Gratitude Isn’t a Gesture—It’s a Strategy!

Why Donor Experience and Frontline Fundraising Must Work Together

The data is sobering: donor retention for first-time gifts has dropped below 20%. That means four out of five new donors walk away after their first gift. In an industry built on relationships, that’s not just a statistic, it’s a wake-up call.

We know that donors should be engaged at least seven times between gifts. Not out of obligation, but because authentic gratitude and transparency builds trust, deepens connection, and lays the foundation for future generosity. And yet, many advancement shops still operate in silos: donor relations on one side, frontline fundraising on the other. The result? Missed opportunities, fragmented messaging, and donor experiences that feel transactional rather than transformational.

Our sector is at a crossroads. If we want to reverse attrition and build lasting partnerships, we must rethink how we work together internally. Because the truth is: strong internal partnerships lead to stronger external relationships.

The Crosswalk We Can’t Ignore

Donor Relations and Gift Officers are not separate lanes—they’re part of the same journey. When we align our efforts, we create a seamless donor experience that reflects both gratitude and impact. We move from “thank you” to “let us show you what your gift made possible.” We shift from stewardship tasks to storytelling of significance.

Demonstrating impact is one of the most powerful tools we have. It’s how we show donors that their generosity matters—not just in numbers, but in lives changed, communities strengthened, and missions advanced.

A Call to Action: Join Us in New York

DRG and KDD Philanthropy have long been committed to elevating the conversation around intentional, authentic donor experiences. This October, we’re bringing our combined approach to New York for a unique discussion that explores the vital crosswalk between Donor Relations and Frontline Fundraising.

This isn’t just another workshop, it’s a strategic gathering for Gift Officers and Advancement professionals who want to build bridges, not just pipelines.

We’ll explore:

  • How to design donor journeys that retain and inspire
  • The role of gratitude in creating meaningful donor experiences
  • Practical strategies for collaboration across departments
  • Real-world examples of impact-driven stewardship

Gift Officers: This is your invitation. Let’s reimagine how we work together—so our donors stay, grow, and feel truly seen.

The opportunity is now. The conversation starts in New York. Will you be part of it?

Use code NYCKDD for 10% off your registration. Register today!

From Inbox to Chatbox: Rethinking Donor Engagement

AI is everywhere right now: You can’t go online, interact with a major company or, in some cases, even order food at a restaurant without engaging with AI. This may be new, but it’s also only the latest evolution of how we interact with technology… and with each other.

Donor interactions aren’t immune from this evolution. I recently had a conversation with an admissions officer in which she really brought this home for me. In the world of higher education, the admissions office is often the first opportunity for a two-way dialogue between the institution and an important group of prospective donors.  

The admissions officer shared that potential students/families do not respond to emails. Although this represents a significant departure from communication norms of just a few years ago, it is a noteworthy shift. These families now prioritize live chat as their primary mode of communication, followed by text messaging. Email, by contrast, ranks a distant third in their preferences.

It’s hard to deny that this example is representative of a much larger societal shift in how we communicate. It’s also hard to deny that we, as advancement professionals, must then shift how we communicate in our work too.

Most of my recent interactions with my primary physician have occurred through an app. I shop online and no longer visit big box stores. My hotel of choice reaches out through text.  The examples are endless.

I know that for many of us in advancement, we were drawn to this field because we love the privilege of talking with our donors, getting to know them and forming connections. But we must recognize that the very concept of “connection” is changing. If we continue to work with donors from our comfort areas, rather than understanding and adapting to our donors’ preferences, we will continue to see shrinking donor numbers.

When was the last time you asked a donor their preferred method of contact … and then ensured that information was collected appropriately into the database, and ensured you followed their preference?

What steps are you taking to add digital engagement beyond email into your donor or prospect outreach for all steps of the donor cycle?

What are you changing to recognize the shifts happening all around us, and using those changes to continue to evolve and excel in your role?

