The One About Asking Better QuestionsHi Friends,
I just got back from Cape Town, where I spent a week facilitating a retreat for ChangeX, an organization I serve as a board member. Traveling internationally in this political moment was its own kind of experience - but that’s a different Note. This one is about questions. Specifically, it’s about something I keep noticing across very different corners of my work: the thing that actually moves people forward is rarely a good answer. It’s a good question. Question Partners At the start of the retreat, I assigned everyone a Question Partner - ideally someone they work with least. The rules were simple. Every day, you ask your partner the assigned question. Not in a session, just whenever you could squeeze it in. You keep a private note of what they say. On the last day, you deliver a two-to-three sentence portrait of your partner based entirely on the questions asked and what you heard. The portraits are read aloud to the whole group as part of the closing ritual. That’s it. One question a day. What I loved was watching it unfold in the margins of the retreat - during breaks, on the walk to dinner, on the bus. People weren’t treating it as an assignment to complete. They were genuinely sitting with their partners, and I kept overhearing conversations where someone would come back the next day with more thoughts on yesterday’s question. The questions didn’t resolve in the moment asked. They kept going. The team put a lot of effort into designing the sessions and activities for the retreat, but what I loved so much about this exercise was how so much of the real work happened in the spaces we couldn’t fully design. AI and a Wall of Post-Its The ChangeX group was 28 people - not a huge group, but in a brainstorming situation, that’s a lot of post-its. On the first day we ran two large group brainstorming sessions - in the first session, we tried to synthesize the themes on the fly. It was slow and messy and there was a bit of floundering. Somewhere between sessions, I remembered I had a tool. For the second brainstorm, we photographed the post-its, fed the images to AI, and had usable themes in minutes. I mention this not as some grand AI endorsement. I’m still what I described in a previous Note as a “healthily ambivalent regular user.” But this was one of those moments where the right tool at the right time made a real difference. The group did the thinking. The AI did the sorting. And we got to spend our time on the conversation that mattered instead of squinting at sticky notes. Since the last Note, I’ve been leaning further into using AI as a thinking partner - specifically using Claude Cowork to develop session scripts, think through organizational design questions, and (full disclosure) brainstorm the topics for this very Note. The pattern I keep returning to is the same one that drives the Question Partner exercise: the value isn’t in the answers it generates. It’s in what happens when something (or someone) asks you a question you wouldn’t have asked yourself. ChairPair Speaking of questions and partners: The Chair Project has entered a new phase. A few updates: since the last Workswell Note we published a Field Memo on the First Seating, we’ve opened up the Second Seating (and I’m happily being joined by friend and rockstar Deb Jospin to deliver this support), and we’ve launched the ChairPair pilot with two pairs. Quick recap: ChairPair is a three-month pilot pairing Board Chairs for monthly reflection. The structure is light: monthly prompts, a commitment to show up, a partner who asks you the questions you’re not asking yourself. What I’m learning about ChairPair, even in the early going, is that there seems to be a combo barrier to lift off. Asking another Board Chair to be your thinking partner requires a small but real act of vulnerability. It means saying, out loud, that you’d benefit from someone else’s questions. For people who’ve said yes to a role that’s mostly defined by having answers, that’s a shift. I had thought that finding a partner would be the biggest barrier, but there’s a baked-in extra snag: you have to consider the possibility that this is something you - and by extension your organization - would benefit from. And given that this isn’t something that generally happens, is never discussed, and I basically made up - it makes the initial leap that much bigger. But it’s the same shift I watched happen at the retreat. When you give people a structure and a partner and a reason to ask good questions, they lean in. They find the time. They come back the next day with more thoughts. One More Thing from the Retreat Maybe everyone already knows about this and I just missed the memo, but the last thing from Cape Town I thought worth sharing was Amazon’s PRFAQ strategy framework. Basically, you start by writing a hypothetical press release as if the product were launching today - the customer problem, the solution, the impact. Then you build out