May I?

I grew up in New York City, specifically The Bronx. (Yes, that uppercase T is part of the official name of the borough that’s at the top right of the NYC map.) There, at a certain age, we played a street game called ‘May I?’ It involved making a creative request to move forward by hops or skips or steps, and accepting an alternative order from the leader. But first, you always had to ask ‘May I,’ or you would be sent back to the starting line.

Well, unlike my young colleagues, I didn’t do well at this game. I enjoyed the creative part, but would forget the ‘May I.’ Still, it was a good experience for a pre-entrepreneur, or a pre-rainmaker, or anyone who would eventually have a greater need to ask for forgiveness than to ask for permission.

But still, there is a cosmic question for which we all need an answer:

When should I start with ‘May I?’ and when can I safely fly into action?

After a lot of thought, and asking a few wise folks what they think, I have concluded that it comes down to one key point: Where does the other person draw their personal boundary line? If you stay outside that line, the ‘May I?’ is optional. But once you cross that border, it’s an imperative.

So, how do you apply this to the creative arts of business?

Just remember that although you have a pretty good idea where your own boundaries are, and you have an idea about the other person’s boundaries, you just don’t know where they really draw the line. Therefore, it’s best to get their permission before launching into your pitch. This leaves a lot of territory in which to introduce yourself via a topic that is related to your ultimate intention, in hopes of encouraging them move their boundary lines just a little closer to you.

And one more point, if I may…

A great deal of that open territory is actually inside your own space. That’s where you can get creative with your questioning, and where you can give yourself permission to move ahead. And that’s how you start becoming great at selling anything from grand ideas to Ginsu knives. Because the first person you have to sell… is you!

Yes, you may. And yes, you can. It’s all your game to play and win!

Happy May!

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