Field Guide
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This customer storytelling framework leverages Command of the Message and Challenger Selling.

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Introduction to customer storytelling

This guide is all about storytelling with a purpose and winning customers. To set the stage, think about a major purchase you've made — a car, an education, a home, etc. Now consider how you made your decision. Most likely, a change in your life caused you to investigate a big new problem or opportunity — a new baby, a need for specialized training, maybe a job relocation — so you had to buy something.

You put a plan together (perhaps with your executive or your spouse!) with your priorities and a deadline that created urgency to buy asap. And you conducted an evaluation based on a set of criteria to ultimately buy one product over another. In short, you traversed the buyer’s journey by answering for yourself three questions:

  • Why Buy Anything?
  • Why Buy Now?
  • Why Buy You?


As an enterprise software product marketer with experience at Okta, Microsoft, Citrix, and a dozen startups, I’ve always been fascinated by companies that successfully create stories that align to the buyer’s journey, from awareness through consideration to decision-making. 

In this guide, we seek to share the instructions for entrepreneurs to create the "perfect" story — one that completely answers the three "why" questions through a compelling, airtight narrative. Our goal is to create a story that resonates so deeply with a customer that the storyteller is viewed as more than a salesperson — they’re viewed as a consultative, trusted advisor dedicated to helping the customer navigate the windy, twisty decision-making process from beginning to end. Once complete, the story lays the foundation for any external conversation and can be used in customer discussions, prospective employee conversations, or more broadly in outbound marketing and thought leadership initiatives.


To be sure, this framework is built from core selling principles taught using Command of the Message or Challenger Selling. In some ways, you could think of this guide as a way for we marketers to "catch up" to be in sync with how highly trained enterprise salespeople naturally sell today. Think of this as a practical how-to guide to creating a story that stays laser-focused on answering the key questions every rep must answer to qualify and ultimately close a sale.


Part 1 walks through how to find the answers to each of the "Three Whys"
We’ve deliberately made this framework simple, but there's a lot of nuance to how to answer these questions correctly, so we’ve broken down each why into two key parts and include examples along the way. Also, Three Why Storytelling is modular and easy to update over time as your company grows and capabilities evolve. 


Part 2 is a step-by-step set of instructions for putting your story together and taking it to market
I like to write out a one-page summary that essentially becomes your north star, the standard talk-track for a customer meeting or other presentation. Once written, building a customer meeting deck, website, white paper, demo script, or any other core messaging deliverable is straightforward.


How a story based on the ‘3 Whys’ aligns to the buyer journey


When I led product marketing at Okta, I was fascinated by how some sales reps crushed their number while other reps struggled, particularly when it came to competing against Microsoft, Okta’s 800-pound gorilla adversary. Some reps had more than 90% win rates, while others were shown the door after repeated losses. In these highly competitive deals, compelling storytelling was essential because the entire narrative had to be airtight to win the deal — especially when going up against a Goliath like Microsoft, the safer choice with huge incumbent advantages.


For context, Okta’s identity product competes directly against Microsoft’s Azure identity product. Both companies have the mission to “be the foundation for secure connections between people and technology" — i.e., the control point for IT in a cloud-first world. As you can imagine, Microsoft was highly motivated to maintain their grip on this winner-take-all control point. Competition was so intense, they booted us from their annual customer event, set up "Kill Okta War Rooms" in Redmond, regularly went over our reps’ heads by leveraging long-standing C-suite relationships, and gave away their software for free when they were in a competitive deal against us. These were — and still are — bare knuckles, take-no-prisoner contests.


To combat this existential threat, we conducted a win / loss analysis for our executive team by interviewing dozens of reps. We looked at product gaps, sales motion gaps, pricing/packaging gaps, business practice gaps, etc. What we found was that successful reps who crushed their number and beat Microsoft regularly did three things to win when selling that unsuccessful reps did not do.

How successful sales reps crush their numbers


Step 1: Align with customers on how their world is changing

Successful reps aligned with their customer on shared beliefs around how their world is changing. In Okta's case, reps would align with customers on one or more of the following beliefs with IT leaders: companies are moving from on-premises to SaaS software, which challenges IT to serve its users; consumerization of IT favors "best in breed" choice vs. vertical software stacks; IT leaders are becoming business enablers vs. implementers, etc. 


Step 2: Identify key business initiatives and hair-on-fire problems

Successful reps were wired into their customers' urgent business priorities and had a broad view of their growth initiatives, as well as their challenges across the enterprise. In Okta's case, successful reps spent a lot of time understanding the urgency behind moving to the cloud, such as the need to rapidly deploy multiple, mission-critical SaaS apps like Office365, Workday, or Box to meet a business unit's needs. If IT could not deploy these applications fast enough, the business / users would go around IT.


Step 3: Prove value and differentiation

Successful reps utilized Okta's business value team of consultants twice as often as their less successful peers to conduct a detailed business justification analysis that demonstrated with quantified, irrefutable proof the unique value of Okta's solution vs. the competition's solution. This included value drivers like time-to-market, cost, and productivity improvements.


Put another way, successful reps won competitive deals by telling stories that answer three key questions, collectively known as the “Three Whys”:

  • Why Buy Anything? A shared belief around how the world is changing and the impact this change has on an organization
  • Why Buy Now? A deep understanding of urgent business priorities and the impact from the organization’s current (in)ability to meet these priorities.
  • Why Buy You? Key capabilities needed to solve the urgent problem AND the unique value your company provides vs. the competition to deliver these capabilities


Why are the “Three Whys” so powerful? Because answering these three questions concisely and completely leads a prospective customer through the three stages of the buyer’s journey to arrive at a decision that your company has the one and only answer to a very urgent problem. Keep in mind, of these three questions, understanding customer urgency is the single most important and hardest part to get right. Here is how the “Three Whys” map to the buyer’s journey and how large, complex buying decisions are processed between the executive and staff functions of an organization:



Aligning your story to the buyer’s journey means you aren’t really “selling” so much as partnering with a customer as a trusted advisor on how they can best achieve their priorities. This approach also gives your story a driving purpose that will put you in the driver’s seat throughout a competitive sales cycle.


What’s more, if we build a narrative that answers these three "Why Buy" questions, we create a strong foundation not only for our sales efforts, but also our entire go-to-market strategy. In part 1, we’ll go into detail on "how" to answer the three "whys." Then, in part 2, we’ll look at how this story provides the blueprint for a story-driven go-to-market plan. The two — story and go-to-market — become synonymous with each other because they are aligned to the same goal: to make the most compelling argument possible for every step of the buying process.

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