Storytelling: Why It Rarely Works in Sales Prospecting

Many a book has been written on storytelling. Especially in marketing. Today, storytelling (as a practice) is creeping into sales prospecting. But is it effective to start conversations from cold?


Many a book has been written on storytelling. Especially in marketing. Today, storytelling (as a practice) is creeping into sales prospecting. But is it effective to start conversations from cold?

Like so many “best” practices this one rarely works for sales reps. Because stories are usually presented:

  • Outside the buyer’s decision-making context (not buying context … the many parts preceding it)
  • Selfishly, in a way tries to force conversation about the seller’s value
  • To help uncover a “hidden pain” the prospect has yet is unaware of

Yes, B2B buyers are concerned more with business value, how your solution is different … less with features and benefits. But until prospects discover, on their own:

  • why buying might be needed,
  • a way to manage their own internal change

… they won’t be in a position to want your story.

In many selling contexts, this reduces your story to a self-centered means-to-an-end: A discussion clients don’t see value in (yet).

Sellers using storytelling as a conversation-starter often suffer. Especially when clients don’t routinely invest in what is being sold.

After all, why would prospects want to hear a story (about a problem they don’t know they have) unless they were ready to consider change? Biased questions create push-back.

In Defense of Storytelling

“Sometimes prospects aren’t willing to open up to sales rep’s questions which are aimed to discover and build pain,” said a colleague who co-founded a SaaS company selling solutions to leaders of sales teams. His targets are often reluctant to invest. The status quo feels just fine.

“Sometimes prospects get frustrated at answering questions without being told why. Sometimes its difficult for prospects to understand ‘whats being sold to them’ and need the context. Storytelling helps prospects resonate with a sales person as they can relate to another customer in the same sector, with the same job title, with similar objectives.”

But here’s the problem: Buyers (who are not buyers yet) aren’t interested in helping you discover pains … and build upon it.

“Qualification or discovery questions on cold calls can sometimes feel like traps to prospects,” says sales trainer, Josh Braun. “How are you going to use this to sell me? Where are you leading me? It’s like when a mall kiosk person says ‘Can I ask you a question?’ You look away because you know they are asking to lead you somewhere.”

Prospects are very good at identifying and resisting your biased questions. Sadly, these are the questions sellers are trained to ask … which serve only their (not the client’s) need.

“This situation happened on a sales call I reviewed for one of my own reps today,” my colleague continued. “The prospect pushed back on my rep’s questions which were aimed at discovering how he could help and where the opportunity existed. As soon as he told a relevant customer story, the conversation changed for the better.”

But did the conversation continue? In most cases they do not. Prospects may get clear on what you’re trying to sell to them; however, they may become less motivated to continue the conversation!

Instead, what if the sales rep asked, “What would need to happen for you to give sales managers a way to monitor and act on how reps are interacting with prospects?”

The “why” is obvious: The rep asks because he’s interested more in the prospects’ current capabilities… less about qualifying them into a deal. By focusing the prospect on their own (lack of) capability there is no need to be put into a defensive posture.

Bottom line: Avoid the push-back completely, save the story for later.

Assume a Neutral Role First

What if your communications technique re-framed: Away from coaxing the prospect into talking about their “why” (which they don’t have), toward a neutral role.

What if you first helped the client realize a problem exists with neutral questions?

The question, “What would need to happen for you to give sales managers a way to monitor and act on how reps are interacting with prospects?” is not asking to consider what they’re missing out on. Instead, it is asking the client to consider a problem (or advantage) they don’t (yet) know exists.

Here is another neutral question my colleague should be asking when calling-in cold: “How are you measuring your sales managers ability to help reps drive qualitatively better sales conversations?”

How, not “are you.” This forces introspection: “Gee, I’m not measuring managers’ ability to help reps communicate better…. why should I be?” Now they’re on a path to developing their ‘why.’

Under your neutral guidance.

If prospects don’t have a need for your tool you cannot nurture that need out of them. You must help them, first, develop a ‘why’ that is not tied to the pre-determined need you have (for prospects to develop a why enabling your eventual sale).

Here are action items for you to consider:

1) Why would a customer who is not, yet, able to initiate the change needed (to bring you in) want to hear a story?

2) What if you, instead, got better at facilitating conversations addressing clients internal decision systems? (helping the champion navigate their internal decision process… and, thus, shaping the RFP)

3) What if you got better at identifying what created the buyer’s status quo — then helped internal champions create a business case within the framework of their decision process?

Stories may be of (better) use when we are invited to share them by the prospect — for their reasons rather than being a means to convince them of something they’re overlooking/not seeing. That feels too much like persuasion.

As Edith Crnkovich, of DXC Technology and self-proclaimed sassy storyteller, says,  there is more value in “having the sales person first seek to understand the customers business issues before launching into a story. I don’t think we spend enough time doing that and this is mostly about asking a lot of questions first.”

What do you think?

Author: Jeff Molander

Jeff Molander is the authority on making social media sell. He co-founded what became the Google Affiliate Network and Performics Inc., where he built the sales team. Today, he is the authority on effective prospecting communications techniques as founder of Communications Edge Inc. (formerly Molander & Associates Inc.) He's been in sales for over 2 decades. He is author of the first social selling book, Off the Hook Marketing: How to Make Social Media Sell for You.Jeff is a sales communications coach and creator of the Spark Selling technique—a means to spark more conversations with customers "from cold," speeding them toward qualification.

2 thoughts on “Storytelling: Why It Rarely Works in Sales Prospecting”

  1. I like the fact that this article questions the ubiquity of storytelling. I keep hearing from people who say, “Everyone tells me I’m supposed to tell a story.”

    But ironically this article would have benefited from a … story! How are people telling stories the wrong way? Are they dialing in cold and then saying, “Hi, is this Ms X? Have I got a story for you!”

    In my Amazon kindle book, Grow Your Business One Story At A Time, argue that sometimes telling a story is a mistake. A story often is the worst way to respond to an objection.

    I also talk about the importance of choosing a story for a strategic purpose, not just to tell a story. The quote from Edith Crnkovich is right on the money: know your audience before you tell your story. Stories easily backfire when you don’t understand the context your audience brings as they listen.

    1. Glad to receive your critical and THOUGHTFUL feedback, Cathy. You’re right about a story to illustrate. The story I tell about my “colleague” is a real life one… so I protected the name of the innocent here. Maybe it didn’t seem story-like enough. Or another is needed for clarity’s sake. Essentially, sellers seem (in my experience) to be telling stories without first earning both the right AND enough interest. As you seem to be indicating. They also seem to be telling stories because they get push-back from clients who say, “wait… what the heck are you (obviously) trying to sell me here?” So they drop a story… to see if the client will realize “oh, yeah… I can relate.” But what happens is the client thinks, “Nice story… and I know why you’re wasting my time telling it…. to size me up for a product/service I haven’t any interest in… and am even LESS interested in now that you’ve wasted my time.”

      What I didn’t cover here is a BETTER way to use stories (in compact ways) using email & phone scripts. Maybe the next piece?? What do you think. I have examples in mind… stories 🙂

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