A very edited version of a question received from a friend/reader:
Q: It's my first year in a new position, and we're working on launching a capital campaign. We really really need a huge new gift from my organization's biggest donor...but I think she hates me. It's messing with my head, paralyzing me with fear, and making it hard to think about anything else. I don't think the campaign will succeed without her, and what if it's my fault she turns us down?
A: OK, so the stakes seem high here, but I don't know if you're making an honest assessment, or whether your fear is leading you to obsess about a worst case scenario.
I'm going to answer two parts of your question separately - the biggest problem you're having is paralyzing fear. That's something you need to fix immediately, because every day you spend motionless makes it that much harder to get started again.
If we were in a coaching relationship, we'd be working on distancing yourself from all your emotions so that you can step back a couple of times a week and think about your campaign strategy objectively...go back to the basics and break down that campaign into a series of bite-sized goals, then channel all of that anxiety into chipping away at your list of tiny steps forward.
If the thing that's tying you in knots is a complicated situation with one donor (even if it's your biggest donor), you need to be able to sit down at your desk (or take a walk if that's a better way to clear your head) and think about all the pieces of the puzzle. You're going to need a base of dedicated and involved smaller donors. What's your plan for reaching the masses? Work on that while your gears are grinding elsewhere. You'll need to scour your existing donors for folks who can be wooed into stretching to new heights of giving, and start the wooing process. You'll need to train and mentor and encourage your board members to get involved. Maybe you need some printed collateral. Maybe you're planning a launch event. The specifics, you'll have to come up with. But there is inevitably a long list of things you need to do, and there's immense psychological benefit to being able to account for real progress at the end of the day (or week, or month). Turn your paralyzing fear into nagging fear. Nagging fears you can live with, or better yet, pin them down and dispel them.
So now let's look at the fear of being hated by a donor. First of all, why do you think this person hates you? Unless there was an actual incident - did you accidentally say something offensive? ("Pregnancy suits you!" "...I'm not pregnant.") Did you do something bad? (Accidentally shatter her grandmother's heirloom and priceless vase by knocking it off the coffee table when you had tea at her house?) If there's no real cause for anger or hate, the odds are that you haven't made that deep of an impression. Actual hate takes energy to manifest and maintain. At worst, you're probably just an annoyance.
There are so very many reasons that two people might not click, and that's without figuring in the fact that you're talking about people who met in a rather artificial circumstance - a paid professional whose job it is to connect the donor to the institution and then ultimately ask them for money. It's perfectly fine to not form a personal, deep connection to every donor. Perhaps this metaphor will help: a great donor relationship casts you in the role of midwife - someone who has a connection with their charge and is honored to be trusted to help the donor bring a new gift into the world. Most donor relationships have you playing the role of translator - speaking to the donor on behalf of the organization, bringing donor concerns and thoughts back to the organization, and hoping that you can speak both languages well enough to communicate effectively. A poor donor relationship makes you a translator with an annoying voice or distracting accent. This should be a comforting perspective: you might not be the translator the donor would imagine or choose, but ultimately, it's not about you. Really.
Except when it is. Sometimes, people really are that crazy, and it's not impossible that your worst fears have manifested in this donor. She hates you AND is willing to hold it against the organization. Very very unlikely, but not impossible.
You are never the only member on the fundraising team. So discuss your fears frankly with the rest of your team - an Executive Director, a Director of Development, Board members...Coach one of them through taking over the relationship, or hear what they have to say about making amends and trying to start fresh. Ask for help.
You might even consider asking the donor. Tell her you fear that the fact that you two have not developed a warm relationship is getting in the way of her longstanding relationship with your amazing organization, and you know how big a role she has played in its success to date (or the impact her involvement has had, how much she's been appreciated...whatever you think matters most to her). Ask if you've offended her. Ask how you can get past your rocky start. Try to find some small common ground (like, say, a passion for the work that your organization is doing) and start fresh.
It may wind up that you need to hand over the relationship to someone else. Happens all the time, so it's important to not feel like that move means failure. Just don't do it from a place of unexamined fear...do it because it makes good sense.
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