcare that shapes the next generation, leadership that’s confined to your org chart is too small for the challenges of today’s economy.

If you’re a CEO, executive, or rising leader wondering how to juggle your core job with board ambitions, community service, and family life – without burning out – this conversation is a masterclass in purposeful over-commitment and community-driven leadership.

Links: 

• Sachin Shivaram
• Wisconsin Aluminum Foundry
• LODGE Cast Iron
• BelGioioso
• New Glarus Brewing – Moon Man
• Union Hotel Supper Club (De Pere, WI) 

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.

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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 management
• There are three main types of meditation, with Vedic meditation being ideal for busy, high-performing leaders
• How a twice-daily 20-minute practice can improve sleep, reduce anxiety, and actually create more time in your day
• Why most meditation apps and monk-style techniques don’t stick for people with jobs, families, and real-world responsibilities
• How meditation helps executives show up as more present, creative, and emotionally regulated leaders at work and at home
• Why becoming a “net giver” (not a “net taker”) starts with stabilizing your own nervous system first

This 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:

1. 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.”
2. 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.
3. 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 overreact
• You’re more present and creative, which makes you better at complex problem-solving and decision-making under pressure
• You can be a more consistent and emotionally regulated leader for your team, your family, and your broader community

Michael 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 Miller
• London Meditation Centre 
• New York Meditation Centre 
• Do Reset: Meditate. Move beyond thinking. Find clarity.
• Why Meditate? Because it Works. 
• Speaking of Meditation 

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This week on The Lift, Ben is joined by Justin Kerr, also known as “the efficiency monster,” a former senior executive at brands like Levi’s, Uniqlo, Old Navy, and Gap. Justin is the author of the “survival guide” How-To series (How to Cry at Work, How to Quit Your Job, How to Write an Email, and How to Be a Boss).

Key takeaways: 

• Over-communication at work reduces anxiety and “status check” micromanagement
• Clear expectations and deadlines are a core leadership skill, not just a nice-to-have, especially when managing up and across teams
• Time management and early-morning routines create more freedom outside of work
• Structured one-on-ones and pre-read agendas make meetings more efficient, build trust with executives, and speed up decision-making
• Small process improvements (like better emails and links) compound into big efficiency gains, so you don’t have to “change the whole system” to make work easier
• Remote work has real limits for learning, feedback, and leadership development, and in-person connection still plays a crucial role in how teams grow

In this episode of The Lift, Justin Kerr introduces us to his niche superpower: known as the “Efficiency Monster,” Justin is obsessed with making work simpler, faster, and less stressful through clear communication, sharp time management, and ruthless expectation-setting.

Justin’s philosophy can be summed up in three words: send more emails.

Not longer emails. Not more confusing emails. But more proactive, specific, expectation-setting messages that keep your boss, peers, and stakeholders fully informed so they never have to chase you for status. That one extra “FYI” or deadline reminder may take another 30 seconds in the moment, but it can save you hours of scrambling, anxiety, and follow-up meetings down the line.

Justin explains why over-communication is not a weakness or a sign of insecurity. It’s actually a high-level leadership skill. If your boss is asking you for status, Justin says you’ve already failed. The anxiety in the system shows up as “just checking in” emails, Slack pings, and surprise questions in meetings. Sending more thoughtful updates up front fills the space before it floods with concerns.

A big part of Kerr’s framework is his obsession with time. He’s a committed morning person and spent two decades in corporate roles without ever working past 5:00 p.m. – not because he was coasting, but because he built his days differently. He’d start extremely early, completing his deep work in those quiet morning hours before the offices started bustling. During that time, he’d send the emails, updates, and pre-reads that made the rest of the day run more smoothly.

For Justin, time equals freedom. Working in corporate America wasn’t selling out; it was a way to fund his creative life, which included bands, record labels, zines, and later, books. All of that was only possible as long as he kept his workday tight and efficient. That meant a radical commitment to priorities. He argues that if you don’t know your top three priorities in life, it’s almost impossible to design your schedule in a way that makes sense.

