The Conversation Factory

My guests today are Rei Wang and Anita Hossain, Co-founders of coaching platform The Grand, which was seed funded by Alexis Ohanian’s firm Seven Seven Six in 2023. Rei is the Chief Product Officer and Anita is the CEO. I met Rei ages ago, in her early days in NYC at General Assembly, where she worked as a Product Manager and Global Community Lead, developing educational opportunities for students. And I was excited to interview her about her work as the CEO of the Dorm Room fund at First Round Capital a few years back to get her perspectives around the intersection of community and product design…especially when the community IS the product. Check out that conversation here. Rei cultivated a vibrant startup ecosystem, mentoring over 250 entrepreneurs on various aspects of business management and fundraising. Their leadership garnered recognition, including the Forbes 30 under 30 award. Rei and Anita met during their time at First Round Capital, where Anita was the Head of Knowledge. While there, she helped hundreds of entrepreneurs connect deeply and vulnerably, to share their concerns and to learn from each other. Anita was also an executive coach with the renowned coaching firm, Reboot, and is a certified Neuro-Linguistic Programming Practitioner. Key Advice for Working Through Challenges Prevention is first and foremost! Speak early and often to reduce buildup, bottling up and boiling over of tensions Make feedback about actions and behaviors, not about the person or their personality Rei suggests that using a simple framework like SBIO is a great way to frame feedback. (Situation or data, the Behavior you see, the Impact it has on you, and the Opportunity for improvement or transformation) Make sure feedback conversations are two-sided, with both partners regularly asking for and offering feedback Anita underscores the importance of Co-Creation of resolutions to challenges instead of telling someone to be different. Working on these tensions with a sense of collaboration can lead to reduced defensiveness. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes  and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links The Grand My previous conversation with Rei Wang

James Rutter, CCO at COOK, talks about fish pie, citizenship, and participation. He emphasizes leadership grounded in play and community. Discusses insights from Peter Block's book and working with Jon Alexander. Highlights the importance of moving away from consumerism and fostering engagement for a meaningful collective vision.

Today I share my conversation with Suzanne Vickberg, aka Dr. Suz. She is a social-personality psychologist and a Research Lead at Deloitte Greenhouse. Along with her Deloitte Greenhouse colleague Kim Christfort, Suzanne co-authored the best-selling book Business Chemistry. But there’s another type of Chemistry - or Alchemistry - that I sat down to talk to Dr. Suz about - shifting the default track of a conversation from protection and opposition to collaboration, Some years ago I interviewed Dr. Elizabeth Stokoe, a Professor of Social Interaction at Loughborough University, who speaks in her book Talk about conversations as having a landscape or a “track” that participants asses and orient to rather quickly…and that we glide down that track, while we monitor the texture of that landscape, and navigate the bumps in the road…so that we can keep things on safely on track. Check out our podcast conversation here and her TEDx talk here. In the opening quote to this podcast, you can hear Dr. Suz describing this process of “landscape orienting” happening very rapidly in a divorce context. Knowing the default path is very helpful when navigating a “hello, how are you?” kind of “small talk” conversation in a non-wierdo-way. Knowing the default track can help make things smooth and easy…when you’re visiting the store, or a bowling alley. And when you don’t know the basics of the track, things can be hard - Doing simple things in a different culture can be surprisingly slippery to navigate when you don’t know the basics of the track.  But sometimes the default path can be extremely detrimental - especially when the default is ineffectual or becomes unconscious and habitual - we keep doing things out of rote, not intent. In business, a common default/habitual conversational path is looking at an underperformer and putting them on a Performance Improvement Plan in order to be able to fire them more easily, A non-default, more conscious conversation is taking the time to learn *why* they are underperforming and helping them actually transform themselves, their work performance and their lives….and in the process deeply benefiting the company and even the community. Seems impossible, right? Or grandiose? Carol Sandford, in her book about Regenerative Business talks about an organization that did just this… a manager discovered that a chronically underperforming and late employee was just functionally illiterate. That employee, once they felt safe to share more, helped that manager learn that many of their employees were facing similar issues. Instead of a PIP, this employee got literacy training, and became an advisor to a new literacy program developed inside the organization, which spread out to the larger community, in ripples of growth and transformation. That is a *non* default conversation - turning a PIP conversation into a community-transformation conversation. On a micro-scale, Dr. Suz’s book tells the story of rethinking or re-designing the “default track” for a very, very common conversation - Divorce. When that word gets said out loud, people find lawyers, put up a shield, and start digging trenches.  There is a better way! It takes effort to deeply empathize with your “opponent” in a difficult conversation. It takes patience and imagination to collaborate with your “opponent” to design a win-win scenario.  But the default design for divorce doesn’t usually create ideal outcomes…just conventional ones. It’s possible to create something better than you can imagine if you create the space for a transformational conversation. Dr. Suz helps break down how “design” in these situations just means really understanding the REAL problem we’re solving and what our IDEAL outcome really could look like… BEFORE we jump to solutions. Also check out my podcast conversation with Adam Kahane, author of, among many other amazing books, the book Collaborating with the Enemy - which is what I know a divorce can feel like. Some of his perspectives take this “divorce by design” mindset into the broader business and strategy arena. Enjoy this conversation as much as I did…and think about how you might transform the most challenging conversations in your life and work. With more conscious creativity and intention, with empathy and collaboration…with more design you can create more of what you really want, just like Dr. Suz did for her own divorce and for her own life. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes  and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links https://www.divorcexdesign.com/ https://www.linkedin.com/in/suzannevickberg/ https://www2.deloitte.com/us/en/profiles/svickberg.html https://theconversationfactory.com/podcast/facilitating-breakthrough-with-adam-kahane

