Surprise and delight: What Valentine’s Day Can Teach Fundraisers

A few years ago, I decided to take back Valentine’s Day and transform what had become an eye-roll holiday into an opportunity to surprise and delight my friends with homemade Valentine’s cards.

I get crafty. This year, I cut, pasted and glued together a google-eyed heart lollipop. Then, I send my homemade cards via snail mail to personal friends who’ve made a difference in my life.

But why am I sharing my construction paper prowess here? Because I think building relationships with high-values donors requires similar thought.

1. Reach out when it’s unexpected. People expect you to send holiday cards — even birthday cards. They don’t anticipate Valentine’s Day cards (especially from friends), which makes receiving a Valentine extra special. Donors expect an acknowledgement after making a gift. When can you reach out in an unexpected way to make them feel super special?
2. Put some thought into your timing.  I chose Valentine’s Day because February days are cold. Winter nights are long. And I personally struggle with seasonal depression and know many of my friends do too. When you reach out during unexpected times, put some mission-related thought into why now. An example: Many refugees who come to the United States without birth certificates are given January 1st as a birthday. If you are an organization working with refugees, what about sending a January 1st birthday card to donors as a way to connect them more closely to your mission?
3. Make it personal. You don’t have to glue individual googly-eyes to make it feel personal. But you do need to think about ways your outreach feels authentic (even at scale). Drop in your business card. Get a fun stamp and personalize each envelope. Or maybe include a link to a song you love in your email footer p.s. Think about how you can put some personality into your outreach so it feels like it’s coming from someone — not an institution.
4. Make it easy. I frequently update my contact list throughout the year so I can easily flag people to receive my cards come February. Keep a clean list of your high-value prospects and your multi-year donors at the ready.
5. Try for at least 2X per year. Right now, I only do Valentine’s Day. But I aspire to add in another special touch. Maybe I’ll send cards on my birthday? (Just like hobbits do — yes I’m a Lord of the Rings fanatic). Or maybe I’ll send something for summer solstice?
6. You’ll get so much in return. When those envelopes start arriving in mailboxes, you’ll be giddy with delight as folks respond with appreciation and love. They now know they mean the world to you. And that’s a precious gift.