I get away with banter as a lot of the time, by the time I speak with a prospect they’ve consumed some of our content and so there’s a level of rapport there.
I think you need to use your emotional intelligence on this one.
At the top of the sales process you mirror the prospects level of communication and friendliness.
I will outwardly tease people or be self-depreciating when it comes time to close a deal though to get them over the line –
“OK, so it seems like you want to make this happen. Are you nervous about having to stare at my ugly mug for the next 12-months? Or is something else stopping you from getting signed up today?”
After a couple of calls it’s absolutely fine to be a little more playful with people.
Email and text communication though is different. It’s more difficult to read your intention when it’s just text and so I rarely banter on those platforms.