Shalene Gupta, Editor, Fast Company: The Manager's AI Survival Guide episode artwork

EPISODE · May 29, 2026 · 18 MIN

Shalene Gupta, Editor, Fast Company: The Manager's AI Survival Guide

from Stumbling Blocks: How Great Leaders Are Made · host Jonathan Block

Shalene Gupta, staff editor for Fast Company's Work Life and Leadership section, interviewed 35 middle managers at some of the biggest companies in the world for her piece "The Middle Manager's AI Survival Guide." What she found is that the contradictory headlines about AI at work aren't actually contradictory. There are two different worlds, and which one you're working in makes a world of difference.One idea sits under all of it, and it matches what I find in my own work. People will walk through almost any change, AI included, when they trust that their leader has their back.In this episode:0:00:00 The question every manager is asking0:01:20 The one-line takeaway from the AI Survival Guide0:02:30 Two universes: the AI race vs. where most of us work0:04:53 Ethan at Meta: "If you think they'll replace you, they probably will"0:06:07 The math: a person vs. $200 to $500 a month in tokens0:07:36 ClickUp's "100x more productive" memo0:08:40 Are we weighing the human cost? (Dimon at Davos)0:09:49 What it feels like to be a middle manager today0:11:48 What the excited managers had in common (and a Georgia-Pacific surprise)0:14:10 Advice for leaders taking teams through AI0:16:26 Advice for the rest of us0:17:07 My takeaway, and a look at next weekLinks:"The Middle Manager's AI Survival Guide" (Fast Company): https://www.fastcompany.com/91531056/the-middle-managers-ai-survival-guideThe Power of Trust, by Sandra Sucher and Shalene Gupta: https://amzn.to/4xdcxUKThe Cycle, by Shalene Gupta: https://www.amazon.com/Cycle-Confronting-Pain-Periods-PMDD/dp/1250882893Shalene Gupta: https://shalenegupta.comShalene Gupta is the staff editor for Fast Company's Work Life and Leadership section, co-author of The Power of Trust with Harvard's Sandra Sucher, and author of The Cycle.Stumbling Blocks: How Great Leaders Are Made is hosted by Jonathan Block, founder of Block Leadership Group, recorded in the Treehouse Studio in Georgia.If this was worth your time, follow the show and leave a review. It's the best way to help other leaders find it.Next week: Retired Vice Admiral Mark Harnitchek, who led the Defense Logistics Agency, on loss, grief, and leadership as a mirror. I'll see you then on The Stumble.

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