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After Taste, Pt 3: The 24-Month Window Is Real

Most Design Leaders Are Sleepwalking.

I want to ask you something directly.

Not as a thought experiment. Not as a conference panel discussion. As a genuine question for anyone leading a design organization right now.

What have you actually changed in the last six months?

Not what you've been reading about. Not what you've been tracking on LinkedIn. Not what you've bookmarked to engage with when things slow down. What have you actually done differently — in how you hire, how you structure your team, how you define the work, how you develop the people already in your organization?

For most design leaders, the honest answer is somewhere between experimenting and overwhelmed. The awareness is genuine. The curiosity is real. But the translation from awareness into structural change — in how the team is hired, developed, and organized — largely hasn't happened yet.

This piece is about why that gap matters — and why the window to close it is shorter than most people are acting like it is.

The Comfortable Position

The watching-and-waiting posture has a logic to it. It's not irrational.

The ambiguity around where AI is actually going is real. The tools are evolving fast enough that committing to a specific workflow or capability set today carries genuine risk of obsolescence in six months. The organizational friction of changing how a team works — rewriting job descriptions, redesigning processes, reskilling people who are already stretched — is significant. And the pressure to keep the current operation running, delivering on existing commitments, maintaining the team's output quality through a period of disruption, is not trivial.

Given all of that, watching and waiting feels professionally responsible. You're not ignoring the issue. You're being deliberate. You're waiting for the picture to clarify before making moves that are hard to reverse.

The problem is that this logic applies at every point in the transition. There will always be more ambiguity to resolve before it feels safe to commit. The picture will not clarify cleanly and completely before action is required. The leaders who waited for certainty before the last major platform shift didn't get certainty — they got irrelevance.

The 24-month window is not a prediction about when AI will mature. It is an observation about when the gap between teams that have adapted and teams that haven't will become organizationally decisive. That gap is already forming. By the time it's visible to everyone, it will already have been determining outcomes for some time.

What Sleepwalking Actually Looks Like

Sleepwalking doesn't look like ignorance. It looks like awareness without action — the state of knowing something is happening and continuing to behave as if it isn't.

Most design leaders are not unaware of AI's impact on the field. They are attending the conferences, reading the articles, having the conversations. The awareness is high. What is low is the translation of that awareness into structural change within their organizations.

The sleepwalking shows up in specific, recognizable patterns.

The hiring process hasn't changed. The job descriptions are still written for the T-shaped maker. The interview process is still portfolio-first. The evaluation criteria are still weighted toward execution-layer craft skills. The organization is still optimizing its hiring for a role that is being restructured by the same forces it's aware of but not responding to.

AI development is optional rather than structural. Teams are offered lunch-and-learns, tool demos, optional workshops. Individual designers are encouraged to explore AI tools on their own time. The organization signals awareness without creating accountability. The result is a bimodal distribution — the self-directed designers who engage deeply, and the majority who don't, with no systematic effort to close the gap.

The team's AI literacy is being assumed rather than developed. Most design leaders, when pressed, will admit they don't have a clear picture of where their team actually is in terms of AI capability. They assume the good people are figuring it out. They assume the gaps will surface if they become significant. This is an assumption that compounds quietly — and announces itself at exactly the wrong moment.

The organizational case for change hasn't been made. Design leaders who are waiting for permission or a mandate from above to change how their teams work are, in most cases, going to wait longer than the window allows. The organizations most likely to give that mandate are the ones that are already ahead. For everyone else, the case has to be made from below — which requires design leaders who are willing to drive change rather than wait for it.

The definition of the work hasn't been updated. The way design work is scoped, staffed, and evaluated in most organizations still reflects the assumptions of the pre-AI model. Projects are resourced as if the execution layer is entirely human. Timelines are set as if the tools available today are the same as the tools available two years ago. The organizational infrastructure around the work hasn't kept pace with the capabilities the work can now draw on.

None of these individually is a crisis. Together, they describe an organization that is falling behind on a trajectory that is not going to reverse.

