Hello Monday with Jessi Hempel

Baratunde Thurston fired ChatGPT. And ChatGPT helped him do it. This week, the Emmy-nominated storyteller, writer and host of Life with Machines joins Jessi in the studio to talk about what it actually means to have agency in a moment when we’re still figuring out the rules and norms of AI.

In this episode, Jessi and Baratunde discuss:

Why Baratunde fired ChatGPT and what the chat bot taught him on his way out

What he means when he says we're not using a tool, we're entering a relationship

The "direction, not perfection" principle for navigating an imperfect landscape of AI companies and choices

Why switching platforms is itself a practice of agency, and proof that you can leave

What AI tools reveal about you that you didn't know you were sharing

The two people living inside every employee at an AI all-hands: the one on-program, and the one who's scared and skeptical

What the kids opting out of AI are trying to tell us

What the internet could look like if we treated it as a public utility instead of a commercial space

Why token-maxing is a "flagrant foul" in an era of climate change

What executives get wrong when rolling out AI, and the questions they should be asking their teams instead

Follow Baratunde Thurston and Jessi Hempel on LinkedIn.

Daniel Pink is a seven-time New York Times bestselling author, a three-time Hello Monday guest, and one of the most trusted voices on motivation and performance. This week, he joins Jessi in the studio to talk about productivity and regret: how to actually get meaningful work done, how to protect your time and attention in an age of infinite distraction, and how to use the things you wish you'd done differently as a map for what you actually care about.

Jessi and Dan discuss:

Why productivity shouldn’t be measured in units of output, it should be measured in meaningfulness

The MIT method: why Daniel writes his single most important task at the top of his to-do list before anything else

How to design your environment for deep focus instead of trying to willpower your way there

The to-don't list: how to treat the things that drain your time with the same seriousness as the things you need to do

Why you probably overestimate how disappointed people will be when you say no, and how to say it cleanly

The SNL rule for shipping work: "We don't go on because we're ready. We go on because it's 11:30."

What to do when your boss keeps changing the priorities

The Pomodoro technique: whether it still holds up, and Dan thanked its inventor in the acknowledgments of one of his books

Why regret is one of the most misunderstood and underused emotions we have

The four core regrets that show up across 26,000 people in 130 countries, and what they reveal about what we actually value

This conversation was originally recorded live and broadcast to LinkedIn Premium members. Premium members can find the extended version here.

Follow Daniel Pink and Jessi Hempel on LinkedIn.

Most of us approach a long break from work with some anxiety. Whether it’s a layoff, parental leave, or a season of caregiving, there’s tension around if and when we’ll return to work and how we’ll explain the gap on our résumé.

DJ DiDonna, senior lecturer at Harvard Business School and author of the new book Big Time Off, wants to change that. This week, he joins Jessi to make the case that stepping away from routine work — for whatever reason, for however long — is one of the most strategic things you can do for your career and your life.

Jessi and DJ discuss:

What a sabbatical actually is, and why two-thirds of them happen because of a negative catalyst, not a choice

Why immediately job-searching after a layoff is like grocery shopping while hungry

The difference between a vacation, a corporate "sabbatical," and the real thing, and why it takes six to eight weeks just to feel like yourself again

What DJ calls "fertile emptiness," and why most of us never let ourselves get there

How to use a sabbatical to run experiments on possible future versions of yourself

The story of a CTO who went to Norway, built a text-to-speech app, and redesigned his entire relationship with work and money

Why functional workaholism is the thing most of us are living with

What AI has to do with the case for stepping back, and why learning from a place of fear versus curiosity makes all the difference

How Jessi's own three-month hiatus from the workplace, during which she wrote a book and raised a newborn, turned out to be a sabbatical she didn't know she was taking

How to start planning for a sabbatical five years from now, even if taking one today feels impossible

Follow DJ DiDonna and Jessi Hempel on LinkedIn.

You can't lead a team through a hard moment if you can't manage yourself first. That's the core of Dr. Becky Kennedy's work. The clinical psychologist and founder of Good Inside built a global movement teaching parents how to navigate the hardest moments with their kids. It turns out those same skills are exactly what the modern workplace needs. This week, Dr. Becky joins Jessi in the studio to translate her parenting playbook for managers, leaders, and anyone who's ever had to deliver hard news, hold a line they didn't fully believe in, or hold it together when someone on their team fell apart.

In this episode, Jessi and Dr. Becky discuss:

Why conviction matters more than confidence, and how to tell if you actually have it before walking into a hard meeting

The AVP method (acknowledge, validate, permit) for regulating your own emotions before they spill into the room

Why self-regulation isn't a two-minute fix, and what Dr. Becky calls "the road to reactivity"

How to separate behavior from identity when giving feedback, and why conflating the two is what makes hard conversations go wrong

Why sturdiness is the key to managing a team through uncertainty and layoffs

The sentence structure to use when you don't have all the answers but still need to show up as a leader

Why empathy requires boundaries, and a tennis court visualization that keeps other people's feelings on their side of the net

What anger is actually telling you, and how to use it productively instead of letting it drive the conversation

Why Dr. Becky is skeptical of the feedback sandwich, and a feedback method to use instead

A simple question managers can ask every week to make upward feedback feel safe and specific

This conversation was originally recorded live and broadcast to LinkedIn Premium members. Premium members can watch the extended version here.

Follow Dr. Becky Kennedy and Jessi Hempel on LinkedIn.

Most of us think of negotiation as something reserved for high-stakes boardrooms—or even hostage situations. But Christopher Voss, former FBI lead hostage negotiator and bestselling author of Never Split the Difference, says negotiation is everywhere: in salary talks, in team meetings, even in conversations with your kids. 

In this episode from the Hello Monday archives, Jessi Hempel sits down with Chris to explore how we can all become better negotiators by focusing on empathy, collaboration, and trust. Drawing on decades of experience, Chris shares practical tools you can use to move conversations forward—whether you’re asking for a raise, dealing with a difficult boss, or navigating conflict at home.

Chris and Jessi discuss:

Why negotiation is really about collaboration and long-term relationships

How to shift from seeking control to building influence

The power of labeling emotions to build trust and lower defenses

Why “no” is often more powerful than “yes”

How to recognize when a negotiation is over—or when it’s time to walk away

Strategies to reframe salary conversations and show your value

This episode was recorded live in-studio. For an extended, behind-the-scenes version, watch on LinkedIn Premium.