How I Moderated My First Mayoral Debate
A peek behind the scenes.
Last night, I served as moderator for a debate between our two candidates for Mayor: Councilors Jake Wilson and Willie Burnley, Jr.
I’m very pleased with how it went!
One benefit of co-producing the debate with the Somerville Media Center is that they recorded and speedily released this very nice video:
Reflections
Rules
As moderator, my first responsibility was determining the rules we’d use.
I got a decent first draft from ChatGPT, though I probably spent about 4 more hours refining them. When I was happy with the rules, I had Claude Code turn them into some pleasant-looking html and published them on my personal website.

I didn’t want to have to remember whose turn it was to answer first, so I brought a printed copy of the run of show, and checked the candidate’s name after each of their responses on this table:
This worked great for easing my cognitive load, and gave me something useful to do with my hands.
Questions
Another critical duty was generating the debate questions.
I have to say I think I nailed this 😄.
I went a little bit bold with my questions. Once or twice I heard near-gasps from the audience, and I could often feel a bit of frisson in the room. I got a great laugh at one point, too. I think I achieved my goal of being a bit pointed, but not needlessly provocative.
To generate my question bank, I asked Claude and ChatGPT with their Research modes on to dig into this year’s Somerville news coverage and generate 40 possible debate questions. Most were pretty terrible, but there were a few gems in there. Out of the 80 generated questions, approximately four made it to the debate. I massaged the language on all four at least a little.
I also solicited ideas for questions from readers of this blog, though I don’t think I ended up using any of them.
The remaining questions came straight from my dome.
You can see the final list here.
Imperfections
Overall, I feel like I pretty much nailed it. I’d give myself a 95%.
Two things cost me those last 5 points:
I didn’t do a dry run with actual humans. There was a rules question that came up during the debate that I definitely would have already resolved if I’d actually tried running a few questions with people. I’m happy with the call I made under pressure, but the blip was avoidable. This was one of the few pieces of Daniel Golliher’s advice that I didn’t take, and I wish I had.
At one point, Councilor Burnley mentioned that I had donated hundreds of dollars to Councilor Wilson’s campaign. I decided to respond immediately after his statement, clarifying that I had made a donation, but subsequently asked Councilor Wilson to refund it, which he had. I’m glad I responded in the moment, and think I handled it fairly well. However, I wish I’d also mentioned that I made that donation before I knew how I intended to engage with Somerville politics, and asked Wilson to refund it once I realized I might conceivably end up moderating a mayoral debate.
Celebrations
Nine months ago, I had no connection to Somerville politics.
Last night, I stood on stage with both mayoral candidates and asked tough questions so Somerville’s residents can determine who they want to govern them.
This project almost died several times. I spent a lot of time unsure if it would happen at all. But it did! And we nailed it. And that feels awesome.
Thanks so much to Joe Lynch and Sean Effel from the Somerville Media Center, Daniel Golliher, and Joel Sutherland. It wouldn’t have been nearly as good without you.




Donated, then withdrew is still donated. You showed your hand in a completely unacceptable way. Sorry, it's an F from me. You had no business moderating a debate.
Full disclosure, I have been following your prep on this substack, and will only watch the debate this weekend. My comment is that I was disapointed in the questions. After solicitating questions from readers, then not using any, makes me think that you are just playing a game and was never going to listen to us anyway. The questions you did ask however I feel had a slant. As mentioned, I need to listen to the candidates replies, and I am still open to making my final choice, I got the destinction on every question, that I knew roughly where candidate Burnley stood, but not candidate Wilson. The more I read through it, I got the feeling that this was a planned for candidate Wilson to get his message out, on questions candidate Burnley had answered, which feels/sounds/smells like it was the plan all along. If I got it wrong, after I watch the full debate, I will update.