Ben Brooks (PILOT) on The Lift: real conversations about leadership, growth, and getting what you want at work. On The Lift, we pull up to see the bigger picture from accomplished leaders who know how to get things done in a rapidly changing world. Host Ben Brooks dives deep into a relevant leadership topic each episode and connects the dots to leave you with powerful distinctions that you can use as a leader.
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Judgment at Work: A Framework for Better Leadership Decisions with Sir Andrew Likierman
Episode 3
Tuesday, February 10, 2026 • Duration 38:38
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:
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.
Toxic Leadership Explained: What Makes a Bad Boss with Mita Mallick
Episode 2
Tuesday, February 10, 2026 • Duration 37:01
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%).
Lead Like a Learner: Helen Tupper on “Squiggly Careers” and the Power of Vulnerability
Episode 1
Tuesday, February 10, 2026 • Duration 38:03
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
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?”
Introducing...The Lift!
Friday, December 5, 2025 • Duration 01:12
Welcome to The Lift, the show about leadership, growth, and getting what we want. On The Lift, we pull up to see the bigger picture from accomplished leaders who know how to get things done in a rapidly changing world. Host Ben Brooks dives deep into a relevant leadership topic each episode and connects the dots to leave you with powerful distinctions that you can use as a leader.
The Lift is hosted by Ben Brooks. Find out more about Ben Brooks and his company, PILOT, here. The show is made by editaudio.
Using Community Leadership to Grow Business: How Sachin Shivaram Invests His Time Beyond the Office
Episode 6
Tuesday, March 3, 2026 • Duration 33:08
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.
Meditation for Busy Leaders: How Michael Miller Uses Vedic Practice to Reduce Stress and Gain Time
Episode 5
Tuesday, February 24, 2026 • Duration 36:50
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:
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.”
Send More Emails and Still Sign Off at 5 P.M.: Managing Expectations, Time, and Teams with Justin Kerr
Episode 4
Tuesday, February 17, 2026 • Duration 40:50
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.
Conflict at work: Amy Gallo on how to have the hard conversation you’ve been avoiding
Episode 17
Tuesday, May 19, 2026 • Duration 39:15
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).
Your best meeting ever: Why meetings are broken and how to fix them with Dr. Rebecca Hinds
Episode 16
Tuesday, May 12, 2026 • Duration 39:28
During World War II, the Office of Strategic Services published a manual teaching ordinary citizens how to sabotage the enemy from within. One of the tactics: hold unproductive meetings.
Nearly a century later, Dr. Rebecca Hinds is dedicating her career to studying why meetings fail – and what it actually costs when they do.
Topic Highlights:
– The WWII sabotage manual that became standard business practice and makes meeting culture work against you
– The 4D CEO test: a two-part filter for deciding whether any given meeting should exist at all
– Why AI is making meetings worse, not better, and the one rule that changes that
– The "meeting doomsday" intervention: what it is and why it works
– The Babble Hypothesis: who's actually perceived as a leader in meetings
Guest Bio:
Dr. Rebecca Hinds is an organizational psychologist, author of Your Best Meeting Ever, founder of the Work Innovation Lab at Asana, and founder of the Work AI Institute at Glean.
The Great Debate: Chief of Staff vs. EA vs. COO with Keziah Wonstolen of Vannin Chief of Staff
Episode 7
Tuesday, March 10, 2026 • Duration 40:36
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.
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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:
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.
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.
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.
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.
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.
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 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.
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:
Sending a written agenda by 5:00 p.m. the day before, so your boss can pre-read and prepare
Printing or bringing that agenda into the meeting, in priority order, to build momentum: quick wins first, harder asks later
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.
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.
