I was reviewing a keynote speech with someone, a CHRO preparing to address top talent from across the globe at a major internal company event.
She’d worked hard on it. You could tell. Every slide considered, every word chosen carefully.
And it was completely wrong for the room.
The language was formal to the point of being stiff. The tone was top-down. The framing was all company, very little human. She was speaking at a room full of high performers from different cultures and generations, people who can smell inauthenticity from three time zones away.
So I said it straight:
“This is not going to fly with your audience.“
She paused. Then: “What do you mean?”
And that’s where the real coaching began.
“Not going to fly” … what it means and why it matters
To say something isn’t going to fly means it won’t succeed, won’t be accepted, won’t land the way you intend. Native English speakers use it constantly in professional settings: in meetings, in feedback sessions, in honest conversations between people who respect each other enough to tell the truth early.
It’s direct without being harsh. It closes the door on a bad idea without slamming it.
In Italian you might say: Non decolla … it doesn’t take off (my favourite, it keeps the aviation feel) Non funziona … it doesn’t work Non va da nessuna parte … it’s going nowhere.
But “not going to fly” has something those phrases don’t quite capture: a kind of calm, confident finality that says, I’m not attacking you, I’m saving you time.
Back to my CHRO
Once she understood what wasn’t working, she was open. We stripped back the corporate language, brought in her actual personality, and reframed the whole speech around what that global audience actually needed to hear: that they were seen, valued, and that leadership was listening.
The difference was night and day.
That’s what English confidence looks like in a coaching room. Not just grammar. Not just vocabulary. Knowing which phrase to use, when to use it, and having the courage to hear it when someone says it to you.
Have you ever sat through a presentation and thought “this isn’t landing” but didn’t know how to say it? Now you do.
