WORKSWELL NOTE #4

The One About Asking Better Questions 

Hi Friends,
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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
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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.