Sasha Dichter

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Tag: connection

  • Pleasantly Persistent

    Someone left me a voicemail the other day in which she said, “I know we keep missing each other, so I thought I’d try again.  And hope that you appreciate my being pleasantly persistent.”  Somehow, the way she said it, it really worked.

    If outreach and building new relationships is part of what you do (and it is, no matter what you do), how you create the next conversation is always top of mind.

    Nearly all of us need to be reaching out more, to be building more relationships and cultivating them with more care.  When you reach out to someone new, especially when you reach out cold, you’re hoping for a “yes” to a first meeting, but more often you get a “no” or, more confusing still, silence.  Then what?

    The tricky thing about silence is that it can sound just like “no.”  But it might mean lots of other things, for example: I didn’t notice your call/email; I’m not sure how serious you are; I really don’t have the time right now; you haven’t explained to me what value I’ll get out of the meeting; etc.

    Take silence as an opportunity to fill in the blank with something other than the self-doubting, “Well, I guess they don’t want to meet with me.”  Instead, persist, and do so in a way that demonstrates how you’ll handle the relationship once they let you in the door.

    I like this notion of “pleasantly persistent.”  It exposes the lie that we’re being persistent enough (we often aren’t), while also giving a simple descriptor of how to build a first connection that will lead to a constructive relationship.  If you’re being pleasantly persistent, you’re communicating a few things: I take this meeting seriously; I know that I’m pushing, and I can tell that you’re a busy person; I will make a good use of your time.    (Also, if you remind yourself that you’re being persistent in a pleasant way, it can help you overcome your own fears that you’re just badgering your prospect.)

    Finally, this is also a good reminder of what you don’t want to be: unpleasantly persistent or quick to give up.  Neither will get you there.

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  • Call it out

    I recently went out to a nice birthday dinner at a new TriBeCa restaurant in New York City.  It’s been open for about a month, and while the food is delicious, the service is still finding its way.  Our waiter was friendly enough, but he would disappear for swaths of time.  At one point, we found ourselves looking longingly at our bottle of white wine, chilling across the room, and discussing exactly how big a faux pas it would be to stand up, grab the bottle, and pour for ourselves.

    But no matter.  It was a jovial night, and we didn’t have anywhere to be; the languorous service gave space for conversation.  But things got worse over main dishes when food arrived for everyone but the birthday girl.   She insisted we all start eating, and after some protest, everyone dug in.  But the clock kept on ticking on the one missing dish, so much so that we considered canceling the order altogether.  Finally, a full fifteen minutes later, when everyone had clean plates in front of them, the tardy pizza finally arrived.

    In a stroke of brilliance, our waiter said, “We knew it was your birthday, and so we wanted to make your pizza extra-special.  That’s why it took so long for us to make it.”

    Poof!  Everyone laughed.  The tension was gone.  What could have been a wrong turn, a souring of our entire meal, became a moment of lightness.

    What our server did was brilliant.  The moment was awkward and tense, and he could have (a) Said nothing; or (b) Issued a standard apology.  But he took a different tack – he made a point of calling out the difficult situation, and did so with humor and grace.  Suddenly we were all looking at this bad situation together, calling it out, and laughing.  The dichotomy between the server and the customer evaporated, and with it, so did the problem.

    There are a lot of situations that are like this, and since I’m in the business of raising money, I couldn’t help but draw some parallels.  Not every conversation is awkward, but there are definitely times people slip into their roles – the potential donor starts acting like the potential donor, and the fundraiser is stuck in the role of fundraiser.  Usually, this is the beginning of the end of a productive conversation.  It’s just plain awkward, and if you don’t break the tension fast you’re finished.

    The thing to remember is that no one likes falling into these roles – they’re uncomfortable to everyone at the table.  So call them out.  Point to the elephant in the room, describe it, make a joke about it, diffuse the situation.  And then go on with your meal.

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