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How to Boss AI

Anna | How to Boss AI, Dallas Payne, Cristina

Exploring how we can lead and grow alongside AI without losing what makes us human.

Platform
Substack
PricingOnly free issuesPublishesWeekly
Issues17SubscribersRead howtobossai.substack.com

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Latest Issues

Recent posts by this newsletter. Browse the email archive.

A Call From The Future

When Dallas called me, it was Friday morning in New Zealand. Thursday evening in New York. She was already in tomorrow.

13 days ago
25
35

The Invisible Scale: What AI Revealed About the Rating System

I sat in a calibration meeting and watched a director argue that a woman on his team meets expectations. She’d outperformed her peers on every measurable metric that quarter. Her projects delivered before due date and client feedback was po...

20 days ago
35
32

I Watched a Business Plan Die in 5 Days

Few weeks ago I posted a note that hit a nerve. I wrote that in the current era, portfolios replace degrees, and careers become skill networks instead of linear paths.

25 days ago
26
13

My AI Isn’t My Boyfriend. It’s My Thought-Compost Bin

I didn’t fall in love with AI. I got tired of melting people’s nervous systems. My brain likes to go far. Fast. Loud. When I am spun up. Angry. Cluttered. Overthinking.

a month ago
32
30

Authors

The writers behind this newsletter.

  • Anna | How to Boss AI

    I help leaders navigate AI adoption from the human side: resistance, identity shifts, judgment under pressure. Advisor to founders and leadership teams who want clear thinking and honest questions about how AI is reshaping their orgs.

  • Dallas Payne

    Navigation training for an AI future. Building boats while sailing them. Making invisible expertise visible. Join the crew ⛵⚓

  • Cristina

    Equal Employment Opportunity Specialist and AI ethics writer | Helping leaders and everyday users navigate AI responsibly | Delivered training to 1K+ professionals | Building literacy for a safer, more human future.

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