On Culture: Leading Without Illusions

Myste Wylde
Aug 15, 2025
7 min read

Dear Culturati Insider,

If you think of artificial intelligence as a mind, you will misuse it. If you think it cannot change yours, you will miss its value. The most effective leaders hold both truths. In last week’s Culturati: LIVE, Geoff Woods showed us how generative AI can be a disciplined thought partner, sharpening judgment, clarifying strategy, and unlocking growth using the CRIT framework: context, role, interview, task.

Separately, our co-founder Josh Jones-Dilworth shared Adam Mastrioanni’s "Bag of Words, Have Mercy on Us", which he called “the best writing about AI all year.” It dismantles the illusion that large language models think like we do. These views are not in tension, but rather depend on each other. To use AI as a true thinking partner, you must first understand that it does not operate like a mind with context from lived experience, personal judgement, and intent, but as a sophisticated prediction engine.

That distinction matters. If you treat AI like it “thinks” or “understands” as we do, you risk trusting it in ways you shouldn’t. If you see it as a prediction engine (software that generates the most statistically likely sequence of words from its training data) you stay grounded. It doesn’t know anything in the human sense, but it can still offer new insights and connections that challenge and extend our thinking. Knowing its limits is what lets you get the most from it, expanding human insight without surrendering human judgment.

That same ability to balance potential and limits applies beyond AI. Inside organizations, proximity and visibility are still mistaken for being productive. Research shows that the real driver of trust and engagement is psychological closeness, how connected people feel to one another. When that is missing, we may see its shadow side: clock botching, where people are physically present but mentally absent. Leaders who normalize mental health discussions, encourage real time off, and connect work to purpose improve morale and protect performance.

Outside the organization, value creation is changing form. The Trumpcoin phenomenon ($60B -> in 36 hours -> from attention) signals that narrative alone can generate capital, power, and influence in a self-reinforcing loop. For younger generations navigating economic uncertainty and AI disruption, this shift has split career strategies, with some choosing stable trades and others gambling on exponential digital wins.

To succeed in this environment, it might be wise to evaluate any illusions harbored around AI, productivity, and where value is created and redesign both culture and systems accordingly. Interpretive AI, able to translate messy, unstructured inputs into consistent, actionable data, is one example of that. While it may not make headlines like generative and agentic AI, behind the scenes it can make a measurable impact. In large organizations, where teams and systems are spread across functions and geographies, those gains can add up to 20-40% higher productivity. The leaders most likely to get work right these days will see the system clearly, name what others avoid, and act with conviction and integrity.

To truth & clarity,

Myste Wylde, COO

Psychological Closeness: The New KPI For Remote Leaders

Forbes

By Alain Hunkins

Summary: RTO mandates may be stalling and with 25% of workdays still remote, physical presence isn't proxy for productivity. Research from Durham University shows that psychological closeness, the felt sense of connection between leader and team, drives trust, engagement, and discretionary effort. Leaders who pair empathy with a clear strategic vision close the perceived distance that erodes motivation, creativity, and retention. Leaders can track it through targeted pulse questions like, "Do you feel supported by me? Do you feel informed about priorities? Do you feel you can reach me when needed?" and then act visibly on what they hear.

READ ARTICLE IN FULL

How to Fight Clock Botching, the Latest Threat to Productivity

Inc.

By Kit Eaton

Summary: Clock botching, a more active form of presenteeism, happens when employees are physically at work but mentally checked out due to burnout, disconnection, or lack of purpose. Presenteeism is being at work but underperforming due to illness or fatigue, while taskmasking is the deliberate performance of visible “busy work” to appear productive. Unlike taskmasking, which can reflect job investment, clock botching signals deeper morale and mental health issues that quietly drain productivity. Founder Guy Thornton warns it often stems from cultures that reward visibility over output, leaving employees stretching basic tasks all day while disengaging from meaningful work. Leaders can counter this by normalizing mental health discussions, encouraging real time off, and ensuring workloads and roles connect to purpose. Research shows every dollar invested in mental health can yield a 5x return through higher retention, lower absenteeism, and fewer errors.

READ ARTICLE IN FULL

The Attention Economy and Young People

No Mercy/No Malice

By Kyla Scanlon

Summary: Young people are navigating a “Great Uncertainty” shaped by AI-driven disruption, political and economic instability, and a collapsing link between traditional careers and security. The Trumpcoin flash ($60B in paper wealth created in 36 hours purely through attention) signaled a cultural tipping point where narrative now creates value, wealth, and power in a self-reinforcing loop. Four forces drive it: privatized and profit-optimized digital infrastructure, algorithms built for engagement over knowledge, brainrot from short-form content, and a generational gap in digital fluency. With 59% of under-30 adults using TikTok and wealth concentrated in older generations (72.9% held by over-55s), younger workers are splitting into a “barbell economy” of stability-seeking tradespeople and high-risk digital gamblers. For leaders, the takeaway is twofold: rethink value creation when attention is the currency, and invest in digital literacy, mental adaptability, and platform reform to prepare talent for an economy where exponential outcomes, not linear careers, increasingly define success.

READ ARTICLE IN FULL

Bag of Words, Have Mercy On Us

Experimental History

By Adam Mastroianni

Summary: Arguably our biggest mistake with AI is how we understand it. We default to treating large language models like people, applying human psychology and social status games to something that is simply a “bag of words” predicting the most relevant text it can find. This framing explains why AI can excel at some tasks, fail spectacularly at others, and never truly “think.” For leaders, the cultural risk is that anthropomorphizing AI fuels misplaced trust, inflated expectations, and poor decisions. A better metaphor keeps AI in its proper role: a tool to automate, scale, and assist, not a mind to defer to. Building a culture around this clarity means training teams to question outputs, know the limits of the bag, and focus human energy on the creative, irrational leaps machines cannot make.

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What Comes After Agentic AI? This Powerful New Technology Will Change Everything

Fast Company

By John Lester

Summary: Interpretive AI is the under-the-radar breakthrough with the biggest potential to reshape enterprise work. Unlike generative or agentic AI, which often deliver variable outputs, interpretive AI can take messy, unstructured inputs (think conversations, reports, legacy code) and translate them into consistent, actionable data at scale. Early deployments in healthcare, insurance, and project management point to 20-40% productivity gains for the half of GDP driven by large corporations. The payoff comes from replacing slow, costly coordination and oversight with automated, predictable processing. Leaders can capitalize on this by moving beyond novelty use cases, building cross-functional adoption strategies, and rewiring work culture.

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In this interactive session, Geoff Woods, author of The AI Driven Leader, shared a transformative approach to using AI as a strategic partner. He reintroduced the CRIT framework (Context, Role, Interview, Task) as a powerful method for prompting AI to ask the right questions, enabling leaders to think more clearly, creatively, and effectively. Through real-world examples, including resolving board tensions and reimagining impossible revenue goals, Geoff demonstrated how AI can unlock growth, accelerate execution, and align strategy across organizations. The session challenged common assumptions, urging leaders to stop delegating AI adoption to IT and instead lead from the top focusing on enterprise value. Participants left with tangible tools, a shift in mindset, and a renewed sense of how to harness AI not to replace human insight, but to enhance it.

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