Complacency doesn't feel like standing still. It feels like winning. Right up until it doesn't.

That's the trap Snorre Kjesbu has spent his career trying to help his organization escape. As SVP & GM of Collaboration at Cisco, he runs a multi-billion dollar business, holds 20+ patents, and is blunt about where this ends: companies that stop pushing themselves don't just slow down. They go out of business.

Topic Highlights:

– The window of opportunity: why being four years too early costs you just as much as being four years too late

– Why chasing the wave you missed is a losing game (and what to do instead)

– The four questions every leader should ask every quarter to stay ahead of complacency

– What an effective “AI forward” team actually looks like

Guest Bio:

Snorre Kjesbu is SVP & GM of Collaboration at Cisco and holder of 20+ patents. 

Episode Links:

Snorre Kjesbu on LinkedIn

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Tom Hardin was a rising hedge fund analyst making good money in New York City when he decided to make a few trades on inside information. 

Then the FBI tailed him at 6:30 AM outside his dry cleaner. In the 18 months that followed, he wore a wire more than 40 times as an informant in the largest insider trading investigation in US history.

What he learned about getting people to finally share what they've been hiding is something no management book has ever taught.

Topic Highlights:

– The three meeting sequence that gets people to stop performing and start telling the truth

– The 10/80/10 model and why the 80% in the middle will follow what the leading 10% does

– How unclear goals create the conditions for ethical drift without anyone noticing

– Why not understanding the difference between a mistake and a bad decision is often how cover-ups start

Guest Bio:

Tom Hardin is “Tipper X,” the FBI's most prolific cooperating informant in Operation Perfect Hedge, and the author of Wired on Wall Street.

Episode Links:

Wired on Wall Street by Tom Hardin

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Just Ben this week. In our very first solo episode, we go deep on the topic Ben has been teaching inside every PILOT cohort since day one, the one that shows up in almost every coaching conversation he has, the one that he considers the single biggest unlock in a career: self-advocacy. 

Knowing what you need, knowing how to ask for it specifically, and being willing to hear no – and knowing when and how to ask again.

Topic Highlights:

– Why the current moment makes self-advocacy more urgent, not less

– The fear of rejection reframe: why if you haven't been told no recently, you're probably not asking enough

– What a specific, “shovel-ready” ask looks like

– The information asymmetry most people miss: your manager almost certainly doesn't know what you need

– The secret menu: why your career’s has more options on it than the one you've been ordering from

Guest Bio:

Ben Brooks is a leadership strategist, career innovator, executive coach, the founder of PILOT, and host of The Lift. He loves travel, making new friends, and of course, his dog, Jetson. 

Episode Links:

PILOT

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“Running is my meditation.” Michael Miller hears this a lot. 

His response: “Knitting is my rock climbing.” 

If you've been telling yourself exercise counts as meditation, this is the episode that gently, convincingly, changes your mind.

Topic Highlights

– The three types of meditation and why the one most leaders try is the hardest and least effective

– How a 20-minute practice twice a day can actually give you more time back, not less

– The difference between being a net giver and a net taker (and why it starts with your nervous system, not your calendar)

– Why Vedic meditation was specifically designed for people with jobs, families, and actual responsibilities

Guest Bio

Michael Miller is the founder of New York Meditation Center and London Meditation Centre, a Vedic meditation teacher with nearly 10,000 students worldwide, and the person who taught Ben to meditate 15 years ago.

Episode Links:

New York Meditation Center

London Meditation Centre

Vedic Meditation

Meditation for Busy Leaders: How Michael Miller Uses Vedic Practice to Reduce Stress and Gain Time

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Most senior leaders got to where they are by being the expert. But Helen Tupper has research showing that the moment you start thinking of yourself as an expert is the exact moment you stop growing. 

If you've been coasting on competence, or are quietly terrified of being a beginner again, this episode is for you.

Topic Highlights

– How expertise quietly kills curiosity, and what to do before it happens to you

– Why the career ladder is a limiting model for both individuals and organizations

– The “mistake moments” team practice that makes vulnerability a daily habit

– The “What? So what? Now what?” reflection loop that turns any meeting into a learning engine

Guest Bio

Helen Tupper is the CEO of Amazing If, an award-winning company with a mission to make squiggly careers better for everyone. She is the co-author of The Squiggly Career and Learn Like a Lobster. 

Episode Links:

Amazing If

Learn Like a Lobster

The Squiggly Career

Values Institute

Lead Like a Learner: Helen Tupper on “Squiggly Careers” and the Power of Vulnerability

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Ask almost any leader if they're self-aware and most will say yes. But research shows only 15% actually are. That gap – between who we think we are and how others experience us – is where most leadership development needs to start. 

