Rethinking what it means to sell

Word association time:

I say “salesperson,” you say ________?


What’s ironic about these stereotypes is that they’re only true if you’re not very good at your job.

As I’ve shadowed sales calls over the past weeks, I’ve realized that the best aren’t “selling” at all in the traditional sense. In fact, I think the most successful salespeople actually view their job as two different roles:

  1. User researcher

  2. Problem solver  

The first requires the ability to listen, empathize, and draw out the underlying problem that you’re solving for. The second calls on your creativity, resourcefulness, and flexibility.

What this approach highlights is that the foundation of the entire process is understanding the use cases and paint points your product needs to address. Which means most of your time should be spent listening and asking thoughtful questions, not talking. I wouldn’t be surprised if there’s an inverse correlation between number of words spoken and deals closed.

This philosophy is helpful on a tactical level too. When you’re fielding questions or handling objections, try taking a step back to understand what’s motivating the concern. Otherwise you miss a valuable opportunity to gather context; it’s like being asked to pack a lunch without knowing if you’re going on a lazy picnic or an eight mile hike. To take a couple of examples:

Customer: “How much do you cost?”


You: “$795 a year for the first five licenses and $125 for each additional seat.”


You: “Annual billing is our most popular option and that’s $795 for the first five licenses and $125 for each additional seat. Are you looking to replace an on-prem server or switch from an existing cloud solution?”

Customer: “We have an on-premise server at the moment.”

You: “Ok, well let’s do a quick calculation of how much you can expect to save over five years…”

Customer: “I need something that’s more secure.”


You: “We encrypt your files at rest and in transit using the same technology as banks — 256-bit AES encryption and SSL for data transfers.”


You: “I’m happy to talk more about security. Can you tell me a bit more about your specific concerns and what your team needs?

Customer: “Well, we work with a lot of external vendors so the ability to set different access permissions is really important.”

You: “I see. There’s a couple of ways you can do that with Dropbox…”

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