Sharing sales and startup lessons from comedy

Alli McKee
Jul 25, 2018 · 5 min read

A year ago, we loaded all of our belongings into a 15-foot U-Haul, miraculously parallel parked on Church Street in San Francisco. We were moving to Los Angeles.

From those first moments on the 10, it was clear that LA wasn’t going to be anything like SF. Up there, billboards offered pithy product promises. “Ask your Developer.”

Down here, “War for Planet of the Apes” and “The Emoji Movie” lined the freeways. While I never thought I’d miss the 101, now I did.

But one Saturday night, after eye-rolling the entertainment industry over dinner again, I ended up at at Westside Comedy for a standup show. By the end, I was laughing so hard that the flyers offering Improv 101 classes didn’t seem so absurd anymore. Improv and standup were the same, right? Being funny was fun. I wanted to be funny. Why not try it? I thought.

Sunday night’s Improv 101 class would be a fun way to turn off my brain, to get away from startups, sales, and everything else.

Turns out, improv wasn’t that. Not even close.

Six months later, I’ve just signed up for my Sunday night Advanced 401 class, and this is just the beginning. Not because I want to be an actor, but because nothing has helped me in sales or startups more than studying Improv.

I share this and some of the highlights from studying Improv hoping that they help your sales and startup teams in the same way that they’ve helped ours.


Sales is about people.

In its core form, it’s about whether you can connect with another person. Can you listen deeply enough to understand your prospect? Can you communicate clearly to that prospect? Can you compel them to change? The goal is to get the prospect to buy.

Improv is the same thing. Except the goal is to get the audience to laugh.

To be a better improviser or seller, here are a few key principles:

1. Yes, And

You’ve probably heard the principle of “Yes, And” before, as the most famous improv principle. Say “yes, and” not “yes, but” or “no, but.” But it goes deeper than that. Ultimately Yes, And is about being brave and being decisive.

Sometimes saying “Yes” is scary — whether it’s doing an accent, or being a character you don’t already know, or singing on stage when you can’t sing well at ALL. It’s all about getting out of your comfort zone.

“And” requires you to make a decision. If you simply say “yes,” your scene (or sale) doesn’t go anywhere. It’s your job to add information and direction to push the conversation forward. Make a decision and commit to it.

2. Point of View, not just Persona

In marketing and sales, we rely on “buyer personas” to better understand our customers. Often these fall in line with the title on their LinkedIn profile. A persona, by definition, is “the aspect of someone’s character that is presented to or perceived by others.” Personas are outside-in.

Improv, though, is about Character. And every good character has a Point of View, which is that character’s “particular attitude or way of considering a matter.” It’s what shows you the world from that one person’s perspective. Point of Views are inside-out.

If you want to really connect with a prospect, start with their persona to guide you, but you have to be able to dig deeper, and exercise perspective-taking if you want to speak their language.

3. Be Specific

A successful improv scene is always specific. The more detailed, the more funny it is. Why? Because it requires real thoughtfulness to generate those details, and it requires shared understanding between the actor and audience. Most of all, it’s rooted in truth. It’s hard to make up specifics on the spot.

One of the reasons sales has gotten a bad reputation is from all the fluff and BS promised by those who came before us. “More Sales” “Faster Growth” “Lower Costs” “Better Business.” Fluff is easy to make up, and therefore hard to trust.

Instead, root your sales conversations in specifics, whether that’s a parallel customer success story or ROI analysis. Whenever possible, go deeper.

4. Be Adaptable

When you initiate a scene as an improviser, you have an agenda. You know who you are, what you’re doing, and what you’re feeling. Let’s say you have the idea to be on a father son fishing trip. But before you’ve said anything, your scene partner enters, bouncing an imaginary basketball. Dammit! you think. There aren’t any basketballs on a boat! This scene is ruined!

But that’s not how it goes. If you have a fishing rod, and your partner has a basketball, how do you adapt to make both true?

New idea: You’re still fishing, but you’re not on a boat anymore. You and your basketball-bouncing partner are now in Dick’s Sporting Goods.

Sales isn’t so different. Often you come into a demo with an agenda, expecting the prospect to ask for A. But then, they ask for C. You can’t throw in the towel completely. You have to adapt.

Be decisive and have a plan, but hold it loosely.

5. Reset Regularly

Whether you have 10 Demo calls in a day, or 10 Scenes in a show, it’s tiring work. Some are going to go well, and others not so well. Some of them you will completely bomb. That’s how it goes.

The trick, though, is to prevent the bad calls from bringing down the rest of them. If you let that happen, the second demo will be shot, and the other 7 will stink, too.

Improv is no different. One teacher I had encouraged us to “Clap it out” between scenes, so we could start fresh each time.

Start off by being present. Do the work. Learn what worked, what didn’t. Then, Clap it out. Do it again.


About the Author: Alli McKee is a student at the Westside Comedy Theater in Los Angeles, and the CEO and Founder of Stick — a communication platform built for B2B Sales and Success teams to illustrate ideas automatically in real time, to have better conversations with their customers. For more, visit www.stick.ai.

Show and Sell

Storytelling is the new Selling. Show and Sell brings together the best of strategy, storytelling, and design to show companies how to sell more, faster with stories that stick. Brought to you by stick.ai.

Alli McKee

Written by

CEO and Founder, Stick.ai - Illustrating Ideas in real time with NLP + ML. Painting and Improv on the side. TEDx Stanford.

Show and Sell

Storytelling is the new Selling. Show and Sell brings together the best of strategy, storytelling, and design to show companies how to sell more, faster with stories that stick. Brought to you by stick.ai.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade