As year-end approaches, you may feel even greater pressure to get out and meet with donors and prospects and ask for a gift.

Meeting with supporters is so important, but also nerve wracking! First, you’ve got to figure out the goal for each meeting. It could be just to reconnect, or share some news or program plans, or to make an ask. Once you know what you want to accomplish, the next step – outreach – often just doesn’t happen.

Making the Difficult Fundraising Asks

Think about what may be holding you back. By acknowledging your fears, you’re more likely to move to the next step and get the meeting. These 5 challenges often make fundraisers and volunteers nervous. Any of these seem familiar….?

1. Not knowing the major donor prospect well enough before the ask meeting. Do your research and gather info on their interests, past giving, support of other causes, and capacity. Consider inviting a board member or volunteer who knows them. Or just be honest and let them know you don’t know each other well but have been meaning to reach out. Remember: cultivation is key to fundraising - don't rush the process! If the timing isn't right for one prospect, reach out in another way and move on to someone that you’re ready to meet with.
2. Not knowing enough about your organization or program. Time to study up! Ask the program or service team questions, go on site visits, review past write-ups to learn as much as you can in advance. Also know it's ok to say "I don't know, but I'll check on that and get back to you" when needed.
3. Not understanding how the ask meeting is likely to go. Pre-meetings are KEY to work through who’ll take the lead, who’ll make the ask, and what to say when asking. It’s also good to think through how the prospect might respond to your request, and questions they may ask.
4. Concern that the ask amount is too high (or too low!) The right ask amount should come from data and your knowledge/relationship with the donor (part art, part science). Look at their capacity, gifts they’ve made to other organizations, past giving to your nonprofit. There should always be a rationale for your ask amount.
5. Fear of rejection - what if they say no!? As a fundraiser you should be hearing no. (If you aren't, the saying goes, you're not asking enough!) Make sure to listen closely when a donor responds to your ask to understand why they aren't giving now. Learn from that! Remember: saying no to the gift is not saying no to you.

Once you’re ready to ask, start with “easier” prospects or donors. This includes those close to your organization like former board members, longtime donors who haven't given in some time, or enthusiastic supporters who are volunteering or attending events regularly.

If ask meetings have been on your KPI list for a while or your major gift line in your revenue summary is looking low, the time is right to reach out and set up meetings. You’ve got this!