Preparing for the Ask

The ask didn’t happen.

It should have. It was supposed to happen. But it didn’t.

You’ve been there, right?

Now, the meeting happened. I set it up so a prospect I’d been cultivating could meet the Dean of our school. And we’d ask him for a gift.

Except, the ask didn’t happen.

Great lunch, great conversation. And at the end…no ask.

Oh sure, we danced around it. Our prospect was probably even expecting it. But no, we didn’t ask.

“Great cultivation!” we told ourselves afterward. But, of course, we knew. It was a missed opportunity.

We hadn’t been in sync. We had no idea when or how to transition. We didn’t ask.

Embarrassing.

And avoidable!

How?

With a little planning. Even a few minutes of pre-ask preparation would have gotten us focused and on the same page.

That should have been my job in this situation, right? I was pretty inexperienced then, but still, I shouldn’t have expected my Dean to know exactly what to do in that meeting. Executives are busy. And they rely on their fundraising professionals to position them for success.

Again, embarrassing.

Today’s post is all about planning and preparing for the ask.

The previous entry in this series covered the psychology of solicitation. We went deep inside our prospects’ heads to consider what truly motivates philanthropy. And we considered how our own “inner game” can impact an ask.

This installment will focus on everything you need to do to get ready for a.

And I don’t mean cultivation!

I mean the actual meeting where you sit down face-to-face with a prospect and ask for a gift.

In fact, this article assumes great cultivation. For more about what that looks like, check out my series on cultivation.

I’ve said it before: 80% of the work in any donor meeting happens before you even get in the room—when you get your game plan together, rally the troops, prepare your materials, and practice.

The same is true for solicitations.

Who, What and Why

Let’s start with the most important pieces.

Who

Who will participate in the meeting? Who will actually make the ask when the time comes? These are among the most critical questions.

First, who from the organization?

Solicitation meetings can involve many configurations of people—executives, fundraisers, program staff. As you prepare for the ask, make sure everyone knows his or her role. Who will make introductions, if any need to be made? Who will transition the group from small talk to the business at hand? If program staff are attending, what will they highlight and how? And finally, who will (clearly and directly) ask for the gift when the time comes?

Now, what about who from the prospect’s side? Will anyone else attend? During cultivation, did you discover who will be involved in your prospect’s decision-making process? Spouse, lawyer, CPA, financial advisor, etc. Some of those people might be in the room.

Any time your prospect includes an advisor in a meeting he is signaling something:

• CPA in the meeting: Your prospect wants to understand the tax implications of the gift.
• Lawyer in the meeting: Your prospect wants to make sure he’s protected.
• Financial advisor in the meeting: Your prospect wants to understand the gift’s impact on his wealth over the long term. Or he’s already thinking about how to facilitate the transaction.

Be ready with documents or other information that will help your prospect’s advisors do their jobs. And be friendly with them! You want these folks on your side.

What

What is the content of the meeting?

Make sure everyone involved from the organization is on the same page.

How much ground has already been covered? Has the prospect already reviewed a proposal from you? Or, is this a meeting to present a proposal? What, now, needs to be discussed?

And, most importantly, what is the specific amount being asked for, and for what purpose?

Also important—leave room for the prospect to talk. Don’t script your delegation so tightly that there’s no room for your donor to get a word in.

And, as a fundraiser, make sure that all involved are comfortable with the “ask and then shut up” when the time comes. Fundraisers are comfortable with this tactic (thanks to years of practice), but it will likely be new and awkward for others joining the ask.

Finally, it’s important to review in advance what you’re not going to talk about. If issues have been resolved along the way, don’t bring them up again. If there are other potential distractions that are best left unmentioned, you’ll want to steer clear on those as well. Don’t borrow trouble.

Why

Why are you asking for the gift?

It’s obvious, but again, make sure everyone involved in the solicitation is on the same page in advance. It never hurts to re-establish your baselines.

And, perhaps more importantly, think about this from your prospect’s perspective. Undoubtedly she will ask herself, Why me? Why now? It comes back to relevance, as we discussed in the last post.

Try thinking of relevance in terms of story—your donor’s life story. The story that she tells herself. That she tells other people. How will this gift fit in?

Big, meaningful gifts become part of the donor’s life story. Here’s an example:

Cancer took my mom way too early. Our household was a little dysfunctional after she died and I made some bad choices in my teens. Good mentors helped me get back on track and I eventually found my way to college. I started the company shortly after graduation and the rest is history. But it was a struggle for a while and I hope that no other kids out there have to have a parent or loved one taken from them by cancer. That’s why I’m so committed to supporting cancer research.