Unfortunately, it almost never does.

Margaret Andrews, who has spent two decades teaching this at Harvard, is here to help close the gap.

Topic Highlights

– Why the best boss you ever had probably wasn't (always) the smartest person in the room 

– Six questions that reveal more about your leadership than any 360 assessment will

– The difference between changing your personality (you can't) and changing your behavior (you absolutely can)

– Why “if you want to change how people think, you have to change how they feel” is the most underused insight in leadership development

Guest Bio

Margaret Andrews is a Harvard executive education professor, founder of The MYLO Center, and author of Manage Yourself to Lead Others.

Episode Links:

Manage Yourself to Lead Others

The MYLO Center

Managing yourself first: Margaret Andrews on self-awareness and leadership

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“You're not a good fit.” 

“The company's going in a different direction.”

Every manager thinks these phrases are legally safe. But according to attorney James Bryton, they're basically an engraved invitation to a lawsuit. And a lot could be avoided if leaders took a different approach to letting people go.

This is part two of our two-part series about letting people go with empathy and dignity.

Topic Highlights:

– The “middle lane” of firing and why it's where most separations actually belong

– Why “not a good fit” is one of the most legally dangerous things you can say in a termination meeting

– The thoughtful approach to choreography for letting someone go

– Why how a termination ends matters more than almost everything that preceded it

Guest Bio:

Dr. Dennis Davis is a clinical psychologist and national training director at Ogletree Deakins. James Bryton is Of Counsel at Littler Mendelson, the world's largest employment law firm, and a former civil rights litigator.

Episode Links:

How to fire people properly - Part 1: When waiting too long goes wrong

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Most leaders know when someone isn't working out, for months – sometimes years. So why does it take so many of them so long to do anything about it? Dr. Dennis Davis has a theory, and it has a lot more to do with the manager than the employee.

This is part one of our two-part series about letting people go with empathy and dignity. 

Topic Highlights:

– The real cost of the “performing-at-35%-is-better-than-zero” rationalization 

– Why the "myth of niceness" is actually the least kind thing a manager can do for an underperformer

– The skill/will matrix: a simple diagnostic tool for knowing whether you have a performance problem, a motivation problem, or a fit problem

– How PIPs are too often used incorrectly, and what doing so says about your organization's integrity

– Why employee success is ultimately contingent on your leadership style

Guest Bio:

Dr. Dennis Davis is a clinical psychologist and national expert in conflict resolution at Ogletree Deakins, a multinational law firm specializing in labor and employment law.

Episode Links:

Ogletree Deakins

Full Article

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How do you work with people you genuinely can't stand? Not someone who rubs you the wrong way in a meeting. Someone on the opposite side of your moral compass. Adam Kahane has spent 35 years finding that answer in some of the most intractable conflicts in modern history. His conclusion? You don't blow the system up. You find the cracks.

Topic Highlights:

– The simple tool for moving from blame to agency in any stuck situation

– What calling someone your "enemy" can actually cost you

– What apartheid learnings say about how systems change from the inside

– Why civility and self-regulation are the most strategic leadership skills you'll ever build

– The Leonard Cohen framework that might be Adam’s best leadership advice

Guest Bio:

Adam Kahane is the co-founder of Reos Partners, a conflict resolution facilitator who has worked in over 50 countries, and a member of the Order of Canada. 

Episode Links:

Reos Partners

Everyday Habits for Transforming Systems

Collaborating with the Enemy

Stanford Social Innovation Review: "Working With Cracks"

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What's the fastest way to kill any chance of actually moving the needle on a big, complex project? According to longtime NYC power broker Kathryn Wylde, it's defensiveness. 

Kathryn knows this because she spent 50 years dragging billionaires, union bosses, and city officials into the same room and getting them to agree on the best way forward. And she’s here to share how she did it.

Topic Highlights:

– The power of a specific ask and why most change efforts fail

– How to reframe a problem so that the people who resist it become its biggest advocates

– Why defensiveness, not disagreement, is the real roadblock, and the one move that eliminates it faster than any argument

– The million dollar leadership advice she gave to Zohran Mamdani 

– The Amazon HQ2 cautionary tale

Guest Bio:

Kathryn Wylde is the former President and CEO of the Partnership for New York City, and the woman the city’s most powerful people call when they need to actually get something done in NYC.

Episode Links:

Partnership for New York City

Kathryn Wylde, Connector of New York’s Powerful, Is Retiring

Full Article

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