As experience design continues to become more widely adopted and utilized by organizations of every size, experience designers of every stripe and specialty are more likely to find themselves presenting their ideas to stakeholders. The broader implementation of UX (including CX, EX, TX, et al) also means ideas are being pitched to a wider variety of stakeholders (everyone from C-suiters to HR managers to customer service supervisors can benefit from user-centered design, after all).
Luckily, pitching to such a broad audience can be made easier by studying the work and ethos of stand-up comedians. These brave denizens of nightly discomfort know a thing or two about tough rooms and how to win over even the most reluctant person staring back at them. Trust me, years ago I thought the path to success was headlining comedy clubs, landing my own HBO special, and scoring a recurring role on Curb Your Enthusiasm.
What I learned over the ten years I spent slinging jokes from Denver to Miami was that the same skills I’d honed landing jokes and doging hecklers had made me a pretty effective pitch man. These days, I spend a lot of my time teaching people how to think like a comic to make a sale. I’ve realized through conversation with the UX people in my life that many of these techniques have special resonance in the realm of experience design. With that, here come five lessons in effective message delivery from some seriously funny people.
Don’t Prepare Too Much Content
My first-ever stand-up gig was at the beloved Comedy Works in Denver. It was New Talent Night and the house was packed. Comedy Works puts a two-minute set limit on all first-timers. That doesn’t sound like a lot of time, but believe me, those two minutes can feel like an eternity when things don’t go right.
My first time on this stage was a huge opportunity and my impulse was to show all of my stuff, cramming 145 seconds worth of jokes into my two-minute set. I couldn’t bear to kill my darlings and the result was a ridiculously rushed set. I stepped on all my laughs because the audience’s laughter was taking up precious time! When I finally got off stage, one of the veteran comedians asked me, “Are you late to catch a train or something? Man, you were going fast up there.”
It wouldn’t be unusual for an experience design practitioner to think that every slide in their deck is crucial. While it might seem like each persona, wireframe, and case study is invaluable, don’t make the mistake of cramming an hour’s worth of content into a 30-minute pitch. Truly great presenters frequently prepare less content than time allotted to present, allowing for organic conversation, improvisation, and opportunities to break the fourth wall. More often than not, these unexpected moments are the ones that stick with your audience, and they can’t exist without room to breathe.
Start with a Story
Great stories create an emotional connection—affecting the part of our brains that releases oxytocin, a hormone that gives us a greater sense of empathy and connection. For this reason, great stories are also memorable. Demetri Martin is one of my favorite comedians, but my retention of his barrage of one-liners is ridiculously low. On the other hand, many of Richard Pryor’s extended bits seem to swim in my head fully-formed because he was such an incredible storyteller. Memorable and emotional are two characteristics that will differentiate you whether you’re on a comedy stage or making your case to weary stakeholders over Zoom.
Every great story consists of three simple things:
- Setup
- Conflict
- Resolution
If your story doesn’t have conflict it’s not a story, it’s merely a series of events. A captivating story doesn’t even have to actually be about your product or service in order to engage your audience, it just has to be a great story that you can connect back to whatever you actually want to talk about. Fortunately for experience designers, the very thing you’re often pitching is a story: the story of a user (setup) not finding what they are looking for (conflict) and how experience design will fix that (resolution).
Communicate Value Before Asking for an Investment
In the months leading up to my overstuffed, storyless debut set at Comedy Works, I’d been reading Zen and the Art of Stand-Up Comedy by Jay Sankey. This is a classic guide that introduced me to the framework underpinning good jokes:
Setup + Punchline + Tag = Successful Joke
In many ways this is the same formula behind a great story. The setup establishes initial context or premise, and the punchline alters the meaning of the setup in an unexpected way. The tag is an additional comment that builds on the punchline. Since I needlessly picked on him earlier, let’s use one of Demeteri Martin’s great jokes as an example.
“If you’re a battery, you’re either working or you’re dead. It’s a shit life.”
- Setup: If you’re a battery,
- Punchline: you’re either working or you’re dead.
- Tag: It’s a shit life.
I love the simplicity of this joke. Without the setup, the punchline has no meaning and the tag adds no heft. The same relationship exists between the value of the solution you’re presenting vs. the investment you’re asking for. Price only becomes an issue in the absence of value. That’s why it’s important to outline your solution’s business and personal value in the slide directly before delivering the investment estimate—giving the investment context up against the value.
