Write Like You’re In The West Wing

(or, the power of listener attention)

Hi everyone, I’m excited to be writing alongside Patrick for The Story Is The Strategy. 

I’ll share a secret about myself since this is the first time I’m landing in your inbox.

In the midst of the pandemic and an enthralling election, The West Wing has been one of my guilty pleasures. In my opinion, it has everything you need for quarantine watching: years of character development, drama and levity in equal parts, and storylines that are compelling, fanciful, and (somehow) emotionally relatable.

Watching the series reminded me that Toby Ziegler is one of my favourite television characters. Not just because of his role as the understated voice of the progressive left in Aaron Sorkin’s fictional, liberal universe. But, because his character is the wellspring of the show’s earnest belief in the power of oratory. 

In Season 2, Episode 16, Toby talks about speech writing to a security guard who’s been assigned to shadow him as he speaks to a group of WTO protesters. It all sounds so quaint in 2020.

Here’s the salient part of their conversation.

Toby Ziegler: “Food is cheaper! Clothes are cheaper. Steel is cheaper. Cars are cheaper. Phone service is cheaper. You feel me building a rhythm here? That’s because I’m a speech writer – I know how to make a point.”

Officer Rhonda Sachs: “Toby…”

Toby Ziegler: “It lowers prices, it raises income. You see what I did with ‘lowers’ and ‘raises’ there?”

Officer Rhonda Sachs: “Yes.”

Toby Ziegler: “It’s called the science of listener attention. We did repetition, we did floating opposites, and now you end with the one that’s not like the others. Ready? Free trade stops wars. Heh, and that’s it. Free trade stops wars! And we figure out a way to fix the rest. One world, one peace – I’m sure I’ve seen that on a sign somewhere.”


In a few lines of dialogue, Toby gives us three key lessons for how we can create and hold listener attention. This works remarkably well for public speaking - whether you’re Martin Sheen playing President Jed Bartlet or walking through a quarterly plan with your team.

1. Building to a point, through repetition

Patrick wrote about this a while ago. The Greek word for this trick is anaphora. By repeating a form (often in a series of three), you immediately force people’s ears to prick up.

It works well in openings or closings, but rarely in between. Need to set context, pique attention, or conclude without sounding trite or redundant? See if you can employ anaphora without cringing.

2. “Floating opposites” (more accurately, chiasmus)

Toby suggests that his use of antonymical verbs (“lowers” and “raises”) is called floating opposites - but it’s just a simplified form of a literary device called chiasmus.

Chiasmus is a form where the grammar of one phrase is inverted in the following phrase. The mirror structure of the device is a simple way to add emphasis.

The most famous use of this might be John F. Kennedy’s imploration - “Ask not what your country can do for you, ask what you can do for your country.”

Much like anaphora, it’s tempting to overuse chiasmus as it is easy to construct and pleasing to the ear. To me, it is best used in the manner Toby employs it - as a penultimate headline. 

Is the second to last slide in your presentation lacking? Need to rouse the room before you come back to your final point? See if you can insert a chiasmus without sounding sophomoric.

3. End with something that’s not like the others

It’s very easy in business communication to land on a conclusion that is both obvious and ineffectual. How many presentations have you listened to that tritely summed up the main points or ended with no call to action?

How to end well is worth a post of its own. But, for now, consider that ending a passage, talk, or presentation with a turn of phrase that’s different to the rest of your points can inspire action and create consensus. 

This doesn’t mean you should end your talk on a totally random point. Rather, find a way to deliver the key message of your conclusion in a way that makes it stand out from the crowd. By showing what it’s not, you make your point even stronger. 

Want more thoughts on how to use chiasmus or end a talk? Reply to this email or connect with me on Twitter.

If you want more help, Patrick and I are both offering free in-person communications help. If you need help punching up a draft presentation, want to know if your pitch deck works, or anything else - feel free to book some time with me (NYC evenings are open) or with Patrick.