I am back with Part 2 of our conversation about fund-raising — although I am sure some of you were hoping I would forget! Not a chance. Now we get to the fun part, the rewarding part, and, of course, the part where you will need to remember the joy of facing your fears. I am thinking again of that nervous camper shivering at the end of the diving board, wanting so much to be brave enough to make her first jump into the chilly lake. You are standing next to her and encouraging her, because you know how great she will feel after she takes this scary step. With a whoop, she leaps in and you both feel the excitement of the moment. She has chosen courage over comfort, and she will take that moment with her into all the scary situations she will face during her life.

Perhaps it is not as dramatic, but you too are facing such a moment in your quest for fund-raising confidence. It is right in front of you, and I will be cheering you on. Trust me, the rewards — not just in actual money raised, but in your moment of facing a fear — will be great. So, let’s dive right in!

We have already covered setting up the systems to support your fund-raising efforts — and, if you want to remind yourself of those steps, do read over the earlier article in this series (Camping Magazine, November/December 2017). I am assuming that you have a tracking system for creating a yearly calendar, for segmenting donors into appropriate groups, for saving important information about individual donors and prospects, and for generating perfect thank-yous at perfect times.

We are now going to zero in on the prospects where the potential is great for major gifts that will be the most useful in reaching your goals. Remember that one of our underlying principles is to treat all donors with gratitude and respect, but know that in most fund-raising work the top 20 percent of your givers give at least 80 percent of your totals, so it makes sense to spend more of your energy bringing them closer to your vision and story. The idea here is to help a donor reach a point of maximum involvement before you invite him or her to make a major commitment to your cause.

My own experience tells me that, while some folks try to short-cut that process with various less time-consuming strategies, building deep and lasting connections with your donors always yields the best results. You can “guilt” a person into giving or create some competition to push folks into writing a check, but gifts extracted with those methods are frequently one-time commitments and made with some element of irritation. Our strategy at the core of sustained support is to build deep and lasting connections between the work of your organization and your donors. In that way, their gifts will continue and even grow over time, because they believe in the work and the mission. If you steward those donors carefully, keeping them informed and sharing with them the vital impact of their support, they will become lifetime givers — and perhaps even more than givers. This dedicated group is where you will find board members, campaign leaders, and individuals who will open doors to others who may become friends of your organization.

So now you have identified a group of prospects who have the potential for making major gifts. A major gift in this instance is yours to define as you will. What you are trying to do is identify in that category a group that you can manage individually with your current staff and volunteers. It does no good to identify a huge group of potential major donors and be unable to do anything with them beyond, say, the mailings you are sending to everyone else. Perhaps you have a group of 20 names beyond your board who you think have great potential and you can steward individually. That is your major donor pool for the year. If you can honestly handle more, go for it, but be realistic about your abilities before you begin.

The first step in the work is to identify a plan for every donor. What will it take to bring this prospect to a point of maximum connection with your organization? It may be that they are past donors with solid connections and a small step — a visit to update them on progress their past gifts have made possible, an invitation to see your program in action, and/or a personal letter of thanks — is all it takes to reach that point.

In other cases, the prospect’s connection may be more tenuous. Perhaps they are a new parent or a neighbor with deep pockets but no history of giving. Here the plan you map out will be necessarily longer, maybe starting with a tour and meeting some key frontline staff. Seeing participants learning, growing, and having wonderful times in your program can be the very best way to build understanding and support. If distance makes an actual visit impossible, perhaps a small gathering for a group of prospects with pictures and stories from key staff or happy campers would give the feeling of being on site. Save time for answering questions and follow up with a note of thanks for being with you.

A next step might be coffee with a volunteer — a board member, for example, who can listen carefully to find out what particularly excited the prospect. Were they interested in camperships for disadvantaged children, or were they more of a “bricks and mortar” donor? What kinds of organizations have they supported in the past and what sorts of gifts gave them the most pleasure?

Now that the prospect has seen the organization in action — or close to it — and has made a connection with another donor whose commitment is high, you can judge if further steps would help to build an even deeper connection or if the prospect is ready to be invited to join the vision and help the cause they have come to understand. If it would help, here is where a personal note from your executive director with an update on something the prospect has expressed interest in might be perfect. Be creative at this point and don’t rush. Time taken to deepen connections always pays off. One warning: Be sure you are not delaying an actual invitation to make a gift because you are feeling chicken to take that step. This is all about donor readiness and not your fear of taking the plunge.