Human relationships have incredible value, and I do not believe technology will ever meaningfully replace those relationships. It will, however, always be essential to how we build and maintain those connections, and as advancement professionals, we’d better not be left behind.

What shifts could you make to meet the moment in how humans use technology to connect?

Stop Making Decisions for Your Donors

How well do you know each of your donors? Truly, authentically know them?

The greatest role of a gift officer is to understand people. To gain deep insight into values, preferences, philanthropic intent and more, and to allow that insight to guide our path toward generosity.

This level of understanding can only be achieved through intentional conversation. And without it, we make assumptions about our prospects rather that diving deeply into the prospect’s greatest interest, their goals and their desired impact.

Time and again, I see gift officers following practices that undercut this process.

We “pitch” – leading with wanting to share about our institution and initiative – rather than asking and listening.

We research rather than outreach, relying too heavily on what can be found versus what can be discovered in conversation.

We assume rather than explore.

Each of these instincts – common ones – holds us back. And it takes courage to overcome them.

Yes, sharing our case and conducting prospect research has its place. These are tools we should wield wisely. But the most impactful tools we have include being willing to make the outreach and the use of thoughtful, conversation-provoking questions.

What inspires you to give?

How did you become passionate about this issue?

What would you like your impact to be?

What was it like to start your own business? 

Does this vision align with what you’d like to see?

Consider limiting your research before contacting a prospect to 15 minutes max (with a goal to get to no more than five minutes). Any more than that is likely a delay, because we find cold outreach intimidating. Or, you think you must know everything there is to know about who you are outreaching to. If this is truly an authentic relationship in the making, you will learn, with them, what they care most about.

But most importantly, consider how you might approach outreach and donor meetings with courage. What would that change for you? Would you make more introductory calls and send more introductory emails? Would you engage in a more authentic conversation with prospects rather than sticking to talking points? Would you learn to love qualification work as much as other stages in the partnership and embrace what it takes to get to this important conversation?

How would it change your work if you stopped making decisions for prospects, and instead embraced the messy, but rewarding and effective, work of engaging?

Two Touches

Advancement professionals think about our donors and prospects regularly – whether we’re wondering if a prospect will fund a gift proposal, a donor will take our meeting request or a faculty partner will tell us if she identifies a new potential prospect. But as much as these prospects and partners may be top of mind, our actions can send a very different message. We get busy, or focused on just a few relationships, and can let months go by without communicating with those we want to draw closest.

This pattern is why I’m a champion of a Two Touches exercise: starting every workday with two outreaches, or touches, to donors or organizational partners. This habit is an easy way to ensure we start every day the right way: focused on relationships! When we begin each day this way, we’re reinforcing discipline and a focus on our most important work: building, enhancing or growing our relationships and the strategies that support them.

These daily touches are simple:

  • A hand-written note card of congratulations on a recent achievement (personal or professional)
  • An email sharing some news that might be of interest (our organizations are diverse, our outreach should be as well!)
  • A note in a birthday card that is truly personal
  • A news release that provides follow-up while rekindling the fire for your institution/organization
  • A text message with a photo of something happening at your organization (e.g. a commencement ceremony, a new wing opening or a new program opening)
  • A message celebrating a program milestone

Every strategy we build relies on a relationship, and every relationship requires interactions both big and small. Focusing on the moves is important, but our strategies need both moves (active fundraising) and interactions (passive fundraising) to truly be successful. The Two Touches technique, when implemented habitually, creates ten small interactions per week – or over 400 per year.

How would these touches strengthen your strategies?

Begin by keeping a stack of organizational note cards on your desk as an easy reminder to keep this important activity front and center. You’ll be glad to see the results of making sure your donors, prospects and partners actually know when you’re thinking of them!

Who are you going to outreach to today?

Handoff Versus Transition

“Handoff” is transactional — It indicates a lack of collaboration, and rarely reflects a thoughtful pathway for someone who is supporting our institutions. So how do we move away from this transactional reference, and embrace our very best work?

