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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Nola Simon is a strategic futurist, and we discuss the evolving landscape of remote work, the importance of trust and connection in the workplace, and the integration of AI with her. Nola shares her insights on building engaged remote teams, the significance of asynchronous work, and the necessity of measuring trust within organizations. She emphasizes the need for strategic foresight in navigating rapid changes in technology and society, and discusses the role of narrative intelligence in leadership. The conversation concludes with practical advice for CTOs on fostering a culture of trust and engagement in distributed teams.
Chapters
00:00 Intro to Remote Work & Flexibility
05:34 Creating Connection in Remote Teams
10:55 Async workflows, documentation, and AI
13:31 Earning trust for knowledge sharing
15:16 Measuring trust via outcomes & psychological safety
29:04 Strategic foresight: scenarios and adaptability in AI turbulence
44:35 Playbook for first-time distributed CTOs
About Nola
Nola Simon is a strategic futurist and a steady voice for leaders navigating the messy, human moments at work. Her keynotes are part mirror, part map—reflective, insightful, and grounded in the lived experience of leading when the future isn’t clear.
What sets Nola apart? She blends sharp systems thinking with a warm sense of humour and a love of pop culture. Whether it’s a tongue-in-cheek reference to a classic sitcom, a playful callback to a viral meme, or a story about the unexpected lessons of a Zoom mishap, Nola uses levity to spark connection and make big ideas stick. Her sessions are as likely to include a laugh-out-loud anecdote as a breakthrough leadership insight.
As host of Hope & Possibilities: A Love Letter to the Future of Work, Nola brings lived experience, quiet power, and a knack for making people smile to every stage. She adapts to the moment—remote, hybrid, or in person—always with clarity, presence, and deep respect for the space she’s in.
Nola invites audiences to question assumptions, explore new perspectives, and leave with a renewed sense of agency, possibility, and optimism about the future of work.
Where to find Nola
• LinkedIn: https://www.linkedin.com/in/nolasimon
• Youtube: https://youtube.com/@nolasimonsayings
• Website: https://www.nolasimon.com
7 episodes
