Improvise your way to more effective sales conversations

Katherine Shao
VP Sales Enablement Practice
Katherine Shao turns her musician’s lens on business conversations – and shares what jazz musicians teach us about effective sales conversations.

The improvisatory nature of jazz is a great analogy for working together. One of my favorite examples of this is a duet by Jerry Mulligan and Paul Desmond who carry on a conversation with their instruments in a tune called “Two of a Mind.”

What’s really going on underneath the dialogue between two or more musicians? And how does that relate to an effective business conversation? Whether musical or spoken, the ad-lib nature of conversation doesn’t just happen out of chaos. Behind every masterful improvisation, there is a structure.

For musicians, that structure is codified into something called a lead sheet. We can play music like it’s a conversation, and the lead sheet provides that minimum guideline of what to play.

If only there were such a construct for conversations between sellers and buyers; agents and customers; decision makers and their peers.

Take salespeople – a group whose success at having good conversations with customers is critical to the success of a business. At many companies, salespeople are given so much content all at once: not just the minimum of what to say, but every single item under the sun crammed into playbooks, training classes, emails, and intranets. In our audits of enablement content across industries, the Oxygen team often observes what we call the Firehose Effect—absurd quantities of mandatory content sprayed at new sellers in a remarkably intense fashion, sometimes for an entire quarter. So instead of tuning in, they opt out. 

To explore an alternative to that unsustainable method, let’s look at the musical lead sheet. Here is a picture of one for a tune called "Killer Joe" by Benny Golson.

"Killer Joe" by Benny Golson

If you aren’t a musician, particularly if you aren’t a jazz musician, a lot of what is on this page probably looks incredibly foreign. Most people will recognize musical notes, but a lot of the other symbols and structure shown here are not universally known. A jazz musician, however, will recognize chord labels or indications on when to repeat the melody. They’ll know how to read the musical notation and play it on their instrument. They’ll even know how to interpret the cryptic jargon that are really instructions on how to end the tune. Instructions that are—as with most jazz—open to interpretation. 

Aside from the cryptic jargon, there’s nothing that dictates how this tune should be played. There’s no tempo, no suggestions for which instrument to use, no strict rules about which musician plays what, when. You can take the same group of musicians and ask them to play Killer Joe in an easygoing swing format, or you can ask them to play it with a Latin groove.

Play the easygoing swing version
Play the Latin groove version

The two versions sound pretty different. But they are the same composition in terms of structure. They have the same melody, harmony, and form.

The lead sheet above is an example of the minimum structure needed to provide instruction to a group of musicians as to what they should play, but not how they play it.

A conversation is nearly impossible to script or prescribe, just as it is impossible to ask musicians to improvise on Killer Joe in exactly the same way twice. With musicians, we assume that they have a certain level of proficiency about the structure and the minimum they need is the lead sheet to be able to play it through, in swing or in Latin, without embarrassing anyone.

Salespeople may need to change the tone or topic of their conversation, depending on whether they’re talking with the VP of HR, or a manager of recruiting, or a CIO. There may be other people on their own team who are part of the conversation. Everyone needs to be on the same page, or it will sound incoherent to the customer.

What if, instead of overwhelming sales people with so much content, we could give them the minimum structure that they would need for their conversations? 

After hundreds of gigs and rehearsals, the best jazz musicians can recall tunes like Killer Joe almost without thinking. At that point, they can move far beyond just playing it straight and experiment with its boundaries, and can deftly engage in a camaraderie that makes it look like they are all enjoying the most nuanced private joke in the universe. 

But it doesn’t take a jazz musician with a Grammy to use a lead sheet. All you need is the fundamentals. High school players, dad-banders, enthusiasts, occasional giggers with day jobs, they can all use these sheets and play at a level where it’s…fun.

Similarly, not all salespeople will be gurus. And no medium-to-large sized company can hope to have a salesforce comprised entirely of master conversationalists. But there is a huge population of sellers who are pretty darn good at what they do. What if we were able to give sellers just the minimum for them to play their part, and make it easier for them to practice, rehearse, perform, and learn? 

What does this “conversation lead sheet” look like? Some initial thoughts:

If we can embrace the improvisatory nature of conversation, perhaps that will provide insight as to what kinds of guiding frameworks would be most helpful for today’s overwhelmed salespeople. 

Want to tune into other music Katherine Shao is listening to? Visit her Spotify playlist.

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