Continue reading

Tackling Your Top Fear: Conflict

At the recent CASE Strategic Talent Management Conference I attended, a fascinating report* was presented that outlined factors that make major gift officers successful, and surveyed fundraisers on how confident they felt in their ability to display those factors.

At the very top of the list — tied with using the phone to secure donor visits — was handling difficult conversations with donors.

The relationships between our institutions and donors are, in our best-case scenarios, long term and deeply personal to the donor. And those factors are a recipe for the occasional conflict.

However, learning to manage those conversations is both deeply effective and satisfying for the fundraisers who must do so. Here are my top strategies for navigating these tricky conversations with supporters:

Remember that you’re an ambassador, not the subject of the critique.

  • We know that we’re not the institution, and a donor’s concern isn’t a judgment of us as individuals … but how we process emotionally can be an entirely different story!
  • One frame that can help us manage this emotion is to think of ourselves as a facilitator: We are not the party who is critical, and we are not the party being criticized. We are here to facilitate a message between those two parties.

Understand when transparency is a gift.

  • Don’t delay when there’s information to share. Perhaps your scholarship naming minimums are being raised, or a program beloved by a donor is going away. Whatever the scenario, it is a kindness to share information proactively and clearly.
  • Have the facts on both what is happening and why it’s happening before you talk with the donor. Otherwise, the conversation will feel incomplete.

Represent the institution professionally but with authenticity.

  • We should never undermine the institution in donor conversations, so we must know how and when to acknowledge our own feelings.
  • Not every issue needs you to share your own thoughts, but issues that are very substantive or when the donor is personally impacted can be an appropriate occasion.
  • Consider language such as:
    • I recognize this is a complicated decision; and while I don’t know that I would make the same one, I understand why it was made.
    • I think very thoughtful people can disagree about this issue.
    • If I can take off my ambassador “hat” for a moment, I will share that I see this issue a bit differently than the institution does. But I also recognize that leadership is weighing some very complicated factors and is making the decision they think will create the best outcome for everyone.

Recognize when your donor may be unhappy.

  • Some donors will tell you when they’re upset about something … but many will not be so direct.
  • When something feels “off,” ask probing questions. For example:
    • Am I hearing some hesitation in how you feel about leadership?
    • It sounds like you may have some thoughts about the event. Would you be open to sharing more?
    • I’m sensing that something may be off in how you’re feeling about your relationship with the institution. Am I correct?

Don’t try to resolve right away: Seek to understand first.

  • Conflict often has layers to it. Perhaps a donor who is upset about a program going away is just upset about the program … or maybe what concerns them most is that they weren’t consulted first.
  • Ask questions to ensure you have a full picture. For example:
    • I understand. Can you tell me more about how you would have liked to see us approach this issue?
    • What would you change if it were up to you?
    • Is there a way we could have managed this differently that would allow you to feel better about the change/decision/program/etc.?

Determine whether the donor is seeking resolution or just needs to be heard.

  • Being heard is a basic human need and can resolve many conflicts.
  • An apology or acknowledgement can go a long way. Offer it freely.
  • Often the donor will respond by letting you know whether the situation is resolved or if they need further resolution. If that’s unclear, ask:
    • I’m really glad you shared your thoughts with me …
      • Can you tell me more about how you’re feeling now?
      • I’d like to offer to arrange for you and the dean to discuss this directly. Is that something you’d be interested in?
      • I think the best outcome would be for you to be able to feel confident in this decision. Is there something else I can do to help with that?

While conflict is never fun, I’ve found that using these tools can make these conversations productive and even rewarding. When we help a donor navigate conflict with the institution, we preserve a relationship that is meaningful to both sides – and that outcome can make the temporary conflict worthwhile.

