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This post highlights the wisdom of campaign expert and Capital Campaign Toolkit advisor, Richard Quinn, shared in a lively conversation with Toolkit co-founders, Amy Eisenstein and Andrea Kihlstedt.

This is the second of a six-part series of posts drawn from discussions with six of the Toolkit’s experts. A full audio discussion of the topic has been recorded for the podcast, All About Capital Campaigns, which you can listen to on your favorite podcast platform.


If you’re heading into a capital campaign, there’s a good chance that you’ll experience some of the most common campaign conundrums. And you’ll be well-served to think about them in advance so when they happen, you’ll know what to do.

3 Common Capital Campaign Challenges and How to Overcome Them

Take a look at these three common campaign challenges.

Problem #1: The Donor Has Decided on Your Gift Before You Solicit Her

Few things are more disheartening than meeting with a donor you think will make a lead gift to your campaign only to have the donor, at the start of your meeting, tell you that she had already decided and hand you a check that is a fraction of what you had planned go ask for.

For example, you might have planned to ask the donor for $500,000 only to be handed a check for $50,000 before you even begin the solicitation.

Here are some things you can do:

Lead with gratitude.

No matter what the size of the gift, let the donor know you are grateful! Do your level best not to look shocked or dismayed.

Then, rather than simply accepting the check and leaving, use the scheduled time to educate the donor about the campaign and where you are in the solicitation process. Your donor may simply not have known enough about the campaign and the gift levels required to make the campaign successful.

So, use the opportunity to educate your donor about where you are in the campaign. You might say something like:

This is the time we are speaking with the people who are closest to us about the possibility of making gifts that will set the pace for the campaign.

Show the donor the and indicate the gifts that have already been committed. Just doing that may lead your donor to reconsider her gift.

Lead with the authority of process.

Your donor might not even have considered their role in the campaign. They may not know that they can make multi-year pledges. They may not have thought yet about giving from other assets beyond their cash flow.

And finally, talk to your donor about being one of your organization’s leaders. Inspire them with the possibility that with a generous gift, they can lead the way toward a successful campaign.

Problem #2: A Campaign Committee Member Recommends a Problematic Volunteer

As you build your campaign committees, you will ask people for suggestions about who to recruit. And sometimes one of your campaign committee members or a board member may suggest that you invite one of their friends to serve.

It’s hard to know what to do when the person they recommend is someone like Jessica. You’ve worked with Jessica before and have found that she talks a good game, but she doesn’t follow through (and she isn’t a generous donor).

You don’t want to offend the board member who made the recommendation. But you aren’t keen on inviting Jessica to serve on the campaign committee.

Once again, lead with gratitude.

Show an interest in your board member’s suggestion and be open to the possibility that you are wrong about Jessica.

Ask your board member why she thinks Jessica would be a good prospect. Share your concerns about Jessica with the board member. If she stands behind the recommendation, you should pursue the possibility — though cautiously.

Drop your preconceptions.

Assume the best of Jessica and then check her out carefully. Meet with her and share the committee job description with her. Be prepared to discuss specific roles and discuss whether she’d be a good fit.

Gather several names of people to recruit and invite two or three current committee members to interview them all and make the selection. If Jessica isn’t selected for the committee role, suggest another way for her to help.

Problem #3: Campaign Chair Who Isn’t Good at Asking

You might wonder how someone who isn’t good at asking becomes a campaign chair. It actually happens more often than you might think.

Imagine that you’ve taken a job as Development Director at an organization where a campaign is in progress. The campaign chair has been around a long time and you assume that he knows how to ask. But it doesn’t take long for you to see that the chair is happy to schmooze with donors at cocktail parties but uncomfortable asking for gifts directly.

Even when you go on solicitation calls with him, he simply doesn’t get around to asking for the gift. And that, of course, puts you in a difficult situation.

For the campaign to succeed, the largest gifts must be solicited effectively. But you don’t feel you can jump in and ask for the gift, even when the campaign chair doesn’t do it.

Here are two things you can do…

First, accept the fact that your campaign chair isn’t likely to turn into a good solicitor. So don’t assume that the next solicitation he does will be better. Instead, try one of these alternate approaches.

1. Assign other tasks to your chair for which he’s better suited.
Find out what your campaign chair is good at and give him tasks that fit his abilities and comfort level. If he loves talking to people at cocktail parties, give him some cocktail party assignments.

You might suggest the names of three people who will be at the party for him to talk to. Ask him to learn as much as he can about those people and to tell them about the new project.

Get him to ask their permission for you to call to schedule a later meeting to discuss the campaign. But tell your chair, in no uncertain terms, that he is not to ask for gifts casually during the party.

2. Select a campaign co-chair.
Talk to the chair about identifying a campaign co-chair whose skills would complement his own and who would take some of the pressure off him. Presented as an opportunity for your chair to relieve some of the burdens on him and to expand the reach of the campaign, he might relish the change.

Then, with the approval of the chair, select someone who has been road tested and excels at the things that the existing chair would rather not do. In recruiting any campaign chair, don’t select someone you haven’t seen in action. And don’t leave it to chance. Hand-select people who will be excellent and then recruit them in a way that they will be likely to sign on.

A Healthy Dose of Generosity and Appreciation Helps Solve Many Problems

The challenges discussed above are just some of the problems you may encounter in your capital campaign.

As with these three examples, most campaign challenges require a big dose of goodwill and generosity combined with a bit of creative problem solving and open communications. If you assume the best of people and involve them in finding the best way forward, you will be more likely to succeed.

To listen the podcast episode that inspired this post, listen to the full discussion here. And check out the All About Capital Campaigns Podcast on your favorite podcast platform.

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