Insider 119: Rare Air


Hello, Insider!

Stuart: Growing up, I was a jazz nerd; still am. I even named my newborn son Dexter (after Dexter Gordon; not the television character). One of the reasons I’ve always loved jazz is because I’m attracted by things with inherent conflicts (salty + sweet, shiny + dull, Brad + Angelina).

Jazz is a juxtaposition between two opposites:
-form and freedom
-structure and solos
-staccato and legato *(yes, I had to look these up, but it works and they rhyme!)
In high school, I was a comedy dork too (jazz and comedy? Hello, ladies!) I noticed that “traditional” jazz (bebop) was similar to improvisational comedy. Jazz has the structure of a song. Comedy has the structure of a scene. Jazz has solos in the middle of songs, and comedy scenes have improvisation throughout.  

The unplanned parts—aka the “improvisation”—creates magic. Structure = freedom. 

Pitching is a little like comedy and jazz. A pitch has a structure in the form of a script and speaking points, but to be truly compelling, there should be elements of improvisation too—even if it’s only in the delivery.  

There’s a golden ratio between structure and improvisation in every talk. It’s just about finding the right balance for you.
As a general rule, I like to be about 80% structured and 20% improvised. Having structure grounds me—ensures that I have a point to my talk and a narrative flow that drives the message. However, knowing I have some freedom within the format encourages me to find hidden moments that will elevate the message. To borrow an idea from Steven Pressfield’s The War of Art, you’ve got to be open to receiving the muse.

What’s the ideal structured-to-improvised ratio for you?

You need to find a blend that works best for you, your style, your industry, who you’re presenting for, and your level of experience. It may not be easy, but you’ll know. That’s a lot, and we’ll dig into how in a future post.
If you’re fairly new to pitching, you might feel more comfortable with a 90/10, 80/20 or 70/30 structured-to-improvised model. It all depends on your level of confidence and what feels the most natural for you—and ultimately, what will help you deliver your message in an entertaining and compelling way.

If you’re comfortable as an extemporaneous speaker, your pitch might best be served through “beating it out” (i.e., choosing 5 key messages or “beats” to share during the course of your pitch in a “connect the dots” format. One “beat” leads to the next, hence “beating it out”). You should still rehearse a lot, but you don’t need to be tethered to a script.
TIP: When it doubt, film yourself pitching/rehearsing your talk and watch it back. How do you come across to you? Learn to coach yourself.
auGi: If you’re just starting out, it’s probably good to write and rehearse every moment of your pitch. This is especially true when you’re first developing a talk of any kind (pitch, keynote, speech) that you plan to give more than once.

As I’ve learned doing solo shows (which have multi-day performances at theater festivals) and keynotes (where I repeat the same basic message over the course of years), those virgin drafts/performances are gonna be rough—like my first ever solo show, SexyNurd: Rockstar Trapped in a Nurd’s Body. Opening night, I bombed hard. Why? Because the script was only 90% complete and I hadn’t rehearsed it all the way through even once (rookie move).

Note: It’s common to make adjustments to a script the entire way through rehearsals and even on the day of a talk/performance. But, those changes should be minimal! At some point, you’ve got to trust your gut.

Stuart: To me, the essence of a great speaker is when they make the words feel "in the moment," but it’s carefully thought through. To watch true masters of this art, find stand-up comedy clips from your favorites and notice how they make their set feel organic and improvised.

However, there are extremes. For example, Dave Chappelle and Steven Wright. Both are hilarious, but they’re on opposite sides of the spectrum (Chappelle seems so loose, it’s like he’s making all of it up. Wright is a master wordsmith, each syllable counts). But the truth is, most of what they’re saying is well-crafted material. It just looks effortless. That’s the magic trick.
auGi: It took several performances and iterations of SexyNurd to “get it right.” Even now, as I’ve moved away from one-man shows and towards keynoting at conferences, I continue to tweak the script and rehearse/memorize for at least 90 days before the conference. During rehearsals, I allow myself space to improvise to find new ways to say something, make my words more conversational, or sometimes completely kill a section because it doesn’t feel genuine. The bonus: my insanely OCD rehearsal schedule creates space to play once I’m on stage because I don’t have to think about the words—they just flow. This is my version of “jazz.”

Stuart: So, how do you transcend the words and share a moment with your audience?

Charlie Parker, the famous Jazz saxophonist, said it best: "Master your instrument, master the music, then forget all that and just play."

So, here’s the hard work: learn from Charlie Parker and first master your script. Practice different ways and rewrite, rewrite, rewrite (this is the 12th draft of this blog post!) Think of your pitch like playing championship tennis: First, you need to nail down the mechanics of your swings. After that, you can stop paying attention to the mechanics and simply play the game.

You won’t move beyond the consciousness of pitching until you’ve internalized the script. That’s the ultimate goal when delivering your pitch—to transcend the script. That way, when you’re in front of the right audience, you’ll have the tools to live “in the moment.” You’ll be free to pay attention to them, create a real connection with your material, and develop the instincts to know when to stick to your script and when you can solo like Bird.

As Claude Debussy famously said, “Music is the silence between the notes.”

It’s the same in pitching: the magic lives somewhere in between the words and beyond the stage.

Trust the process, and you will be set free.


Before we go, we just want to say Thank You. 2018 was a fantastic year for us at Pitch DNA. We had the chance to work with clients around the U.S. and even internationally! This is also the first year we published 12 issues of the Insider just for you (we love it, too). Thank you for reading our articles and sharing them with friends. We’re so grateful that you’re part of our growing community.


As always, we love hearing from you about what you want to read next. Drop us a line: and, or @stuartpitch on Twitter.

Have a great holiday. We’ll see you in the new year!

Stuart & auGi

PS. Read our top Insider post of 2018.