*Advancement Resources Feb 2020: Early Career Success Factors for Major Gift Fundraisers

Building a Bridge: How to Effectively Transition Prospects

Advancement officers are, typically, quite familiar with the idea of transferring a prospect from one portfolio to another. This is most easily done when transitioning a new prospect without an existing relationship. In those cases, it’s easy for a different colleague to reach out and introduce themselves.

But what about when you do have a relationship? When a prospect or donor that you’ve gotten to know just isn’t the right fit for your portfolio, do you know how to provide them with a bridge to a different team member?

Let’s be clear about why we may need to bridge a prospect to someone else’s portfolio. It may be that the individual’s passions more closely align with a colleague’s area of focus. They may not be right for your role, or the area you represent. Or, that their giving patterns and opportunities suit them for the portfolio of a planned giving or leadership annual giving portfolio.

Is it easier to just make the switch on the back end and let your colleague reach out? Yes.

Is it more respectful and supportive of retaining the relationship to make that transition and introduction personally, sharing the shift with the prospect? Absolutely.

But this is where it’s very easy to be at a loss for words. Which is why it’s important to think through the language you use when you create a bridge for a prospect to another colleague.

My tip is this: Never focus on gift level.

Prospects do not want to feel they’re being sorted and assigned in that way. And we do not do handoffs! Instead, focus on interest and demonstrate that you’re getting to know the prospect as an individual and want them to have their best match.

Here’s what this may look like:

  • I’d love to introduce you to my colleague, Victoria. You shared about your passion for theater, and Victoria represents the theater program. She works to foster generosity with community members like you who are fellow arts lovers. [For a prospect qualified for another area.]
  • May I introduce you to my colleague, Jacob? He runs our President’s Leadership Society, which I think would be a great fit for you based on your interests that you’ve shared with me. I know he would love to get to know you and share more about how community members can get involved through that program. [For a prospect who is an annual leadership giving candidate, not a major giving candidate.]
  • Would you be open to me introducing you to my colleague, Alexa? She’s a part of our larger team who works to engage our supporters, particularly those like you who have long-term relationships with us. [For a planned giving prospect.]

These options are definitely more work! But they’re also more effective for the work we’ve dedicated ourselves to doing — developing meaningful, thoughtful relationships between supporters and the institution we represent.

Do you use bridge language with your portfolio transitions? Share how it works for you and what tips you have for others!

Creating Your “Unhooking” Strategy

Work events: Whether it’s a gala, a homecoming event for university parents, a campaign launch or any other community-facing event, there’s a belief among folks who aren’t frontline fundraisers that we just love to attend these. That we’re naturals at introducing ourselves, making conversation, working the room, and using it to move strategies forward. What many of us know, of course, is that this is not true, and that events often push us outside of our comfort zone, requiring us to be even more intentional in order to be strategic.

So we use that intentionality to introduce ourselves, make conversation, and to make that conversation purposeful, in support of philanthropy at our institution. There’s a lot of talk in our field about “hooks” to engage supporters in meaningful ways around our role and philanthropy, and those can come into play for events too.

But in a recent conversation with a professional new to advancement, we began discussing “unhooking” — exiting event conversations that are lovely, but not strategic or in alignment with our role of introducing or reaffirming the importance of philanthropy.

Imagine you’re working an event. You’re chatting with a fantastic supporter, one whose annual support is thoughtful but who will not be growing that support. Or you’re chatting with someone who is in someone else’s portfolio, and you are not able to move that relationship forward yourself.

How do we as fundraising professionals “unhook,” or exit the conversation gracefully, but with intention? I shared a few examples with the colleague of how we can leave the conversation with as much strategy as we entered it:

  • “It was so nice talking with you! I don’t want to stop you from visiting with our other guests/going to the food stations/etc., so I’ll let you do that. But thank you so much for your support of our organization. It makes such a difference, and I’m really glad you can be here for us to show you how you’re making a difference and say thank you!”
  • “I’m so glad we were able to connect! I’d love to introduce you to my colleague who works with alumni and supporters of our school of engineering, as I know she would be very glad to chat with you. Let me introduce you – she’s right over here.”