two sets of FAQs: one addressing customer concerns (usability, pricing, setup) and another exploring the internal feasibility, viability, and organizational implications. From there you reverse-engineer: what would need to be true for your PR and FAQ docs to come to pass? What would need to get done? And who would do it? Admittedly, I’m a sucker for a good framework, but I thought this was particularly playful and doable, and I figured some of you probably missed it like me. Ironically, I no longer shop at Amazon, but I’m happy to borrow their planning tools for world domination. The Thread Across all of this - Question Partners in Cape Town, an AI sorting post-its, Board Chairs finding the nerve to call a peer, a planning framework that starts with the questions your customers would ask - I keep landing in the same place. The most useful things I’ve encountered lately don’t give you answers. They give you a better question. And then they give you someone with whom to think about it. Got a Good One? Now it’s your turn. Send us your favorite question ([email protected] - include your t-shirt size and your snail mail address!) - the one you come back to, the one that always opens something up, the one you ask at dinner parties or in one-on-ones or when you’re trying to actually get to know someone. We’ll pick our three favorites, turn them into tees in the store, and send each of the three winners a shirt with their question on it. OK, that’s what I’ve got for this fourth Workswell Note. As always, thanks for reading - and, of course, if any of this sparks a question, I’d love to hear it. Peace! #jill P.S. The Valkyries’ season is underway and I’m just silly excited about it. Also, Ted Lasso is back August 5th - this time coaching the AFC Richmond women’s team. If you’ve never seen the dart scene (Season 1, episode 8), do yourself a favor and watch it. “Be curious, not judgmental” - plus the left-handed reveal - might be the best thing ever said about questions on television. P.P.S. One of my favorite Substacks is Pádraig Ó Tuama’s and his most recent post (that I read after I wrote this, I swear!) is about asking yourself the question “What’s something nice that someone said to you?” and turning it into a poem. So figured I needed to share.
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Prepared, not HeroicHi Friends,
We’re wrapping up the First Seating of The Chair Project this week. Whenever I close out an experiment, I find myself asking the usual questions: What worked? What didn’t? What surprised me? What’s next? But this time I’ve been thinking about something bigger. How much of the human condition boils down to caring deeply about outcomes that are only partly within our control? A lot of adulting seems to involve finding ourselves in situations where we’re “in charge” of unmanageable/unreasonable situations. We may imagine ourselves acting heroically in the movies we play in our head, but it almost always turns out that taking responsibility involves working well with other humans and being at least somewhat prepared. Heroism, such as it is, turns out to be kind of mind-blowingly un-sexy. Also, maybe a bit of a myth. At least to the extent that willingness is underestimated as a key ingredient. Responsibility without full control Governance is structured around this truth. Boards are shared by design. Authority is distributed. No one gets to steer alone. And yet we often talk as if the goal is efficiency: fewer voices, faster decisions, less friction. But shared responsibility creates friction. It slows things down. It requires conversation and compromise. It can feel inefficient. We’re living in a moment that glorifies speed and certainty. But responsibility is relational. And relational work is rarely efficient. Almost six years ago, my father-in-law had a heart attack while out on a walk. He was saved by a middle school science teacher who happened to be running by - not even on his usual route. He knew CPR. He acted. EMTs arrived. And while the doctor said that less than 5% with his particular blockage generally survive, my father-in-law staged a full recovery. It still feels like a miracle. But what really happened is simpler: a person who was prepared stepped in. Every January since, I’ve renewed my Red Cross CPR/First Aid training. Not out of obligation, but more in an “oh, this is how it works” way. Someone else took responsibility for someone I love. That’s how the chain continues. (Though I will admit that the thought of actually needing to use my CPR training mildly terrifies me.) Chairs (and the quiet kind of leadership) The gift of the Chair Project so far has been spending time with people who have said yes to an extra layer of responsibility. No one forced them. None of them are chasing glory. At some point, they just had their own version of “Oh. This is how it works.” I was having coffee with my friend Paul Jansen from UC Berkeley Haas the other day and Paul, who studies governance, shared