CEO and Founder, Kasa.
Some people are born for the stage. I wasn’t one of them. As a kid, I didn’t do theater, and back in my days as a green associate at a private equity firm, I gave presentations but never volunteered. I wasn’t great on my feet. One day at a Monday morning stand-up, someone called out sick, and I had to cover for them last minute. I flubbed it. Turning on a dime to speak in front of a big group wasn’t something I was good at, so I decided to do something about it. With a recommendation from a trusted colleague, I signed up for improv classes.
I went to a very well-known improv comedy group. I didn’t know it then, but this was like signing up for intramural basketball and playing against Lebron James. A-list actors and comedians had gone through the program, and I was in over my head. But, it turns out that many of the lessons I learned from improv have been indispensable in my role as a founder and CEO of a company in the accommodations industry.
Taking An Indirect Path To Big Results
In improv, you always build in uncertainty. You discover the scene and the characters over time while uncovering and solving problems in real time. That practice will be familiar to anyone who has ever built something hard and new.
The principles of improv often challenge our conventional wisdom. In one exercise, we were asked to do everything we could to not make the audience laugh. Intuitively, one might think a serious scene would achieve this. Yet, the more earnest we became, the harder the audience laughed. This counterintuitive outcome mirrors a truth in business: Sometimes, the indirect path yields the most direct results.
Take sales, for example. I’ve found that when you focus less on the hard sell and more on genuine engagement, your effectiveness skyrockets. By openly discussing a product’s limitations, you foster trust with potential customers. By prioritizing learning about a customer’s needs over pitching, you can truly advise if your product can be a solution or build trust by suggesting you are not the right fit.
And here’s another twist: To build a product that addresses a large market, I believe you are better off starting out building something perfectly that a very small group obsesses over than building something imperfectly that a much larger group merely likes.
Allowing For Some Improvisation
Drawing parallels between the world of improv and business strategy, I also began to reflect on the balance between meticulous planning and on-the-spot improvisation. In the corporate realm, should our approach to achieving goals be akin to rehearsing a Broadway show, where every last detail is planned and choreographed? Or should we, much like in improv, set a general theme and adapt as the “scene” of the business landscape unfolds?
There is no one-size-fits-all approach, of course, and the answer differs depending on the level of change and uncertainty in an industry. For my company, I’ve found that having an overarching strategy and set of goals (or themes of a scene) combines well with working agilely to adjust the specific approaches to achieving those goals. We’ve had a very clear direction of striving to become the accommodations brand of choice for property partners, guests and neighbors alike since the beginning, but if we tried to map out precisely how we’d accomplish that goal from the start, we would have never gotten started.
Listening More Than Speaking
One of the paramount lessons from improv that resonated deeply with my business journey is perhaps the most counterintuitive: Improv is about listening, not speaking. Every scene has multiple stakeholders (actors), and the key is to really listen. If you don’t tune in before acting, you get misaligned with others on stage, and the scene flops.
This principle became especially crucial for my team during the pandemic. There was no playbook for how a hospitality company should navigate being in the eye of the storm of a global disaster. Our ability to not only survive but also thrive was rooted in our commitment to listening. We engaged each of our property partners and adjusted more than 45 contracts in just two months. I spent every day from 6 a.m. to midnight in deep conversations with our partners. Through this genuine engagement, we found mutually beneficial adjustments to our contracts and have built a strong foundation with our partners, which has helped grow the business significantly.
I’m always amazed at how often the lessons from improv have guided me since that day I couldn’t improvise in front of my team. I still remember the intensity of my feelings: My heart was beating quickly, my mouth dry and I couldn’t muster anything to say. It felt like a deep failure in front of people I respected. And yet, it was this moment that is at the root of my learnings with improv.
While I no longer attend improv classes, their principles continue to shape my actions daily, guiding both my personal leadership style and the strategic direction of my business. This journey from that day of failure to now underscores a universal truth: It is often from our most challenging moments that we derive our most profound insights and achievements.
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