Be Connected: Behind-the-scenes with Eoin Cannon, Mayor Walsh's Chief Speechwriter

In this edition, we speak with the man behind the curtain (quite literally), Mayor Walsh's speechwriter Eoin Cannon. We caught up with Eoin shortly after the Mayor's final State of the City address to chat about the collaborative process of preparing the Mayor for major speeches (as well as the day-to-day events and appearances that populate his busy schedule), how he learned to write for Mayor Walsh's voice, his tips for dealing with writer's block, and more. 

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Eoin, I’m so glad you agreed to let me interview you for this segment. I just want to start with a sincere thank you, and congratulations on yet another fantastic State of the City address. I know I say this every time, but that was the best one yet.  And as you know, I completely lost it when the Mayor thanked you by name. 

I sort of lost it too! I was operating the teleprompter and was so overwhelmed, I bowed my head for a moment. Dave Burt from the Cable Office, who sits next to me, said he was afraid I was passing out and he’d have to take over. I mean, no speech writer ever expects that. The job requires what one FDR adviser called “a passion for anonymity.” But Mayor Walsh is who he is, showing gratitude and sharing success are what he does.

You’ve been writing for Mayor Walsh since the very beginning, and you have a special relationship as a result. How did you get so good at writing for his unique voice? 

It was a trial by fire at first, a relentless schedule of events where you can hear every single time a line doesn’t work or simply isn’t used, and you have to keep adapting and adjusting. 

Yeah, sorry about that (Full disclosure for our readers: My last role was Mayor Walsh’s Director of Scheduling and Advance).

But Mayor Walsh’s voice is very good training for a writer, because his style is direct, concrete, personal, and relational, all the things effective writing should usually be. Both of us having Irish parents might help a bit as well. You are taught to never sound full of yourself but you can be sentimental when called for.  

What led you to this career in the first place?

Mayor Walsh brought me into public service, as he has so many others. I was an academic interested in things the mayor worked on, including cities, recovery, and labor. I was a fan of his when he was my State Representative, so I volunteered to do some writing on his 2013 campaign and one thing led to another.  

I worked closely with you and your team when I was in the Mayor’s Office of Scheduling & Advance. And I’ll be the first to admit, his schedule is...I don’t even know how to describe it properly. Borderline impossible? An extraordinary feat of human endurance and willpower? You’re the wordsmith, help me out. 

It’s like something out of Greek mythology, the labors of Hercules but with ribbon cuttings and coffee hours instead of slaying monsters. 

Nailed it.

I learned early on not to take a breather when an event gets cancelled, because it usually gets replaced by two more.  

How do you, [and speechwriters] Maura, and Nancy keep up with the volume of events and appearances at which he’s scheduled to speak? 

We divide up the workload, plan out our deadlines, and are ready to adapt to whatever comes. Speaking of adapting, I’ve got to say Nancy and Maura have done an incredible job during the pandemic. 

They are rockstars. 

Most of the Mayor’s speeches became video recordings, and many COVID-related PSAs have been needed. On top of our many other tasks, they write and tape dozens of messages every week, with Stacia Sheputa from the Press Team. We do get a ton of support -- from each other, from Scheduling and Advance, from the Press team, from the whole Mayor’s Office and every department we work with. Everyone is great about understanding our deadlines and needs when we reach out. 

There’s so much ground to cover in a major speech like the State of the City or the annual Chamber of Commerce address. Can you share some insight into how a speech like that comes together?

I put together an outline to start the conversation, but the Mayor usually has a main point and a sequence of issues and/or announcements in mind already. I write a draft based on that conversation, then get feedback and input from him and members of the cabinet over a series of drafts and practice sessions. By the very end, it’s usually just him and me tweaking the final language. 

When you’re drafting or rehearsing a speech, do you know which lines are going to stand out and/or stick with the audience after the fact? 

You do try to come up with memorable lines that simplify complex issues, without getting too caught up in snappy one-liners that can sound cheesy or inauthentic. You want it to have some sense when pulled out of context. 

What are your favorite topics to write in Mayor Walsh’s voice? 

Anything around second chances and helping people who might have felt lost find hope and change their lives, whether through recovery, job training, affordable housing, or what have you. That’s really at the core of who the mayor is. To be fair, though, that's usually when he puts the notes aside and speaks from the heart. 

How has his style and delivery changed or evolved over the years? 

Like anyone who goes from occasional public speaking to constant public speaking, he’s gotten more polished. But the fundamentals of his style haven’t changed. He’s a natural at building up a point around a repeated line that draws different people into shared understanding. 

That’s such a good point, now that you said it I can totally hear it.

And he’s able to be open and vulnerable in ways that create authentic connections, and inspire confidence that someone who genuinely cares is leading the city.

The State of the City address Mayor Walsh gave on Tuesday will be his last. It was an incredible speech impeccably delivered by a man who’s vision, hard work, and generosity changed the course of so many lives — mine and yours included. It’s an emotional time for us all. How did you feel when he was delivering that final speech? How are you feeling now? 

Emotional for sure, but I had to focus on the job at hand. More than anything, I’m proud that we work for a leader and team who were so good at supporting working families that the country came calling in its time of need.  

That’s an excellent way to put it. You’ve always been a rock for the Mayor and everyone around him, myself included. Thank you for everything. Before I start to cry (again), are you up for a quick lightning round? 

Sure.

Favorite Presidential speaker or speech? 

I often return to Lincoln and Kennedy’s inaugurals. But I have a soft spot for FDR, because of the way his major speeches told the story of a country discovering cooperation as the only way out of the Depression.  

Best written show on television?

I shouldn’t say Veep, should I? 

Oh my god my roommates and I have been rewatching Veep and it occurred to me that every single line is a joke. There isn’t a single sentence that is just like, exposition.

I also like to revisit a brilliant BBC show from my childhood called Yes, Minister. It’s about a cabinet secretary…

What’s the best way to deal with writer’s block?  

Accept that the first draft may suck, but it's better than a blank page, and you have a job to do, so you have to start somewhere. Then be willing to show colleagues your awful first draft, because rather than judging you they will offer help. The best writing usually comes in the rewriting. 

Who would you rather write a speech for, Edgar Allen Poe or George Washington?

Poe. It would be a nice change to unleash the inner weirdo. 

I knew you were going to say Poe. 

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Got a suggestion for our next behind-the-scenes interview? Let us know!

About the interviewer:

Erin Santhouse joined the City of Boston in 2014 as a scheduler for Mayor Walsh. She is currently a Project Manager for the HR Transformation and the lead content strategist for Be Connected. In lieu of providing further biographical information, she suggests googling “Kelly Kapoor quotes”.