New Year Fundraising Questions Every Nonprofit Leader Will Want to Consider
A good question is said to be worth more than a good answer, and I believe that wholeheartedly. The best fundraising plans I have seen over three decades of practice did not begin with strategies or tactics. They began with honest questions — the kind that open a dialogue rather than close one down, that surface assumptions rather than reinforce them, and that invite the people closest to the work to share what they actually know.
John Tukey — the Princeton statistician who coined the word "software" and whose box plot remains a standard tool of data analysis — put it this way: "An approximate answer to the right question is worth a great deal more than a precise answer to the wrong question." For fundraisers, that observation cuts to the heart of why so many development programs plan carefully and still underperform — not because the planning is unsound, but because the questions behind it are the wrong ones.
What follows is a framework for the internal discovery process that every development team deserves — a structured set of questions to explore with staff and trustees before the planning work begins. It is designed for the start of a new year, but it is equally useful at the beginning of any new planning cycle, after a significant organizational transition, or whenever a development program feels like it is working harder than it should for the results it is producing.
Why Questions Come Before Plans — and What the Best Fundraisers Understand About That
Advanced fundraisers probe before they plan. They investigate their strategies and practices not because something has gone wrong but because continuous inquiry is what keeps a fundraising program responsive rather than merely habitual. The questions below are not evaluations — they are invitations, directed at the staff and trustees with whom you work, and their purpose is internal discovery rather than judgment.
Questions that open rather than close a dialogue are what help development professionals connect more genuinely with the aspirations of donors and funders, improve cultivation strategies, and focus solicitations on what donors actually care about rather than what the organization assumes they care about. As knowledge and detail accumulate through this inquiry, strategies become more precise and relationships become more genuine — and the organization's fundraising capacity grows not just in technique but in wisdom.
A note on process: if you are new to this inquiry approach, consider sharing your proposed list of questions with someone you trust — or someone skilled at facilitated conversation — before using it with your team. The questions work best when they feel like dialogue rather than audit, and the calendar context for when to run them matters as much as the questions themselves.
Where This Process Fits in the Fundraising Year — and When to Run It
The inquiry process described here sits at a specific moment in the fundraising calendar — the transition between what just happened and what comes next. For most organizations, that moment arrives after the year-end giving season has closed. Year-end is the most revenue-intensive period on the fundraising calendar, and the habits, assumptions, and relationship dynamics it surfaces are the raw material for the planning that follows.
If you have not already done a thorough review of your year-end results, start there before running this inquiry. The companion post on this blog, The Last Four Days: When Online Giving Quintuples, describes how to maximize the final days of the year-end giving season, and The Annual Fundraising Review: Questions That Drive Greater Revenue Every Year describes the post-season review that should precede this internal discovery process. For those planning the full arc of the year — including the summer months that many organizations underutilize — Does Fundraising Slow Down in the Summer — And What Should You Do About It? and How to Set the Right Fundraising Goal offer complementary frameworks for the months that follow.
The inquiry described here sits between the review of the past and the strategy for the future — the bridge between what you have learned and what you will decide. With that context in place, here are the questions worth bringing to your team.
The Questions That Surface What Your Fundraising Program Actually Needs
The questions below are intended to be explored with the staff and trustees involved in the fundraising program — not answered by the development director alone, and not treated as a checklist. The most productive version of this process involves sitting with each question long enough for honest responses to emerge, documenting what is learned, and looking for the patterns that surface across different conversations. I encourage you to adapt this list to your organization's specific situation, adding questions that open doors for your team and removing any that don't fit where you are right now.
Why do we need to raise funds — and how urgent is the need? This sounds like a question with an obvious answer, but it rarely is. The urgency behind fundraising — whether the organization is maintaining a program, expanding one, or navigating a financial strain — shapes every subsequent strategy. A development director who is clear on urgency communicates differently to donors than one who is operating on autopilot.
What would happen if we don't raise the required funds? Naming the consequence of falling short is one of the most clarifying acts in fundraising planning, and most organizations avoid it. The answer to this question is often the most compelling thing the organization could say to a donor — and it is often the thing that never gets said.
