For better or for worse, AI is already here. What should HOA boards ask about it?

Every service company seems to say it uses AI now. Management companies, accountants, vendors, software providers. The phrase is everywhere, and it tells a board member almost nothing on its own.

In this episode of The Uncommon Area, Matthew Holbrook sits down with Chris Lema, CEO of Motivation Code and a longtime technology executive, and Brad Perry, chief information officer for Action Property Management and the architect behind SnapHOA, to talk about what separates real AI capability from a buzzword.

Their answer comes down to three things: the data a company owns, the context it gives the AI, and the people who check the work.

Chris opens with a story from his time as a technology executive at a hosting company. He kept two data scientists on staff at about $150,000 each, working in a windowless room the team called Vegas because nobody inside knew what time it was. Years later, his own team read a report he had produced and asked if he had outsourced it to a data scientist. He had. One data scientist, named Claude.

From there, Brad explains why that kind of power only helps if the AI understands the business. In community management, nearly everything depends on unit count. But in a master association with sub associations, do you count the same homes twice? Until someone defines that rule and teaches it to the AI, every answer built on it can be wrong. The same goes for whether an association keeps its books on a cash or accrual basis. As Brad puts it, too much data without context can actually produce incorrect information.

The conversation then turns to software. Chris has watched companies drop subscription tools and build their own with AI, and he has a blunt take: most people shouldn't build software, just like most people shouldn't build their own house. He walks through what happens when a platform that looked great for ten customers lets the eleventh see someone else's data, and why anyone building software has to be more excited about maintenance than new construction.

The conversation also tackles:

• How AI has moved from generating text to agents that take action
• Why two companies that both "use AI" can be doing very different things
• How managers, residents, and board members each need different, filtered information
• Capturing the unwritten rules experienced staff carry in their heads
• Who should and shouldn't build their own software with AI
• What multi-tenancy is and why it matters to clients
• How APIs and MCPs connect the systems a management company runs on
• What to ask a provider that says it built its own platform

Chris closes with the story of how he went from HOA skeptic to HOA fan after moving from California to Houston, when his new association patched a wall behind his house before he even knew it was cracked. His point: AI frees up time, and what a company does with that time is a choice.

Key Takeaways

Ask what "we use AI" means. The phrase covers a wide range of practices. The details are what matter.

Context beats volume. An AI that doesn't know how your association counts units or keeps its books will make assumptions.

Unwritten rules need to be written down. Much of a company's judgment lives with experienced people. It has to be captured before AI can follow it.

Prototypes are not platforms. A tool built quickly with AI can be a useful starting point, but security, multi-tenancy, and long-term maintenance take real expertise.

Watch what the saved time is used for. The best use of efficiency is putting people toward better service.

Questions Boards Can Ask a Provider

1. What does using AI mean in your day-to-day operations?
2. Who defines the rules and context your AI follows?
3. How does a person verify AI output before it reaches our board?
4. How is our association's data kept separate from other clients' data?
5. How long have you been building your own software, and is it central to your roadmap?
6. What do your people do with the time AI saves?

About Chris and Brad

Chris Lema is the CEO of Motivation Code and a technology executive whose career stretches back to the early days of the internet.

Brad Perry is the chief information officer for Action Property Management and the architect behind SnapHOA, the proprietary software platform Action Property Management uses. He has spent about 30 years in technology.