A simple guideline for when we ask for something that matters to us – the first no isn’t a no.
No just happens to be the default response. It almost doesn’t matter what we’re asking for – a change in compensation, an upgrade of some kind, or for someone’s time. No is the answer we’ll get 80% of the time.
And, in nearly every case, it pays to ask again.
If we’re able to better modify our ask to something that we think they might be more amenable to, that improves our chances some more.
“I realize that x may not be possible. Any chance we could do y?” works like a charm because it shows we care enough to ask again.