something that really stopped me: he believes that nonprofit boards should aspire to have at least 25% of members imagining themselves as future Board Chairs. His logic is simple. When people see themselves as potential leaders, they behave differently. They don’t sit back waiting to be directed. They lean in. It may be aspirational. But what would shift if boards named that expectation out loud? What would change if more of us assumed responsibility for the health of the systems we’re part of; not as heroes, but as steady partners? The Gift of a Hard Conversation A few weeks ago I facilitated a staff conversation for a client about their external partners. On the surface, it was about partnerships. Underneath, it was about values. Some staff were feeling uneasy about the ethics of a few partnerships - worried about the possibility of greenwashing and wanting more clarity about how partners were selected. They weren’t naïve about the organization’s financial realities. They understood that leadership has to make hard decisions to keep the work funded. But they wanted to understand the process. They wanted to know where their voices fit. What was striking wasn’t the tension. It was the tone. The conversation was civil. Generous. Thoughtful. Staff acknowledged the constraints leadership operates under. Leadership listened without defensiveness. They were transparent about trade-offs and open to exploring ways to involve staff in future decisions. No heroes. No villains. Just humans trying to steward something they care about. It reminded me that responsibility gets complicated precisely when values and viability intersect. Someone has to weigh mission against money. Someone has to protect integrity. And rarely is that weight carried by one person alone. Or, at least, it shouldn’t be. When responsibility is shared, and the process is visible, trust has a chance to grow. A couple of invitations In the midst of all this reflecting on responsibility, I’m preparing to moderate a conversation at the Commonwealth Club with my friend and Holocaust survivor Marion Fredman about her nonfiction children’s book A Time to Hide. Marion has been a source of counsel and love since the early days of launching the Museum of Children’s Art (mocha), and I’m genuinely honored to share the stage with her. Her family’s story is one of endurance and moral courage - not cinematic heroism, but ordinary people making hard, relational decisions in impossible circumstances. If you’re interested in attending - either virtually or in person, the link to tickets can be found here. And one more invitation, of a very different sort: many of you know I host a monthly gathering informally known as Community (Not Necessarily) Lunch. In April, instead of conversation over sandwiches, we’ll be running a live simulation using the Operation Outbreak platform at the Playworks offices in Oakland on April 1 at noon. It’ll be hands-on, slightly chaotic, and a fascinating way to experience how systems behave under pressure. If you’re curious and want to join, just send me an email. For a little inspiration on the power of gathering with others, check out Ezra Klein’s interview with Priya Parker. I really appreciate the idea that the antidote to authoritarianism is connection. What’s Next In March we’ll be launching the next iteration of the Chair Project: a three-month pilot supporting pairs of Chairs. A bit of structure. Monthly prompts. A commitment to reflect. Nothing heavy, just steady practice. #ChairPair My guess is that the hardest part won’t be the structure - it will be finding a partner. While we’re not going to be matchmaking, we will be encouraging/supporting folks in reaching out through their networks (asking their EDs for possible referrals, posting on their LinkedIn pages, posting on the Workswell LinkedIn page). Keep an eye out for the launch announcement - as is my nature, I’m guardedly optimistic. That’s what I’ve got for this edition of the Workswell Notes - thanks for reading. #jill P.S. There’s no metaphor here - I just think everyone should see Victor Wembanyama casually kicking basketballs out of the net. It’s astonishing. Seriously, he’s barely jumping. P.P.S. Yes, of course there are new t-shirts (including multiple versions of The Chair Project tee). Check them out here. Learning alongside othersSince 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. 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?” On Dopamine, Tees, and ZombiesHi Friends,