This conversation also dives into one of Justin’s favorite tools: the structured one-on-one meeting. In his view, you cannot be truly good at your job without a recurring 30-minute one-on-one with your manager. But it’s not enough to just “show up and chat.” He recommends:

1. Sending a written agenda by 5:00 p.m. the day before, so your boss can pre-read and prepare
2. Printing or bringing that agenda into the meeting, in priority order, to build momentum: quick wins first, harder asks later
3. Treating that time as your responsibility to manage, not just something the boss drives

This approach works at every level, even for the C-suite. Executives, Justin notes, are often lonelier and more uncertain than people realize. They want clarity, confidence, and structure from their leaders, not more ambiguity.

Justin breaks work down into two simple domains: people and process.

• People: relationships, trust, triggers, and individual differences. We all bring our family histories and emotional wiring to work; a manager’s tone or look might trigger old childhood patterns. Without self-awareness, it’s easy for simple feedback to spiral out of control.
• Process: the repeatable workflows – emails, forms, slides, approvals – that either make work easier or wildly inefficient.

According to Justin, most people are waiting for some “grand organizational redesign” to fix broken processes. But real progress comes from small, local improvements: adding the right link to an email, creating a simple agenda template, or sending a pre-read to a difficult stakeholder so they can’t derail a meeting with “I’m hearing this for the first time.”

Finally, Justin shares his hot take on the future of work: Remote work doesn’t fully work – at least not for everything. While digital tools can streamline process and documentation, he believes leadership, learning, and relationship-building still require in-person time. In his view, AI and automation should handle more of the process work. But the human side, including feedback, trust, creativity, and culture, happens best when people are actually together.

If you’ve ever felt buried in Slack messages, frustrated by vague expectations, or stuck in a cycle of last-minute requests, this episode will give you practical and immediately usable tools to change the dynamic. 

And yes, you may walk away sharing Justin’s belief that the secret to an easier work life might just be three deceptively simple words: send more emails.

Links: 

• Justin Kerr
• How To Write The Perfect Email class (CreativeLive)
• Justin Kerr on Instagram (@mrcorpo)

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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 instinct
• Applying judgment principles requires context and flexibility, not rigid rule-following
• Awareness of personal biases and emotions strengthens decision-making
• In the age of AI, judgment is a critical human advantage, helping leaders assess nuance, break patterns, and adapt when situations don’t fit the data
• Strong leadership judgment depends on execution, not just analysis — a decision isn’t “good” if it can’t be carried out in the real world

In 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:

1. Relevant knowledge and experience. What do you truly know that applies here – and what are you assuming?
2. Awareness of context. Every decision happens inside a specific moment: politics, timing, incentives, constraints, hidden agendas.
3. Trust. Are the people, data and inputs reliable? Are you over-trusting a “confident” source?
4. Feelings, beliefs and biases. You’re not a machine. Your emotions and worldview shape what you see as “obvious.”
5. How you make the choice. Slow down or speed up? Consider alternatives or commit? Who stress-tests the decision?
6. 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 Mita Mallick, leadership strategist and the author of The Devil Emails at Midnight: What Good Leaders Can Learn From Bad Bosses (and also a self-proclaimed former bad boss). 

Key takeaways: 

• Bad bosses are created, not born: Toxic leadership behaviors often emerge under stress, pressure, and unexamined power rather than from personality alone
• Managers have an outsized impact on employee mental health, influencing wellbeing more than doctors or therapists and nearly as much as a spouse or partner
• Poor management training fuels toxic leadership: many first-time managers are promoted for performance, not people-leadership skills, leading to micromanagement and fear-based control
• Developing confidence and identity outside of work helps protect employees dealing with a toxic boss, by reducing burnout and restoring agency when leaving isn’t immediately possible 
• Self-awareness and vulnerability are critical leadership skills 
• Feedback, reflection, and accountability are essential to becoming a better boss

According to this week’s guest, Mita Mallick, bad bosses aren’t born, they’re made. Mita brings a rare combination to the conversation: she’s lived the worst of it. She’s studied the patterns, and she’s also willing to say out loud what most leaders won’t – that she, herself, has been a bad boss 

One of the most haunting examples from her career is about a boss she nicknamed “Medusa,” known for screaming, public humiliation, and unpredictable tantrums. Her point in sharing isn’t shock value; it’s the reality that this behavior often gets normalized as “just how they are,” especially when fear-driven leadership produces short-term results.