As you’re preparing for the ask, particularly if it’s a gift amount that will require the donor to sacrifice, consider again how the gift would become part of her story. It’s a valuable exercise because very often it will evoke language or images that you can use in your ask.

When and Where

We covered the more strategic stuff; let’s pivot to tactics.

When

It goes without saying that you need to get a date on the calendar in order for the ask to happen. And this may take some coordination depending on how many people need to be involved.

Use your best judgement. If you’re aware of major life events or big trips on your prospect’s horizon, propose dates and times accordingly.

Be careful though. You can go too far in assuming it isn’t a good time to meet. Generally speaking, you don’t want to say “no” for your prospects. When in doubt, ask for the meeting. Just be prepared to work around your prospect’s schedule—business transactions, legal proceedings, family events, etc.

Also, before reaching out to a major prospect—whether for the first meeting or the tenth—do a quick Google search on her just to check the headlines. This might not be necessary for most retirees, but it is a good practice for public figures and executives. A few years ago, a colleague of mine Googled her prospect (on a whim) right before picking up the phone to request a meeting. As it turned out, he had just been fired! She gave him a little space before circling back.

Where

Where will you meet and make the ask? Do you need to meet again? Can it happen over the phone?

Some of the fundraising guru’s out there who will tell you that you should never ask for a gift at a restaurant. I think it depends on your prospect. And it certainly depends on how large a gift you’re asking for.

Leadership annual fund gifts to join your giving society? Sure. Ask at a restaurant.

Gift of a lifetime to name a new building—probably better to meet at the prospect’s office.

Anytime you want your prospect to review a proposal or some other presentation, it’s probably best to pick a quiet space that’s free from distractions.

Most importantly, you want your prospect to be comfortable. And thanks to your good cultivation, you know a lot about her personality and how much discretion she prefers. Tailor your choice of location and approach to suit the prospect and the nature of the ask.

Other Questions

Stewardship

Do you know how your prospect likes to be recognized? This is particularly important when it comes to naming opportunities.

Some donors love having their names on things. Others wouldn’t dream of it. Maybe you touched on this in your cultivation. If so, good.

One of the easiest ways to learn what your prospect thinks about naming is to talk about what other people have named, particularly his close associates. Start this conversation and, more likely than not, your prospect will volunteer his own feelings on the subject.

Why do you need to know this? Well, if it matters to your donor, you’ll want to highlight a naming opportunity in your ask. If it doesn’t, you’ll know to emphasize other things.

The same principle applies to other aspects of stewardship, including publicity, acknowledgement, celebratory events, treatment of gifts made in honor or in memory of someone, thank you gifts, and special access. As you’re planning for a solicitation, consider if and how early discussion of stewardship could strengthen your ask.

Learning your prospect’s motivators is important work and will largely happen during the cultivation stage. But don’t stop at, Why would this person give? Also consider, How would this person want to feel after making the gift? Your prospect might already have a vision for what it would be like and how good it would feel. A better understanding of those daydreams will help your ask. Who does the donor envision would thank them? In what way will her name be “in lights?” Will there be a big party?

Timing

You’ve heard the phrase “timing is everything.” Well, it’s certainly true in fundraising. Don’t be afraid to ask about timing, particularly during your cultivation, or leading up to an ask: “When would be a good time to talk to you about participation in our campaign?”

There are any number of factors in your prospect’s world that will drive her decision to make a gift now versus later, particularly if you’re asking big.

And, similarly, as you prepare for your solicitation, plan to continue clarifying timing—timing of the decision, the timeframe for completing the pledge, etc.

Assets

Another “what” question you’ll want to consider is: What assets might your prospect use to make the gift?

So be sure you’re not focused exclusively on cash. If you are, you’ll miss out on some major opportunities since only a fraction of wealth in America (around 10%) is held in cash.

During your research and cultivation, you’ll likely learn more about your prospect’s assets. Be prepared to help your prospect think creatively about using stock, real estate, life insurance, or other assets to make a meaningful gift.

Marketing Materials/Collateral

Fancy brochures or slick proposals are never going to get you a major gifts. Why? Because marketing pieces can’t build relationships. Earning a donor’s trust, demonstrating a project’s relevance to him, and helping him feel confident in its impact—these happen over time and with lots of face-to-face contact.

So, use your nice campaign materials to supplement your ask or presentation. But don’t rely on them to do the heavy lifting. They’re most effective as background information.

