how to boss AI | Substack

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And why AI Adoption is about letting your ego die

Mar 30 • Anna | how to boss AI and Dylan Oh

An Honest Conversation About the Workplace and the Future

Watch now | A recording from Anna | how to boss AI and Peter Benei's live video

Mar 26 • Anna | how to boss AI and Peter Benei

53:20

Patriarchal and Matriarchal Leadership

How organizations reward one kind of leadership, run on another, and call it a culture problem

Mar 24 • Anna | how to boss AI

There’s Nothing Left In The Tank

And AI Hasn’t Even Started Yet

Mar 19 • Anna | how to boss AI

Live from the Wellness Barricade

On barricades, AI races, and the cost of staying sane

Mar 15 • Anna | how to boss AI

The AI Education Industrial Complex

We are entering a 'second wave' of AI de-programming. This is slowly showing up as people become more familiar with the tools and realize that 'viral…

Mar 10 • Anna | how to boss AI

What AI Requires From Leadership and Organizations

Watch now | Cappuccino & Connections Live with Maribeth & Anna

Mar 7 • Anna | how to boss AI and Maribeth Martorana

34:16

The Builder Who Stopped Waiting for Permission

A conversation about shedding armor, getting messy, and why dreaming is free

Mar 5 • Anna | how to boss AI and Elena | AI Product Leader

The Linguistics Lounge - Let's Talk About Accents

Watch now (54 mins) | Thank you Jen Benford, Hodman Murad, Emma Klint, Chief Absurdist Officer, JJ, and many others for tuning into my live video with…

Mar 2 • Anna | how to boss AI, The Strategic Linguist, and Cristina

53:50

February 2026

The AI Readiness Live: Key Takeaways

Watch now (36 mins) | A recording from Anna | how to boss AI and Joel Salinas's live video

Feb 27 • Anna | how to boss AI and Joel Salinas

37:14

Something Big Is Happening. Now What?

And the Panic Is the Wrong Response

Feb 20 • Anna | how to boss AI

A Call From The Future

A conversation with Dallas Payne

Feb 13 • Anna | how to boss AI and Dallas Payne

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