How to Lead and Scale a Distributed Team That Actually Works with Charity Majors

Charity Majors is a writer, speaker, and the co-founder and CTO of Honeycomb, an observability platform for debugging and optimizing distributed systems.In this episode of Distributed, Jack Hannah talks with Charity about the realities of leading and scaling a distributed company. From why remote work is not best for every situation to the communication tax of distributed management, Charity shares what she has learned about building effective teams, fostering trust, and staying connected in a remote environment. She also reflects on her own leadership journey, from CEO back to CTO, and how greater self-awareness and empathy have shaped her approach to work and life.—Where to find Charity Majors:• Bluesky: https://bsky.app/profile/charity.wtf• LinkedIn: https://www.linkedin.com/in/charity-majors/• Website: https://charity.wtf/—Where to find Jack Hannah:  • LinkedIn: ⁠⁠⁠https://www.linkedin.com/in/jack-hannah/⁠⁠⁠• Website: ⁠⁠⁠https://tuple.app/⁠⁠⁠—Timestamps:(00:00) Intro(01:15) Why remote work isn’t best for everything(03:20) What Charity learned from her viral Bluesky post on RTOs(08:33) Why distributed teams need more and better management(11:33) How to get the most from a remote work experience as an engineer (14:30) Why 10x engineers matter less than 10x teams(18:06) How trust and psychological safety drive high-performing teams(20:58) Signs of a healthy organization for job seekers(24:17) Charity’s transition from CEO to CTO and the challenges of down-leveling(26:31) When stepping back in your career can be the right move(30:44) How self-awareness transformed Charity’s approach to leadership and life(34:42) Rapid-fire round —Referenced:• Honeycomb: https://www.honeycomb.io/• Charity’s post on Bluesky about RTO policies: https://bsky.app/profile/charity.wtf/post/3lq4cgak3vk24• How 37signals handles communication, meetings, and setting work boundaries: https://tuple.app/distributed/How-37signals-handles-communication-meetings-and-setting-work-boundaries-with-Rosa-Gutierrez• In Praise of “Normal” Engineers: https://charity.wtf/2025/06/19/in-praise-of-normal-engineers/• Christine Yen on LinkedIn: https://www.linkedin.com/in/christineyen/• Simon Willison’s blog: https://simonwillison.net/• Dr. Cat Hicks' newsletter, Fight for the Human: https://www.fightforthehuman.com/