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Don’t Be Boring

3 min readJune 2, 2021

It’s a cardinal sin to be boring in sales.

It’s not your value proposition that’s initially interesting to your buyer. It’s you.

Creating a working connection with a buyer, or a human, demands that you demonstrate a sincere interest in them as a person. It also demands that you be interesting to them in return.

Which is hard to do if you’re boring.

Take the mythic ‘sales conversation.’ That first substantive interaction between buyer and seller. Think about how boring these are for buyers.

Sellers are armed with a pitch and a scripted list of questions to ask. These are the same questions buyers have heard from every single salesperson they’ve spoken with. Boring.

Sellers use these questions as shields so they aren’t forced to engage at a deeper level with buyers (which could expose their limited expertise or the fact that they aren’t interesting…)

In this scenario the typical outcome of this first sales conversation is not a conversation at all. It’s an interrogation. It’s safe. And, boring.

Buyers are human beings and quickly form associations in their minds. ‘This salesperson was dull and boring. His company must be boring. Why would we want to do business with them?’

However, if you overcome the scripted questions trap, your buyer will want, at some point, to learn something about you. Not just your company. You.

This is a key moment that can unlock the door to the connection that differentiates you from other sellers.

This is your cue to be interesting.

Are you ready?

Researchers have found that three of the essential ingredients to make yourself interesting to another person are:

  1. Being interested in the other person;
  2. To be well-informed;
  3. To stray outside your comfort zone.

These factors go hand in hand. What’s the point of being interested and informed about a wide range of topics if you’re too afraid to step outside your comfort zone to talk about them with a buyer?

Unfortunately, sellers these days are trained to believe that buyers don’t have the time to talk about anything that isn’t directly related to the business at hand. So they feel the pressure to keep it strictly business.

Which is wrong. And boring.

Only a fraction of the value of the initial sales conversation (and I mean conversation) is about the transaction. It’s more about connecting and engaging the interest of another person.

Remember: Sales is what you do; it’s not who you are.

So, once your conversation with a buyer ends, what are they going to remember about you? Better yet, what do you want them to remember about you?

That you were a robot that competently asked a series of predictable questions? You can be competent and dull, uninteresting and uninspiring at the same time.

Or, that you were an interesting person? That you added value to the moment through your questions, insights and personality. And that you’re someone they want to invest more time with.

Think about the people you meet in your own life. In your personal life outside of sales.

If someone is interesting, you decide you want to spend more time with them. If someone is boring, you decide to avoid them.

Your buyers are no different. Which one do you want to be?

Follow Andy on LinkedIn.