For a lot of people, work feels especially chaotic right now.. Projects start and don't finish. Layoffs happen, then reorgs, then new strategies, and through all of it, managers are expected to have the answers. Caroline Webb spent 25 years coaching leaders through exactly this kind of turbulence. She's a behavioral scientist, a former economist and the author of the new book Leadership Intelligence: Science-Backed Strategies for Mastering 21 Everyday Management Challenges. This week she joins Jessi to talk about what the science of the human brain tells us about leading through uncertainty.

In this episode, Jessi and Caroline discuss:

• Why the current moment hits a stress trifecta — demanding, uncontrollable and unpleasant — and what that does to your team's brains
• The "know-be-do" framework: how to lead people through uncertainty when facts are in short supply
• Why naming how you feel is one of the most powerful things a leader can do and what affect labeling actually does in the brain
• What "measured authenticity" means, and why "terrified" is not a word you want your manager to use
• How to be honest with your team when you know more than you can say
• Why letting projects die quietly is one of the most demoralizing things a manager can do, and what to do instead
• What Astro (Google X's moonshot factory) does when it kills a project, and why it works
• The "when-then" method for taking the sting out of worst-case scenarios before they happen
• "Compassionate clarity": what it means in practice when layoff season arrives
• Why walking people out of the building immediately is almost never necessary and what a seasoned CHRO said about it

Follow Caroline Webb and Jessi Hempel on LinkedIn

Join us for Hello Monday Office Hours, Wednesday at 3pm EST

Listen to Caroline’s previous Hello Monday episode on how to have a good day at a bad job

We spend a lot of energy trying to optimize our time, but what happens when we're forced to surrender to it? Writer, meditation teacher and lifetime student of Buddhism Sebene Selassie has been living with cancer for more than twenty years. In that time, she's learned something most of us spend a lifetime avoiding: how little control we actually have, and how to find joy anyway. This is the third and final episode in our month-long series on time. We’ve discussed how we spend our minutes, our days, our months and our years. Today you’ll hear about how we make the most of all of it..

In this episode, Jessi and Sebene discuss:

• Why a cancer diagnosis at 34 became the entry point to a deeper spiritual life, and eventually, to teaching
• The tight relationship between fear and control, and how Sebene has spent twenty years slowly loosening her grip on both
• What Sebene’s ticking clock has taught her about the present moment
• The difference between joy and happiness, and why joy is available even in the hardest moments
• Why meditation isn't about feeling better, and what the saccharine corporate version gets wrong
• The paradox at the heart of Sebene’s book You Belong: A Call for Connection
• How grasping for time is often just grasping for control, and what we miss when we do this
• What it means to show up to life openhearted, fully as yourself

Follow Sebene Selassie and Jessi Hempel on LinkedIn.

Join us this Wednesday at 3pm EST for the return of Office Hours!

Being busy and being productive are not the same thing. Cal Newport, computer science professor at Georgetown and author of Slow Productivity: The Lost Art of Accomplishment Without Burnout, has spent years making that case. This is the second of three episodes from the archive that we're revisiting this month on the subject of time. In it, Cal joins Jessi to zoom out and ask: what does it really mean to get meaningful work done over the course of our weeks, our months, and even our years?

In this episode, Jessi and Cal discuss:

• Why "pseudo-productivity" — using visible activity as a proxy for real work — was always a bad idea, and why mobile computing made it unsustainable
• How the pandemic pushed knowledge work past a breaking point
• The administrative overhead trap: why agreeing to too many things at once is slowing you down
• How to say no to new work without actually saying no, and why transparency is the key
• Why boredom is essential
• What your phone has to do with short-circuiting the most human productivity tool we have
• Cal's rule for his kids on smartphones and social media, and the age he thinks unrestricted internet access becomes safe
• Why doing fewer things at once will get you to the finish line faster
• What AI tools like ChatGPT are actually good for, and what Cal is waiting for them to do instead
• The difference between technology that helps you do things faster and technology that takes things off your plate entirely

Follow Jessi Hempel on LinkedIn.

