Your manager has been telling you for three years that your work is excellent. Then one day you're let go. Nobody saw it coming except the person who signed your reviews. James Coyle has watched this play out more times than he can count. His take: that's not a performance problem. That's a leadership failure.

Topic Highlights:

– Why avoiding the hard conversation is always more expensive than just having the hard conversation

– The ethos behind the “tell me how people get paid” principle

– What basketball taught James about self-awareness (and why most players always think they're one of the best two on the team)

– The three-bucket framework for deciding what to do with underperformers

– The difference between an average employee and a great employee

Guest Bio:

James Coyle is the EVP, President Marketplace of OPENLANE, a leading digital marketplace for wholesale vehicles, and a former senior leader at Amazon during its most aggressive growth years.

Episode Links:

OPENLANE

James on LinkedIn

How To Fire People Properly: When Waiting Too Long Goes Wrong

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You know the feeling of researching a hotel for three hours and still not booking it? The Points Guy Brian Kelly has made a career out of knowing exactly when to stop doing research – on flights, on investments, on the decision to quit your job – and just make it happen. For Brian, it's about knowing when you have enough information to move.

Topic Highlights:

– How Brian made the biggest decision of his life with no mentor, no banker, and no blueprint

– Why the worst-case scenario you're afraid of almost never exists

– What corporate boardrooms and bad travel decisions have in common

– How to take a great leap without burning the bridge you might need later

– Why he thinks many executives aren't using AI enough to see what's coming

Guest Bio:

Brian Kelly is the founder of The Points Guy, New York Times bestselling author of How to Win at Travel, and one of the most-visited travel media personalities in the world.

Episode Links:

The Points Guy

How to Win at Travel

point.me

seat.aero

insuremytrip.com

Hetrick-Martin Institute

Rainbow Railroad

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Ben Brooks usually asks the questions. This week, he's the guest, and The Lift's Executive Producer, Steph Colbourn, takes the host chair to dig into the nitty-gritty of management.

Leadership gets the TED Talks while management gets the eye rolls. But here's the inconvenient truth: 70% of the employee experience is determined by one thing - the quality of their manager. Problem is, we've been talking around management for years.

Topic Highlights:

– The Pilot Six: Ben’s framework to define what good management actually looks like

– Why “getting promoted to manager” is too often Latin for “I'll make more money” but no one tells you about what you're actually signing up for

– The story behind the employee who stuffed papers between the keys of Ben's keyboard just to get his attention

– What Ben's own 360 feedback revealed about where he's still a mediocre manager (and what he's doing about it)

Guest Bio:

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

Episode Links:

The Lift

PILOT

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What do you do when the President of the United States, the Senate majority leader, the Secretary of Energy, and an army of lobbyists all want you to say yes – and your answer is no? Robert Powelson has been in that exact position.

In this conversation, Rob shares what it actually costs to hold the line – and, what it buys you.

Topic Highlights:

– What Rob said in a three minute 4th of July phone call with the Pennsylvania governor that upended the pressure campaign around Uber

– Why Rob, a lifelong Republican, voted to kill the Trump administration's coal bailout proposal

– Why the invisible infrastructure holding your daily life together is more vulnerable than most people realize

– What it means to spend your credibility wisely when you only have a finite amount

– The relationship habit Rob credits for leaning on in the face of the toughest calls

Guest Bio:

Rob Powelson is President & CEO of the National Association of Water Companies and a former member of President Trump's Federal Energy Regulatory Commission.

Episode Links:

Rob’s LinkedIn

National Association of Water Companies

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Ben went to Salzburg for two weeks of “pure PTO” vacation. He ended up spending the first day and a half locked in a hotel room, heart rate elevated, surrounded by sticky notes.

In today’s episode, we cover incompletions: the tasks that haven't been done, the conversations that haven't happened, the decisions still open. And why they are probably quietly costing you, your coworkers, and your organization more than you realize.

Topic Highlights:

– What "attention residue" is and why your brain stays at work long after you've left the building.

– Why incompletions don't just drain you personally – they quietly stall entire organizations.

– What being on the receiving end of someone else's incompletion actually does to them.

– The 20-minute microdose you should take before any vacation, big deadline, or leadership transition.

Guest Bio:

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

Episode Links:

The Lift

PILOT

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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 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.

This is one of our favorite episodes from earlier this year. It originally aired on May 19, 2026.

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

Conflict at Work: How to Have the Hard Conversation You’ve Been Avoiding

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Have you ever had this thought? “I have an HR problem. They’re too slow. Too reactive. Too focused on process and compliance.”

Here's an uncomfortable possibility: the HR you're complaining about may just be the HR you bought.

If you've only ever funded HR for compliance and recruiting, don't be surprised when that's all you get. Part two in our series about getting the most out of your HR function is about what you're responsible for as a business leader, and how to fix it when it’s broken.

Topic Highlights:

– The HR-to-employee ratio you should be targeting

– How to make the case to a CFO who only cares about EBITDA

– The three questions to ask to find out if you've got a real HR partner

– Why AI is the best argument for investing more in HR, not less

Guest Bio:

Trish Steed is CEO and principal analyst at H3 HR Advisors, and a former HR executive across Big Four, healthcare, and IT. Steve Boese is an H3 HR co-founder and a program chair of the HR Technology Conference.

Episode Links:

Part 1: The Hidden Weight of HR

H3 HR Advisors

HR Happy Hour Media Network

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Most executives think of HR as an order window. Fire this person. Hire that one. Fix the culture. Improve the managers. But underneath that fictional menu is a function absorbing things no one ever puts on a report: the weight of every employee's hardest moments, handled quietly, while still being expected to move the business forward.

In part one of this two-part conversation, we pull back the curtain on what HR actually carries.

Topic Highlights:

– Why treating HR like an order menu is the most expensive mistake executives make

– What HR partnership actually looks like

– The value of involving HR in strategy upfront

– Why shifts in employee output might not be about performance

– The most underused resource in your benefits package

Guest Bio:

Trish Steed is CEO and principal analyst at H3 HR Advisors, and a former HR executive across Big Four, healthcare, and IT. Steve Boese is an H3 HR co-founder and a program chair of the HR Technology Conference.

Episode Links:

H3 HR Advisors

HR Happy Hour Media Network

From Worst to First by Gordon Bethune

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