But Mita makes the business case that too many companies avoid: when a boss behaves badly, teams lose clarity and momentum. People stop taking smart risks, communication gets distorted, and, eventually, performance suffers. Toxic leadership doesn’t just hurt feelings; it breaks productivity and execution.

One of the most jaw-dropping moments in the conversation is the mental-health data Mita references. Research from UKG’s Workforce Institute showed that managers impact employees’ mental health (69%) more than doctors (51%) or therapists (41%), and about the same as a spouse/partner (69%).

That statistic reframes “bad boss behavior” as more than an HR issue. It’s a leadership and wellbeing issue with real consequences, and it explains why so many people DM Mita long, painful stories asking how to survive a toxic manager.

Then layer on a structural problem: Many organizations promote high performers into management without teaching them how to lead. “Congratulations, here’s a title and a team of 10. Now figure it out.” That “doing → directing” transition is where micromanagement, perfectionism, and fear-based leadership often begin.

Ben asks the question everyone wonders: If bad bosses are the worst kept secret in a company, why are they still there?

Mita is blunt: It’s often not HR’s call. HR may document patterns and advise accountability, but the decision to protect a high-performing toxic leader frequently sits with the CEO or business leadership, who can justify it with numbers, relationships, history, or convenience. The message to the organization becomes results at any cost, favoritism wins, and (thus) the culture is negotiable.

But in today’s workplace, where employees can post, rate, leak, and speak, senior bad-boss behavior is increasingly public and reputationally expensive.

This episode isn’t just for people enduring a nightmare manager; it’s also a mirror for leaders. Mita offers a practical self-check:

1. Trust your internal moment of knowing. If you ended a Zoom and felt that post-meeting wince because you snapped at, dismissed or got sharp with someone, sit in the silence and name it. Repair starts with admitting it.
2. Look for the signals you’re ignoring. People go quiet around you. You’re the last to know what’s happening. Exit interviews (when done well) leave breadcrumbs.
3. Ask for feedback with structure, not vagueness. Instead of “What should I work on?” (which can feel unsafe in a power dynamic), try: “Here’s what I’m working on, can you tell me what you’ve noticed?”

When it comes to escaping a bad boss, Mita knows not everyone has the privilege to resign on the spot. So she recommends a survival strategy that protects your future:

• Keep your resume ready (always).
• Start networking before you’re desperate.
• Identify internal transfer options when possible.
• Decide your expiration date (“I can do this for another 6 to 12 months.”)
• Rebuild confidence outside of work – volunteer, coach, return to a hobby, create something. Toxic bosses shrink your sense of self; your life outside work needs to expand it again.

Poignantly, Mita shares how grief after losing her father intensified her “bad boss” tendencies and how vulnerability (not oversharing) can create context that reduces misinterpretation and increases humanity. The goal is not to excuse damage, it’s to stop repeating it.

If you’ve ever wondered how bad bosses get made – or worried you might be on the path to becoming one – this conversation gives you language, tools and a framework to lead with more clarity, courage and care.

Links: 

• Mita Mallick 
• The Devil Emails at Midnight 
• Managers Impact Our Mental Health More Than Doctors, Therapists — and Same as Spouses
• Hogan Assessment 

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 project
• Vulnerability accelerates learning and leadership growth
• Personalized, “squiggly” career paths drive engagement and adaptability
• Turning 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 tools
• Diversifying how and where you learn leads to longer-lasting growth

In 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:

1. “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.
2. 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 Lobster
• The Squiggly Career
• Amy Edmondson on Psychological Safety
• Employee Coaching and Development for the Hybrid/Remote Workforce 
• 3 ways to measure your adaptability - and how to improve it | Natalie Fratto
• BookTrust
• Harvard Business Review article on impact managers have 
• Values Institute
• How 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.