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The Ballad of the Cowardly Salesperson – Sandler Training

Verse One – Prospecting

The Cowardly Salesperson looks at their prospecting plan for the week and rolls their eyes. The told their manager what their manager wanted to hear when they built their plan. The Cowardly Salesperson believed that they didn’t need a plan because they had “great relationships” and their company had a “great reputation” so all of their business would come through referrals or inbound leads.

When the Cowardly Salesperson did make a prospecting call they cycled through the same list of people who were happy to take the Cowardly Salesperson’s call or meet for a free (to the prospect) lunch, but never actually buy from the Cowardly Salesperson.

What the Cowardly Salesperson’s manager didn’t understand was the Cowardly Salesperson took rejection personally and, when they spoke with a gatekeeper or someone who could say “yes” instead of only “no” or “I’ve got to talk to my boss” they felt like a child who had to please their parent. That belief prompted them to say and do things that weren’t in their best interest, like agreeing to email information or accepting “we’ll call you back,” yet they added those prospects to their opportunity report because one of those opportunities “might close someday and I want credit.”

Verse Two – Selling

The Cowardly Salesperson managed to get a meeting with a prospect. They spend the time their prospect gives them talking about the reasons why their prospect should buy today including all of the new features their company is adding “soon.”

They find out how much time they have with their prospect when their prospect cuts them off mid-sentence and says, “sounds good, how about you send me a proposal and some references and I’ll get back to you.”

The Cowardly Salesperson rushes back to their desk and spends the rest of their day working on that proposal, ignoring their prospecting activities, emailing it to their prospect as they wrap up their day believing that their prospect will “appreciate their effort in getting a proposal back so quickly.”

A little more than one week passes and the Cowardly Salesperson’s prospect, who they confidently told their boss was “a sure thing,” hasn’t responded to their emailed proposal. The Cowardly Salesperson leaves multiple messages, voice and text, with their prospect over the next two weeks, their tone sounding increasingly desperate and aggressive with each message.

When the Cowardly Salesperson’s prospect does call back, offering profuse apologies about being “busy,” the Cowardly Salesperson offers a discount at the beginning of the call believing that they need to “add value” so the prospect will close. When their prospect does agree to buy the Cowardly Salesperson tells their manager it was because of their “great relationship” with their new client.

Verse Three – Client Development

With a new client in their book the Cowardly Salesperson regularly offers additional services for free to “build the relationship,” but doesn’t ask for introductions because they “haven’t earned the right.”

One day their client calls to say that they are switching to a competitor. The Cowardly Salesperson takes this personally because of “all the things they’ve done” for their client. In desperation they offer extra discounts, services and promise their company will “do better.” When those pleas fail to move their client the Cowardly Salesperson aggressively reminds their client of the features-and-benefits of their product and all of the features-and-benefits that will be added “soon,” which only the Cowardly Salesperson cares about, and defending their price, performance and customer service.

When their manager asks why their client switched the Cowardly Salesperson tells their manager that their client “got a better deal” then tells their manager that their company “needs to lower prices to be competitive.”


Sandler said sales take “guts and humor.” Support your team to have guts in all three phases of selling by coaching them to stretch their comfort zone in small ways daily. As the C.S. Lews quote goes, “isn’t funny how day by day nothing changes, but when you look back everything is different.”

Until next time… go lead

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