Peter and the Wolf Webinars Peter and Peter & The Wolf: The Wolf's Guide to AI Phone Systems

Thinking about switching to an AI phone system for your property management company? In this expert-led webinar, Wolf Crosskey breaks down the pros and cons of AI phone assistants, what features actually work for property managers, and where most systems fall short. Before you choose a VoIP or AI phone solution, read this recap to learn what questions to ask and which tools to consider.

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Wolf didn’t hold back in this webinar diving deep into the reality and hype of AI phone systems in property management. Whether you’re already using smart VoIP or just considering switching from an archaic setup, this session unpacked what’s working, what’s failing, and what’s still missing from today’s AI phone tech.

💡 Here’s what was covered

1. Why are people still calling you?

If tenants and owners are calling, it means your self-serve options didn’t work—and layering on AI without fixing the root issue is like putting lipstick on a broken system. It's time to rethink your content, onboarding, and communication strategies before ever considering automation.

2. What AI should be doing—and what it isn’t (yet)

Wolf explored where current AI phone tools fall short—especially around true integration, personalization, and real-time data access.

Wolf outlined what a true “AI-powered phone system” should look like: a tool that knows who’s calling, what they’re likely calling about, and routes them accordingly—all in real time, with natural language. 

 

🧠 Other topics touched on:

  • Smart VoIP vs PBX: What “smart lines” actually mean today
  • AI phone assistants: what they can do (maintenance triage, basic routing) and where they hallucinate
  • Why mobile-first matters more than ever—and why staff keep reverting to personal cell phones
  • Integration pitfalls: what to ask vendors about AI training, data flow, and privacy during your demos
  • AI hallucinations: when bots blend owner/tenant/vendor data and give dangerous answers
  • AI use cases that do work: lease inquiries, after-hours emergencies, and voicemail summarization
  • Critical security questions to ask before giving AI access to your property data

🔍 Top Questions Asked by Attendees:

  • “How do I connect my current phone number to one of these AI tools?”
  • “Are there any AI phone systems that truly integrate with LeadSimple or AppFolio?”
  • “Can AI actually reduce call volume—or will it make my staff’s job harder?”
  • “How do we train AI without sacrificing compliance or customer experience?”
  • “What’s the best place to start if we’re still using a legacy phone system?”

👀 So… What's The Status on AI Phone Systems?

If you’re ready to rethink your entire communication flow—starting with why your phones are ringing—this webinar will shift how you evaluate tech from now on.

 

Learn how LeadSimple is evolving with AI integrations. Book a call with us today. 

 

 

Miriam Kusa

Author: Miriam Kusa

Miriam Kusa is the Content Marketing Manager at LeadSimple. She creates content with the aim of empowering property managers to succeed in their businesses. Outside of work, you'll find her playing a game of tennis, diving into personal development books, and exploring all things health and wellness.