Jay Ruparel, Co-founder and CEO of VOICEplug AI, talks about using AI for natural language ordering in restaurants. He discusses the responsible use of AI, the benefits of AI in repetitive tasks like fast food ordering, and the importance of quality datasets for AI learning. Jay highlights the balance between AI tools and human connections, effective meeting strategies, and the power of asking insightful questions for team interactions and AI ethics.

Kevin Bethune, multidisciplinary design executive, discusses the importance of embracing creative approaches and the need for bold leadership to optimize curiosity and creativity. They also highlight the lack of diversity in design and innovation, particularly in black representation. Kevin's book, Reimagining Design: Unlocking Strategic Innovation, explores the cone of possibility and the S curve as models of thinking. They discuss rewiring organizations to embrace design thinking and the concept of opening the aperture in strategic foresight. Additionally, they emphasize the importance of diversity, intent, and belief in design, as well as handling ambiguity and navigating non-linearities.

Emily Levada, Chief Product Officer at Embark Veterinary, discusses managing organizational emotions, particularly during layoffs. Topics include transparency and trust, polarity mapping, managing negative emotions, regular check-ins, driving resilience and creativity, and the value of challenge and psychological safety.

My guest today is Jason Knight, the creator, host, producer, editor and promoter of the One Knight in Product podcast, a B2B SaaS product consultant, and fractional Chief Product Officer for companies that have gotten to product market fit and need help scaling their product team. Jason is also the founder of My Mentor Path, an inclusive, accessible and cloud-based mentorship service.  Sandra Monteiro, a Product Manager at SAGE Publishing and a mentee of Jason’s, joined us halfway through to share her own experiences with mentoring, how she found her way to working with Jason as a mentor and what some of her learnings and insights from working with Jason as a mentor have been. She also shares her thoughts on what mentees should be thinking about as they search for and work with mentors. We explored Jason’s mentorship journey and why mentorship matters to him, the challenges of Industrializing mentorship pairing and productizing the matching of the lopsided mentorship marketplace. We also touch on how to measure the impact of the work and the subtle and important difference between Mentoring and Coaching. Jason suggests that many people who say they want coaching really want mentoring from someone who has “been there and done that”…and that great mentoring leverages coaching mindsets and skills in a practice he affectionately calls “centering”. Some fundamental questions we explored were the differences and relative merits of FORMAL vs INFORMAL mentorship as well as working with someone INTERNAL vs EXTERNAL to your Organization One of the big insights Sandra shared was shifting her expectations on the nature of the mentoring relationship from one centered around SOLVING vs conversations centered around TOOLS (ie, being offered relevant examples, learning materials and frameworks, holding space for emotional distance, and being offered broader context for challenges). Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes  and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Sandra Monteiro Jason Knight https://www.oneknightinproduct.com/bio/ https://www.oneknightconsulting.com/ My conversation on Unapologetic Eating and Living with Alissa Rumsey is here

Dr. Onyinye Balogun and Eve McDavid, co-founders of Mission-Driven Tech, discuss the disparities in gynecological cancer outcomes and the importance of collaboration and communication in their co-founder relationship. They also emphasize the need for equity in healthcare, increasing awareness about gynecologic cancer, and finding the right connections and supporters for their mission.

