Last night was one of the first nights I’ve had a bit of down time for myself in a while and accidentally happened upon Comedy Central’s First Annual Comedy Awards. Why it took them so long to come out with an awards show, I don’t know, but I’m happy they finally got around to it. Without a doubt, the awards show was a pleasant surprise as I’m a huge fan of well-delivered lines of wit but I’m also a hopeless tangentialist in lively conversations and have a strong affinity for improvisational comedy (theater).

After having my fill of good laughs, I started plugging away at my late Sunday night work again but this time for the alumni association, The Wharton Club of New York. After having transitioned out of my previous volunteer position as the Web Committee Chair at Dance Parade, I’ve taken on an investor contact role for the association’s 1st annual Alumni Business Showcase (ABS), which was formerly called the Wharton Alumni Business Plan Competition. This year the focus has shifted from being a competition and more about making the process more efficient for young, promising companies to meet and potentially get funded by accredited seed and angel investors.

In order to acquaint myself with the entrepreneurial applicants vying to pitch at the showcase, I reviewed their profiles and found many of them to be pretty impressive and finished by wondering what could help other aspiring entrepreneurs to be successful with their ideas and their messaging. Words like “creative,” “innovative,” and “unexpected” came to mind to describe what future entrepreneurs might bring to the world’s table and then I recalled my classes in improv. Besides the improv giants like Avery Schreiber, Viola Spolin and her son Paul Sillis, founder of Chicago’s famous Second City troupe, we, too, can be improv experts in our entrepreneurial endeavors over brainstorming sessions with our teams by employing just some of the key principles they helped lay the groundwork on.

1. Come Prepared

Doing things “off the cuff” or “playing things by ear” doesn’t mean acting in blithe ignorance of events happening around you nor does it mean rehearsing a specific script of expected outcomes, because life and business rarely offers us the luxury of total predictability. What it does mean is to come trained, practice your craft, internalize certain structures and modes for when it comes time for your hyper-awareness to translate to action or thought, like that of improvisational jazz artists.

2. Be Willing to Screw Up

With so many variables at-play, be prepared to screw up and screw up big. By letting go of any fear of missteps will allow you to take on big risks more freely. Without that risk-taking behavior, the adrenaline, the rush and the potential upside to a venture can fall into the trough of the banal and of little return. Beyond the fear of failure, this is where everyone inherently understands that in order to be wildly successful, they have to be willing to fail spectacularly.

3. There Are No Mistakes

After you get over your fear of failure and fear of success, you’ll soon realize that they weren’t actually failures – just interesting choices. One well-known series of thousands of “failures” until he finally got it right is Thomas Edison’s goal to find a suitable filament to make the incandescent electric light a viable, commercialized device.

4. Understand What You Control and What You Don’t

More or less, the only thing you can really control are our own choices. Although we might influence others, they ultimately make their own choices. What this forces us to do is stay more attuned to their queues, signals and frameworks to focus on how to keep the flow of creativity going as opposed to slowing down progress by trying to convince them to seeing things your way.

5. Be Honest and Don’t Object to Others’ Honesty

Although general ethical and moral lines are already drawn as to what’s right and wrong, the process of acting and reacting shouldn’t be bound by the judgment of others when coming up with new ideas. In short, there are no “stupid ideas,” just interesting choices that may lead to unexpected or challenging opportunities that may be a bit of a “stretch.”

6. Stay in the Moment

By dwelling on what happened in the recent past or being distracted of potential issues in the near future, the opportunity for you to stay aware of your surroundings and to respond to such inputs will be lost and potentially irrelevant (i.e., lack of timeliness of information). I’m not saying totally ignore either them, just be in the moment for when you need to act, because thinking of the past and future is what the “coming prepared” step is all about – thinking of frameworks that have worked well and thoughtfully poking through the “what if” scenarios.

7. Be a Good Listener and Observer

Coming up with good ideas doesn’t mean that you’re the one that’s constantly talking and throwing out suggestions. It’s actually the process of listening to and observing others to then creatively express or act, when what you’ve trained for can build upon what others have offered to you. To effectively deliver, you have to be an acute, active listener.

8. Favor Action over Inaction

Taking action requires specificity and specific action requires commitment to the action itself. That’s why a lot of blathering over glossed-over commentary can be really “cheap,” ineffective and very difficult to build upon.

9. Trust and Teamwork

Although we instinctively trust ourselves for choices we make out of self-interest, we have to be willing to trust others AND ourselves to make choices that are in the interest of the ecosystem around us.  Even if you end up digging yourself into a hole, there are infinite number of choices and combinations that you and your team can make to help dig you and the collective team out.

10. Always Take on the “Yes, and” Attitude

This doesn’t mean to be passively compliant but to be willing to accept someone’s honesty as a gift for you to build upon. It’s also a direct acknowledgment of their idea/feelings and an affirmation of trust that the offer’s integrity is intact before building interesting choices on top of that.  Sometimes just incorporating this one principle in a brainstorming session can make bits of “magic” (or genius) percolate.

As a quick example of just some of these principles in-action, I’ve included the Best Comedy Actress for TV acceptance speech by one of my favorite comediennes, Kristen Wiig, at the Comedy Awards Show (2011).

For some reason, Comedy Central doesn’t seem to be supporting its video embeds anymore (see above), so I had to circle back and use a more recent example. This is both Kristen Wiig and Will Ferrell “yes and-ing” it like the rock stars that they are.