Today, I sit down with Tracey Ivanyshyn, a serial entrepreneur, culture builder, corporate grief educator, death doula, and co-founder of Kindness at Work. After more than 25 years leading purpose-driven businesses and a team of over 100 people, Tracey has turned her attention to helping organizations build trust, belonging, and the capacity to meet loss with greater humanity. Tracey and I met on Necker Island, where a remarkable group of people came together around Richard Branson and the work of Virgin Unite. We begin with some joyful memories from that time, but our conversation soon becomes deeply personal. I share what it was like to lose my father while I was struggling with clinical depression and anxiety following a serious infection. Tracey offers a thought that’s stayed with me: grief tends to wait. When we can’t face it immediately, it doesn’t disappear. It waits until we’ve got the capacity to feel it. That understanding leads us into Tracey’s work helping companies learn how to support grieving employees. Most leaders haven’t been trained for these moments. They feel responsible for finding an answer, yet grief can’t be fixed. Tracey explains that often, our task isn’t to solve anything. It’s to witness, listen, and build systems that prevent a grieving person or overwhelmed manager from having to invent a response in the middle of a crisis. We also explore her work as a death doula and the “goodbye year” she shared with her mother. Tracey helps families ask the questions we tend to avoid, preserve their love stories, and thoughtfully shape the final days of a person’s life. Her reflections raise two questions worth asking long before the end: Am I loved? Have I loved well? What really stands out to me is how naturally this connects to leadership. Tracey draws a sharp distinction between being nice and being kind: niceness avoids friction, while kindness tells the truth with care. She saw that principle create loyalty, strengthen culture, and increase the value of the companies she eventually sold. Now she and co-founder Fiona Stevenson are bringing that mission to the inaugural Workplace Kindness Awards, hosted at Nasdaq MarketSite in New York City on November 12, 2026, with Claude Silver as keynote speaker. Key TakeawaysI was struck by Tracey’s insight that grief tends to wait. When other circumstances prevent us from processing a loss, the grief often returns when we’ve finally got room to feel it. I learned that leaders don’t need to fix grief. They need the courage and presence to witness it, ask caring questions, and stay with someone in an experience that doesn’t have a simple answer. Tracey’s framework moves organizations through three stages: grief awareness, grief literacy, and grief readiness supported by training, policies, and practical systems. I loved her idea of creating an employee “operating manual” before a crisis, including how each person prefers to communicate and be supported during difficult times. Small signals can remove enormous uncertainty. A blue or white flag on a desk or video-call background can tell colleagues whether a grieving person needs space or welcomes connection. Tracey showed how remembrance can become part of workplace culture through the story of a two-sided memorial bench: one side for quietly connecting with a colleague’s legacy, the other for signaling a need for companionship. Her work as a death doula demonstrates that thoughtful questions about sights, sounds, people, stories, fears, and unfinished conversations can bring greater intention to the end of life. The questions “Am I loved?” and “Have I loved well?” aren’t just questions for our final days. Asking them now gives us time to change the answers. I came away with an even clearer distinction between niceness and kindness. Niceness avoids discomfort; real kindness means telling the truth with care. Tracey’s business experience shows that a people-first culture isn’t separate from performance. The loyalty and trust her companies created contributed directly to their value when she sold them. Addressing Relevant IssuesThis conversation matters because grief enters the workplace whether or not our policies, managers, or cultures are prepared for it. People don’t stop being human when they arrive at work, and loss doesn’t remain neatly outside the office. When leaders avoid grief because they’re afraid of saying the wrong thing, grieving employees can experience that silence as isolation. Tracey offers a more capable model of workplace leadership. We can prepare managers, create humane bereavement practices, learn how people want to be supported, and give colleagues simple ways to communicate their emotional capacity. None of this requires lowering standards or avoiding difficult truths. It requires greater skill. The same principle applies to kindness. I don’t see kindness as politeness or conflict avoidance. Real kindness makes honest communication possible while preserving another person’s dignity. In an era of strained trust, uncertainty, and constant organizational change, that’s not a decorative cultural value. It’s part of how strong leaders and resilient organizations function. Why This Episode MattersThis episode matters to me personally. My father’s death has continued to teach me about love, grief, and the stories we carry about losing someone. Tracey gave me a way to see that grief with more patience and less judgment. It waits for us, and when it arrives, our job isn’t necessarily to make it go away. I also care deeply about Tracey’s work because it connects humanity with effective leadership. She isn’t talking about kindness from the sidelines. She built companies around it, saw it create extraordinary loyalty, and watched it contribute to their value. The Workplace Kindness Awards give us an opportunity to recognize people already leading this way and help make their example more visible. I hope this conversation encourages you to support that mission and to ask some of life’s important questions while there’s still time to act on the answers. Resources MentionedTracey Ivanyshyn on LinkedInKindness at WorkWorkplace Kindness Awards — November 12, 2026, at Nasdaq MarketSite in New York CityLife Review and Love Story QuestionsReimagine GoodbyeTell Love StoriesKindness.org — charity and science partner for the Workplace Kindness AwardsClaude Silver on LinkedIn — Chief Heart Officer of VaynerX, keynote speaker, and author of Be Yourself at WorkThe Five Invitations: Discovering What Death Can Teach Us About Living Fully by Frank OstaseskiCentre for Sacred Death Care100% Human at Work and Virgin Unite Connect & SubscribeIf this conversation made a difference for you, please subscribe to Live Like a Leader, follow the show, and share this episode with someone who’d appreciate it. I’d also be grateful if you left a five-star review, along with a short comment about what you enjoy about the show. Reviews help more thoughtful leaders discover these conversations, especially on Apple Podcasts. You can find the show and more episodes at livelikealeader.show. Next StepsTake a few minutes to explore Tracey’s life review questions. Choose one person you love and ask a question you’ve been postponing. Record the answer if they’re comfortable with that. The conversation may become part of your family’s lasting story. I also invite you to learn more about Kindness at Work and the inaugural Workplace Kindness Awards. Consider who deserves to be recognized for telling the truth with care, creating belonging, or showing up for people when it mattered most. ----- Tracey Ivanyshyn has spent her life building things that matter—companies, cultures, communities—and most of all, belonging. For over 25 years, she led a group of purpose-driven businesses known as much for their award-winning performance as for the people-first culture she cultivated within them. Leading her team of over 100 employees was a great joy in her life and an incredible teacher. And when approached to sell the companies to a larger aligned competitor, she found her own transition to spaciousness and a new chapter. Now Tracey transforms workplace cultures through the power of kindness. She helps organisations build trust where it's been lost, culture where it's been strained, and emotional safety where it's most needed. As a corporate grief educator, she is also quietly pioneering a new model for how we show up for one another in times of loss—at work, and beyond. She and her co-founder Fiona Stevenson have created the Workplace Kindness Awards - hosted at NASDAQ in NYC in November. Ready to make your communication a match for how good you really are? John K. Bates provides private executive communication coaching and leadership development for accomplished leaders and teams. His programs have earned 92+ Net Promoter Scores with organizations including NASA, Johnson & Johnson, Google, Intuit, and Boston Scientific. Explore private coaching and leadership programs: https://executivespeakingsuccess.com/ Build your communication practice with John’s free weekly mini-trainings: https://johnbates.com/mini-trainings/