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Writer's pictureMark Olivito

Playing Both Sides: The Profile of Jimmy 2 Times

Updated: Jul 1, 2022

I’ve profiled a few business types on the blog.

A Yankee game where unknown players had each other’s back, in the greatest brawl in Baseball History.

All profiles of common business types that create Excellence, or in some cases, anti-Excellence.

Now I present: Jimmy 2 Times.


There’s a difference with business Jimmy and the Jimmy from Goodfellas.

Jimmy in the business world doesn’t say the same thing. He says different things, 1 message to your face, and a different message NOT to your face. When the different message comes back around to you, and it always does, you wonder who you are dealing with? And trust falls rapidly.

It could be over a business decision, feedback on a meeting, conflict within an office, forwarding (or BCC’ing) an email with a completely different tone or message, or simply trivial matters.

Regardless of the topic, 2 Timers pose on of the best TRUST KILLERS in business, when people choose to be inauthentic in their communication.

I have never seen this under-handed technique work in business. MAYBE it works outside of business where hours with multiple people are not as constant. Not in the hotbox of business.

It is why people can’t stand politicians; they don’t know where they stand.

There are reasons why many companies have a “No Gossip” policy: It kills morale and erodes trust. I’ve never worked in an organization that does, but certainly see the merits.


Like most areas of leadership, confronting the 2 timers comes down to a choice: Do you drive a better outcome by dealing with it, or ignoring it?

Usually ignoring a problem is NOT a recipe for fixing it.

  • Set your expectations clear and often: Authenticity is EXPECTED, not just appreciated

  • The Leadership Dare: 2 Timers always erode trust and hurt results. They always get found out. If you like this kind of high risk behavior, feel free!

  • Handle one on one when it happens: Usually don’t need to address more than once….

All Relationships start with a foundation of trust. The quickest way to build it is to “Do what you say you will do.” The reverse is also true. Multiple it by 10 when the message is different, AND it’s also behind someone’s back.

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