Herding Squirrels Ep 08
w Allison McHenry
Former CTO: Hired, LaCalle Group, & Spafinder Wellness 365
I sat down with Allison McHenry (CTO at Daily Kos, formerly NYT, Meta, Daily Beast) for a conversation about leading through uncertainty—and she dropped some serious wisdom about career paths.
About Allison McHenry
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: "When externalities of uncertainty make everyone from leadership straight on down feel afraid, insecure, concerned about am I going to lose my job... people tend to push their anxiety down the leadership team."
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. That empathy and that desire to support people... that's like the thing that everything else comes from."
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."
Connect with 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.
