[TMA] Skepticism, not cynicism, in this liminal moment

Last week, Jack Dorsey announced that his company Block will be laying off 40% of its workforce, from 10,000 to 6,000, with the rationale:

...something has changed. we're already seeing that... intelligence tools... paired with smaller and flatter teams, are enabling a new way of working which fundamentally changes what it means to build and run a company. and that's accelerating rapidly.

Anything so drastic incurs response, and what I've seen has varied quite wildly. Pavel's latest newsletter claims AI is a smokescreen, with many links that show Dorsey is motivated simply by cost reduction and profit maximizing.

Judd Antin relates that he's heard how Dorsey is a dumpster fire as a leader,"Propping up a business stuck in neutral by firing 40% and blaming AI is a trick."

These takes have merit. But explaining away the AI claim strikes me as premature. As Hang shares,

From what I’ve heard, Block has built some of the best AI design ops tooling and processes in the market. These are the folks who I’d actually consider to be ‘AI-first’ and ‘AI-native’. While many others over-exaggerate the RoI of AI usage, I do believe Block has made it work. 

Even if Dorsey is behaving in some bad faith, the underlying premise, that AI-enabled teams can produce more with fewer people, is becoming credible.

Stories are emerging of how product development teams are evolving as they embrace these tools. I'm grateful for Z, Design Operations Lead at Cloudflare, sharing real data from how these teams are behaving:

Data from my own organization:

📊 50 people accessed Figma last Tuesday

→ Only 4 were UX designers

→ The rest: PMs and marketers

🔧 All 30+ designers now have dev environments

And her takeaways:

✅ For practitioners: This is the best time to be a practitioner. You can think and build across the stack. Contribute wherever you see gaps. The artificial boundaries are gone.

⚠️ For leaders: Disorientation. Traditional org structures don’t map to the work anymore. How do you maintain clarity and quality when everyone does everything?

Z's comment put me in mind of Stanley McChrystal's seminal book Team of Teams, which I coincidentally cited a week ago in the first episode of LIMINAL. McChrystal's core argument is that in a networked, fast-moving, chaotic environment, the traditional leader—the confident decision-maker at the top of a hierarchy—becomes a liability. Information moves too fast, context is too distributed, and decisions need to happen where the work is actually occurring. The leader's job evolves into: enabling, connecting, informing, creating the conditions under which teams can make good decisions without waiting for permission.

Z has been sharing her teams' experiences, providing uncommon insight into how organizations can adopt these new ways of working. Start here and then read forward to learn how Cloudflare's design org has largely moved off of Figma and designing in code.

[Side note: Are others sharing such details of their transformations? If so, please let me know.]

And while it can feel like things are moving awfully quickly, companies like Block and Cloudflare are outliers on the far early end of the adoption curve. Consider legacy enterprises still running SAFe, still toiling in feature factories—after a decade of evidence that these approaches undermine the work they're meant to support. If they can't shift into superior development practices, the odds of them effectively embracing an acceleration layer like AI are not good.

A couple weeks ago, I posted how there are many possible futures. I'm probing liminality because we're in the middle of something that we don't know where it leads. Jesse and I dropped the second episode of LIMINAL this past weekend (Apple, Spotify, any podcatcher, website), as we continue to mull what it takes to navigate and maintain resilience during these uncertain times.

We discussed how a non-negotiable for any leaders is to maintain positivity. This isn't toxic positivity, wearing rose-colored glasses and ignoring the very real challenges your teams are facing. But it is optimism, a belief that there are better ways forward.

What this past weekend's reading has brought to mind, is that leaders need to avoid cynicism. In a liminal moment, where we don't know where we're heading, cynicism proves regressive, smugly refusing the shifting context. It's reminiscent of Thomas Kuhn's The Structure of Scientific Revolutions, where an explanatory model becomes reified as a belief system, resistant to accepting new approaches and evidence. The cynical takes on Block have some of that quality.

Leading through liminality requires curiosity, healthy skepticism, and pragmatism. A desire to experiment, learn, discern, and iterate. To meet the moment where it is, not where you want it to be. A willingness to call bullshit on evident snake oil, but also to embrace that which moves things forward.

What I ask is, like Z, please share your stories, so that we can all learn from each other.

[Plug] Helping through this liminal moment

The discombobulation of these uncertain times leaves teams struggling to know where to best put their action. I help teams and their leaders regain clarity, driving shared understanding, shared principles, and rebuilding trust. If this can be of service to you, don't hesitate to reach out.