Most of us are convinced we don't have enough time. Laura Vanderkam argues that we have enough time, we just aren’t using it with enough intention. This month, we're revisiting our series of episodes on time, and how we make the most of it. We’re starting here, with the bestselling author of numerous books on time management and the host of the daily four-minute podcast Before Breakfast. 

In this episode, Jessi and Laura discuss:

• Why 5 PM on Thursday is actually the exact midpoint of your week, and what that reveals about the time you're losing
• How Laura has tracked every half hour of her life since April 2015, and what nine years of data taught her
• The biggest time waster of all (it's not email or your phone)
• Effortful fun versus effortless fun, and why doing a little of the first before the second changes everything
• Why you should give yourself a bedtime, and how most adults are already getting more sleep than they think
• The case for moving for 10 minutes by 3 PM every day
• Why busy people need a hobby
• The Friday punch list: how batching your small tasks protects your best hours for the work that actually matters

Follow Laura Vanderkam and Jessi Hempel on LinkedIn.

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.

We tend to talk about AI and the future of work as a young person's game. Dr. Myechia Minter-Jordan, CEO of AARP, is here to challenge that notion. A physician turned healthcare executive turned nonprofit leader, she joins Jessi in the studio to talk about ageism, AI, and what it means to not just stay relevant, but to move ahead, in the second half of a working life. 

In this episode, Jessi and Dr. Minter-Jordan discuss:

• How the fifty-plus workforce is upskilling faster than other generations
• How to reframe experience as an asset in a job search, and why soft skills are having a moment
• The move Dr. Minter-Jordan made that surprised everyone: going back to business school in her thirties, while practicing medicine
• Why mentorship is one of the most powerful tools an older worker has for demonstrating value, and why stepping back from it is a mistake
• How Dr. Minter-Jordan got her current job as CEO of AARP
• What the trillion-dollar caregiving economy means for employers, and why the policies aren't keeping up
• How to approach AI without feeling overwhelmed: start small, stay consistent, and focus on what's relevant to your field
• Whether you should de-age your résumé
• How to be strategic about timing a career pivot, especially when you have real responsibilities
• What Dr. Minter-Jordan would tell a thirty-five-year-old building a career for the long arc

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

Follow Dr. Myechia Minter-Jordan and Jessi Hempel on LinkedIn.

“It’s not your fault.” This is the message Alissa Quart has spent over a decade trying to get people to believe when it comes to economic hardship. Right now, it feels harder than ever to embrace.

Alissa Quart is the executive director of the Economic Hardship Reporting Project, the nonprofit Barbara Ehrenreich built after writing her groundbreaking exposé Nickel and Dimed. A journalist herself, Alissa is the author of seven books, including Squeezed: Why Our Families Can’t Afford America and Bootstrapped: Liberating Ourselves from the American Dream. She's spent over a decade reporting on class, caregiving, and economic precarity.

In this episode, Jessi and Alissa discuss:

• Why "insecurity" is a more honest and unifying framework than "affordability," and how it builds solidarity across class lines
• The data behind it: 52% of US families are now financially insecure by one measure, and nearly half of workers lack confidence they could find a job they'd want
• "Apocalyptic insecurity": the new framework Alissa and economist Lynn Parramore developed to describe how employers use AI dread to manipulate workers
• The Frederick Taylor parallel: how AI is repeating the logic of scientific management, a century later
• "AI brain fry": the exhaustion of performing enthusiasm for AI at work while feeling something very different about it personally
• Why losing the narrative of generational progress is its own kind of psychological injury
• The AI dividend, universal basic income, and what a modern New Deal could look like
• Why naming the problem matters: how failing to recognize insecurity as systemic — rather than personal failure — can curdle into self-blame and even disordered coping
• What Alissa tells her own daughter about finding agency in an uncertain future

Follow Alissa Quart and Jessi Hempel on LinkedIn.