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Making the Most of Each Holiday Connection

There you are, standing over the punch bowl at the holiday party, chatting with a former board member or a volunteer you haven’t seen for a while. She’s just walked through your new offices, recalled the early days, inquired about how various programs are going now. She’s reconnected.

Would you be prepared, right there in that moment, to delicately suggest some ways she could be of help to your organization?

Maybe she’s not ready to jump back in to a major volunteer role, but she could host a little Point of Entry or dessert gathering in her home after the holidays—just to help you spread the word. No fundraising, of course!

Or those dear friends of hers you’d just love to meet—could she arrange that lunch for all of you to get acquainted?

The foundation board she sits on—can she help you arrange a meeting with the grants officer?

Her firm’s volunteer department—don’t they look for volunteer opportunities for the employees all year round?

Will you be arriving at the holiday party informed about the guests and armed with your mental list of opportunities for involvement?

If not, get to work!

You may need to brainstorm with your team to be sure your list is broad enough. If you know the guests who’ll be coming to the holiday events, you may be able to get very specific: someone to chair the big event next year, someone to help you launch the computer program, or that new young professionals group you’ve been wanting to start.

Play a game to see how connected or reconnected you can become in each conversation you have over the holidays.

It’s the time for reconnecting and then planting a seed that can be nurtured and grown next year and in the years to come.

Your goal with each holiday interaction is to connect enough in each conversation so that your last sentence can very naturally be: “I’ll call you after the holidays to talk more about it.”

Happy Holidays!

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Capturing Names at a Holiday Banquet

Leaning Too Heavily on Your Board?

Q: How do we capture the names at our annual holiday banquet fundraising dinner and can we use it as a Point of Entry Event? We expect to have over 200 people, and we do a great emotional program about our work, but we’ve never been very successful at getting people to give us their cards for more info.

Neil in Massachusetts

A: In order to consider an event a real Point of Entry, people must be invited personally by someone they know, they must attend knowing they are coming just to learn about your work, you must have time to do the full Point of Entry program, and you must have permission to follow up with all of the guests afterwards.

Your holiday banquet is a great example of what we call a Point of Entry Conversion Event, which is often a great feeder strategy for your Points of Entry if you can successfully follow up with attendees and invite them to come.

At a moment in the program when you have people’s attention, have your emcee say that you wouldn’t be doing your job if you didn’t take a moment to share what the support raised at this event will make possible for the mission. Have them introduce your Visionary Leader, who should give a brief Visionary Leader Talk. Following the Visionary Leader, you should have a testimonial from someone who was supported by your organization.

Once those two program pieces have happened, the emcee should come back out and say that people have now gotten a glimpse of what your work is about and that some of them might find themselves wanting to get more involved. Then direct them to cards in the center of their table or under their plates, which they can fill out to indicate that they would like to talk with someone from the organization. You will then follow up and invite the people who gave you a card to a Point of Entry.

To shortcut the process, you can recruit your table hosts to become Ambassadors who agree to host and fill one private Point of Entry Event after the holiday banquet for those guests who want to attend.

Have the dates for their private Points of Entry pre-scheduled for January and work with each person to invite the folks they bring to the banquet back to a Point of Entry in the new year. Tell the hosts that it will be a great way for their guests to learn more about the organization and feel proud of what their support has allowed them to do.

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The Lifelong Donor

What do we mean by lifelong donor? Does it mean we have to wait a whole lifetime before they make their first gift? Does it mean they take a lot of extra care and maintenance that your organization may not be prepared to give?

Let’s start with the word “lifelong.” That sounds like a long time! Think of other lifelong relationships you have—with friends and family, perhaps with work colleagues. You’ve been through a lot together—good times and bad times. You’ve had moments when you wondered why you stayed connected to this person. Yet something has endured. There’s something about these lifelong relationships that makes them worth it. They add tremendous richness and breadth to our lives.

Now imagine that your donors put your organization in that category. The people and the work are important enough to them that they want to stay connected long-term. We each have organizations like this. I will always have a fondness for the hospital where our two children were born. I consider myself a lifelong supporter of the quality healthcare they provide. The same goes for my alma mater, my faith organization, the search-and-rescue organization that airlifted my sister out of a terrifying wilderness experience, and the schools that have done such a terrific job of educating our kids.