Thank you for subscribing! When I first shared this idea, I figured most people would be too overwhelmed (and maybe a bit skeptical) about adding one more thing to their inbox. Instead, the response was so enthusiastic that my dopamine system got quite the workout with each new Substack notification. Modern life does have a knack for hijacking our brain chemistry. I’ll keep this brief-ish, quarterly-ish, and experimental. My goal isn’t perfection - it’s to learn, share, and connect. I often nudge folks I’m working with not to lose sight of their why and my why in writing these Notes is to share what I’m learning in the hope it’s useful. I also want to get better at this act of sharing, and the best way I know to get better at anything is by actually doing it. Finally, I love building things with other people, and my not-so-secret desire is that these Notes spark ideas and connections that lead to more of that. I’ll admit, I’ve struggled with this first edition. I expected maybe 40 sign-ups; 160+ made the stakes feel higher. Suddenly my desire to learn was in conflict with my desire to be useful. Of course, I know the answer is to keep going - it’s exactly what I tell the organizations with whom I work. But few things are more humbling than being forced to take your own advice. Experimentation as an Antidote to VUCA Fittingly, experimentation is the theme for this first Note. Most of the organizations I’m working with now are feeling paralyzed by the extra-VUCA world we’re all navigating (Volatility, Uncertainty, Complexity, Ambiguity). VUCA isn’t new - the term dates to the Cold War - but it feels especially resonant right now. Leaders are trying to make choices about staffing, strategy, or how to interpret institutional players, all while knowing the future is basically unknowable. My antidote? Experiment. Do something. Do something small. Signal that you don’t know if it will work. And, most importantly, invite other people into the process of figuring it out. Yes, it feels vulnerable. Most experiments don’t “work” in the purest sense - but they all succeed if they teach you something. The critical piece, and the one most often overlooked, is what you do with those learnings. A Founder Transition Case I’m currently helping a group through a founder transition. Nothing dramatic has happened yet - they’re only just forming their Transition Committee. But I’ve been interviewing super-volunteers, showing up at meetings, and volunteering myself. Most importantly, I’ve been asking people what they think and communicating back what I learn. What’s striking is how much people appreciate simply being asked, heard, and given visibility into the process. They understand we’re experimenting, that the path forward isn’t yet clear, and that they - and their questions and reflections - are part of it. While we can’t predict the future, communicating openly about experiments creates opportunities for others to connect and engage, making it more likely you’ll land somewhere good and that those involved will feel invested in the outcome. Even for an organization already inclined toward innovation, incorporating experimentation into succession planning can feel a little unnatural, but it can also dramatically increase creativity, comfort with risk, and collective engagement. Jill’s Tee Shop Another (admittedly random) experiment: Jill’s Tee Shop. I’ve long loved designing t-shirts, and what started as sharing my own designs has quickly morphed. Whenever I bring it up, friends share stories of tees they’ve loved, made, or wanted to make. Now the shop is growing to include guest artists, friends’ bands (a legit reason for me to say merch), and new collaborations I haven’t even imagined yet. It’s become a quirky little lab in storytelling, self-expression, and play - with cotton as the medium. If you’ve got an idea for a tee (or a related project), send it my way. What I also love about this experiment is the learning it has generated. Back when I was a d.school fellow, our projects became the platform for all our applied learning. The Tee Shop has been the same, nudging me to experiment with AI, push deeper into Canva, learn about UTMs, and explore ethical sourcing. Do I need all these skills? Probably not. But like drinking water, sleeping, or getting outside, learning new things just makes everything else better. Easter Egg: Because experiments are more fun with surprises: the first five people who fill out this quick form will get a free mystery t-shirt from Jill’s Tee Shop. Guaranteed to be quirky. A Resource to Know I’ve been part of Stay Resolute, a community of advisors and consultants offering two hours of free support to nonprofits navigating tough challenges without the budget for outside help. It may sound too good to be true, but it really is just good humans wanting to do something and offering time. If you know a group that could use this, please send them this way. A Playful Tip Because it’s back-to-school season: one of my favorite ways to get my kids talking about school was to ask, “Which teacher would be most likely to survive a zombie apocalypse, and why?” The answers were consistently hilarious and revealing. It’s also a good reminder that sometimes the best way to learn isn’t head-on, but through a playful openness that invites things to reveal themselves. That’s it for this first Workswell Note. Thanks again for being here. |
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