It’s Not Quite Funny Or Die, But Improv Works To Fuel Powerful Innovation

Tina Fey’s “Bossypants” was the inspiration for to try out improv techniques to invigorate its team. Here’s what happened when they got off their duffs and found their inner monkey saddles.

It’s Not Quite Funny Or Die, But Improv Works To Fuel Powerful Innovation

When we last checked in with, the grandaddy of question and answer platforms was changing direction. Moving a 15-year old general purpose search model to one that uses proprietary, semantic search technology to deliver answers from its own content banks, community, and experts, was no simple task. Nor did Ask’s move to mobile happen overnight. 


But change is good, says Ask’s chief product and technology officer Lisa Kavanaugh, as evidenced by strong results. Traffic is up 35% thanks to product development and enhancements to the site and mobile. There have been 2 million app downloads and triple-digit growth on the mobile site month over month last year. 

“We are hyper-efficient at playing within the boundaries,” Kavanaugh says, “and we needed to look for ways to be more innovative.” And then CEO Doug Leeds challenged staffers to come up with some big, new ideas. Kavanaugh laughs as she recounts what happened next. “We got back a proposal to get brand-new office chairs. It’s just one glaring example that we were not breaking out of that mental shuffle,” she recalls.

It was enough to make Leeds take a different approach. Kavanaugh says he’d been reading Tina Fey’s Bossypants, which points out how improvisation can lead to more creative thinking and innovation. “He’d seen it sprinkled in other management books, but that was the tipping point to really investigate.”

Kavanaugh confesses that she and other members of the executive team were “a little scared” to try improv as visions of having to perform like the cast of Who’s Line Is It Anyway? took hold.

When the Ask team finally dove in (with assistance from Sue Walden at ImprovWorks!) they discovered something totally different. “It was really transformative,” says Kavanaugh. “Folks said it was the most impactful training session in their entire career.”

What It Isn’t


For skeptics and those who suffer from performance anxiety, Kavanaugh says they should rest assured that there is no “deer in the headlights moment of having to perform on stage.” Or be as instantaneously hilarious as Drew Carey and his cronies when riffing off suggestions from the audience.

What It Really Is

Working with the foundation of improv, says Kavanaugh, various exercises are designed to keep participants present in the moment and not think ahead. “Every idea is a great one. It’s accepted with gratitude and built upon. It’s a shift out of analytical space rather than bulletproofing an idea based on what won’t work. I do this all the time in my own head and some of the best ideas never see the light of day.”

How It Works

(It’s called a monkey saddle, don’t judge.)


The exercises range from simple warmups where everyone walks around (improv is big on standing, says Kavanaugh, as apparently sitting on your duff blocks creative juices) and points to an object but must call it by any other name than what it actually is. “It’s a complete mind scramble that shifts you out of that thought process and wakes you up,” she explains. 

Once everyone’s brain is sufficiently scrambled, they’re ready to move on to brainstorming. These group exercises are designed to get ideas on the table without judgement. For example, a problem is introduced and participants note down possible solutions on index cards. The solutions are scored in teams of two and what remains at the end are a vetted selection of the most effective opportunities to solve the problem.

Time Suck?

Not at all, says Kavanaugh. The exercises are timed so everyone can move through to the resolution quickly. The example above took 15 minutes to find five great solutions. 

Roll Out

“Our culture was to move fast and deliver quickly and while we did that very well we were looking for the next crazy idea, the big leap. We were only looking to a small percentage of the organization to think that way.”


So rather than just do one or two sessions and call it the end of training for top brass, Leeds took the improv idea to the next level. Kavanaugh says Ask’s intranet has a log of exercises and videos so every person in the company can use it. “Doug doesn’t do anything in a small way. We made this a pillar of culture and every Friday we are training this muscle with a repository of tools,” she says. Meetings often start with improv warmups and new hires are encouraged to participate in sessions, too. 

Results Oriented

Kavanaugh says she’s really excited to see people interacting in a new way. In a brainstorming session with engineering to improve quality and reduce bugs, she was pleasantly surprised to hear the best solution come from the head of HR, who was encouraged to attend. “She was applying her way of thinking and motivating people with bonuses tied to performance,” says Kavanaugh. Offering a bonus to someone for fixing a bug turned into an aha moment. The same thing happened at a recent hackathon, which not only drew record participation but coaxed solutions from finance and legal departments. “The bonds of trust and common skillset and language of improv allow us come together and leverage that.”

In rolling sessions, Ask staff kick an idea around and keep building. “The trick is to go as far as you can, even if it’s completely ridiculous. There are nuggets you can get something from. Then we let it marinate for a week, put them up on the wall again and get back together continue to build, evolve, morph, shrink so what you come out with in the end is much more exciting.”

But Is It Funny?

Kavanaugh says whether anyone is trying or not, certain exercises like the object naming do tickle the funny bone. “I called something a monkey saddle once, and that got a lot of laughs. I can’t tell you how many people say, ‘I don’t even feel like I am working.’ There’s sense of trust and when you feel safe all kinds of amazing things emerge.”


Here’s Lisa Kavanaugh discussing innovation versus growth on 30 Second MBA:

About the author

Lydia Dishman is a reporter writing about the intersection of tech, leadership, and innovation. She is a regular contributor to Fast Company and has written for CBS Moneywatch, Fortune, The Guardian, Popular Science, and the New York Times, among others.