Digital Trends: 05.15.26

Hi all, hope my Canadian readers enjoyed a sunny long weekend.

This time of year is sort of funny. Maybe it’s a Toronto thing. Since the end of February, I’ve had about a dozen people I’ve been emailing with who all sign off the same way: let’s wait for patio season and have a proper catch-up. Well friends, that time has come. Looking forward to some patio drinks. And if you’d like to connect on a patio soon, reach out.

In the spirit of learning about AI together, I’ve got another short video for you. My goal is to keep making these badly enough that you can tell there’s no AI avatar involved. This one’s about a small aha moment: I realized just how many different things I can start building web apps for using vibe-coding. Here’s a quick demo of something little I made in the video below.

As I mention in the video, here are a few folks that share helpful resources on vibe-coding: Futurepedia, Jeff Su, Nate Herk.

AI & Search Marketing

It’s pretty amazing how quickly people have adopted AI for researching products and services. Our familiarity with Google, plus the fact that AI chat looks so similar from a UX perspective, has likely fuelled this. New research shows 44% of online buyers now start their journey in an LLM or split between AI tools and traditional search, and that number skews higher among younger cohorts. That AI-generated traffic is also doing more once it lands: in March 2026, it converted 42% better than other sources, a sharp reversal from March 2025 when it converted 38% worse. Is AI-generated traffic more valuable?

Marketers are responding. Many are leaning into AEO, making sure their sites are LLM-readable, and developing AI-native content. Mondelez has shared how they are making this a priority. For those who want to make sure they show up in AI search, OpenAI just launched a self-serve ad platform. Free users of ChatGPT have started seeing display ads on relevant queries this past week (below is one that served to me on a search for hotels in Toronto). A lot of the lead-up framed this as a hit to unbiased AI results, but seeing it in the wild, it feels close to the search experience we are used to. Not too disruptive. Will be interesting to see how it well it performs.

AI & Work

Microsoft released a new report on how AI is reshaping work that’s worth a skim. What stood out to me was the role of culture and managers in driving adoption. When managers actively modelled AI use, employees reported a 17-point lift in AI value. When managers created psychological safety around experimentation, that jumped to 20-points. A good reminder that it’s not just about individual training.

The workforce impact continues to play out in different ways. Some tech leaders are using AI to be almost omnipresent: Mark Zuckerberg is reportedly building a digital avatar of himself for employees to access. This article looks at the downstream effects when a manager seems to trust AI more than their team – a new blind spot for many leaders.

The workforce itself is shifting too. Employers can be skeptical of how reliant AI-native new hires are, but those who help an organization figure out practical AI use can be really valuable. I think about this a lot: if you’re a young person trying to break into a company, being able to explain and navigate AI within teams in a smart, clear, and inclusive way will make you super-valuable to an employer.

And what will the office even sound like as more of us use voice-to-text? Alone in a closed office it works great. But what happens when everyone stops typing and starts talking? If you’re keen to trial voice-to-text, I recommend giving Wispr Flow a try.

Cool Beans

  • Break Mode: I know it’s a bit of agency award-bait, but I love this concept from Ogilvy: a special edition KitKat packaging that puts your phone into a smartphone jail so you can truly have a break.