There is very little they need to do to keep me as a donor. I already consider myself to be a lifelong supporter of their work, and in most cases, they don’t even know that. They certainly don’t fawn over me and make me feel as if I could become one of their special major donors.

My story is typical. We each have a handful of organizations like this in our lives—organizations we truly love and to which we are lifelong donors.

Who are those donors for your organization? Who is already out there that cares about your work that much? With them, you have deep permission—permission that you are most likely not even using. I say that to the extent to which you are not fully “taking advantage of” the deep permission you have with these donors, you are not serving them.

We had a woman in one of our workshops who was the director of a major American art museum. She had done a brilliant job of cultivating her donors over the years. She proudly told me that she had at least 20 donors who were ready to give her a minimum of $1 million each. Yet she was afraid to ask them.

As we were meeting in her beautiful office one day, her assistant came in to tell her the sad news that one of these wonderful donors had just passed away—never having been given the opportunity to make a major gift to this institution that she had loved her entire life. Instead, an additional million or ten went to her heirs or to taxes. What pleasure that gift could have brought that woman, to know the lasting impact she would have made on the museum.

Perhaps this story sounds familiar. Whether your donors are ready to give you millions or thousands or hundreds, every organization has donors with whom you have this deep permission—donors who consider themselves to be lifelong supporters of your work.

Your job is to find out who they are, nurture the process, and then ask them to give to whatever it is that most moves them. Furthermore, your job is to develop a pipeline of donors in this category so that the person who comes along after you will have inherited all those well-cultivated potential donors. You are on a scouting mission for lifelong donors, donors who truly get it about your mission and are giving for the right reasons. Then you’ve left a real legacy for your organization.

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Holiday Wish List Tune-Up

What Size Tables for the Ask Event?

Q: We always feel so overwhelmed with people’s generosity at holiday time. Do you have any suggestions to help us feel more prepared?

 Stewart in New Jersey

 A: Maybe it’s time to take out the old Wish List and give it a tune-up. After all, these are your holidays too! What do you really want for your organization? What are you wishing for?

Ask each department, staff subgroup, or staff member to list their top five needs. Have them be as specific as possible, from soup to nuts: band aids, diapers, computers or office equipment, gas for the van, a new music instructor or counselor, playground equipment, or even a new gym.

Then compile them all into a single Wish List. You might consider listing them by area or department: “The nursery is wishing for X, the maintenance staff is wishing for Y.” It will let people know that you really need these items.

Print them up on pretty holiday paper. Make enough copies so that you can distribute them generously throughout the season. Have them at your front door. Insert them in your newsletter. Have a little basket of them at your holiday parties and other events. In other words, let people know what you want and need so that they can fulfill your wish.

Get started now. This is the helping season.

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Making the Ask

This week’s feature is an excerpt from The Benevon Model for Sustainable Funding: A Step-by-Step Guide to Getting it Right, Second Edition. For more information and to buy the book, visit our store.

Remember, first and foremost, that in the Benevon Model, the Ask happens only after the donor has been educated and inspired about your work, has indicated an interest in becoming more involved, and has been cultivated personally before being asked for money.

The process of asking is fun and natural. The biggest challenge is to remember that it needs to be a dialog between two people who already know each other.

Before I go to ask someone for money, I always put myself in the donor’s shoes. How would I like to be approached by one or two key people from the organization, knowing full well what they want from me? I recall that this is an organization I love and will feel excited to support. It feels as though I have guided myself through the cultivation process. In fact, the process has felt very natural. I am wondering why no one has asked me to give until now. I have given many readiness signs to this group, hosted an event in my home, and invited friends to Point of Entry Events. This is one of the two or three places I want to give my money. I love these people and support what they are up to.

To provide some encouragement for what may lie ahead as you enter the cultivation and asking process, let me share two heartwarming Ask stories from our alumni groups. One group had a lunchtime major Ask for $1 million scheduled with the executive director and the board chair (who was also a major donor), but on the day of the appointment, the donor had to cancel. Rather than postponing the meeting, the donor called that morning to apologize, insisting on knowing how much money the organization needed. Despite the executive director’s attempts to hem and haw and reschedule the lunch so the Ask could take place in person, the donor persisted and the nervous executive director finally blurted out, “We were planning to ask you to give $1 million toward the capital campaign for our new building.” The donor replied, “I’d be delighted to do that—just send me all the paperwork.”

