Willie Jackson

I help teams and organizations find harmony, bringing compassion and levity to the hard work of changing how people work together. Lately that includes teaching leaders to manage their AI agents as well as they manage their people.

I started as a technologist, then spent fifteen years on a harder problem: how do you get people to actually change? Most of what I’ve learned is below, one essay at a time.

Over the years, I’ve…

1. 5th grade

   Sold mistletoe door to door in the fifth grade (and learned what happens when you run out of product)

2. 2010

   Deployed enterprise software across the country for Accenture, then walked away from the cubicle in 2010 with no plan

3. [YEAR]

   Was CTO of The Domino Project, Seth’s publishing experiment powered by Amazon

4. 2015

   Built the tech behind Seth Godin’s altMBA, now 7,000+ alumni in 100+ countries

5. 2015

   Ran a magazine for Black men out of Harlem and published 400+ stories in four years

6. c. 2015

   Sat across from a new client who started telling racial jokes at our kickoff meeting

7. 2017

   Gave a talk in Berkeley, got recruited as hire #3 at ReadySet, and stayed six years

8. 2017–24

   Led ReadySet trainings from Portland to Portugal for 200+ organizations

9. [YEAR]

   Went house hunting on HGTV

10. 2026

    Started managing AI agents like direct reports (and taught one to run the servers in my closet)

Solid links are published. Dotted links are essays I haven’t written yet.

What I write about

Holding the room

Facilitation, feedback, and what actually happens between the agenda items. A teacher’s turning pointFeedback for you and for meAct like you want to be thereHow I open a room in the first five minutesThe session that didn’t land, and what I changedFacilitating across five generations and a dozen countries

Managing humans and agents

Direction, trust, and context, whether your report is a person or a model. Agentic ManagementTrust and ego in managementUnnecessary heroicsAI upskilling is a management problem, not a training problemWrite your agent’s onboarding doc firstWhat 450 managers taught me about the first 90 days

The Seth Godin years

Building the altMBA and The Domino Project, and what shipping weekly does to you. Building the altMBA: learning infrastructure for 7,000 peopleThe Domino Project and publishing at internet speedWhat Seth taught me about shipping

Media and identity

Abernathy, Black leadership, and who gets to tell the story. A love letter to Oak BluffsThe Fierce Urgency of CompassionFour years of publishing a magazine for Black menSelling sponsorships against other people’s writingWhere Abernathy’s writers went next

Culture work

Six years and 200+ organizations of inclusion work, and what actually stuck. Six & ChangeFrom Day OneA message for the momentWhat inclusion work actually changedDoing culture work after the backlashHire #3: growing a consultancy from the inside

The portfolio career

Accruing assets, starting before you’re ready, and pivots nobody planned. Accruing AssetsWhat’s in a Power Circle?The problem with waitingFrom IT consultant to facilitatorLeaving the cubicle in 2010What I’d tell myself at 30 about portfolio careers

Tinkering

Vibe coding, home servers, and doing an impression of a software developer. The vibes are rightI let an AI run the servers in my closetMy résumé is a website nowCross-posting to LinkedIn in an afternoon

People and places

Weak ties, mutual introductions, and the places that made me. Strengthening weak tiesMutual introductionsYou just had to be thereJacksonville made meWhat House Hunters International leaves outField notes from the Delta Sky Club

Recently

• 04-27

  Agentic Management There are surprising similarities between managing AI agents and managing direct reports. An agent is like having a smart, eager recent MBA graduate with extremely high competence and aptitude, but little initial context and experience.

• 04-24

  A tale of two comfort levels I once worked with an executive facilitator who insisted on feedback after every project, regardless of the outcome or stakes.

• 04-23

  The vibes are right Vibe coding is a hilarious term, and I don’t have a better alternative, but thanks to Claude Code, I’ve been having a lot of fun lately doing an impression of a software developer.

• 04-20

  Strengthening weak ties Social pressure is a powerful force that dictates our behavior to a significant degree. Many of us regularly encounter new people—in our favorite cafe, in our neighborhood, and at the gym.