Okay, to be fair, I don’t think for a moment that Simon has it wrong. In fact, I am as big a fan of his Why message as anyone. It’s just that in order to achieve true sales clarity, his idea needs to be taken a bit further. 

I’m sure you’re familiar with Simon’s message, but here is a brief overview. 

Simon makes the point that there are three key elements to any COMPLETE sales message – Why, How, and What. 


Your What is the most basic element of the sales message – it is comprised of the products/services you sell. Everyone tends to understand this and can explain it reasonably well. The primary problem here is that this is the part of the sales message where most salespeople start. This a problem because it makes you sound just like everyone else.  

I watch agencies/producers all the time who go out and accumulate a long list of Whats (the next technology, compliance, communication, HR, insurance solution) in an attempt to differentiate themselves. They get so excited about What they have to offer, and they make their capabilities presentation the primary attempt to differentiate themselves.   

You will never differentiate yourself with a What. Even if you get to a new solution first, the advantage will be temporary and brief. You know as well as I do, competitors will go out and procure it (or something close enough from the perspective of the buyer) as soon as they see you have it. 


This is where true competitive differentiation takes place. Your How is your unique value proposition, a differentiating process. Basically, your How is something about the way you work that gives you an advantage over your competitors. My experience is very few can articulate this clearly, and I think that’s because very few have created that kind of advantage. 

It is the process of How you use your Whats that is your ultimate competitive advantage. 

Instead of focusing on the Whats themselves, your How should focus on the problems your Whats solve: analyzing which of those problems afflict the prospect, and a detailed plan of execution of How you will use those Whats. 


As Sinek is so famous for observing, “People don’t buy what you sell, they buy why you sell it.”  

Your Why is your purpose, your belief, your cause – it is the emotional driver that motivates and rewards you. By sharing your Why, you make yourself attractive to those who have a similar Why, pulling them to you emotionally. What a powerful connection! 

Sinek argues that once a prospect finds themselves emotionally attracted to your Why, then all that’s left is to help them rationalize/validate their decision/connection by sharing your How and What. 

An emotional connection isn’t enough 

Oh Simon, if only it were as simple as Why – How – What!! The “failure” of his idea is that it can be driven by potentially unchecked emotion. Because of that, it leaves salespeople exposed to misaligned clients and, to make matters worse, an inefficient pursuit of those misaligned clients. 

Emotion is a powerful force. But, like with any powerful force, it can be either constructive or destructive. Emotion not held in check leads to irrational behavior and a blind pursuit. 

Even when someone is aligned with your Why, there are two additional filters to apply before exposing them to your How: Who and When. 


Sinek’s idea of Why is a powerful starting point. When you find someone with whom your Whys align, there is an emotional connection and that provides unbelievable potential. However, just because there is an emotional connection, doesn’t necessarily mean there is ideal alignment. 

And, because emotional connections are so strong, they can actually cloud judgment, causing you to pursue wrong-fit prospects/clients. Therefore, it is critical to establish objective criteria to filter through the emotional connections to identify where there is also a cerebral/logical connection. 

Determine the worthiness of the potential client: 

  • Are they the right size? 
  • Can they be profitable? 
  • What is their buying style? 
  • Would you enjoy working with them? 
  • Do they even need what you are selling? 

It is really easy to get excited when you realize you share a Why with someone. But, don’t let that lead to an irrational pursuit. Just like Simon says, the prospect will validate/rationalize their emotional connection to you as you share your How and What. However, this is a two-sided relationship. You need to validate/rationalize your emotional connection to them by asking the questions above. 


Finally, once you have the Why and Who alignment, it is important to consider where they are from a timing perspective. Is there a traditional decision-making timeline they follow that you need to be aware of? Or is there a traditional timeline that you are looking to avoid/break? 

Your How applied, even to the right Who, at the wrong time, loses its potency. 

Way too often, insurance advisors are showing up at exactly the wrong time -- renewal. I know this happens because it is the easiest time to get the prospect’s attention. However, as someone competing for the role of advisor, this timing puts you at a huge disadvantage. 

There are two critical decisions business owners need to make around their benefit program: The carriers they will use, and the advisor who will advocate on their behalf to those carriers.  

At renewal time, they have no choice but to make a decision about the carriers. Expecting them to also make a second big change of advisor is unfair and overwhelming to them and, worst of all for you, puts you at a disadvantage. 

You must take the conversation off renewal (your How is what makes this possible) and allow them to focus on what it is you purport to do – bring them better results. When you have established a strong How, as described above, you can get them to focus on what makes you different as opposed to what makes you just like everyone else. 

It’s all about the pipeline 

Using all of these filters to determine who you are willing to pursue takes great discipline. The key to finding such discipline is keeping a healthy pipeline of prospects. 

I know, I know!! Yes, this is a bit of a Catch-22. You can’t have a healthy pipeline of prospects without going through these filters, but it’s hard to be disciplined with the filters until you have a healthy pipeline. 

There is no “easy” when it comes to prospecting. As you start to build that healthy pipeline, you are going to have to dig extra deep to find the discipline that may not yet be natural.  

However, as you build that pipeline of prospects, it's beyond empowering when you get that right match:

  • People with whom you share an emotional driver (Why)
  • Those who fit the criteria of your ideal client (Who)
  • The ones who have the time to focus on making a decision about you as an advisor (When)
  • Prospects who appreciate you focusing on their problems (How)
  • Businesses that can benefit from the solutions/services you offer (What) 

So, with all due respect to Simon Sinek, a complete sales message isn’t complete until it addresses Why, Who, When, How, and What. Take the time to add in the Who and When elements and you are going to leave your competition with a whole different Why, How, and What. They’ll be asking: 

  • Why didn’t I get the business? 
  • How can I be more like them? 
  • What in the world just happened? 


Photo Credit: olegdudko

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