David Hoffman built and sold big-data and data analytics company Next Big Sound to Pandora in 2015. He's now building Beam, which helps people create shoppable mood boards for DTC brands. David reflects on his experience with mentorship and the long arc of the conversation that is being a co-founder and being in community. We unpack the Techstars motto "give first" and discuss the power of the Techstars community and the importance of community relationships in entrepreneurship. We talk through the complex evolution that is founding and scaling a startup, his experience doing just that with Next Big Sound, and the challenges of becoming a leader inside a growing company. One challenge is always scaling culture as a company scales, and David outlines some of the routines and structures that helped in defining his startup's culture. David also shares some insights on the post-startup-sale emotional roller coaster and the decision to build another company. Some of my other favorite insights from David: Living the “Give First” motto requires approaching everything with curiosity. “Grown ups” is a construct: When it is your idea and your company, you can make the decisions you need to make. Your Culture is made of your routines, whether it’s Friday bagels or snap-clapping after people share wins. Your MVP product can be much, much more simple than you think if it creates value for your customers. David’s nuanced reflections are a gift, and I’m so glad he sat down for this conversation. Head over to theconversationfactory.com/listen for full episode transcripts, links, show notes  and more key quotes and ideas. You can also head over there and become a monthly supporter of the show for as little as $8 a month. You'll get complimentary access to exclusive workshops and resources that I only share with this circle of facilitators and leaders. Links Beam

My guests today, Ryan Horrigan and Armando Kirwin, bonded over their mutual fascination with the future of entertainment and their desire to do something innovative, which led to the creation of their current company, Artie. We talk about pivots and micro pivots and staying sane through the million tiny conversations Cofounders need to navigate. Ryan, the CEO, and Armando, President and co-founder of Artie have a pretty radical vision for the future of social media— namely, to make TikTok, Instagram, Twitter and other social media apps the gaming consoles of the future. Before co-founding Artie, Ryan served as Chief Content Officer of the Comcast-backed VR & AR startup Felix & Paul Studios. He oversaw the development and production of feature films, including Academy Award Best Picture Winner “12 Years A Slave.” at Fox/New Regency, and is a two-time Emmy Award winner for immersive entertainment projects he produced with President Barack Obama and NASA, as well as a Peabody Award winner. Armando has been in the VFX world for over fifteen years, working with numerous award-winning directors, including two-time Academy Award nominee Lucy Walker,  Sundance Grand Jury prize nominee Sandy Smolan on The Click Effect, which was nominated for an Emmy; and Imraan Ismail on The Displaced, which won the Grand Prix at Cannes. He also produced Take Flight, starring Benicio del Toro, Michael Fassbender, and Charlize Theron. His most recent VR film, Nothing is Safe (2022), was an official selection of the Cannes Marché du Film. While movies are a wonderful industry, they both saw the power and potential of gaming as a storytelling platform - and a financial juggernaut. If you didn’t know: According to a report by SuperData Research, the global gaming market was valued at $159.3 billion in 2020. This includes revenue from console games, PC games, mobile games, and esports. Let’s put that into perspective: the music industry was valued at $19.1 billion in 2020, and the movie industry at $41.7 billion. That means the gaming industry is more than three times the size of the music industry and almost four times the size of the movie industry. TikTok used to be where people just watched videos (as of this writing, TikTok and Netflix are nearly tied for eyeball-hours). Now, hundreds of thousands of people are playing games on TikTok thanks to Artie and the technology breakthroughs that make streaming app-quality games from within social media apps possible. But how did they get here? Through a million micro conversations about data, signals, stakeholders and what it all means. Artie is where are are today not because of one big pivot, but many, many micro-pivots over the course of years. Pivots impact the team - who you needed on staff  when you were focused on one path isn’t always who you need when you’ve decided to shift directions. Communication between departments and involving the team more is important - which means being intentional about regular check-ins and interdepartmental communication, but eventually, it comes down to the co-founder conversation - owning the choices that need to be made and moving forward, all while making sure you stay healthy and sane. Pivots vs Shaping Clay I loved this metaphor from Ryan, where he suggested that, from the outside, to investors, bloggers and customers, a company may have pivoted once, or a few times. From the inside, there are daily conversations, where the product is being shaped like clay, remade, refocused, almost constantly. “Listen to your body, have a Coach and a Therapist” This was one of my favorite insights from this conversation. It’s not often that men talk openly about mental health and needing support. Ryan and Armando both have a coach (although they meet with that coach separately) and Armando advocated for having a therapist, while Ryan discussed how they got much much more intentional about listening to their bodies and taking down time. Armando suggests that therapy focuses on self-awareness, learning about yourself and your patterns, while his coaching focuses on future outcomes and goals. “You have to care deeply about your people, but at the same time, you can't care about what they think of you” Ryan quotes what he describes as a harsh-sounding notion from  Dick Costello when he was at Twitter: In Ryan’s experience, when you make a tough decision, you can't worry about everyone's collective feelings (even though you DO care about them as people and teammates). You have to make the decision that you, as the leader, believe needs to be made. As a founder, you have to make and own tough decisions. Ryan points out that, at the end of the day, you can't ignore tough decisions. You can’t have someone else do it for you. He suggests that while these moments are hard, it’s helpful to focus on the people who are still with you and the ultimate goals you’re trying to achieve. Links https://www.artie.com/