I relearned sales from a stand-up comedian

I’m not joking

Happy New Year!

I’m thankful 2020 is over. There were stretches of days, weeks, and months when it felt like the world was changing every 24 hours. I got laid off. My basic assumptions were challenged. I felt grateful for my privilege.

2020 taught me a lot, particularly about the importance of adapting to change.

I spent a lot of last year trying to unlearn bad sales habits that I picked up over the past few years, and then reteaching myself best practices. I looked to the people around me for inspiration.

One of those people is my friend Simon Fraser, who is on an extended road trip throughout the United States, performing stand-up comedy and stopping at every municipality named London along on the way.

Simon stayed with me for a few weeks over the summer, using Columbus as a temporary home base while visiting the London’s of Ohio (population 9,904), Kentucky (pop: 7,993), Indiana (pop.: unknown), and Michigan (pop.: 3,048).

During this time, I got to witness the day-to-day life of a stand-up comedian and think about how his habits, practices, and processes could make me better at sales & marketing. Here’s what I learned:

Discovery

Picture a random person performing stand-up for the first time. What do they say? There’s a reason why they’ll likely lead with “How’s everyone doing tonight?” or ask a couple sitting in the first row if they’re on a first date. The comedian is feeling out their audience, trying to see what will get laughs and what will flop.

The analogy in SaaS sales is called discovery. A sales rep asks their prospect discovery questions to better understand what they need to do to run an effective and successful sales process.

Discovery is one of (if not the) most important stages of every sales process. Don’t underestimate it. A bad discovery call can kill an entire deal. A well-run discovery call should feel like a good cocktail conversation, not an interrogation for the prospect.

Simon, and other stand-up comedians, retaught me that discovery should be a two-way street. A stand-up comedian asks questions to allow their audience to get to know them. They’re establishing early rapport and making themself likable. A comedian knows that they’re not going to get the crowd to laugh if they give off a bad first impression.

Similarly, the discovery process in sales is an opportunity for prospects to meet the seller, not just the other way around (which is how we typically think about it).

Founders and sales reps should stop treating discovery like a checklist. Think big picture. Discovery is about getting to know your prospects (and vice-versa), not taking detailed notes… that’s what call recordings and Salesforce are for.

Don’t stick to the script

I used to think that stand-up comedy was entirely improvised. Anyone else?

Stand-up comedians don’t just get up on stage and make jokes about whatever comes to their mind for the duration of a set. Improvisation does still have an important role in stand-up comedy, though.

As much as stand-up comedians meticulously prepare and practice, they know that not everything will go to plan during a set. They accept that some new material will make their audience laugh, while some is bound to fall flat. Maybe someone in the audience has too much to drink and starts heckling... A good comedian can improvise and seamlessly go back-and-forth between spontaneous quips and prepared jokes.

Seeing Simon riff in response to flopped jokes, hecklers, and technical difficulties at bars in Ohio, Indiana, and Kentucky made me realize how important improvisation is in sales too.

The ability to go off-script is the difference between a conversation with and a presentation to your prospect. Good sales reps don’t read from a script or talk about every point in their slide deck. Good sales reps listen and respond to their prospects.

Take, for example, objection handling during a sales call. Though it’s important to prepare responses to common objections and questions, remember to respond to the question you’re being asked, not the one you would like to answer. Giving generic replies that don’t actually answer your prospect’s specific objection/question is a quick, surefire way to lose their trust.

The worst thing a sales rep can do is avoid their prospect’s question/objection. Good sales reps embrace uncertainty and improvisation by pausing and asking their prospects for feedback throughout a pitch. They meet interruptions head-on and use improvisation to tie their responses back to their original meeting agenda.

Practice, practice, practice

Simon practices a lot. Like a lot, a lot.

When he’s not performing or writing, he’s analyzing his sets. Simon records all of his performances and watches them over and over with the scrutiny of an art film critic. He pours himself into these hours-long review sessions as much as he does into his actual performances. He brings the same dedication and intensity to each film analysis session, regardless of if he got a standing ovation or didn’t get as many laughs as he was hoping for.

Seeing Simon watch hour-after-hour of his sets made me reflect on my relationship to practice in sales. I couldn’t remember the last time I had just watched or listened to one of my meetings from start to finish (and not in the background while doing other work), much less took notes and analyzed my sentences the way my friend and aspiring stand-up comedian does.

Good sales reps don’t stop practicing their pitch just because they’re fully ramped or smashing their quota. Bad sales reps forget to (or avoid) practice after their onboarding/training period.

Another one of Simon’s inspiring practice habits is how and how much he asks for feedback. When writing and preparing sets, he’d often ask me if I thought his new jokes were funny or not. He’d ask me what material I specifically liked and what I didn’t like in his sets. I’m not a stand-up comedian, but he valued my opinion and brought me into his creative process.

Simon’s process of gathering and implementing feedback motivated to do the same for sales. I stopped asking colleagues and managers for general feedback (e.g. “How do you think that call went?”) and started focusing on my specific strengths and weaknesses.

When asking for feedback, start small (to the tune of a few sentences or a deck slide). When trying to rework sections of your pitch, practice in front of others and ask for their feedback as you incorporate it back into a full presentation/demo.

The art of the callback

A callback is when a comedian tells a joke that refers to one previously told in their set. Callbacks are usually told at the end of a set.

What makes a callback so funny is that the reference is meant to be forgotten, then instantly remembered. Even after a 60-minute set full of many good jokes, an audience will immediately remember an earlier line when a comedian delivers a callback to perfection. It’s tricky to get right, but when it lands, a comedian creates audience rapport that’s second-to-none.

A callback can make the difference between an audience remembering how funny a set was versus how funny a few jokes were. Stand-up comedians are performers, not joke-tellers, which is why having a good callback or two is so important.

Need an example and got an hour? Dave Chappelle delivers a callback masterclass in his Netflix specials from 2017.

Watching Simon toil over his callbacks and strive for a Chappelle-esque one was energizing. More specifically, this forced me to think about how to use callbacks in sales.

A callback is actually one way in which good sales reps make themselves stand out to their prospects. Have you ever been a prospect/buyer on a sales call and the sales rep brings up a point that you shared with them during discovery? It’s one of the most reassuring/best feelings I’ve experienced as a buyer because it makes you feel so heard and respected as a buyer. A callback in sales will make you “wow that was a good call.”

This is another reason why I think discovery is the most important part of any sales process. Was this a callback in itself?

We can all learn something about SaaS sales from someone who has never sold SaaS. For me, it was from a stand-up comedian or two. Who will make you better at your job in 2021?

Thanks, Simon!