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  • Writer's picturelauramccartytufano

Overthinking It

Last week, I posted about a client wordsmithing her email to a donor, and she asked if she was overthinking it.

I have a confession to make: I overthink things. A lot. Particularly when it comes to face-to-face donor visits. I think about where we are meeting. Is the vibe of the place right for this prospect? What about the noise level? What about the type of food they have and the type of seating they have? Is it too dark in there? Is the parking convenient? Is the location convenient? Does my clothing/hair/makeup make me seem professional and respectable to this particular prospect?

Does my email project a cheerful, friendly tone? Does my phone voice portray a great passion for our cause?


Most of those questions are actually appropriate to ask yourself, but that last one used to trip me up big time. Years ago, I came across the Asking Matters website, where these wonderful folks have created a matrix of asking personalities based on dual spectra of introvert/extrovert and analytic/intuitive. You can take a quiz to find your asking style, and it’s one of my favorite things to recommend to clients.

Unsurprisingly, my quiz results came back with the asking style of Mission Controller. Mission Controllers, according to Asking Matters, are methodical and observant, excelling in doing their homework and always being prepared. The downside is that Mission Controllers rarely feel prepared enough to make an ask.

Big downside.

Having identified that weakness, I spent years working on it. I’d study all the organization’s materials and try to be as prepared as humanly possible. Eventually I had to become comfortable with the idea that I might not have an answer to every single question a donor has. And in fact, the more face-to-face donor visits I had, the more I realized donors got more from our meetings if I was a good listener than if I was a good fact-giver. Donors got more from me bringing a genuine excitement for the mission than an encyclopedic knowledge of the subject matter.

Years later, I returned to the quiz. I’m still a Mission Controller, but I’ve built myself a solid standing in the Rainmaker category as my Secondary Asking Style.

I know too many organizations and too many development professionals that want to get everything just right before they do any asking. They’ll spend a year creating major gift societies and recognition levels and brochures but never ask for any major gifts.

I firmly believe that the basic infrastructure needs to be built before you ask. For example, before you start asking for gifts, you need to have procedures nailed down for processing gifts, recording information, and receipting donors promptly. YES--be prepared.

BUT, especially when it comes to major gifts, don’t let the details (beyond basic infrastructure) be your excuse for not getting out of the office and talking to your donors. Not every meeting is an ask, anyway! Go have coffee and find out what makes your donors tick. It’s probably not the brochure you’re designing or the giving levels you’re agonizing over (it’s definitely not).

With every fundraising effort, it’s a good idea to think things through. It’s a great idea to recognize when overthinking things is stopping you from actually raising money.

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