Billboard Insider’s Dave Westburg moderated a panel on AI and out of home at last week’s OAAA Independent Summit.  Some excerpts from the discussion.

OAAA SVP Andy McDonald on AI legal issues

Every organization needs a corporate AI policy. If you don’t have one, you need one. It should address acceptable and prohibited uses, what employees can and can’t do with confidential company information, and whether the AI tools you’re using are open-source (where inputs may become part of the public training corpus) or a walled-garden service where your data stays protected.  You also need to think about HR applications. Some jurisdictions restrict or regulate using AI to screen job applications, and discriminatory outcomes—even unintentional ones—can create legal exposure.  Most importantly: always have a human review AI output. Never assume it’s accurate. Look at how large corporations have structured their AI policies, borrow what’s useful, and consult an attorney.

Digital Strategist and Landmark Partner, Erica Glotfelty says AI is changing search

SEO is shifting. Previously, a Google search returned a list of links. Now there’s an AI overview at the top, and many users are going directly to platforms like ChatGPT or Claude to ask questions—“who sells billboards in Ocean City” rather than typing a keyword into a search bar. This changes not just where people find you, but how. They may get the answer they need from the AI overview without ever clicking through to your website.  What this means practically: everything you’ve been doing to rank in search is still valuable, but you need to add a new layer. Focus on findability and quotability. Create FAQ content that directly answers the questions your prospects are asking. Think about what information AI systems are likely to surface about your company and whether your website content supports that. The goal is to be the source that gets cited.

Mile Outdoor VP Marcus Danneil on introducing AI to Mile High Outdoor

I’ve broken our journey into phases.

Phase 1: The Search Engine Phase.

When you first start, you treat it like Google. You type a quick question, get an answer, and think “what’s the big deal?” You get stuck there for a while. But then you start experimenting—uploading something unexpected and seeing what comes back. Those “aha moments” are when you realize this is something fundamentally different from a search engine.

Phase 2: Using AI at Work

The natural entry point is writing. Cleaning up an email, breaking through writer’s block, drafting a document you’ve been putting off. Always review what comes back and add your own voice, but the efficiency gain is immediate.  A specific example: I was about to start lease negotiations with a major real estate developer in Denver. I drafted my email, then asked AI to rewrite it in the language of someone who works in his industry. It came back with something more credible and polished, and it launched the conversation on a much stronger footing.

Phase 3: Better Prompting

I read the book “Co-Intelligence” (probably outdated now, but valuable at the time), took an online course called Cursive, and watched YouTube tutorials. Getting educated on prompting changed everything.  Here’s the difference good prompting makes. My original lease comparison prompt was: “Please read this redlined lease and show me the differences between our original and the redline.” Basic, functional. After learning more, my prompt became: “You are John, a 30-year tenured in-house attorney who specializes in leases and billboard law. You work for a 20-person out-of-home company and are an expert in negotiation, especially when it comes to lease language. For the duration of this conversation, remain in this character. Review both leases, bullet-point all differences, and provide suggested language for all redlined conflicts so we can meet in the middle.” The output was dramatically more useful.

Phase 4: Agentic AI

I’ve been experimenting with agentic AI—systems that can think and act proactively on your behalf. I built one agent and uploaded our brand guidelines, asking it to specialize in putting together presentations that stay consistent with our fonts, colors, and style. It looked promising. But then I got nervous about how much system access I had granted it, and I deleted it. We’re approaching this carefully.