The Mid-Year Gut Check: Are You on Track or In Denial?

Welcome back to NPQ’s fundraising advice column, Ask Rhea. Rhea Wong is a fundraising expert and professional coach, exuberant author of Get That Money, Honey!, host of the Nonprofit Lowdown podcast, and an unfailingly encouraging voice in a sometimes-bleak landscape. Rhea wants you to succeed, and she’s here to answer your questions.

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Dear Rhea,

It’s early June. Our fiscal year ends December 31st. My board chair just asked if we were on track to hit our annual goal. I said yes. But the truth is, I have no idea. We’ve raised about 40 percent. We have a CRM [customer relationship management software]. We have reports. We do moves management. And I still cannot tell you where the money is.

Summer is here, and I am starting to panic. How do I know if I am actually on track?

Signed,

Wondering in Wyoming

Dear Wondering in Wyoming,

Real talk: hope is not a plan. And “feels okay” is not a forecast.

Here is what I want you to hear first. You do not have a capacity problem. You have a clarity problem. You have the CRM. You have the reports. You have moves management. Yet, you still cannot see where the money is. More staff and more tools will not fix that. The issue is not how much you are doing, it is that you cannot see where the money is leaking out the back door.

June is the moment to find the leak. Not December. Not October. Right now. By August, you have run out of runway. By October, you are managing a crisis. This gut check, done honestly in the next two weeks, is the single most important move you will make this fiscal year.

Why June Matters More than December

Most fundraisers think December is the most important month. They are wrong.

December is when gifts close. The work that determines whether they close happens in June, July, and August. Major donors do not decide on December 28 to write a six-figure check. They decide in the summer, when they are reviewing their giving plans and talking to their wealth advisors. The organizations that show up in those summer conversations get the gifts in December. The ones that go quiet now stay quiet later.

The summer lull is not a real thing for donors. It is a real thing for fundraisers, who go on vacation, lose momentum, and stop reaching out. Donors are still living their lives. My advice is to be present while everyone else is vacationing.

Find Out Where the Leak Is*

The summer lull is not a real thing for donors. It is a real thing for fundraisers, who go on vacation, lose momentum, and stop reaching out.

Walk every stage of your major gift process, and at each stage ask one honest question. Where you cannot say yes confidently, there is your leak. For ease, I’ve outlined the stages and questions you may want to ask at each respective one:

1. Engagement: Are you delivering real value to the donor before asking for anything in return? Not a newsletter. Real value. If donors are not engaging, the leak is upstream of everything else, and nothing downstream will work.
2. Preliminary qualification: Are donors on your list qualifying, or are you cold-calling a random list and hoping for the best? A wealth screen tells you someone has money. It does not tell you whether they care about your work.
3. Complete qualification: Are you discovering donors’ deep values and the specific victory they want to achieve? Most fundraisers skip this. They jump from “this person is rich and interested” to “let’s get them on a site visit.” That skip is a major leak.
4. Caseload management: Do you have mutually agreed touchpoints, a shared plan for how the relationship moves forward? Not just a calendar in your head. A plan the donor has actually said yes to.
5. Proposal: Are you presenting a calibrated, aligned gift that is not a guess? If you are pulling numbers out of thin air, the proposal stage is leaking. A real proposal is co-created with the donor.
6. Stewardship: Are you proving to them that their gift achieved the impact that enhances their story of self? Donors do not give again because they got a thank you note. They give again because their first gift made them feel like the kind of giving person or entity they want to be.

The “no’s” and the “sometimes” are likely where your money is leaking.

The Numbers That Predict December

Once you know where the leak is, look at the metrics that predict whether you hit your number. Track these, update them weekly, and then review them with your board. Below are the considerations you should keep in mind after the questions above are addressed:

• Permission gained. How many prospects have explicitly said yes to being in your major gift process? Names on a list do not count.
• Qualified prospects in pipeline. How many have been confirmed for capacity, interest, relationship, timing, and permission?
• Active cultivation moves. How many cultivation activities are on the calendar in the next 90 days, with names attached?

Proposals out. How many written proposals are sitting in front of donors right now? Total dollar value? Realistic close rate?

• Commitments in. How much has actually been committed for the second half of the year? Not raised. Committed.
• Stewardship check-ins. How many existing major donors have heard from you in the last 60 days in a way that was not an ask?

If you cannot pull these six numbers from a single document in under two minutes, you have a systems problem that you must solve with structure. Effort will not save you and feelings do not pay salaries.

The Two-Hour Gut Check

Block two hours. Close your email. This is the most important meeting you will have this quarter, and it is with yourself. In this meeting, do the following:

• Write down your annual goal. The number you committed to your board. Not the softer one in your head.
• Write down what you have raised year to date. Banked. Not pledged. Not warm. Banked.
• Subtract. That is your gap. Look at it. Sit with it.
• List every prospect with a real shot in the second half of the year. For each one, write the dollar amount, the probability (high, medium, low), and which of the six stages they are in.
• Add up the high probability column. If it is bigger than the gap, you are on track. If it is smaller, you are not. There is no middle ground.
• Pick the top five from the medium column. Write the next specific actions and the date. Put them on the calendar before you stand up.
• Be ruthless with the low probability column. Some come off the list. Some go back to qualification. Some need a different relationship lead. Make the calls now.

And do all of this before July 1st.

Win the Summer

Donors are not lulling—fundraisers are. Here is what works:

• Host, do not chase. Backyard gatherings, casual lunches, walking meetings. Donors are more available than you think. They just do not want a formal site visit in July.
• Hit the right windows. The first two weeks in June and early September are the strongest cultivation moments of the season. Plan your two biggest summer touches there, not in mid-August when nobody is anywhere.
• Send fewer, better updates. A handwritten note, a phone call, a one-paragraph personal email. That is what gets remembered.
• Brief your board before they travel. They will be going to donor dinner parties and beach houses. Give them three sentences about the work, two questions to ask, and one specific person to mention you to.
• Clean your data. If your CRM is a mess in June, your fourth quarter will be a mess in October.

What Your Board Chair Should Be Asking

Your board should not be asking, “Are we on track to hit our numbers?” That is the wrong question.

New campaigns do not close gaps in the back half of a fiscal year. Disciplined cultivation of qualified prospects, moved through a clear pipeline, does.

The right question is: What is the dollar value of qualified, committed, and high probability revenue currently in our pipeline for the next six months, and where is our system leaking?

If you can answer that in 60 seconds, you have a system you can govern. If you cannot, you have a hopeful list, and your board won’t be able to do its job either.

A board that asks for clarity on pipeline metrics and leak points is doing its actual job. A board that nods and moves on to the program update will be surprised in December.

You Do Not Need More Activity—You Need More Honesty

James Clear has a line every fundraiser should tape to their monitor: “You do not rise to the level of your goals. You fall to the level of your systems.” If your system is messy, unclear, or unused, that is what you will fall into. Your goal will not save you in December. But your system will.

The temptation right now is to look at the gap, panic, and announce a new campaign. Resist this temptation. New campaigns do not close gaps in the back half of a fiscal year. Disciplined cultivation of qualified prospects, moved through a clear pipeline, does.

Ten qualified prospects, methodically advanced over the next 90 days, will outperform a hundred new names every single time.

So pull out the spreadsheet. Run the numbers. Find the leaks. The math always tells the truth in the end. The only question is whether you find out in June—when you can still do something about it—or in December when you cannot.

The time to find out is now.

You can find more insights and resources from Rhea at rheawong.com.

*The six-stage diagnostic is drawn from the Engagement Fundraising Operating System, used with permission by MarketSmart.