The moral of that story is to never underestimate the power of the highly personal donor-cultivation work you will be doing. This same executive director, who has now raised over $10 million for this campaign, calls me often with amazing success stories and to ask me, “How can we attract and cultivate more of these wonderful donors who truly understand and appreciate our work?”

But let’s suppose you aren’t getting millions of dollars over the phone. Let’s assume you’ll need to go out and meet with people to ask. What else does it take to be successful when you ask?

We worked with one very shy executive director of a children’s home who, even after many cultivation visits and practice Asks, could barely bring himself to make the Ask for $100,000. His 27-year tenure with the organization was a testament to his love of the children and the work of the organization. We suggested that when he goes out to make the Ask, rather than nervously anticipating all the ways things could go wrong, he should pause to recall his larger purpose. “Imagine the little kids, tugging at your pant legs as you walk out of the office, saying, ‘Do it for us, Bob! You can do it! We need the things the money will buy.'”

He became a fearless, highly successful asker after that, and yes, he secured that $100,000 gift—for the kids!

Once you have completed your preparation and practice Asks, you need to put it all aside. At this point, asking should be nothing more than nudging the inevitable. You are asking people who already know and love your organization. You already know they have what you are asking for. You already know they are emotionally connected to you.

I recommend you go into the Ask with an entirely different agenda: in those few minutes, see how related and connected you can become with the donor. It is all about listening for every cue and being much more focused on what they are saying right now than on what you should say next.

The key to a successful Ask is you being a real human being—not a robot with a script, but a regular person who truly cares about this organization and this donor. The more authentic you can be, the better. Asking someone for money is an intimate occasion. It can be serious, playful, short and to the point, or long and drawn out. No two Asks are ever the same, because no two people are the same. I recommend you approach it more like your first dance with your new, lifelong dance partner. You may step on each other’s toes, grumble and laugh a bit, but eventually you will get it right. As with dancing, one person is the leader. In asking for money, it should go without saying that the donor is the leader.

Even after doing all your cultivation, some donors may say no to part or all of what you ask for. Your job if they say no is to thank them for being a friend of your organization and to ask if there are any other ways they would like to be involved. Then your job is to figure out how to ask them again in exactly the way they want to be asked, for exactly the thing they do want to say yes to. And then you ask them again, or have the perfect person ask them, so they say yes and feel great about it.

If they say yes and don’t feel great about it, it’s not a “win.” You don’t want to leave them with any sense of having been manipulated into giving more than they were comfortable giving. You don’t need their contribution that badly.

You want each donor to feel as though they have sprinkled fairy dust on the most worthy organization in the world. You want each donor to feel so good about giving to you that they have no need for others to even know they did it. You want them to feel as if supporting your organization is a source of personal pleasure for them.

You must let them know how excited you are to receive their gifts. You cannot be just a little bit appreciative. Let them know right away that their gifts are a big deal to you. Then you will have made a real friend. You have allowed them to truly contribute and feel the way you feel when you know you have made a real contribution.

Cultivating lifelong donors and connecting them to your work is the real nugget of the Benevon Model. Once established and nurtured, that personal connection becomes the driver of the relationship. Rather than giving out of guilt or obligation to a friend who is on your board, these donors have chosen to become—and remain—involved with you, for their own reasons. Multiply that by hundreds, even thousands of donors, and you can begin to see over the horizon to long-term sustainability for your organization.

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Is One-on-One the Only Way to Ask?

Ask Benevon: The Ask Event is Not a First Date

Q: If someone has attended our Point of Entry and gotten involved but can’t come to our Ask Event, is one-on-one the only way to ask them to join our Multiple-Year Giving Society? What about our year-end annual appeal or other special mailings?

 Amber in California

 A: Yes, asking one-on-one is the only way. Do not send a letter asking people to join your Multiple-Year Giving Society for $1,000+ a year for five years.

