It’s not too early to begin planning your fundraising strategies for the fall and end of the calendar year.  You’re probably already thinking about your mail appeal.  But what about person-to-person major gift fundraising? For most nonprofits, the lion’s share of money comes from the smallest group of people. Many of these folks respond well to in-person cultivation. Not to mention being asked to give by people who they know, like or admire.  Board members can really help you out in this regard.

The late summer months are a great time to plan to hold an “inspiring philanthropy” (aka board fundraising training) session for your board and/or advisory board members; then provide volunteers with assignments so they can hit the ground running! These sessions are best held in September/October – in time to fire folks up for year-end major gift asks.

Whether you do this virtually or in person this year, it’s an important board engagement strategy. I’ve run sessions entitled “How Philanthropy Can Be as Addictive as Chocolate.”  I’ve even offered chocolate tastings at these events (if you’re going virtual, you could mail some sample chocolate kits in advance). I’ve found folks enjoy this approach so much more than “Fundraising Training Sessions,” so you’ll get a larger turnout. Plus you’ll energize folks a lot more than if you start from the perspective of: “this is your chore; you must do it, even if you hate it.”  Your goal is to get your board members to LOVE facilitating philanthropy!

Consider inviting an experienced fundraiser and meeting facilitator to run the session. Why hire a facilitator? While you can definitely do it on your own by following the tips below, I often find board members are more receptive and open-minded when an outsider is brought in.  They listen more.  They believe more.  They are more relaxed and less combative.

Sorry, but it’s just the nature of the beast.  And, since you’re going to be raising major gifts, it will be money well spent! If you do hire a facilitator, I suggest you tell them this is the type of agenda you’d like to follow:


A. Ask folks to describe why they became involved with your organization, and what continues to keep them passionate and inspired. Give each person a turn if you have a small board; otherwise, pair folks up and have them break into new pairings several times (you can do this virtually using breakout rooms). Your objectives are to:

(1) get folks comfortable telling their own story, and

(2) fire folks up from listening to other people’s stories.

Usually folks will have a personal connection to the cause.  Or they’ll have an outcome story to tell – something they remember from having been involved with you over a period of time.

B. When storytelling has concluded, ask the group for feedback. 

(1) How did it feel?

(2) What did they learn?

(3) Did telling their story feel at all scary?

(4) Did it feel less scary than asking for a gift?

(5) Do they think they could consider reframing ‘fundraising’ as ‘storytelling’ moving forward?

Could they maybe move from ‘fighting’ (e.g., “It’s time for me to hit your up” or “twist your arm”) to ‘inviting’ (e.g., “I’ve got a great opportunity for you” or “Would you like to join us?”)


A. Discuss why you do fundraising. To create happy endings! For your organization, for those who rely on you, and also for your supporters. Make this another opportunity to frame what you’re doing as storytelling. You’re helping prospective donors visualize the story of your cause. Think about the people, animals, places or values you’re trying to sustain, restore or heal. Talk about connecting to the donor’s own personal narrative through your collective narrative.

Talk about the need people have to enact their values and be part of something larger than themselves.

B. Discuss the fact donors are empowerers. They give the stories you tell happy endings. They help those you serve stand up and fight, becoming heroes in their own right. Your job is simply to facilitate their empowering philanthropy.

This is a noble, rather than an evil, pursuit. Asking isn’t begging.  Asking isn’t taking something away.  Asking is giving folks an opportunity to join in something wonderful.


A. Discuss what folks are afraid of. Usually it boils down to two things: (1) fear of rejection, and (2) fear of looking dumb/unprepared. Begin by asking folks what words they associate with fundraising. Then ask them what words they associate with philanthropy. You may be surprised with the results.

Talk about how to overcome their fears.

B. Destroy the money taboo. People think fundraising is about money, and they hate to talk about it. Persuade them it’s not about money. It’s about outcomes.

Money is just a symbol of what it can accomplish.

C. Help board stop wallowing in negativity about fundraising. Consider asking them the following questions:

1. What are you telling yourself that keeps you focused on the negativity?

2. What will you have to give up to leave the painful associations behind?

3. What will you gain from leaving the pain behind?

4. Who benefits from you staying in pain and self-pity?

Usually what folks are telling themselves is that fundraising is begging.  Overcome that argument this way.

What they think they’ll have to give up is freedom from an onerous chore.  Overcome that argument this way.

What they need help understanding is they’ll gain a boatload of satisfaction by helping others enact their values. You can help them become inspired this way.

In the end, it should become abundantly clear to everyone that when board members don’t engage enthusiastically in fundraising, no one benefits.  It’s a lose (for the organization)/lose (for the board member)/lose (for donors denied an opportunity to passionately invest)/lose (for those who rely on your mission continuing to thrive).

But it’s easy to turn philanthropy facilitation into a win/win/win/win once board members understand the very special role they play.

Want to feel more confident of your major gift fundraising skills?

I highly recommend the Certification Course for Major Gift Fundraisers. There’s also a companion course for fundraising managers and executives. Whether you’re new to this, or just want to upgrade your skills, you’ll find everything you need here and walk away with tons of practical strategies. It’s a well-constructed course using principles of adult learning, and you can work at your own pace (within reason). If you can’t make the live calls, they are recorded for you. Upon completion of the course you’ll become a certified Veritus Scholar. Check it out; it’s one of the best things you can do for yourself professionally — and what you learn will inform the rest of your career.

BTW: The next course begins August 26th, just in time to help you with year-end fundraising. If you enroll by July 26th you can save $200 automatically when you register! If you forget, and miss the “early bird,” no worries. You can use my exclusive discount code — just for Clairification students — and still save $100. Pretty sweet! Make sure to use this link and CA5 at checkout.

To your success!