Workswell Note #2

Learning alongside others 

Since my last Note, I’ve been thinking a lot about how often the most meaningful learning happens with other people. Not in a classroom or a training or a carefully structured retreat, but in those moments when we’re sitting beside someone - sometimes literally, sometimes metaphorically - trying to make sense of something together. It occurs to me that much of my work this past year, across some very different contexts, has had this shared-learning energy running through it. And as we move into the new year, I’m returning to that energy more intentionally.

Which brings me to something new I’m working on: The Chair Project.
If you’ve ever worked with a nonprofit board (I suspect many of of you have), you know how much rides on the Board Chair, especially when things get tough. The Chair sets the tone and tempo, shapes the conversations, holds the boundaries, partners with the Executive Director, and, generally without acknowledgement, ends up being the emotional barometer of the entire governance ecosystem.

It’s a role that carries outsized influence and almost no support.

Over the past year, in my fractional work, interim roles and conversations with friends, I’ve been noticing a pattern: Boards don’t necessarily need more training; they need Chairs who feel grounded, clear, and not alone. So, in true Workswell fashion, I’ve decided to run an experiment.

I’ve started developing a simple practice framework that I’ll be testing in January and February to see if it helps Chairs engage with a bit more ease. Instead of one amorphous job description -“lead the board” - the framework is an attempt to break the work down into five distinct stances a Chair moves among. It’s not about perfection; it’s more about having a map.

To explore this in the real world, I’m launching a First Seating (it’s possible I’m taking the Chair thing a bit too far) with a few Board Chairs who raised their hands to be part of the prototype. Together, we’ll work through a short series of conversations: a profile session, an alignment session with their Executive Director, a couple of micro-coaching moments, and a wrap-up reflection to capture what we learn. No homework. No heavy lift. Just structured noticing.

And because every good experiment needs a little bit of joy, each participant in the First Seating will receive the inaugural Chair Project tee. Just in case you were wondering…

Plays well With Others
A few people have asked me to write a little more about some of the groups I’m currently working with, and there were two bits of news/recent developments I especially want to share.

Operation Outbreak: Earlier this month, Time Magazine ran a piece on Operation Outbreak’s efforts to rethink how young people learn about epidemiology and public health. I’ve been working alongside their team as they are becoming an independent nonprofit. It’s been a lesson in collaborative design: helping shape governance, culture, and systems while learning from people who often think very differently than I do.

Ownership Capital Lab: Meanwhile, Ownership Capital Lab launched its EO Roadmap (you can download it here) a strategy for organizing capital and field infrastructure to support employee ownership transitions at scale. Being part of that team - exploring capital structures, storytelling, and field-building - continues to teach me how movements are shaped not just by big ideas, but by the practices and relationships that carry them.

A Moment of Empathic Joy: Noticing and celebrating leadership done well
While I don’t work with the Golden State Valkyries, my devotion is real. Watching their journey unfold - particularly the leadership they’re modeling - has been a steady source of learning and inspiration. I’m hardly alone in clocking their profound bad-assery, which made it especially fun to attend the WISE celebration honoring Valkyries GM Ohemaa Nyanin as their 2025 Woman of Inspiration. Ohemaa is a proud Playworks Board member and friend and deserves all the love.

And yes… tees
The tee experiments continue! Since the last Note the Shop has grown a lot, including some great guest tees (including a Steph Curry tee designed by my son), collaborative tees with Interim Executive Services, Crimson Goes Blue and Parole Whiskey, and a brown “Worry Less” sweatshirt that I’m basically living in these days. You can check them all out here! And, of course, if you have a tee or sweatshirt idea, please reach out.
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Across all these projects - boards, outbreaks, employee ownership, hoops, tees - I keep coming back to the same thing: we learn best when we’re learning with other people. I think that’s the part of the Chair Project that I’m most excited about: a chance to sit beside a few Chairs and notice what the role is really asking of people. I’m excited to see where this goes - and what we create along the way.

Thanks, as always, for reading and for being part of this ongoing adventure of making things work well.

Warmly,
Jill

PS An unsolicited endorsement: I remain healthily ambivalent about AI—and also a regular user. I just finished Jeremy Utley’s AI Bootcamp and found it genuinely useful. It nudged me away from treating AI like a shortcut machine and toward treating it more like a thinking partner. Less “do this,” more “what if?”