As an experience designer, you’ve probably already asked questions during discovery that uncovered the value your proposition will bring. Clearly communicating the value your solution presents is the setup that makes your investment ask (I’d advise never calling it a “price,” “cost,” or “fee”) an effective punchline. For a tag, you can always find examples of competing organizations that have suffered by not investing properly in experience design.
Know How (and When) to Improvise
One of my favorite gigs as a stand-up was to host, or emcee. There are basically three components to the job:
- Make the comedians look good
- Keep the show rolling energetically
- Occasionally “call the room” from the audience’s point of view (if they’re thinking it, you get laughs for calling it out)
This third directive is basically a fancy way of saying “improvise.” It’s critical to be able to perform effectively without any preparation or planning. My improv spirit animal was always David Letterman. As a host, Letterman clearly loved crowd work. He knew that bad ideas can often be a bridge to better ideas if you are open to letting go of your plan and staying present in the moment with your audience. To Letterman, chaos wasn’t something to eliminate but rather something to relish in.
When pitching to stakeholders, chaos (or at the very least something unexpected) can lurk at every turn. Maybe you’ve spent hours on your slides, obsessing over every word, image, phrase, as you sequence your presentation. Then, in the midst of that presentation, you start reading your stakeholders’ body language and sense you’re missing the mark. Or worse, what if the lead stakeholder doesn’t want to see the slides you’ve prepared and wants answers now to a question you don’t address until slide 12.
There are times when you need to stick to your guns and muscle through the presentation. More often than not, however, you need to read the room and go with the flow. That means letting go of your agenda and all the hard work you’ve put into your slides. Sometimes the worst thing you can do is not heed the perceived and direct feedback your audience is giving and plow on with your slides because you’ve invested a ton of time on the deck.
For inspiration on keeping your cool and pivoting with panache, watch Letterman wrangle one of the most squirrely quests in the history of The Late Show, Crispin Glover. During his manic 1987 appearance, the agitated actor runs roughshod over the typical interview structure, culminating in a roundhouse kick that looks to pass inches in front of Letterman’s face before Dave calls it off early.
While this clearly isn’t Letterman’s best interview, it is memorable and emotional (good story, remember) and even through Glover throws his whole body into derailing the conversation, Dave salvages the experience by doing some self-deprecating riffing with his bandleader and filing the leftover minutes with a postscript—asking the audience, “Hey, would you want to have dinner with the guy?”
Different Stakeholders Respond to Different Approaches
If you were pitching an experience design initiative to stakeholders 10 years ago, you probably had to lay a lot of groundwork—explaining the basic precepts of user-centric design, talking about the importance of research, hinting at the structural overhaul an earnest effort might entail, etc. These days, far more people in leadership roles have a sense of what UX is and what it will likely require from their organization. There are also a growing number of high-level decision-makers with a direct background in experience design.
Getting a sense of who you’ll be pitching to beforehand can be of great advantage. You don’t want to end up boring a CTO with information they already know or skimming past something your audience hasn’t even heard of. There’s also the possibility that you might be pitching to a diverse crowd in terms of their understanding of UX. What to do?
In his Netflix special 3 Mics, comedian Neal Brennan delivers a trio of different sets in a single show using not one, not two, but … wait for it … three microphones. Brennan deftly moves between them, using one to read one-liners from index cards, another to talk more seriously about dealing with depression and his relationship with his father, and the third for traditional stand-up comedy.
This approach can work well when pitching to a mixed audience, though you’ll take a more understated approach. Brennan makes dramatic transitions between mics, killing the lights and leaving the room dark for a few moments before spotlighting whichever zone he’s moved to. While you’re certainly welcome to experiment with light switches and a collection of mics, it can really be as simple as picking three different spots in front of your audience that you can move between.
When you’re standing stage left, you can talk UX nuts and bolts to the in-crowd. As you move to the center the subject matter might be more high-level stuff that everyone can latch on to. Stage right is the place to unpack basic concepts for noobs. You don’t need to address your maneuvering and the significance of each area. Your audience will likely adjust on a subliminal level to the informational differentiation going on.
I call this “moving with purpose,” and it’s one more thing that good comics and good presenters have in common. Now, I encourage you to take these tips out into the wild, both in meetings with stakeholders and—if you’re ready—open mic night at a comedy club.
