Facing Discouragement and 3 Common Mistakes in Fundraising Conversations
It is so easy to feel discouraged right now.
There are a million reasons to.
When I was a kid, my brother and I did a lot of yard work with my dad. When the weather was nice enough, you were likely to find us on a basketball court in a park somewhere. And if you couldn’t find us playing hoop, we were probably in the yard pulling weeds, laying bark dust, or mowing.
I remember one time when my dad went in on some river rock with a neighbor just a block away. Early Saturday morning, roughly 2 tons of river rock were dumped on our neighbor’s driveway. Easy. We would take our half over the weekend, and I’m guessing we saved some money under this simple scheme.
The only thing was that the neighbor lived down a short but steep hill.
Which meant my brother and I would be pushing a wheelbarrow full of river rock up it. I was a late bloomer, and around this time, I was one of the shortest in my class. So this was no easy feat. On top of that, my brother always tried to outshine me, proving that although he was shorter, skinnier, and younger, he could beat me at anything (even if he had to cheat!).
All I can recall is the heat from the furious sun beaming down on me and sweat trickling off my chin as I leaned as far in as I could to the steep incline to force the wheelbarrow forward and up the hill multiple times. I’m sure it wasn’t this many, but it felt like my brother and I had to climb it over 100 times each that weekend.
On at least a few of those rounds up and down, I was ambitious, and I filled the wheelbarrow too heavily. As I used all my strength to try to push it forward, it rolled back just a couple of steps, giving me a quick but intense scare. If it rolled over me, I would hurt myself, and if it tipped over, I would be embarrassed, and my brother would clown me for weeks.
So I paused. I sat on the curb midway up the hill and caught my breath. I felt guilty at first, like I had failed. But then I realized there was no rule against taking a break during this chore. As long as the rocks made it up to our yard, it’s all good.
After a couple of minutes, I wiped the sweat from my forehead and stood up from the curb just as I saw my brother turning the corner, a little extra motivation to keep forging ahead. I kept going, and he would not pass me.
The rollback was scary for a moment, but it was a sign of progress. If I hadn’t made it up the hill at all, there would be no gravitational force pulling the wheelbarrow against me. And if I hadn’t ambitiously pushed to the limit of how much weight I could carry, I wouldn’t know my limit, nor would I have discovered that taking a short break halfway up the hill would allow me to go even beyond that limit.
The rollback right now is real. The temptation to sulk is natural.
I’m recalling that summer childhood lesson to remind myself that there is no progress without struggle, as Frederick Douglass said.
Taking a break can also be powerful. I believe it is necessary in any journey toward real change. It can be what restores our energy enough to push through to see the next big societal shift we are working for and to reclaim what it means to be human together.
Three Common Mistakes in Donor Conversations
Even for those with fundraising experience, it’s easy to fall into common mistakes and bad habits in conversations with donors. I’ve been guilty of all three myself, and it takes real practice and planning to avoid them consistently and get the best possible results from every fundraising interaction. Here are the top three that I’ve noticed that are easiest to get in the way - and the easiest to address with preparation.
Talking too much.
We do it either to cope with our nerves, to unconsciously avoid a potential rejection, or to follow the mistaken assumption that more information makes our case stronger. If you’ve overwhelmed the donor or crowded out the ask, you’ve weakened the meeting’s impact. That doesn’t mean you’ve lost them for good — it just means more work to get back on track.
Forgetting the Emotional Connection
We’re conditioned as nonprofit leaders to speak to the funder frameworks for responsible, impactful, and innovative organizations. As a result, we can get bogged down describing our sustainability strategy, equity approach, theory of change, and governance practices — and forget to lead with vision, story, and emotional connection to the work. To fix this, make it a rule to always describe impact: what it looks like for just one person, family, or neighborhood, even if it’s just a sentence or two.
Not Preparing for the Conversation
You plan to keep it casual and not put pressure on the meeting. You’ve talked about your organization a thousand times by now, so what’s there to prepare for, right? Wrong. You should walk into every conversation — even the introductory ones — with a sense of what you want to learn about the donor, what questions will get you there, and what next step makes sense to offer, like a follow-up meeting, an event invitation, or program materials. Preparation is key to making the most of each donor meeting, even if the goal is a relaxed vibe.
None of this is easy to master alone — it takes practice, feedback, and a plan. That’s exactly why we launched the Own the Ask Fundraising Academy: to help leaders build real confidence and a real strategy for raising 4- and 5-figure gifts through individual donor cultivation, instead of waiting for a foundation to swoop in and save the day.
Interested in learning more? Click here to schedule an overview call.
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