Each of these further build the groundwork for the individual relationship by reinforcing the role of events and/or advancement professionals. I’d argue that each of us can build our impact even more by making sure we have the thoughtful “unhooking” language that works for us at the ready.

What language do you like to use? We would love to learn your tips and tools.

Keeping it Simple

I was recently conducting an assessment that will lead to a strategic plan outline for a client. As a part of the process, I had the honor of speaking with a handful of passionate stakeholders: alumni, parents, trustees and donors. Each showed up with incredible passion for their institution, and a deep-rooted desire to support the growth of a philanthropic program.

As we discussed the approaching fall season and all that comes with it — sporting events, homecoming and reunions, campus productions — I kept hearing a message from these committed stakeholders: “keep it simple.” And throughout these conversations, that message kept echoing in my ear.

Now, we know that the things that look “simple” to our supporters often are much more complex for those of us implementing them.

But there’s a message in here that I think we need to hear. A question for each of us to reflect on: How do we take time to slow down to truly create engagement opportunities that will support our greatest outcomes — building relationships that lead to philanthropy?

Our to-do lists and moving through the actions is at exact odds with what we are consistently hearing from our most important stakeholders. But are we listening?

As we plan for filling an athletic suite or a homecoming lunch, are we aligned with what our most important stakeholders are looking for? Are we discussing the desired outcomes through their lens, or ours?

Keep it simple is actually a request. Think about what’s often most important to those returning to campus or attending a regional event: a conversation with a beloved professor, the opportunity to walk through storied halls or favorite campus landmarks or seeing old friends and laughing about memories.

Fall events provide an opportunity to build pride and passion for our institutions and our vision. It is the conversations that happen after these events where our best work in philanthropy can come to life.

How can we keep it simple so that we focus not on our to do lists, or how busy we are, but make time for the most important interactions?

As you plan for fall, ask yourself: Are you creating spaces for meaningful, memorable interactions? And how will you build on those interactions to create deep-rooted, long-term relationships on behalf of our institutions?

Time for a “Donor Vacation”

With summer fully underway, many of us are also thinking about vacations. We are also focused on fiscal year end — thinking about what we’ve accomplished and what we’d hoped to do better — while planning for the new year.

The thing I hear most frequently from those that I talk with when reflecting on the prior year likely won’t surprise you: “I need to spend more time with our greatest stakeholders.” And yes, we all do. 

Strategically managing philanthropic partnerships requires time and attention. There’s simply no shortcut for this — our most essential work.

In the past, I’ve talked about calendar management; but one discussion isn’t enough to ensure we put enough time, care and thought into our donors and potential donors. We must continue to focus on prioritizing our most important responsibility: building relationships that lead to philanthropic generosity.

Last week, I was on a call with a wonderful fundraiser, relationship generator, and manager. She shared that she has told her team that for the next 60 days, she will be minimizing participation in 1:1 meetings and the institution’s standing meetings, and will be doing a calendar overhaul to ensure she is dedicating real time and attention to prospects and donors.

I love that she has built trust with her team (reduced meetings with exception to donor strategy and hurdles), is role modeling prioritization of our most impactful responsibilities, and is looking to move things off her plate that have created “bad habit creep.”

One of her colleagues actually said, “How lucky, you get to go on a donor vacation.”

A donor vacation! My new favorite word, concept, and habit! And I want it to become yours too!

We must never stop asking: How can each of us take things off our plates so that a donor vacation becomes a norm? Yes, this supports the essential prioritization of donor engagement. But thinking of it as a donor vacation also allows us to reset how we think about our roles and our time, providing better focus and reminding us of the joy and privilege of connecting passionate and generous community members with causes they care about.

How can you build a donor vacation into your summer? And how can you use the good habits you build during this focused activity to provide additional focus and rigor all year long?