Here we are! We have built the prospect’s connections, and they are practically begging to help. They understand your work and its importance to your participants; they have met key players and trust the organization to steward funds carefully. No more standing shivering on that diving board. It’s time to move to an actual ask!

As you can see, there is nothing “cold” about the call you are about to make. You may be unsure about the size of the gift a donor is ready to give, but, at this point, you should have no doubt about that donor’s connection with the cause. Perhaps the donor has already made a small gift or has told you she is excited about your work. You should be feeling a strong connection with her. If another volunteer or staff member has an even stronger connection, perhaps they are the right person to take the next step. Sending the right person — or people — to pay a visit may make all the difference.

One other step: You may be wondering how large a gift to ask for. (Yes, it is almost always more effective to ask for a specific amount or a range than to leave the question open.) There are many ways to figure out a reasonable ask amount. Check your own records or public information on the web to see the size of the donor’s past gifts. Your ask should be a bit of a stretch for the donor, especially if you are inviting them to make a multiyear pledge. You want to invite them to support your cause with an amount that is not insanely high but also doesn’t bring them into a gift category much below their capability. I remember a meeting early in my career when I asked a donor to consider a gift of $25,000 to my organization. He instantly wrote a check, handed it to me, and then said, “You need to know, if you had asked me for $250,000, I would have said yes.”

Time for your first dive! You can tailor these steps to reflect your own style, but here is how I would go about a visit.

Call or email to set up an appointment. If bringing a good additional person makes sense, do it, but never bring more than two people. Say you would like to come by to talk about your organization and ask if there is a good time for about a 45-minute chat in the next ten days or so. Coming to a person’s home or workplace is often better than a coffee shop or other location where you may be interrupted.

Bring any materials that help you make your case, such as a capital campaign brochure, an annual report, and a few pictures or words from a grateful participant.

Arrive on time, and enjoy a few minutes of gracious chit-chat while settling in.

Thank them for the time and for getting to know your organization.

Tell them why you are there. Perhaps you are starting to raise funds for a new building or working hard on getting your annual fund to a new level. Perhaps it is a campership campaign that is on your list. Whatever the purpose, describe it succinctly and share why it will make a difference in the lives of the folks you serve.

Tell them how others — your board, for example — have already given. It is always easier for donors to commit if they know they are joining other dedicated givers. A 100-percent commitment from your board is almost a must before inviting others to step up.

Now you can use these words: “I hope you will consider supporting our organization with a gift in the range of . . . .” Give a modest range so the prospect has a bit of a choice as they think through their response. Sometimes, particularly in a capital campaign, you will have created a table of gifts indicating the range of gifts you will need to reach your goal. In this instance, you can indicate the range you are hoping they will consider on the table itself.

Important step here: Be quiet! If you are anything like me, you will want to back-pedal here, lowering the expectations and filling the silence. But let them make the next move. There are three possibilities for what happens next.

The prospect gives an enthusiastic yes. You thank them profusely and give them the appropriate paperwork. You hurry back to the office and send them a grateful written thank-you, and you record the highlights of the conversation in your tracking system.

The prospect says they will need to consider the gift and perhaps speak with their spouse before committing. Again, express gratitude and ask if you may call in a few days or a week to see how the considerations have gone. Keep the ball in your court here. Don’t say you will wait to hear from them, but make the next contact yours to initiate.

The prospect says they are not in a position to give at the moment. Again, thank them graciously on the spot and send them a thank-you for their time. Handling a rejection well can sometimes lead to a gift later when the time is better for the donor.

That’s it. You jumped in and the water is fine. Think through the meeting and give yourself a giant pat on the back. Also, reflect on what went well and what you might have done better so the next visit will be even smoother.

One last critical point: Once you have secured a gift, stewarding that donor kicks into high gear. Keep this supporter close with regular communications and many thank-yous. Remember that a donor well-cared for is likely to become an even more generous friend. Keep up the connections, making them even stronger over the years, and you will have made a lifetime giver to the cause.

You have taken the first and most difficult leap. From now on, you will still have butterflies the night before any visit, but with a strong foundation and a courageous history, you are ready for even the high diving board!

Photos on pages 42–43 courtesy of Rolling River Day Camp, East Rockaway, New York; and Green River Preserve, Cedar Mountain, North Carolina.