Grading my own 2018 predictions about AI assistants

Synthetic users and AI personas came up as something In October 2018, fresh from hosting the Emerging Tech track at the Boye conference, I wrote a post on this blog about how AI assistants would change business. Assistants, at the time, could set a timer and mispronounce your calendar. Writing about them reshaping commerce felt slightly reckless.

Eight years is long enough. Most predictions die politely - nobody checks them, including their authors. I'd rather grade mine in public, because the pattern of what held and what didn't turns out to be more useful than any of the individual claims.

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Sesimi wins CMS Idol by solving the last mile of content

Creating content is only part of the challenge. The harder part for many organisations is turning content, data and assets into the banners, advertisements and videos needed across a distributed network, without losing control of the brand along the way.

That was the practical problem at the centre of the winning CMS Idol demonstration at CMS Connect 26 in Montréal last month.

It was the first time that Sesimi, an Australian platform for brand management and content automation, had joined the conference. Michael Thompson represented the company in a demanding format: six minutes, a working product and no slides to hide behind. Using the example of a car dealer, he showed Sesimi generating banners, social media advertisements and video while maintaining control of approved assets, templates and brand requirements.

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Some Conversations Only Happen When We Show Up

Some conversations only happen when we show up

This week, I stayed home while our team brought the community together in Bjerringbro, Boston and Toronto.

Matthew Garrepy led our digital leaders and CMS experts in a charming Boston art gallery. Julian Mills brought employee experience leaders together in Toronto, while Peter Dahlstrøm Andersen visited the Grundfos headquarters with our UX researchers.

This was quite a change for me. I have spent this week of September in Boston for more than a decade, without missing a year or a bowl of clam chowder.

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To label or not? AI-generated content and the EU AI Act

AI is already part of many content workflows. The harder question is whether, where and how its involvement should be disclosed.

New transparency requirements under the EU AI Act have prompted strong reactions, new tools and plenty of uncertainty. The rules are narrower than some headlines suggest, while important practical questions remain unresolved: Should the label apply to a paragraph, a page or an entire website? What about translated or AI-assisted content? And when is human editorial oversight enough?

By the time we meet, the initial turbulence may have settled a little. This member call is an opportunity to look at what has become clearer, what remains uncertain and what content teams can sensibly do without overreacting or waiting for perfect guidance.

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Where Art Meets AI: Inside Boston's CMS Experts & Digital Leaders Meeting

Boston has always been a beacon for creativity and innovation, and that undeniable spirit is thriving in the SoWa Art + Design District. It was the perfect backdrop for our recent Boye & Company CMS Experts & Digital Leaders meeting, which was held at the charmingly eclectic New England Art Center.

Surrounded by a vibrant pastiche of paintings and sculpture, we hosted a diverse group of leading minds in the content management and digital experience field, where we discussed the continued impact of AI on every aspect of our work.

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The memory you need to build for AI

AI works well when it understands the context in which it is operating. Yet much of that context has never been written down.

Systems carry years of decisions, exceptions and compromises that may look like mistakes to anyone—or any AI—without access to their history. The obvious correction can easily break something that was done deliberately.

Before CMS Connect 26 in Montréal, Andrei Kalamkarov wrote about the memory he was building for AI. His conversations at the conference expanded that thinking: perhaps this is not only about helping an AI work with one system, but about preserving institutional memory more broadly.

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Does AI make content modelling more important?

Do we still need websites in the age of AI? That was one of the more provocative questions raised during the latest Benelux Digital Leaders Peer Group, organised by Boye & Co and hosted at Crossphase Presenter in Leiden on 27 August 2026. It was also only one of many.

Around the table were digital leaders, agency owners, content specialists, platform experts and people responsible for some complex digital environments. The afternoon moved from a mid-year reality check on AI and the CMS market to changing content roles, the state of content modelling, and the practical challenge of deciding what comes after a fragmented CMS landscape. Tridion came up often enough during the introductions to trigger a few shared memories, and judging by Janus Boye’s reaction, possibly a few flashbacks too.

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The Ghost in the Content Tree

You go to edit a page. The CMS stops you politely: this item is locked by jsmith. You check. jsmith left the company in 2022. 

If you have run an enterprise CMS for any length of time, you have met a ghost like this. A lock with no owner, holding a piece of content hostage, left behind by someone who is no longer here. It is a small thing. It is also more revealing than it looks.

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The joy is in the making

Back before AI filters could turn any photo into a sketch, I was pretty handy with a pencil or a piece of charcoal.

