EVENT

Workday Rising Keynote (September 2025)

Brown's September 2025 keynote at Workday Rising — where she introduced the concept of straddling the paradox of humanity and technology as the defining leadership challenge of the AI era.

Brown's September 2025 keynote at the Workday Rising conference represents one of her most direct public engagements with the AI transition. The keynote introduced the formulation that the future belongs to those who can straddle the paradox of humanity and technology — a framing that maps directly onto You On AI's refusal to resolve the question of whether AI is dangerous or wonderful in favor of the harder question of whether the user is worth amplifying. The talk was delivered to an audience of several thousand business and technology leaders and provided the first systematic statement of how Brown's vulnerability research applied to AI-specific leadership challenges. Its arguments were subsequently elaborated in her October Fortune summit remarks, her Aspen Ideas engagement, and the BetterUp research partnership announced in April 2026.

*Workday Rising Keynote (September 2025)*

In The You On AI Encyclopedia

The keynote's central claim — that paradoxical thinking is huge — framed the emotional challenge of the AI transition as fundamentally a test of ambiguity tolerance rather than a test of strategic analysis. Brown argued that the leaders who would navigate the transition successfully were not the leaders with the best AI strategy but the leaders with the best emotional infrastructure — the capacity to hold contradictory truths about the technology without collapsing into either triumphalism or catastrophism, the willingness to admit uncertainty while still making decisions, the practice of vulnerability as operational capability rather than personal disposition.

The talk's framing of AI as a seductive alternative to human vulnerability anticipated the more pointed formulation Brown would deliver at the Aspen Ideas Festival and the Fortune summit. The argument: AI does not force humans out of vulnerability; it offers them an exit. The machine provides confident answers. The machine does not judge. The machine does not require the emotional reciprocity human collaboration demands. Professionals afraid of being vulnerable find in AI not a threat but a relief. The exit is the deepest danger — not because the machines force the withdrawal but because they make the withdrawal less costly in the short term.

The keynote also introduced themes Brown would develop in the BetterUp research: that AI investment without corresponding investment in trust, development, and culture produces technical capabilities without the human infrastructure to make them operational. The billions flowing into AI tools will not pay off if the organizations deploying them have spent decades engineering out the vulnerability, trust, and courage the tools' effective use requires.

Origin

The keynote was delivered at Workday Rising on September 16, 2025, in Las Vegas. Brown's engagement with Workday on AI and organizational culture continued through subsequent research collaborations and informed the arguments of her October 2025 Fortune summit remarks.

Key Ideas

Paradox-straddling. The future belongs to those who can hold the contradictions of humanity and technology simultaneously.

Paradoxical thinking is huge. The emotional challenge of the transition is fundamentally a test of ambiguity tolerance.

AI as seductive exit. The technology offers a way out of human vulnerability that feels less costly than vulnerability in the short term.

Emotional infrastructure. The leadership challenge is emotional infrastructure, not strategic analysis.

Investment reframe. Technical AI investment without relational infrastructure investment produces capability without operational capacity.

In The You On AI Encyclopedia

Origin

Key Ideas

Related Entries

Further Reading