VIDEO EPISODE 56: The Curious Leader's Guide to Better Questions in Family Systems with Jon Bassford

In this episode of Grey Minds Think Alike, host Ali Kessler speaks with Jon Bassford, a two-time bestselling author, TEDx speaker, and founder of Lateral Solutions, about why systems can appear functional yet produce poor outcomes, and how fear, comfort, and habits undermine innovation and change. Bassford shares his background in law, association management, and tech startups, and explains how The Curious Leader emphasizes asking better questions to find root causes rather than treating symptoms. The conversation also addresses family-court flaws, including the host’s experience advocating for Greyson’s Law in Florida after her son’s death, and discusses what individuals can control through self-care, therapy, mindfulness, exercise, and reducing conflict. Bassford outlines child-centered co-parenting principles from The Co-Parenting Secret: It’s Not About You, focusing on intentional communication, letting go of animosity, and building a supportive “village.” 00:00 Welcome and Guest Intro 01:16 Jon’s Career Path 02:32 When Systems Quietly Fail 03:30 Family Court and System Limits 06:13 Advocacy and Greyson’s Law 06:34 It’s Not About You 07:06 Real Co-Parenting Examples 08:43 Intentional Divorce Mindset 10:09 Letting Go of Animosity 11:31 Boundaries With High Conflict 13:06 Mindfulness and Narrative Control 16:24 In the Moment De-Escalation 18:19 Beyond Meditation Therapy 18:43 Choosing Your Support 19:03 Therapy and Accountability 19:23 Venting Without Poisoning 21:01 Regulating Stress and Recovery 21:41 Curious Leader Co-Parenting 23:03 Fixing Transition Problems 26:03 Fighting for 50 50 27:57 Keep Focus on Kids 30:03 Build the Village 30:17 Wrap Up and Resources 31:01 Coaching and Consulting Offer 32:00 Final Goodbye About Jon Bassford: Jon Bassford is a 2x best-selling author, TEDx speaker, and founder of Lateral Solutions, where he helps organizations scale with clarity, discipline, and operational integrity. As the creator of the Trust The Process consulting method and The Curious Leader framework, Jon works with leaders to identify hidden breakdowns in systems, improve decision-making, and create more effective, structured environments. With a background as a former VP and COO, Jon has advised startups, nonprofits, and growing organizations, helping them move from reactive chaos to intentional, sustainable performance. He is also the author of The Co-Parenting Secret: It’s Not About You, which focuses on building more respectful, child-centered co-parenting relationships through mindset and communication. The Co-Parenting Book - https://theco-parentingbook.com LinkedIn -   / jonbassford   @ jonbassford https://jonbassford.com/books/ About Ali Kessler Ali Kessler is a writer, marketing professional, passionate parent advocate, and founder of Greyson’s Choice, a 501(c)(3) created to raise awareness about the risk of domestic abuse on children. Greyson’s Choice was founded by Ali Kessler in memory of her sweet, vibrant, and fearless 4.5-year-old son, Greyson, who was murdered by his biological father in a murder-suicide during an unsupervised, court-approved visit in Ft. Lauderdale, FL, in 2021. This came just hours after her petition for a domestic violence injunction was denied by a Broward County judge, citing that the “petitioner has failed to allege any overt acts by the respondent which would constitute domestic violence under Florida Statute.” Ali’s advocacy efforts culminated in the successful passage of Greyson’s Law during the 2023 legislative session. This bill now requires the court to consider threats against ex-partners or spouses when making child visitation and custody determinations in the court, expanding to include the following factors: evidence of domestic violence, whether a parent in the past or currently has reasonable cause to believe that they or a minor child is, or has been in imminent danger of becoming the victim of domestic/sexual violence by the other parent, even if no other legal action has been brought or is currently pending in court.