In high school, I had a penchant for figure drawing, and spent many hours trying to capture ephemeral poses with live models in studio classes. I won a few awards for it, actually - and carried that love of gestural creation into college.

Of course, not long after, I succumbed to the internet bug, trading in paper for pixels, carbon for code. I had a fine arts concentration and even produced a thesis portfolio show, but eventually my brushes took a back seat to the zeroes and ones.

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San Francisco Digital Leaders: Cracking the Code on AEO

CMS Critic was on the scene in San Francisco for some deep learning, and the human algorithm was front and center.

I was fortunate to facilitate a lively conversation with a diverse set of minds from across the industry as we explored the AI frontier. Meeting in person like this always leads us down unexpected corridors, and that’s exactly what happened at yesterday’s Boye & Company West Coast Digital Leaders group.

AEO was the central throughline, and for good reason: every brand and business is aiming to influence the answer engines, and I’ve been carefully following many vendors in the CMS and DX space as they launch new offerings.

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Inside CMS Connect 26: AI, Content, and What Comes Next

Maybe there was a fly in the AI, but the first day of the Boye & Company CMS Connect 2026 conference was anything but buggy.

I had the honor of kicking off the third annual edition of our summer event in the ever-charming foothills of Montreal, where I shared some of the patterns surfacing in my coverage on CMS Critic.

Jeff Goldblum’s classic sci-fi film “The Fly” served as my thematic backdrop, reflecting the unforeseen consequences as agentic AI mutates everything. But that was just the beginning, and this assemblage of digital explorers was treated to some powerful presentations throughout the day.

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Why don’t people say anything real?

In Elizabeth Strout’s new novel The Things We Never Say, the teacher Artie asks a memorable question that has stayed with me over the past few months:

“I wonder why people never say anything real.”

Later, he comes to understand that “it was a private thing to be alive”.

There is something recognisable in the distance between those two observations. Much of what matters inside an organisation remains private, even when many people are experiencing the same uncertainty. Difficult decisions are presented as settled. Experiments become success stories. Doubts are removed before the work is shared.

Perhaps that is why the most useful professional conversations rarely begin with polished answers. They begin when someone says something real about what is working, what is difficult and what they still do not understand.

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Structured content management in the AI era

Most organisations have spent years creating knowledge. The challenge today isn't simply producing more content, but making sure people can find it, understand it and, increasingly that AI systems can too.

The way content is structured has become just as important as the words themselves. Whether you're publishing knowledge base articles, press releases, documentation or blog posts, clear structure makes information easier to navigate, easier to maintain, and far more useful for both human readers and machines.

Zoltán is co-founder at Lombiq Technologies and an open-source maintainer

In this member call, we'll explore practical approaches to structured content management in the AI era. We'll look at how to identify recurring patterns across documents, formalise them where it makes sense, and build content that is easier to reuse, maintain and discover.

The call is hosted by Zoltán Lehóczky, co-founder and managing director of Lombiq…

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No developer, no problem

Building digital products has changed dramatically.

For years, bringing an idea to life meant assembling a team, securing a budget, and committing months of development. Today, AI and modern no-code tools have lowered many of those barriers. Yet many great ideas still never make it beyond the planning stage.

This raises an interesting question: if technology is becoming easier, what actually determines whether a product gets built?

Karla Fernandes is a product designer and educator with 25+ years of experience building digital products.

In this member call, we'll be joined by Karla Fernandes who will explore how product thinking, design judgement, and rapid experimentation are changing the way digital products are created. Rather than focusing on the latest AI tools, we'll look at the mindset behind designing, building, shipping, and continuously improving products in a world where one person can accomplish what once required an entire team.

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AI Engineering Maturity: What 1,300 Engineers Told Us About How They Really Work with AI

Earlier this year I wrote about the AI Engineering Maturity Model — a five-level framework for understanding how engineers actually work with AI, from ad-hoc chatbot use all the way through to bounded autonomous workflows. This post is the first set of results.

We all feel that the use of AI in software engineering will be transformative, and there are a lot of enthusiastic evangelists around. Going behind the hype reveals a much more mixed picture of adoption. My goal was to get behind the great anecdotes and get an honest, org-wide picture of how engineers are really using these new tools.

For those who haven’t seen the original post: the AIMM is a five-level maturity scale scored from 1.0 to 4.0. L1 (Explorer) is where engineers are experimenting individually with AI tools. L2 (Tool Adopter) is active, habitual use — IDE plugins installed, regular AI interaction — but practice is still individual.

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