Hello Monday with Jessi Hempel

Rest is essential. It’s like food or water; without it, we die. As today’s guest points out though, it’s also a sacred practice.

In today’s rerun conversation, originally held live on Hello Monday’s Office Hours, Octavia Raheem joins Jessi Hempel to talk about, and to practice, rest. Octavia Raheem is a rest coach, yoga and meditation teacher, and author. Her latest book is called Rest is Sacred: Reclaiming Our Brilliance Through the Practice of Stillness.

She and Jessi discuss:

How rest sparks creativity and connection

Rethinking productivity through rest

How to build micro-rest practices into your days

The power of rest for self-reflection, personal growth, and clarity

Then, Octavia leads us in a transformative guided rest practice that combines mindfulness, relaxation, and breathing techniques.

Follow Octavia Raheem and Jessi Hempel on LinkedIn.

AI didn’t decide to reshape work. People did. And that distinction matters more than we like to admit. Dr. Rumman Chowdhury says the real story isn’t about machines replacing humans. It’s about the choices people in power are making—and the agency the rest of us still have. In today’s episode, Jessi Hempel and Rumman unpack what responsible AI really means, why fear is the wrong default reaction, and how workers, leaders, and everyday users can shape a better technological future.

Rumman Chowdhury is a leading expert in responsible artificial intelligence and algorithmic accountability. She previously led responsible AI efforts at Accenture, served on Twitter’s product team before it became X, and advised governments in the U.S. and U.K. She is the co-founder of Humane Intelligence, an organization focused on independent AI auditing and public participation in technology oversight.

Rumman and Jessi discuss:


Why AI isn’t “happening to us”—and how leadership decisions shape its impact


What responsible AI looks like inside real companies and products


The rise and fall of trust in Big Tech and Silicon Valley


Algorithmic bias, content moderation, and the limits of internal oversight


The root of why we fear AI


The difference between techno-optimism and techno-solutionism


How individuals can reclaim agency by understanding and engaging with AI

If you want to hear more from Dr. Rumman Chowdhury listen to her recent Ted Talk here. 

Follow Dr. Rumman Chowdhury on LinkedIn

Follow Jessi Hempel on LinkedIn

Watch on YouTube: https://bit.ly/hellomonday-LI-video-youtube 

Watch/Listen on Spotify: https://bit.ly/hellomonday-LI-video-apple 

Listen on Apple: https://bit.ly/hellomonday-LI-video-spotify

Every day is filled with negotiations. Here’s how to start winning them. Any conversation that has a want or a need is a negotiation. It's critical to approach even the low stakes negotiations with the same tools that will win high stakes conversations. But what if the key to better outcomes isn’t pushing harder, but listening better?

In today’s episode of Hello Monday, Jessi Hempel sits down with Jonathan Smith, negotiation instructor and co-author of Fight Less, Win More, to break down why negotiation is really about empathy, trust, and disciplined listening. Drawing on The Black Swan Group’s negotiation framework—made famous by Never Split the Difference—Jonathan shares practical tools for navigating conflict, building influence, and getting what you need without damaging relationships.

Jonathan is a business strategist and negotiation expert who has spent years teaching leaders, managers, and teams how to communicate in moments that matter most. His work focuses on tactical empathy, emotional intelligence, and the everyday negotiations that shape our careers and lives.

Jonathan and Jessi discuss:


Why every difficult conversation is a negotiation


Tactical empathy and how to help people feel truly heard


The “core four” negotiation skills: labels, mirrors, dynamic silence, and summaries


How low-stakes practice builds confidence for high-stakes conversations


Managing tone, emotion, and self-regulation 


Why listening is a discipline—and how it improves trust and influence


Using AI as a preparation tool without losing human connection

If you want to go deeper on these tools listen to our episode from September, 2025 with The Black Swan Group's founder and CEO, Chris Voss. 

Watch on YouTube: https://bit.ly/chrisvoss-hm-youtube 

Listen on Apple: https://bit.ly/chrisvoss-hm-apple 

Watch/Listen on Spotify: https://bit.ly/chrisvoss-hm-spotify

We will be launching the Hello Monday Book Club soon. If you’re interested in joining, send us an email at [email protected] and let us know!

Want an easy framework for winning any pitch? We’re pitching all the time—at work, at home, and everywhere in between. But most of us are doing it wrong. We lead with logic, credentials, and data, when what people actually need first is connection.

In today’s episode of Hello Monday, Jessi Hempel sits down with Danny Fontaine to unpack what makes a truly great pitch—and how to persuade with emotion, not just information. Drawing on decades of experience in experiential sales and storytelling, Danny shares a framework for captivating any audience by helping them feel seen, understood, and invested before you ever make your case.

Danny Fontaine leads an experiential selling team at IBM and has closed millions of dollars in deals across industries. He is the author of Pitch: How to Captivate and Convince Any Audience on the Planet and hosts a UK-based podcast called “Pitch Masters” on modern selling, persuasion, and communication at work.

Danny and Jessi discuss:


Why pitching is really about connection, not performance


How emotional storytelling builds trust and influence


The “backfire effect” and why logic alone doesn’t persuade


How to determine which opportunities are worth pitching—and which aren’t


Why the audience, not the seller, should be the hero of every pitch


Introverts, ambiverts, and why confidence isn’t what makes a great salesperson


How AI can help you prepare without losing authenticity

We will be launching the Hello Monday Book Club soon. If you’re interested in joining, send us an email at [email protected] and let us know!

Ambition. Is it a dirty word? Do you love the term, or hate it? In this Hello Monday episode from the archives, Jessi Hempel sits down with two incredible colleagues at LinkedIn, Hayley Saltzman and Ahyiana Angel, to explore how our understanding of ambition evolves, and what it means to chase personal growth rather than external validation.

Hayley Saltzman is an Editor at Large at LinkedIn, focusing on vertical video strategy. Ahyiana Angel was the Podcast Ad Ops Producer at LinkedIn and the host of her own podcast called Switch, Pivot, or Quit. Together, they reflect on how ambition is often shaped by external expectations and how true fulfillment comes when we start living for ourselves.

In this episode, Jessi, Ahyiana, and Hayley discuss:

The tension between extrinsic and intrinsic ambition

Our gendered notions of ambition, and how society’s definition of ambition is often limiting for women

What happens when you quit a dream job to pursue something more aligned with personal growth

The relationship between fear and ambition

Practical tips for reconnecting with your own ambitions and self-worth

If you've ever questioned what success and ambition truly mean for you, this episode is for you. Whether you're navigating career transitions or redefining what ambition looks like in your life, we hope this conversation will inspire you to live and work authentically.