If you blend in the higher Multiple-Year Giving Society giving levels into your normal annual appeal letter, it will confuse people who have been accustomed to being asked for smaller gifts in the annual letter.

Once someone joins your Multiple-Year Giving Society, you should take them off your direct mail list and cultivate them personally as a major donor.

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Five Tips for Cultivating “Expiring” Donors

It happens. Five years ticks by quickly. Before you know it, the wonderful donors who made those generous five-year pledges (of $1,000 or more per year) to join your Multiple-Year Giving Society have just made their third year’s pledge payments and no one from your organization has gotten to know them yet. In fact, they are still complete strangers to you.

Take this as a serious wake-up call and get to work. Set up your donor cultivation plan now, starting with the donors who are nearest to the end of their five-year pledge payoff cycle. If you don’t get to know them and cultivate them systematically now, you will lose most of them at the end of the five years, if not before.

I’m always surprised when people tell us they don’t want to “bother” these loyal Multiple-Year Giving Society Donors. They think they should invoice them dutifully each year, call them at the start of the sixth year, and ask them to re-up on their pledge. That is precisely the opposite of what is needed.

The whole purpose of having donors who make five-year pledges at this level is not for your organization’s financial security. After all, if a donor does not pay their annual pledge, you are not going to take legal action against them. Rather, the purpose of the giving society is to identify those donors who want to be closer to the organization. These donors did not have to make a five-year pledge. They could have opted to give the same amount of money one year at a time. By joining your giving society they are communicating something critical: they want to give to your organization, they want to stay connected to you over the next five years, and they expect you to give them updates, ask for their advice, and include them in major milestones in the life of your organization.

In other words, you should interpret their five-year pledge as their permission to stay connected with them.

We say you should have two personal contacts per year with each donor in your giving society, plus attendance at one Free Feel-Good Cultivation Event. If you have fifty donors, that would be 100 personal contacts. A telephone conversation (not just leaving a message) counts as a contact. But the best contacts are one-on-one and in person, focusing on the donor’s particular area of interest.

Even if your donors are in their third year of their pledge cycle and you have never reached out to them to talk with them or meet them in person, it is not too late. But you need to get going quickly. Here’s how:

  1. Invite a small group of five to seven Multiple-Year Giving Society Donors to a special, private “CEO Golden Hour” with your CEO and board chair in the CEO’s office. Offer a full one-hour Point of Entry Event either before or afterwards. This is a mission-focused event (not merely a nice social event), like a group of five donors having a light lunch.
    • Start the hour by having the board member and CEO thank them for their gifts and give specific examples of what their gifts have made possible.
    • Have a testimonial speaker from one of the programs that benefited from their gifts talk about how your organization changed their life for the better.
    • Resist the temptation to share only the positives. Have your CEO and board members share some of the actual challenges they are facing as well. These donors need to hear your needs and know that their money is making a difference—and will continue to be needed after their first pledge is paid off.
  2. Follow up within two to three days to get their feedback and ask if they would like to serve as an Ambassador by hosting a private Point of Entry for ten or more of their friends or colleagues in your offices, their home or workplace. Tell them you can bring the Point of Entry to their home or workplace if needed. If they prefer not to be an Ambassador, how else might they like to become involved?
  3. After they serve as a successful Ambassador, invite them to host a table at your upcoming Ask Event and fill their table with the same friends and colleagues they invited to the Point of Entry.
  4. If they are not able to come to one of your private lunch events, find another way to meet with them in person, ideally at your offices or program site where they can see your work in action.
    • Offer to meet with them one-on-one or arrange a private meeting with your CEO if appropriate.
    • At the very least, talk with them on the phone and ask them what interested them in giving to your organization.
    • Establish enough of a personal connection so that you will have something to refer back to in future contacts.
    • Set a date for a subsequent contact after each contact.
    • Do not close out their record—always schedule a next step.
  5. Before your next Ask Event, you can approach a small group of these donors to ask them to increase or extend their pledges. For example, you could tell them you are looking for five donors who will each extend their pledges for five more years or increase from $1,000 a year to $5,000 a year as a leadership gift to inspire other donors to do the same thing next year (either at your Ask Event or in a follow-up phone campaign to “expiring” donors who do not attend the Ask Event).

