Season 13 Episode #5. Week 2 of the 28-Day AI Challenge Relationships & Communication with Michael Fanning
Mon Feb 02 2026
Welcome back to the Windermere Coaching Minute! This week, we're diving into Week 2 of our AI Challenge series, focusing on the heart of real estate: relationships and communication.
Golden Rule Reminder: Never input confidential client information into AI - no names, addresses, or financial details.
Day 8 - Draft Communication TemplatesCreate scripts for common conversations like price improvements, expired listings, and market updates. Example: Build a framework for discussing price adjustments that's empathetic yet data-driven, turning difficult conversations into strategy sessions.
Day 9 - 90-Day Relationship Nurturing PlanDesign systematic touchpoint strategies for different database segments. Integrate AI planning with your tools: Cloze CRM for automation, Cloze Ghostwriter for email sequences, Express Docs for handwritten notes, and Maxa for social media. AI designs the strategy; your tools execute it while maintaining your authentic voice.
Day 10 - Navigate Challenging Client SituationsUse AI as a judgment-free thinking partner for difficult conversations. Practice boundary-setting, reframe frustrations, and develop language that maintains relationships while addressing tough issues.
Day 11 - Role Play Listing PresentationsLet AI act as a skeptical seller to practice objection handling. Work through commission questions, marketing plan challenges, and experience inquiries - all available 24/7 with no judgment.
Day 12 - Identify Success PatternsAnalyze your best client relationships to understand what makes them successful. Discover your sweet spot and where to focus your energy for replicable results.
Day 13 - Transaction Stage TemplatesCreate text/email templates for every transaction milestone: offer accepted, inspection scheduled, appraisal ordered, clear to close. Stay consistent without starting from scratch each time.
Day 14 - Reflect & IntegrateEvaluate which tools saved you time and improved client conversations. Understand how AI, your CRM, and personal touch work together to create a systematic relationship engine.
As James Clear says, "We don't rise to the level of our goals, but we fall to the level of our systems." AI helps you be more thoughtful, organized, and consistent - but YOU bring the authenticity and build the trust.
What AI Should Help With: Communication templates, relationship strategies, conversation practice, follow-up systems, CRM campaign design
What AI Should NOT Replace: Genuine personal connection, professional judgment, actual client data handling
Commit to 10-15 minutes daily. Stay curious, look for opportunities, and remember: AI handles structure, your tools handle execution, so you can focus on building authentic, lasting relationships.
Connect: Email fanning@windermere.com to be featured on our podcast. Rate, review, and share if you find value!
Be awesome, help somebody, and make it a great day!
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Welcome back to the Windermere Coaching Minute! This week, we're diving into Week 2 of our AI Challenge series, focusing on the heart of real estate: relationships and communication. Golden Rule Reminder: Never input confidential client information into AI - no names, addresses, or financial details. Day 8 - Draft Communication TemplatesCreate scripts for common conversations like price improvements, expired listings, and market updates. Example: Build a framework for discussing price adjustments that's empathetic yet data-driven, turning difficult conversations into strategy sessions. Day 9 - 90-Day Relationship Nurturing PlanDesign systematic touchpoint strategies for different database segments. Integrate AI planning with your tools: Cloze CRM for automation, Cloze Ghostwriter for email sequences, Express Docs for handwritten notes, and Maxa for social media. AI designs the strategy; your tools execute it while maintaining your authentic voice. Day 10 - Navigate Challenging Client SituationsUse AI as a judgment-free thinking partner for difficult conversations. Practice boundary-setting, reframe frustrations, and develop language that maintains relationships while addressing tough issues. Day 11 - Role Play Listing PresentationsLet AI act as a skeptical seller to practice objection handling. Work through commission questions, marketing plan challenges, and experience inquiries - all available 24/7 with no judgment. Day 12 - Identify Success PatternsAnalyze your best client relationships to understand what makes them successful. Discover your sweet spot and where to focus your energy for replicable results. Day 13 - Transaction Stage TemplatesCreate text/email templates for every transaction milestone: offer accepted, inspection scheduled, appraisal ordered, clear to close. Stay consistent without starting from scratch each time. Day 14 - Reflect & IntegrateEvaluate which tools saved you time and improved client conversations. Understand how AI, your CRM, and personal touch work together to create a systematic relationship engine. As James Clear says, "We don't rise to the level of our goals, but we fall to the level of our systems." AI helps you be more thoughtful, organized, and consistent - but YOU bring the authenticity and build the trust. What AI Should Help With: Communication templates, relationship strategies, conversation practice, follow-up systems, CRM campaign design What AI Should NOT Replace: Genuine personal connection, professional judgment, actual client data handling Commit to 10-15 minutes daily. Stay curious, look for opportunities, and remember: AI handles structure, your tools handle execution, so you can focus on building authentic, lasting relationships. Connect: Email fanning@windermere.com to be featured on our podcast. Rate, review, and share if you find value! Be awesome, help somebody, and make it a great day!