How to Convert an Acquaintance to a Prospect without Being Awkward

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How should you approach a casual acquaintance and open the dialogue about working together?

This is the quintessential “asking for the first date” question – major awkwardness potential here! When I was an advisor I was successful using a few methods – depending on how well I knew the prospect. Here is how to maximize your chances of success before, during, and after the ask.

Warm them up for the ask

To take the edge off “the big ask,” one of the best ways to give your prospect an idea of what you do is to include them on your newsletter distribution list. But make it a highly personalized newsletter that reflects your brand, not some boilerplate, overly technical piece.

I piqued the interest of several of my acquaintances, and it did lead to prospects setting up meetings, through my email newsletter. I used extremely creative subject lines, for example, that displayed my character. Example: “Conveyor belt of money.” I remember I walked into the computer room at the Harvard Club and one of my acquaintances who happened to be on the newsletter list said some joke like, “You’d better let her use that printer before you – don’t get in the way of her conveyor belt of money!”

Years later in a casual conversation he brought up that his girlfriend needed an advisor and requested that the three of us set up a meeting. See how that warmed him up?

Connect on social media, also. This way they see your updates and have an idea of what you’re about. Just as with the newsletter, generic content will just give them the impression that you’re “one of those advisors.” Show your personality.

The LinkedIn instant messenger feature is a great way to transition them into a phone call. It’s a casual way to reach people. You can tell when they’re online by seeing if their profile displays a solid green dot. If you see the green dot, you know they’re logged on – so that is a great time to hit them up on chat and see if you can somehow get them on the phone. This is LinkedIn’s best kept secret, and one that not enough people use in their sales work.

Lastly, don’t go into this interaction cold. Get ready for the dialogue and practice your rebuttals. If you’re too embarrassed to ask anyone to role play with you, then record yourself saying your pitch into your iPhone and play it back. Keep doing it until you’re happy with what you see/hear.