How to Hack Storytelling for Non-Raconteurs

Storytelling is marketing’s latest mantra to engage prospects and convert customers. And who’d have guessed that for the last 100 years sales reps have been doing just that.

For B2B sales, success comes down to who tells the best story: And not just the best side splitting, drinks at the bar yarn but also business stories with vulnerabilities, threats, and successes.

Sales storytelling is required multiple times in different types during selling stages.

But not all of us are natural storytellers: We can’t all tell anecdotes in a skillful and amusing way. And if it’s not in our DNA, we’re not likely to feel comfortable the few times we awkwardly swing at it.

Storytelling has different types

That’s a conundrum for non-raconteur sales reps; who need to tell stories, but don’t feel they’re the best storyteller in the room.

And yet storytelling is how humans communicate, connect, and work together. That’s why now, in the 21st century, business gurus are parsing dark matter on what has been with us since our species communally worked to survive. Go figure.

For all the current hype about storytelling for marketing and selling, there appears a lack of guidance for non-raconteurs. For example:

  • What type of story to tell?
  • When to tell it?
  • How to tell it?

The simpler place to start the hack is with the type of story and when to tell it. How to tell a story is nuanced and complex, so we’re tabling that for later.

The following places storytelling types and timing within sales stages for non-raconteurs to first comprehend and then do something about it.

Storytelling Types

5 Storytelling Types

Not all storytelling is the same; different types are needed in different sales’ stages. Here are five broad definitions placed in their sales stage. Of course these aren’t the only types, but sticking to the simpler ones makes for a more actionable hack and keeps us out of the weeds.

1. Personal, Ice Breaking Stories

This is the classic storytelling type told by an individual who could only be a sales rep because they tell such damn funny stories. However, when these stories are explained, they’re no longer funny. So here’s the non-funny explanation: Stories like this may be:

  • Humorous without crossing socially acceptable boundaries for that audience (keep it clean)
  • Self-deprecating to help place audience above storyteller & remove barriers
  • Trying to get the audience laughing with, rather than at something
  • Pointing to some mutually recognized absurdity
  • Speaking to an unrecognized subconscious truth that hasn’t been mentioned yet

This type of storytelling always happens live, most often in person, but can also take place over the phone where customers’ time and familiarity permits.

Storytelling Cautionary Tale

2. Industry-Challenge, Cautionary Tales

This storytelling type addresses a common challenge in the industry where a threat finds a vulnerability and the result is catastrophic, or very costly/painful in the least, e.g., damaged brand reputation, decimated employee morale, regulatory failure with intrusive oversight, etc.

This doesn’t mean the story is told with lightning and thunder. But it is an industry insight shared to forewarn prospective customers.

It’s used to raise awareness about customer risks they didn’t know they had. And it builds suspense by not letting customers off the hook by providing the answer to averting that catastrophe…at least not yet.

This type of storytelling can occur in different modes, such as in person, phone, direct email, ads, and in social media and blog posts.

3. Industry-Challenge, Cautionary Tales with Generic Fix

This story adds the answer to the 2. Industry-Challenge, Cautionary Tale. And that answer is purposefully in general terms rather than as free consulting. It takes place in person, phone, direct email, ads, social media, and blog posts, and is primarily about building up the sales rep’s credibility.

Customer-specific Cautionary Tale

4. Customer-Identified, Cautionary Tales

This storytelling type is the next iteration in the Cautionary Tale series. In it, a particular customer is named and their situation described; vulnerabilities, failures, and consequences.

NOTE: this story type does not include the fix; it’s another cliff hanger intended to generate curiosity to pull customers to the next stage.

The customer protagonist in this story is not the customer the rep is pursuing. Also, there’s only a few situations and sales stages to use this story type in, and they’re dependent on the level of:

  • Detail relating to confidential info (public domain that can be shared)
  • Relationship trust with customers hearing the story (so they don’t feel as if the rep is dissing a peer)

As you can see by the caveats above, this story type is not used to a general audience but to targeted prospective customers. It’s used to heighten sales rep credibility by providing the most relevant and comparable insights: Not just generic industry insights but the directly applicable situation and consequences facing that particular customer sitting across from the rep.

This type of storytelling occurs in person, phone, and direct email.

Specific-fix Cautionary Tale

5. Customer-Identified, Cautionary Tales with Specific Fix

This final storytelling type should be the most powerful, where the specific solution to the Customer-Identified, Cautionary Tale is added. And the fix is the sales rep’s (firm’s) specific solution.

In this story the two caveats of confidential detail and relationship trust become ever more critical. Without both, it’s possible for reps to blow a sale when it’s already far down the pipeline.

This type of storytelling should only be in written responses in proposals and told live during presentations. These are the high-reward situations with greater confidentiality that come with the biggest payoff.

When to Use Different Types of Storytelling

Storytelling types work best when they’re appropriate to the sales stage. For example:

Storytelling Hack Matrix Type by Stage

1. Personal, Ice Breaking Stories — help build individual rapport, begin personal relationships, and work best during the early sales stages. Once personal relationships are established and the opportunity moves into business aspects, the less critical they become, helpful but not critical.

2. Industry-Challenge, Cautionary Tales — help establish industry credibility and create curiosity for moving the sales’ conversation along the stages. Without a fix attached they’re for early stage usage, further along the stages, customers will expect insights into solving issues, which is when number 3 and 5 are more useful.

3. Industry-Challenge, Cautionary Tales with Generic Fix — helps credibility and next-stage curiousity, but also shows insider knowledge of what’s happening in the industry. Now, it’s more than knowing the issues and consequences, but also includes knowing the fixes — although at this point in generic terms only.

4. Customer-Identified, Cautionary Tales — provide greater credibility because of the specificity, rather than talking about generalized industry goings on. These storytelling types can be used early and late to set the context for industry insight but not typically during the nitty-gritty details of a specific bid opportunity.

5. Customer-Identified, Cautionary Tales with Specific Fix — are the proof that the sales rep’s firm can deliver on whatever is being professed in the proposal and presentation stages. They show the sales rep’s (firm’s) solution fixing a similar problem to the ones being addressed by customers in these stages. Although this type of storytelling is sometimes called “Case Studies,” they’d better be much more exciting than the name implies. Just spouting templates populated with nouns isn’t going to do the trick.

Storytelling Hack There You Have It

And There You Have It

That’s most of the storytelling hack. Knowing the types of stories and when to tell them are at least half the battle. Hopefully, when you next read about “storytelling” in marketing, sales, or branding you’ll have a sense of context and place, before worrying about how to tell it.


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