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“Why Buy Anything?” is the first question to answer in customer storytelling and can be thought of as a two-part formula for defining the “Big Problem”: start with why plus align on a shared view of impact.

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I’m a huge fan of Simon Sinek’s Start with Why. Brilliant in its intuitive and empathetic approach, Sinek’s book has single-handedly flipped sales and marketing conversations from leading with what a company does to why they do it. If you haven’t watched his TED Talk, stop reading and take a few minutes. My favorite line is “Martin Luther King didn’t give an ‘I have a plan’ speech. He gave an ‘I have a dream’ speech.” 


By starting with why, we align on shared beliefs around what’s changed in the world to form a tight connection with our audience that builds the relationship foundation and trust needed throughout the rest of the journey. It also allows you to quickly disqualify those who aren’t ultimately aligned to your views.  

Our first sales leader at Okta disqualified 70% of prospects who didn’t view a cloud-first approach as strategic.

One very effective approach to answering Why Buy Anything? is framing the shift through an authentic founder insight. This works best when the founder has deep domain knowledge of the shift that’s occurring. One of our portfolio companies automates compliance in the cloud. Their two co-founders ran IT ops for several companies including Starbucks and have been through 50 audits. They have a powerful founder insight that provides instant credibility with a buyer. Who wouldn’t want to work with someone who has such deep knowledge around such a painful problem?


Once we align on what’s changed, we introduce the impact that change has on an organization — the size or magnitude of the problem. Again, if this assertion is backed by an authentic founder story, even better.  

The 3 components for answering Why Buy Anything?

1. Authentic insight

2. Shift in the world order

3. Empathetic impact statement

Examples of how to answer Why Buy Anything?



  1. Authentic insight: “As the former head of engineering at Salesforce, the first software-as-a-service application, I saw that….”
  2. Shift in the world order: ... as the world moves from on-premise applications to SaaS
  3. Empathetic impact statement: … IT needs to rethink how they deliver services to employees



  1. Authentic insight: “As the head of cloud product management at Splunk, I saw…”
  2. Shift in the world order: hyper-growth cloud companies that provide data rich services are creating huge log files ...
  3. Empathetic impact statement: these logs are quickly becoming unmanageable by traditional players Splunk and ElasticSearch.


This approach introduces the problem statement not as your opinion, but rather as an insightful belief that invites shared understanding around where the world is heading, supported with credibility from you, the founder. Using this approach means you’re far less likely to be talking at someone but rather pulling up a chair, sitting down, and having a conversation as equal partners setting out on an important journey.


Think of Why Buy Anything? as a two-part formula for defining the “Big Problem”:


Start with why: a shift based on beliefs or authentic founder insight
Align on shared view of impact


You’ll know you have this right when you’re able to natural segue into a discovery question like “is this how you see the world?” and the prospect spends a few minutes either aligning with your view or presenting another worldview.

If the latter, you may want to qualify out the opportunity. In my experience, whenever we found an "on-premises hugger" who held onto the notion that cloud SaaS was dangerous and the exception to the rule, we moved on quickly! Assuming you’re getting the head nods and maybe even expansion of your belief in their words, let’s move on to Why Buy Now? — the most urgent question your company needs to answer.

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