He doesn’t mean it. He really doesn’t. But if he does, then he’s an asshole and like your girls, I’m wondering why you haven’t dumped him yet.

No, I’m not drunk. I’m referring to the challenge number 8 and the fact that his tone suggests he’s God’s gift to the world. Like he’s never wrong. As if his opinion is the only one that matters. Like everyone needs to know that he’s got more blessings than the rest of us.

It’s not always his choice of words. It’s when he chooses to say them and the tone he uses.

You know what I’m talking about. Where friends and family are left trying to figure out if he was just trying to be nice or if he’s actually a clinically diagnosed douche bag.

He speaks with so much conviction that even if the person he’s talking to is right, his tone will make them question the validity of what they just said. Why does he do this? Because its how he has to speak to persuade clients to sign on the dotted line. In the world of executives, regardless of gender, conviction = confidence and confidence sells. It sells when it is time to persuade the big wigs to hand over a promotion. It sells when he needs to persuade an absolute dick to stop being an absolute dick at work without getting losing his job. You might recognize this conviction as the same tone that often makes people call you a bitch if you use it.

He’s also expected to make judgements in his leadership capacity at work. Not only that, but he’s in an environment where everyone makes it a point to show interest in his judgement of anything and everything. I call this the Kardashian effect. The Kardashians can usually get away with doing some pretty outrageous stuff. Somehow, making a sex tape made Kim famous. Why? Because everyone cared. Similarly, this phenomenon gives him the false sense that he can completely turn off his filter before opening his mouth…and then it just never turns back on. Its more unfortunate than the suffering our American friends are enduring at the hands of Donald Trump. Speak of the devil! He’s a perfect example of a man with a filter that is permanently in the off position.

Once upon a time, I introduced an executive boyfriend to my parents.

He asked them what they were doing on the weekend to make casual conversation. Like every weekend, they said they were going to attend a group meditation session (my folks are quite spiritual). Harmless at first, but the discussion ended up somehow becoming about my parents’ spiritual beliefs. Him and his tone let my parents know exactly what he thought about this very intimate thing they just shared with him. And as he was doing so, his words were orchestrating the formation of one of the worst “WTF” looks I’ve ever seen on my mom’s face. It was like he was a snake charmer and the more words that came out of his mouth, the closer my mom got to actually biting his head off.

Your executive man doesn’t know that he’s not being well received by your loved ones, so how do you a) tell him and b) get him to throw some humility and grace into his interactions with them?

You can’t exactly tell him that nobody in your life likes him because of his tone or choice of words. Take the opportunity to speak up and point out to him when he says things that are borderline inappropriate. Think of him as Sheldon from The Big Bang Theory when he was learning how to pick up on sarcasm. His friends coached him for a bit every time someone said something sarcastic. Eventually, Sheldon stared dishing sarcastic remarks like a pro. Be sure to specify to your executive man whether his tone or choice of words are the cause of judgemental whispers between your loved ones.

Next you’re going to have to get him to work out that filter switch. On. Off. On. Off. Do this by offering suggestions on what he could’ve said or how he could’ve said it differently instead. Then tell him that he actually has to stop and think about what he wants to say and how he wants it to make the other person FEEL, not what he wants it to make them DO. Believe it or not, this is VERY difficult for men to do, executive or not. Tell him that if he’s not sure how something he’s thinking of saying will be received, it is probably best he that he takes mom’s advice. “If you don’t have anything nice to say, don’t say it.”

Or he can follow my more updated version of that advice.

“If you don’t know that what you want to say is nice, have a few more drinks and then say it so that people blame the alcohol. That way all of your sins will be forgiven.”

Let me know how it goes with your not-so-friendly giant! The Candy Jar is the best way to get in touch with me. 🙂

Here’s the next challenge.



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