Mid- to high-production value marketing collateral signals to prospects your organization is serious about an initiative. It can add a sense of concreteness to a campaign. But, again, brochure typically aren’t enough to help a prospect see a specific role for him or herself.

Objections, Deferrals, and Declines

Not every ask you make will be greeted with an enthusiastic, “yes!”

(If they are, you’re not asking enough people—or you’re not asking for large enough gifts.)

Anyone who’s been in fundraising any length of time knows that sometimes your prospect will have follow up questions, doubts, or reasons she can’t (or won’t) make the gift.

As part of your planning process, you’ll want to do your best to anticipate any objections your prospect might offer. Here are some common ones:

“It’s just not a good time for me to make a commitment like that.” Or, “I can’t get involved at this time.”

This is a tricky one because timing is often used as a polite way to say “no.” Does your prospect truly want to give but can’t now because of some obstacle? Or, is she actually declining your proposal and just softening the blow?

Be prepared to extend the conversation and understand issues related to timing. And, of course, be ready to offer as much flexibility as you’re able. Your prospect might think you need all the money ASAP, whereas you’re merely looking for a commitment. A multi-year pledge or an open-ended pledge might be just the flexibility your prospect is looking for.

“That’s a larger gift than I’m prepared to make.”

Again, be ready to go deeper. Would flexibility around timing help here too?

If the amount is truly the barrier, be prepared to reminder your prospect that the organization would value her involvement and ask what size of gift she would be comfortable making.

In my experience, most asks don’t result in a firm “yes” or “no” from the prospect. Be ready to hear one of the following: “Let me think about it for a bit,” or, “I’ll need to talk it over with my spouse.”

Both are versions of “I’m not sure yet,” which is a normal response to a major gift ask. In either case, be prepared to clarify timeline with your prospect for your follow-up and her eventual decision. The next post in this series will offer some specific suggestions for what to say in response.

And, of course, sometimes you get a “no”—your proposal is declined. Maybe it will sound like this:

“I value the work your organization does and I appreciate you updating me on this project, but I’m not going to be able to get involved.” Or “….but I’m not interested.”

Again, be ready to seek clarity. You want to learn whether this is truly a decline, or merely an objection. So ask if there’s a particular part of the proposal that is preventing the prospect from moving forward.

If your proposal is in fact declined, stay professional. And remember, in fundraising, the first “no” isn’t always the final answer. Don’t give up the long game just because you experience a set-back in the short term. Keep the door open.

Practice

And finally, practice. I know it sounds a little strange, but trust me, things that sound great in your head will sound different when you say them out loud.

So, get comfortable saying them out loud before your meeting. Roleplay with a colleague or practice in front of a mirror.

But. Don’t memorize.

You want to be familiar enough with your “product” and your “pitch” to be conversational. But you don’t want to sound like you’re reciting your lines. Prospects see through this. And they’ll feel like you’re trying to sell them something.

Practice is also useful when there’s a group of people involved in the ask. You’ll want to make sure you at least talk through your choreography. Who will serve what role? How do you anticipate the conversation will unfold?

Sometimes senior executives will bristle at the idea of a “rehearsal” or “role playing.” They’re often confident in their people skills and ability to wing it when the time comes. If this is actually true of the executives you work with, great!

Sometimes, however, confidence in this area is not supported by reality. So, what do you do when you know practice will help but your ED won’t go for it?

Schedule something innocuous like a “briefing” or a “walk through.” Generally speaking, executives like being “briefed.”

And in your briefing, rehearse without calling it “a rehearsal.” Just lead by example. You might say something like, “And after we sit down and chit chat for a bit, I’ll transition us by saying ‘Well, Jim, we’re glad to have had this opportunity to update you on our big project. You’ve been such a wonderful supporter of ours over the years, and I hope you’ll choose to get involved in this effort. Can we share an idea with you?’”  You’ll be pleasantly surprised how others follow suit if you model a role play!

In Closing

Whew—long post! You made it to the end.

Just remember, most of the work for any solicitation happens before you even get into the room. There’s no substitute for being prepared. And good preparation will give you confidence.

Now, will the actual meeting follow your script? Probably not. But know that the planning process is indispensable. It will give you a blueprint and will keep everyone on the same page. And you’ll be prepared for (nearly) anything that comes your way.

Is there anything else that you’ve found to be important as you prepare for an ask? If so, leave me a note in the comments section.

The next post (or perhaps two) will focus on how to ask, and more specifically, exactly what to say when asking, addressing objections, seeking clarity, etc. See you in a month or so!

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