Key takeaways
How property managers can put AI to work
- AI will not replace you, but people who use it might. Phil uses AI to draft notices, review contracts, and check invoices, which multiplies how much he can produce.
- Start small. Paste an email into ChatGPT and ask it to check the tone and professionalism. Build from there until you hit its limits.
- Keep a human in the loop. AI still makes mistakes, so experienced property managers need to review its work, especially anything financial.
- Smaller firms can move faster. Without layers of approvals, small companies can adopt AI now and compete on pricing, speed, and flexibility.
- Educate your boards. The best results come when boards understand the plan as well as you do and can make confident decisions together.
About the guest
PS
Phil Sobkow
Property Manager, Charter Property Management
Phil is a condominium property manager with Charter Property Management in the Calgary area. A former elementary teacher, he has spent about 12 years in condo and rental management, including time at Sierra (now Associa) and FirstService, and is an enthusiastic everyday user of AI tools.
Episode summary
In this episode
Phil Sobkow moved from teaching into property management after chatting with a commercial property manager at the restaurant where he worked part time. He credits his growth to mentors he made a point of learning from at every company.
Phil explains how he uses AI today, from drafting notices and summarizing 45-page contracts to double-checking invoices, and why he sees it as an infinite team of assistants. He also shares where AI still falls short and how property managers can get started.
He talks about keeping communication manageable across thousands of owners, educating boards on capital planning, what he looks for in a janitorial partner, the kind of property he would love to manage, and the book that shaped how he sees people.
Chapters
- 0:00Introduction
- 2:08About Charter Property Management
- 3:37Phil’s path into property management
- 9:25From rentals back to condos
- 12:42Learning from mentors
- 18:21What makes a good property manager
- 21:31How AI is used in property management today
- 24:44Will AI replace property managers?
- 28:28Why AI favours smaller firms
- 30:40AI and financial review
- 35:06How to get started with AI
- 38:54Communicating with owners and boards
- 43:21Educating boards on capital planning
- 47:08Choosing janitorial partners
- 54:11Dream property
- 58:17Book recommendation
Jump to a chapter (16)
- 0:00Introduction
- 2:08About Charter Property Management
- 3:37Phil’s path into property management
- 9:25From rentals back to condos
- 12:42Learning from mentors
- 18:21What makes a good property manager
- 21:31How AI is used in property management today
- 24:44Will AI replace property managers?
- 28:28Why AI favours smaller firms
- 30:40AI and financial review
- 35:06How to get started with AI
- 38:54Communicating with owners and boards
- 43:21Educating boards on capital planning
- 47:08Choosing janitorial partners
- 54:11Dream property
- 58:17Book recommendation
From the conversation
Transcript excerpts
The way I view it it’s like having an infinite team of administrators and assistants that I can… give tasks to and then it comes back to me just to review it.
Phil SobkowPlay from 0:07
Start small. Use it for just helping with your writing. You can copy and paste an email and just say hey like can you check this for tone, professionalism…
Phil SobkowPlay from 0:46
Anyone who’s had success in this industry, I think you’d be a fool not to… mimic them, study them…
Phil SobkowPlay from 9:02
Looking for a cleaning partner your board will be happy with?
We’ll walk your building with you and send a written cleaning scope and price. Free, no obligation.
Read the conversation
Full episode transcript
Show transcript
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FAQ
Questions about this episode
How should property managers get started with AI?
Phil recommends starting with ChatGPT. Begin with simple tasks like checking an email for tone, then keep pushing it until you find what it cannot do. That hands-on practice is how he learned.
What does Phil look for in a janitorial company?
Price matters, but he starts with how happy the board and owners are with the people in their building. He looks at the quality of the relationship, reliability, and mutual respect, and connects boards with others who have had good experiences.
What book does Phil recommend?
The 7 Habits of Highly Effective People by Stephen Covey. The paradigm shift story in the first chapter taught him to look past the surface of a conflict and see what the other person is going through.
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