Q: I've been cultivating this one prospect for a few months, and I can't figure out where we are. I thought I was clear about my interest in getting her to support my organization, but I think she thinks we're friends. We're about the same age, and I really do like spending time with her...but I can't afford to spend all this time on a prospect who's not going to pan out, you know? I feel like I'm wasting company time on a personal relationship. But I'm afraid that she'll hate me if I tell her that the only reason I've been having lunch with her is that I want her money.
A: In amicitia nihil fictum est, nihil simulatum, et quidquid est, in est verum et voluntarium. In friendship, nothing is fiction, nothing is fake, and whatever it is, is true and voluntary. (Cicero)
I ran across that quote a week ago and knew there was a reason I wrote it down. These are good words to live by for cultivating friendships, and good words to live by for cultivating donors. Sometimes those sets overlap, sometimes they don't - but until you let go of the fiction you're allowing to seep into this relationship, you can't have a relationship that is true and voluntary.
Do you want a real friendship with this person? Hold onto that answer a minute.
One of the biggest perks of frontline fundraising is getting to meet some truly amazing people. Sometimes you're going to hit it off, you'll have a good rapport and a lot in common, and you will wind up with a personal friendship (whether or not you wind up with a major donor). But, and I can't stress this enough, you're not there to be someone's friend. That's not the job.
If you're working with a prospect, you need to be true. That's a rather poetic way of phrasing it, so it's open to some interpretation - honest? direct? open? gentle? authentically concerned about their feelings? unafraid to expose your genuine self? Any and all of those are fairly good advice. And they are essential for maintaining the voluntary nature of your relationship.
A donor has to support you because they want to. There can be complicated reasons that folks "want" to support you - they might want to support the mission; they might want to support your organization's leadership; they might want to impress someone on your board; they might want to feel good about honoring a deceased loved one; they might want to get their name on something; they might want to do something nice for you, their friend. You can think of more reasons - but they boil down to wanting to give, based on true and voluntary reasons.
If you feel you compelled to hide your own feelings, you're undermining this whole system.
Now, I'm not talking about neglecting to discuss politics with a donor you know is on the other side of the political spectrum. Unless you're a political fundraiser, that's irrelevant. Treat donor relationships like your distant relatives at Thanksgiving dinner - you know you don't see eye to eye on a lot of things, but you go out of your way to not pick fights and to talk about things you know you can both discuss pleasantly. You're representing your organization.
What I'm talking about is remembering that YOU are representing your organization.
Now let's get down to brass tacks. You feel like you're spinning your wheels with a prospect because you don't know if she's going to ever become a donor. I'm *not* going to criticize or analyze your methods that lead you to say that you thought you'd been clear that you're looking to turn her into a donor. I don't need to. Donor communication is very simple - if they understand what you're saying, you've communicated. If they don't, it doesn't matter how reasonable your attempt was, you need to try again, differently.
Tell your prospect that you always like seeing her, but that you're concerned about doing so on company time without a clear agenda, and then set one. Tell your prospect that you enjoy spending time with her, but want to make sure that she's getting everything she needs to make a decision about supporting your organization or project X this fiscal year. Tell your prospect that you are very concerned about meeting your fundraising goals for the year, and why that's so important to all the work your organization does, and that you'd love to meet her if you can help her come to a decision, but otherwise, you'll have to catch up after the fiscal year ends. Keep trying to communicate until you succeed. Make sure you don't try avoidance as a tactic, either as a way to not take too many meetings or to avoid awkwardness after you've communicated that you don't have time for endless personal lunches on company time.
You'll notice that I didn't suggest that you offer to move your socializing to after-hours.
IF you want to actually be friends with this person, you can put that into your true and voluntary communications. Go for it. Your prospect can say no (in which case you respect that utterly); it's their choice once you ask. But we all go through times in our lives where we don't have enough time to spend with friends we've known for years, and we've all met folks that we like well enough when we see them for work but don't want to spend extensive time with. If you don't actually want this prospect as a personal friend, don't make the offer.
Socializing with prospects and donors is a fine line. You must always walk a tightrope between professionalism and authenticity. You are not there to make personal relationships, you are there to connect people to your organization...but someone who suppresses all personality or manufactures one just for the occasion is going to do a poor job at building those institutional ties. You are always obligated to build relationships on behalf of your organization. Sometimes you will incidentally form personal friendships in the process.
Allow me to offer one final thought: when you conduct yourself as I'm suggesting, you'll be left with true and voluntary relationships. But that also means that you cannot be all things to all people, and that truthfully, some people want something else. Your honesty and clarity will help them see that they don't feel compelled to support your organization. Get used to letting them go and being grateful for the separation. If you trick them into thinking you/your organization are something you're not, you might get a gift, but ultimately you'll wind up unhappy. If you twist your mission or programs or organizational focus to please a donor, you'll regret it. If you bring in a donor who will not actually value what you're doing, they will regret it...which means you will too. Unhappy donors are far far worse than amicably parted prospects.