Two weeks ago, I re-shared a popular blog calling out how snobbish we can be about sales opportunities. Someone then reminded me that there was a follow-up to that blog and asked would I share that?

Of course, but a quick commentary first.

Years ago, I had a salesperson on my team (briefly, as you will see why) who struggled with understanding his role as a customer advocate. He took it too far. Rather than focusing energy on qualifying prospects before engaging, he tried to “sell” his leads to his own employer.

“These guys are great. If we do this one small thing for them, I know we will get more of their business.”

You can imagine some of the tricks he employed like “discounting by omission” and offering ridiculous “value-added” services for free. “I didn’t see a price for that, so I assumed we did it for free,” he explained earnestly.

He didn’t know any other way to sell than to sell himself as a pleaser.

There’s an Operational counterpart to this over-pleasing persona. I call them Obstaclists who often manifest as the Operations Manager who tears down any opportunity that involves even a modicum of outsourcing or other inconvenience.

“This thing sets up at 5am. We can’t afford to do that all the time. We should be charging triple time and put a stop to these requests.”

You know this person too, right?

These people are actually rare, but they make a lasting impact wherever they appear.

This week’s blog post has a lot of dialogue from very reasonable people trying to do the right thing for their companies and customers.

However, as the title suggests – they have gotten ahead of their customer’s expectations in the wrong way.

It’s the top match of the night: Pleaser Battles Obstaclist