Improv and the Art of Selling

by Kat Koppett


Improvisers create without a script or the chance to revise their performances. They work collaboratively to entertain diverse audiences by taking their suggestions and building stories, scenes, whole plays, on the spot. Sound scary? Increasingly, businesses are recognizing how similar their tasks are to those of the improviser. As the world moves faster and becomes more global, there is less time to plan and more need for collaboration. So business people are turning to improv for help. You see, in order for improvisers to succeed at their ridiculous endeavor, they live by certain principles. Principles that can be useful to anyone who must create, collaborate and build relationships with others.

These days, with more sophisticated customers and more complex products abounding, sales people, especially, can benefit from these techniques. Successful sales encounters are dependent on an ability to read customer personalities and needs, instill trust, and cultivate creative solutions. Let us take a closer look at some of the improv principles that can help sales people succeed.

Build Trust

The greater the risk, the greater the necessity for trust. Improvisers risk humiliation in front of hundreds of people each time they perform a show. Customers can have even more at stake. Imagine, the financial well-being of their organization may depend on the products they buy. Their jobs may hang in the balance. A sales person may be able to make a quick sale once by tricking a customer into buying something that does not meet his or her needs, but to have long-term success, he or she must be able to able to establish empathy and credibility. Here are some ways to do just that:

  • Get to know your customer – Intimacy breeds trust. Spend some time learning about the people you sell to. What do they do, like, think about, when they are not at work? Let them get to know you. We do not like to reveal ourselves to people who do not reciprocate.
  • Follow through – Real trust is not created until the rubber hits the road. If you want to sell to a customer a second time, make sure you deliver at least as much as you promised the first time. (More if possible.)
  • Create a safe environment – If you can lower the perception of risk, you will increase the willingness of others to engage. When you are asking people to take chances, they must feel safe. When possible, give customers a chance to test the waters.
  • Make your partner look good – It is only by focusing on your client’s needs that you can fulfill your own. How can you help them sell the idea to their superiors? How can you help promote their agendas? Think of your customer as your partner. When he gets what she wants, you get what you want.

Be Spontaneous

What many people label wit or cleverness in improvisation is simply a willingness to say whatever comes to mind. Spontaneity is the fuel of creativity. And creativity is at the heart of problem-solving. Problem-solving is, in turn, at the heart of a sales interaction. Craig Harrison, sales consultant and trainer in California says, “So often we are bound by rules and regulations, restrictions and proscriptions. Sometimes we’re so bogged down we can’t respond to the issue at hand.” The best salespeople pay attention, trust their instincts, and go with the flow. They solve personal and practical problems as they arise, rather than sticking to a prescribed method or structure. To increase your spontaneity:

  • Be silly. Creativity is, by definition, a departure from the status quo. You can always preface a suggestion with “I know this sounds crazy, but…” Try it before you reject it.
  • Be Obvious. Sometimes we reject ideas because we believe they are not creative enough. When you articulate the obvious, either you are voicing something that everyone is thinking, but no one else has the courage to say, or you are contributing something that seems very obvious to you, no one else has thought of. Both have value. In addition, by simply naming something you notice, you may uncover an important need or objection. Facial expressions and body posture tells us a lot. Trust your impulses when you think you see a clue.
  • Celebrate Failure. In order to create, we must take risks. In order to take risks, we must be willing to fail. Bad ideas may spur great ones. Generate ideas collaboratively with your customers, and give a prize for the worst one.

Say “Yes, And…”

Once we have taken the risk of offering up an idea, we must be willing to accept and build on it. Harrison says, “So often we are apt to respond to comments, suggestions and inquiries with some variation of “Yes, but…” The impact is immediate: whatever “offer” being advanced is now qualified, mitigated, diminished or otherwise muted.

Your customer’s world of possibilities has just been restricted. The idea in question, once ripe with potential, has now been shackled.”

An improviser who forgets everything else can still perform well, simply by following the “yes, and” rule. If spontaneity is the fuel of creativity, saying “yes, and…” is the engine. It turns impulse into workable solutions. And it builds connection and trust along the way.

To improve your “yes, and-ing” skills:

  • Remind yourself and your partners of the rules of brainstorming when generating ideas
    • Separate idea generation from idea evaluation
    • Quantity over quality
    • Record without discussion
    • Build on other’s ideas
  • Explore when and why you say “no” to ideas. Can you work through some of the blocks? Can you negotiate with your supervisors for more leeway? Who has the power to say “yes”? How can you encourage them to do so? Focus on underlying needs rather than specific solutions.
  • Pay attention in your non-business contexts. How often do you say “no” there? Why? Say “yes” sometimes, just to see what will happen


People love stories. That is why they read novels, watch television, go to the theatre, and gossip. The appetite for stories in humans is nearly insatiable. So, improvisers work hard to become good storytellers. Stories are more than just entertainment, however. Story is meaning. The way we make sense of the world is by linking little bits of data together into a connected whole. Stories deepen learning, enhance retention of information, and give us a context for all of our daily choices and activities.

Here are some ways to use stories effectively in sales:

  • Frame Value. Andrew Kimball, of QBInternational, says, “The only reason that anyone buys anything is because they perceive it as fulfilling a need. ‘Value’ equals needs fulfilled.” It is our job as sales people to link the features and benefits of our products to the needs of our customers. Story is an exceptionally good tool for framing value. When we are evaluating a new product, service or option, our tendency is to see how it fits into the overall narrative of our lives. Talented sales people weave beautiful stories for us, showing us just how their offerings will lead to happy endings.
  • Pique interest. No matter how brilliant your information is, if people are not engaged, they will not absorb it. Stories can be used to break the ice and establish credibility and empathy. They can add humor, suspense and drama. Look for opportunities to tell stories whenever you are presenting.
  • Gather information. Stories can provide information about expectations, assumptions, and values. Have your customers share stories about their current situations and concerns. Asking for examples and anecdotes will provide much richer information than simple statistics or bulleted objectives.

Selling is an art. Take these tools, then, from the art of improvisation and apply them to your work. Trust yourself, and others will trust you. Take risks and you may discover genius. Work with your clients to develop relationships, and you will expand your range of selling opportunities. And the most important lesson? Have fun along the way.

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