Above all, reach out to these donors now, by telephone. Do not wait until the next event, the next “right time.” Include them in your organization’s family right away. Make sure they know how much you value them. And vow, in the future, to cultivate your five-year pledge donors starting the day after they make their pledge, rather than waiting until their pledge is close to “expiring” before you get to know them.

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Rate of Pledge Pay-Off

Recognizing Major Donors

Q: What percentage of Multiple-Year Giving Society pledges ($1,000 or more for five years) do people actually pay off?

Mary in Oklahoma

A: The rate of pledge pay-off is typically about 95%.

While that might sound exceptionally high, put yourself in these donors’ shoes. They feel connected to your organization because you keep in touch with them personally. They never become strangers. They only become closer friends of the organization’s family.

In addition to attending at least one Free Feel-Good Cultivation Event during the year, all Multiple-Year Giving Society Donors are cultivated one-on-one two times per year. Many choose to become Ambassadors and then Table Captains in subsequent years. By inviting their own friends and family to their private Point of Entry and the Ask Event, they are deepening their own resolve about the good work of the organization.

Not paying off their pledge is never a consideration for the great majority of these donors. In fact, many Multiple-Year Giving Society Donors pay them off early and increase the amount of their pledge or extend their existing pledge after the initial five years.

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The CEO Golden Hour—Option 3: One-on-One Meetings with Donors

This is the third and final feature in our three-part series entitled the CEO Golden Hour, highlighting the top three things your busy CEO can do to impact donor cultivation and major gifts if they are willing to dedicate merely one hour a week to this critical process.

I’ve also included here some general thoughts about how to integrate this CEO Golden Hour process into the life of your nonprofit organization.

What does it mean to “cultivate” a donor and how would a busy CEO find the time to do that even if they knew what to do?

This is a question we are asked regularly by the groups in our Sustainable Funding Program, now that they have an ever-increasing number of donors in their Multiple-Year Giving Society.

Rather than merely invoicing donors and expecting them to dutifully make their pledge payment for each of the next five years, these wise CEOs and development directors have discovered that with a high-touch system of personalized contacts, even the busiest of CEOs can begin—and even enjoy—the donor cultivation process!

Option 3: Personal lunches, dinners or visits with the sub-list of donors that have expressed further interest during the CEO personal phone calls or small group lunches. CEO may make donor visits one-on-one or accompanied by a board member or your major gifts person.

Purpose: To get to know each donor better and to feel more connected to them.  Likewise, each donor should feel more knowledgeable about and more connected to the organization.


  • CEO’s assistant, major gifts person, or development director:
    • Phones the donor and invites them to lunch with the CEO. “Sheila would love to update you on some of the current developments here at our center and get your input on a few things.”
    • Sends the guest list with two to three sentences about each guest, including last gift, person who engaged them, bucket area of greatest interest, and any other recent participation.

Suggested Agenda:

  • Greeting
  • Thank you for past support, including one or two specific, human examples of what their support made possible
  • Ask/talk about their “bucket” area of greatest impact. For example, in a senior center, is it meals, social, or healthcare? Give examples of new developments in that area
  • Share challenges the staff are facing and ask questions about how the donor’s expertise might relate to each challenge
  • Ask what is going on in the donor’s life: family, business, other community interests
  • Be genuine, open, and be sure the donor does 75% of the talking
  • Make a plan for getting back in touch with the donor to follow up on any action items discussed and talk about a next date for another meeting
  • Thank the donor
  • Put all notes in database and take prompt action on any suggestions or open items
  • Keep things moving: don’t let too much time pass before the next contact—two to four weeks at longest

General Comments:

  • Whether in your phone calls, small group lunches, or one-on-one meeting with donors, if people ask how else they can help, be sure to invite them to become an Ambassador.
  • Keep using this precious hour of your CEO’s time for any of these three activities. At the end of three months, ask your CEO if she would be willing to increase to two hours a week.
  • By then you will have seen how much coordination time this takes from your development director or major gifts person as well as the volunteers on your cultivation committee.

By then, you no doubt also will have seen how much these simple contacts have deepened each donor’s connection to the mission, which is the whole purpose of donor cultivation.