Why the Window Is 24 Months

The 24-month framing is not arbitrary. It reflects a specific set of dynamics that are converging in a way that will make the gap between adapted and unadapted organizations impossible to ignore.

The first dynamic is capability acceleration. Figma is still Figma — the anchor of most design workflows hasn't changed. But the ecosystem around it has exploded. The number and capability of AI tools available to designers today is unrecognizable compared to 18 months ago. The toolbox has fundamentally expanded, even if the anchor is the same. Organizations building genuine fluency across this expanded ecosystem now are compounding that advantage with each new iteration. Organizations that aren't are compounding the deficit.

The second dynamic is talent stratification. The designers entering the workforce now were trained largely the same way designers have always been trained — the curricula haven't fundamentally changed. But they are entering a completely different environment than that training was designed to prepare them for. The senior designers who are actively repositioning are the ones developing the capabilities that will be increasingly rare and in demand: genuine orchestration fluency, curatorial speed, the ability to operate in the curation-orchestration-curation-presentation model. The organizations developing these capabilities internally will have a meaningful advantage. The ones that aren't will find the talent market for this profile increasingly competitive and expensive.

The third dynamic is client and stakeholder expectation. The speed and volume that AI-augmented design teams can produce is already changing what clients, product partners, and executive stakeholders expect from design. As more organizations operate at the new pace, the ones that don't will find their output looking slow by comparison. This is not a distant threat. It is already happening in pockets of the industry. Within 24 months it will be a broad expectation.

Together, these dynamics describe a window — a period in which early movers build compounding advantages while late movers accumulate compounding deficits. The window doesn't close all at once. But at some point, the gap becomes structurally difficult to close rather than just difficult. That point is closer than most organizations are behaving as if it is.

The Cost of Inaction

The cost of inaction in this context is not immediately visible, which is part of what makes it dangerous.

Teams that haven't adapted are still producing work. They are still meeting their commitments, still satisfying their stakeholders, still maintaining the appearance of a functioning design organization. The deficit accumulates below the surface — in velocity, in the volume of conceptual directions they can explore, in the number of people required to do the work — and in the talent that drifts toward organizations that offer more capable and interesting working environments.

By the time the cost of inaction becomes visible — by the time it shows up in a performance review, a budget conversation, or a talent crisis — it has already been building for months or years. The organizations that avoided it didn't do so by reacting when it became obvious. They did so by moving before it was.

There is also a compounding effect on the people in the organization. Designers who are not developing AI fluency are not standing still. They are falling behind relative to the field, relative to their peers, and relative to their own career trajectories. Design leaders who are not creating the conditions for their teams to develop these capabilities are, in effect, making a career development decision on their team's behalf — and not a good one.

What Moving Actually Looks Like

This is not a call to wholesale restructure a design organization overnight. Dramatic pivots made under pressure and without clear direction tend to produce confusion rather than progress.

Moving looks like a series of deliberate, incremental changes that accumulate in the right direction — and that are made with enough conviction to actually stick.

It looks like rewriting one job description to describe the role as it is becoming, not as it was. It looks like adding one evaluation moment to your interview process that is specifically designed to surface curatorial judgment rather than craft execution. It looks like having one honest conversation with your team about where AI fluency is expected to be in 12 months and what support is available to get there. It looks like running one project with an AI-augmented workflow and using what you learn to inform how you run the next one.

None of these is a transformation. Together, over 24 months, they are.

The design leaders who will look prescient at the end of this window are not the ones with the most sophisticated read on AI's trajectory. They are the ones who started making deliberate moves before they had complete information — because they understood that waiting for complete information is itself a choice, and not a neutral one.

A Direct Question

If you've read this far, you're not sleepwalking. Awareness is the starting point.

The question is what comes after awareness.

Not what you're planning to change. Not what you're considering. What you're actually going to do differently — this week, this month, in the next quarter — that reflects an honest engagement with what this moment requires.

That question is worth sitting with. The answer, whatever it is, is the beginning of a real response to what's coming.

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