🟣 The Questions Have Changed

The conversations I have with media CEOs have shifted over the last 18 months. The topics are different, and the anxiety underneath them has shifted too.

Some of that is predictable. AI changed the tenor of every industry conversation. But the more interesting shifts are quieter. They show up in what CEOs are asking about, not what they're reacting to. Here's what I'm hearing now that I wasn't hearing two years ago.

The word "audience" is being used more literally

In 2024, "audience" usually meant reach. Total unique visitors. Email list size. Social following. It was a scale metric dressed up in softer language.

In 2026, CEOs are starting to use the word more precisely. They want to know who their audience actually is — by segment, by behavior, by economic contribution. They're asking how many of those anonymous visitors are actually known. They're asking what percentage of their email list is engaged versus dormant. They're asking who shows up for the flagship newsletter versus the vertical newsletters, and whether those are the same people.

That's a different question than "how big is our audience." It's the question of an operator who has figured out that size without shape is not an asset.

Retention is showing up in CEO conversations for the first time

For most of the last decade, retention lived one or two levels down from the CEO. It was a CMO metric, or an audience ops metric, or a subscriptions team metric. The CEO asked about growth.

That's changing. More CEOs are asking about churn directly. They want to know the curve, not just the number. They want to know which cohorts disengage in the first 90 days versus the ones that stick for years. They want to know what the leading indicators look like before a subscriber cancels.

The shift makes sense. When acquisition gets harder — and it is getting harder, on every channel — every point of retention is worth more. CEOs who aren't personally tracking churn by cohort are flying blind on the single most important variable in their long-term economics. A growing number of them have figured that out.

The AI question has matured

In 2024, the AI question from CEOs was usually some version of "what tools should we buy" or "how are other media companies using this." Vendor-scanning questions.

In 2026, the question I hear more often is "what work should stay human." Which parts of the editorial operation should be explicitly protected. Which parts of the audience relationship should never be automated. What the brand loses if AI creeps into places it shouldn't.

That's a more mature question. The first version assumes AI is a tool you deploy. The second assumes AI is a force you manage.

Board-level conversations now include audience economics

This one surprised me. Two years ago, audience metrics rarely showed up in board packs outside of a marketing appendix. The board talked about revenue, margin, pipeline, maybe a high-level traffic number. Audience was a functional report, not a strategic one.

I'm now seeing audience show up as its own line of discussion. Engaged audience size. Revenue per engaged reader. Retention by cohort. Concentration risk — how much of the audience relationship depends on platforms the company doesn't own. Some of this is being driven by the fact that attribution itself is getting noisier, which is forcing boards to look at audience in more structural terms than they used to.

The CEOs driving this aren't doing it because a consultant told them to. They're doing it because they figured out that their valuation conversation, their capital allocation conversation, and their M&A conversation all need this language. The board members who matter are asking for it.

Nobody is talking about pivots to video anymore

Mostly a joke, but only mostly. The era of strategic pivots driven by platform algorithm changes is fading. CEOs have been burned enough times — by Facebook referral traffic, by pivot-to-video, by Google algorithm shifts — that platform-dependent strategy is out of fashion in the conversations I'm having.

What's replacing it is a more durable question: what can we build that doesn't depend on a platform we don't control. Owned distribution. Direct audience relationships. First-party data. The language is less exciting. The underlying business is more defensible.

The pattern across all five shifts is the same. The industry conversation is maturing faster than the industry's operating models are. CEOs are asking better questions than their reporting systems can answer. They know their audience is more valuable than their dashboards suggest, but they don't yet have the instrumentation to prove it.

That gap is where the next few years of advantage gets built. Not in another tool, another channel, another pivot. In finally building the operating picture that lets a CEO talk about their audience the way they talk about the rest of the business — specifically, economically, and with the math to back it up.