What about our past fundraising has worked well? Before changing anything, name what is working. The strategies, relationships, and communications that have produced results deserve to be understood before they are modified or replaced. Many organizations abandon approaches that were beginning to compound simply because they felt familiar.
Do we know as much about our donors and funders as we could — and how can we learn more? Donor knowledge is not the same as donor data. An organization can have a fully populated CRM and still know very little about why its most loyal donors give, what they hope to accomplish through their giving, and what concerns them about the future. This question invites both a data audit and a relationship audit.
What is the right amount to spend on the fundraising program to achieve our revenue goal, and is it reasonable based on industry standards? Underinvestment in development infrastructure is one of the sector's most persistent and most costly habits. This question surfaces it directly and places it in the context of what comparable organizations invest, rather than what feels comfortable to the board.
Can our fundraising approach be done differently to increase the return? This is the innovation question — the one that invites the team to think beyond the familiar. It does not require a dramatic answer. Often the most productive responses are modest: a different sequence in the cultivation process, a different format for the annual appeal, a different ask strategy for a specific donor segment.
Based on your experience and donor research, what is your plan to raise the required funds — and what are the intended and unintended consequences of that plan? The consequences question is the one most planning processes skip. Every fundraising strategy has side effects — on donor relationships, on staff capacity, on organizational reputation. Naming the unintended consequences before the plan is implemented is far less costly than discovering them after. Beyond these seven, three additional questions have proven so consistently useful across different organizations and different planning moments that they deserve their own space.
Three Questions Every Development Team Finds Indispensable
Beyond the foundational seven, three questions have proven indispensable in any honest fundraising planning conversation, regardless of the organization's specific situation or the moment in the calendar.
Are we investing enough in retaining the donors we already have, or are we primarily focused on acquiring new ones? Donor retention has become one of the most consequential metrics in fundraising, with retained donors typically giving at rates three to four times higher than first-time donors. Organizations that focus primarily on acquisition while underinvesting in stewardship are running a program that leaks as fast as it fills. This question forces an honest look at where the development budget and the development team's attention actually go.
How dependent is our revenue on any single source — and what would happen if that source changed? Revenue concentration is a risk that many organizations do not examine until a major funder reduces a grant, a government contract ends, or a founding major donor passes away. The question is not whether diversity is desirable — it is — but whether the organization has an honest picture of its current exposure and a realistic plan for what to do about it.
Are we using new tools and technologies to deepen donor relationships, or simply to produce more volume? Every generation of new fundraising tools — from direct mail software to email platforms to AI — creates the same essential question: are we using this to communicate more authentically with donors, or simply to communicate more? The teams that ask this question before they deploy a new tool tend to use it more wisely than those that discover the answer after the fact.
How to Turn Internal Discovery Into a Fundraising Action Plan
Asking the right questions is the first step. What happens after the inquiry determines whether it was worth the investment of time.
When you have conducted your internal conversations — with program staff, with the executive director, with board members, with the development team — document what you learned. Compile the findings into a succinct report that names the key insights, the recurring themes, and the tensions that surfaced across different conversations. Include your own recommendations. Share that report with the decision makers in your organization before the planning process begins in earnest.
The report is not the plan — it is the foundation the plan should rest on. A development plan built on genuine internal discovery is one that the people who contributed to it are more likely to support, because they can see their own knowledge reflected in it. And a plan that has been honestly tested against the right questions before it is finalized is far less likely to be derailed by the answers it never sought.
The organizational alignment that makes ambitious fundraising possible is not built through strategy documents or board retreats alone. It is built through the sustained, honest, generous act of asking the people around you what they know — and then listening carefully enough to let their answers change what you decide.
What questions have proven most valuable in your own planning process — and what has the inquiry surfaced that surprised you? Share your experience in the comments section of the website.
This post is offered freely for educational purposes. Please share it with executive directors, board members, and development staff who may find it useful — provided the author's byline remains intact: By Laurence A. Pagnoni, MPA. Reproduction in publications, training programs, or institutional materials requires attribution.
