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

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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

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People with a best friend at work are *seven times* more likely to be engaged in their jobs. Yet most leaders spend zero budget, zero strategy, and zero intentional effort on workplace friendships.

Tom Rath has done the research to understand the power of friendship at work, and how leaders can better foster it.

Topic Highlights:

– Why Gallup's employee engagement prompt "I have a best friend at work" is its most predictive

– The exact number of close relationships we actually need, despite high-achievers chronically under-building this number

– Why Tom thinks his book about work friendships is his worst seller

– The psychological barrier that’s creating a friendship recession for men in midlife

– The "one coffee pot in the office" approach to designing workplaces that create connection

Guest Bio:

Tom Rath is a workplace researcher, author, and one of the most widely-read voices on human wellbeing of the last two decades, with over 10 million books sold worldwide.

Episode Links:

Books by Tom Rath

The Start-Up of You by Reid Hoffman

True North by Bill George & Peter Sims

Little Bets by Peter Sims

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Here’s a scorching hot take: modern workplaces make it nearly impossible for employees to forge real connections. But according to third space culture expert Adam Tanaka, it’s not the connections themselves that are impossible – it’s the space where they’re (not) happening in.

So we took this episode into a wood-fired Finnish sauna pop-up on the Brooklyn waterfront to test his theory.

Topic Highlights:

– The power of physical space design to create real human connection

– The case for wellness as infrastructure, not luxury

– What the "dinner party rule of six" tells us about why most meetings and offsites fail

– The analog advantage: why real human experience offers an exponential premium in an AI-saturated world

Guest Bio:

Adam Tanaka is the COO of Therme Group US, a global wellness infrastructure company. Adam holds a PhD in urban planning.

Episode Links:

Therme Group

Culture of Bathing (Substack)

Building a park in the sky (Robbie Hammond’s TED Talk)

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No one loves a genuine truth bomb more than kids – unfiltered, no social contract, no concern for how it will land.

Ginny McCormick has spent her career figuring out what that kind of radical honesty, and the play that produces it, can teach the rest of us.

Turns out the principles that work in the playroom work just as well in the boardroom. We just forgot them somewhere along the way.

Topic Highlights:

– Why "clarity always wins over complexity"

– The "first pancake" ritual: a team practice for normalizing failure that actually works

– Why structured gamification at work is inauthentic and what real play actually looks like in an adult environment

– What children's unfiltered feedback reveals about the feedback loops most organizations are missing

– The one parenting skill that every leader should be stealing right now

Guest Bio:

Ginny McCormick is the Chief Experience Officer (CXO) at tonies, a screen-free children's audio platform operating in over 100 markets globally. She is a veteran of Disney, Mattel, and Hasbro.

Episode Links:

tonies

Play by Stuart Brown

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When was the last time someone on your team told you something you didn't want to hear? If you have to think about it, you have your answer (too long ago).

Too many leaders have spent their entire careers avoiding conflict, and now they're running teams where nobody tells them anything useful, nothing real gets decided, and everyone is very, very pleasant about it.

According to Amy Gallo, this isn't harmony – it's dysfunction with better manners.

Topic Highlights:

– Why the cost of staying silent is almost always higher than the cost of speaking up

– The "eight-lane highway to harmony" metaphor about conflict avoidance

– How AI is quietly making us worse at disagreeing with real humans

– The important difference between being liked and being respected

– The practice of "conversational receptivity"

Guest Bio:

Amy Gallo is an expert on workplace conflict and feedback, a contributing editor at Harvard Business Review, and the author of Getting Along: How to Work with Anyone (Even Difficult People).

Episode Links:

Getting Along: How to Work with Anyone (Even Difficult People)

Radical Candor

The Five Dysfunctions of a Team

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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.

Episode Links:

Your Best Meeting Ever

The Surprising Science of Meetings

The Simple Sabotage Field Manual

Asana Anatomy of Work Index

Full Article

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