While you’re here, my column yesterday re Jack Dorsey’s attempt to move the goalposts on how aggressive you can get about AI and jobs.
time.com/charter/7382...
04.03.2026 02:43
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While you’re here, my column yesterday re Jack Dorsey’s attempt to move the goalposts on how aggressive you can get about AI and jobs.
time.com/charter/7382...
If you're falling into the hype cycle but not using the tools, you not only risk getting it wrong, you're telling your team (yet again) "do what I say, not what I do."
My column today in TIME:
time.com/charter/7382...
69% of c-suite leaders are using AI less than an hour a week. 28% of them don't use it at all: zero, zilch, nada.
At the same time, 50% of CEOs say they fear for their jobs if they don't make progress on leveraging AI in 2026.
All hype, little lived experience.
This is a restructuring play, not a universal AI productivity playbook.
Shades of Twitter, where when Jack was CEO “absent” was the word most often used to describe him and he took the blame for bloated headcount.
Where do you think this goes next?
My column in TIME:
time.com/charter/7382...
It’s about shifting the Overton Window.
Jack’s also got other motives. He’s selling AI-enabled tech products to businesses. As their web site puts it, “The next era of computing will run itself.”
Block also is 2X larger in 2025 than it was in 2020, while the stock had dropped 75% in the same period.
Jack Dorsey is trying to move the goal posts on AI and layoffs.
Block’s 40% cut in staffing is likely to inspire other leaders to follow suit, just not as extreme.
Like Elon’s 80% cut at Twitter inspired 10-20% cuts and Andy Jassy’s demand for 5 days in office led to 3 day demands in most of tech.
Not to mention a return to normalcy on trade deals that aren't negotiated based on whims and applied based on who transits the White House with the best golden statue.
What happens next with tariff rollbacks and other efforts by Trump to replace them, only time will tell.
But given the US economic growth in 2025 was almost entirely dependent on AI-related spending, it would be excellent news to see a boon outside of tech.
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Tariffs didn’t reduce the trade deficit (~$900b in '25, same as '24). Manufacturing jobs continued to shrink in '25.
They put a regressive tax on consumers and created not just challenges but massive uncertainty for businesses, which resulted in a weaker economy and weaker job market.
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Bad news: US economy only grew 1.4% in Q4.
Good news: Supreme Court has (finally) determined that President Trump's tariffs weren't legally imposed
That's a win for consumers: the Federal Reserve found that "nearly 90 percent of the tariffs’ economic burden fell on U.S. firms and consumers.”
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"The bottleneck isn’t tech. It’s everything around it: organizational change, complexity of real-world jobs, new work AI creates, regulatory friction that slows adoption. ..Pace of disruption will be set by the slowest-moving force, not the fastest. Every year counts for workers’ ability to adapt."
Grappling with fear vs hope on AI's impact on jobs?
Start with a dose of reality: Jacob Clemente digs into Matt Shumer's essay for the @sfstandard.com
sfstandard.com/2026/02/14/a...
Interested in hearing from more leaders grappling with #AI? Check out Charter’s Leading with AI Summits.
→ Tuesday Feb 10th, #NYC and online
→ Tuesday Feb 4th, #SF and online
Virtual registration is still open for Feb 10th, and it’s FREE:
www.charterworks.com/events/ai-su...
Brandon Sammut at Zapier: “We’re at 97% adoption. We might be 10% of the way there” on transformation.
Leaders are grappling with the messy middle of AI: usage is not results.
More often than not, stress being applied from top to bottom, making change harder:
www.charterworks.com/the-ai-chall...
Do we need managers?
Foursquare redesigned to focus on team performance. No more eng manager titles, strong tech leads, team coaching and systems for perf and career dev.
Will it work? Will it scale? Let me know what you think.
In today’s @sfstandard.com:
sfstandard.com/2026/02/03/f...
“Speak out, [and] you are quite likely to get retaliation from the government. If you don’t, you are going to really lose trust with your customers and employees.”
The cost of silence is going up. Leaders finally, tentatively, start to find their voices.
www.charterworks.com/how-to-respo...
Some of both? I think it’s the SF zeitgeist in AI startups at the moment.
Personally not a fan…
In the dotcom era, the influx of banker bro types into tech was followed by the bubble bursting. B2B became "Back to Banking," B2C was "Back to Consulting"
Will the modern tech bros usher in AGI and the last-ever gold rush, or will we get B2B 2.0?
@sfstandard.com
sfstandard.com/2025/09/29/t...?
Giving someone a meditation app to help with burnout is like treating a third-degree burn with a bandaid.
What works? Learn to recognize the signs, clear priorities, and opportunities to grow -- not just taking breaks.
👉 sloanreview.mit.edu/article/the-...
Image credit @omarwhatworks.bsky.social
Just a reminder of how hard Trump had to work to mess up this economy.
It’s not AI-driven automation that’s killing the job market, it’s tariffs and uncertainty.
The big hope of Big Tech is to compound it by cranking up AI-driven losses.
Otherwise, an economy propped up by AI investment collapses.
We are so screwed.
open.substack.com/pub/theworkf...
Why do women have a far greater preference for remote and hybrid work than men? It’s not just that they’re far more often the primary caregiver.
It’s that bias and discrimination are twice as likely to happen to a woman on-site than working remotely.
theworkforward.substack.com/p/return-to-...
Stack ranking and removing the bottom XX% is back in vogue, esp in Big Tech.
As a reminder, here's the org chart that resulted in at Microsoft in the 2000's: internal competition.
Research on why it backfires long term, and alternative paths:
theworkforward.substack.com/p/stop-ranki...
The best leaders embrace being uncomfortable. They know that challenges that test us today become our biggest accomplishments tomorrow -- that's how we learn and grow.
My interview with Izabella Lorenz:
theworkforward.substack.com/p/learning-w...
Leaders demanding more output (code, emails, content) without understanding how AI actually works or investing in proper implementation.
The drive for efficiency squeezing out all time for human connection - leaving users alone with their bot “coworkers.”
theworkforward.substack.com/p/when-chatg...
It's not the tools; leaders must:
1. Invest in training; 5-10 hours brings adoption from 18% to 82%
2. Leaders have to roll up their sleeves. Engaged leaders drive 2X higher adoption.
3. Focus on outcomes, not outputs. Carve out time for connection.
theworkforward.substack.com/p/when-chatg...
Average percentage of time spent per activity among developer tasks -- shows less time coding, more time on other activities including new ones like prompting, reviewing and waiting on AI
Those perceptions of productivity gains might not be real: recent research found developers estimated they were 20% more productive using AI tools, when they were actually 19% slower.
Five major studies on AI adoption recently dropped. The findings are insightful & alarming.
The employees getting the biggest productivity gains are also 2X more likely to quit, with 88% higher burnout rates.
Even scarier? Heavy AI users say they'd rather chat with ChatGPT than their colleagues.
If we invested half the energy spent debating office attendance into fixing how we spend our time, we'd have higher productivity – and lower burnout.
We keep stumbling into packed calendars and ending weeks frustrated.
Want to do something about it?
theworkforward.substack.com/p/the-meetin...
The CEOs who are AI arms merchants aren't the only ones telling employees to adopt or else, but they're certainly the loudest.
Thanks @emilypeck.bsky.social for talking to me about your latest:
www.axios.com/2025/06/20/a...