Allison McHenry is currently serving as the CTO of Daily Kos, a progressive political blog. Previously, she was CTO at The Daily Beast, and has also held leadership roles at Meta and The New York Times. She most loves thinking about ways to enable teams to use technology to move socially conscious businesses forward.

Key Moments & Timestamps

00:00 – 01:11 – Personal Introduction Build

Allison builds a rotating model representing herself in the center trying to connect with her four daughters – two older ones in London and San Diego, and five-year-old twins at home.

01:26 – 03:11 – Best Team Experience: The New York Times

Discussion of leading the standalone product group at NYT, introduction to Paloma Medida’s BICEPS model (Belonging, Improvement, Choice, Equality, Predictability, Status), and creating zero-to-one subscription businesses during a challenging time in media.

05:13 – 09:17 – Worst Team Experience: Leadership Under Pressure

Allison’s powerful model of anxiety cascading down through organizational layers during uncertain economic times, exploring how external pressures create internal dysfunction and the challenge of maintaining team cohesion when basic security needs aren’t met.

09:30 – 10:56 – The Evolution of Leadership

How remote work has required more intentional communication, cultural sensitivity, and leader availability, while also building trust through flexibility.

10:56 – 13:35 – AI’s Impact on Media and Teams

Deep dive into how AI is transforming the media landscape, from Google’s AI summaries affecting search traffic to the existential question of whether AI can replace entry-level positions, and the industry’s struggle with data usage and monetization.

13:38 – 14:41 – Staying Grounded as a Leader

Allison’s approach to managing information overload and maintaining strategic perspective while still being able to “turn it off and watch a movie, hang out with the cat.”

15:05 – 17:02 – Advice for New Leaders

A powerful model showing two viable leadership paths (management vs. technical leadership), emphasizing self-awareness from the Master Trust equation, and the fundamental principle that leadership is ultimately about caring personally for people.

Key Topics Discussed

* BICEPS Model: Belonging, Improvement, Choice, Equality, Predictability, Status as team motivators

* Leading Through Crisis: Managing teams during economic uncertainty and external pressures

* Remote Leadership Evolution: Increased intentionality required for distributed team management

* AI’s Disruption of Media: Search traffic impacts, data monetization challenges, and job displacement concerns

* Leadership Self-Care: Balancing information consumption with mental health

* Career Path Flexibility: Supporting team members in finding their authentic leadership style

Notable Quotes

On team motivation during crisis: “That externality of uncertainty makes everyone from leadership straight on down feel afraid, insecure, concerned about, am I going to lose my job? How am I being evaluated? Is this business even going to be around? There’s a lot of anxiety.”

On cascading pressure: “When that happens, what I’ve observed is people tend to push their anxiety down the leadership team. So they want to get more micromanaging, they want to get more in the weeds with what people under them are doing.”

On remote leadership: “You have to be a lot more intentional about communication. If you’re working with people in multiple time zones and multiple localities, you have to be much more culturally sensitive.”

On AI’s unprecedented impact: “The change with AI has been the single biggest shift I’ve seen in my career. I mean, I’ve never seen anything change so much in the past.”

On leadership fundamentals: “No matter what you’re doing, this is a people business and you have to care personally about your people. And that’s like the thing that everything else comes from is, you know, that empathy and that desire to support people.”

On self-awareness in leadership: “Knowing yourself and having that self-awareness is so critical to whether this is even what you want to do.”

Where to find more Allison

* LinkedIn: Alison McHenry

Herding Squirrels is a podcast about modern teams, exploring how leaders navigate the complexities of today’s workplace through hands-on LEGO® Serious Play® conversations.

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