It makes my day when you email me with questions! Especially descriptive, situational questions with a comedic flare like this gem from a female executive:

“I have started a new job in a senior position in a brand new start-from-scratch business and have other executives, who are not in my direct business unit, who have said on introduction, “Let’s get coffee and chat.” Now these are senior men and I’ve been grappling with whether these are pleasantries or serious gestures? Then if I do set these up, what the heck do you talk about? Or maybe I’m just over-thinking it?”

My reply:

“This made me smile. Yes, you are overthinking it! Whether they meant it or not (which I believe they did) what matters is if you wanted them to mean it. Assuming you do (cause you should), then you act as if they did mean it and take them up on it. Leverage curiosity, ask advice, talk about the weather – you will find things to talk about.

Go have lunch!”

Sometimes we get in our heads and talk ourselves into or out of something. It’s hard to stop overthinking it. What matters is what you want out of it.

Overthinking holds a lot of us back. But really, what do you have to lose?

And more importantly, what could you have to gain that you don’t even know about until you try it?

My advice: stop overthinking it! Always have the conversation. You never know what those new connections will bring you!