Category: Best Practices

We often find that our coaching conversations follow themes. And over the past few weeks, one topic has surfaced again and again: habits. Habits for ourselves, habits with our donors, habits with our natural partners, habits with our team members.

Advancement work asks a lot of us: curiosity, confidence, courage, patience. But as fundraising continues to evolve, one trait consistently separates high performers from everyone else: habits that create structure, discipline, and authentic connection in our work.

High-performing fundraisers are not simply more talented. They are more intentional. More anchored. More consistent in the routines that keep donor relationships moving forward and keep teams aligned.

And the habits that matter most are surprisingly simple, but deeply powerful.

• Calendar Blocking: Protect time for your most important work. If it is not on your calendar, it is not real.
• Sacred Outreach Time: Outreach should never be the first thing given away. Treat it with the same respect as a donor meeting: block it, name it, and honor it.
• Next-Step Discipline: Place every next step directly into your CRM or calendar. Momentum is built through clarity, not memory.

But structure alone is not enough.

The most effective fundraisers pair disciplined habits with authentic engagement — the kind that builds trust, deepens understanding, and strengthens collaboration.

Authentic Engagement with Donors

Authenticity is not a tone; it’s a habit. It shows up in the way we listen, the way we follow through, and the way we stay curious. The strongest donor relationships grow from consistent, genuine connection, not from perfectly crafted pitches.

One of the most powerful habits you can build is asking thoughtful, open-ended questions that help you truly understand your donors:

• Impact Questions: “What impact feels most meaningful to you right now?”
• Values Questions: “What part of our mission resonates most deeply?”
• Experience Questions: “What has shaped your connection to this work?”

Questions are not a tactic; they are a discipline. They create space for donors to share what matters most and they give us the insight needed to steward with intention.

Timely Feedback Loops with Natural Partners

Strong advancement work is never done alone. Natural partners — program staff, leadership, volunteers, board members — are essential to donor movement. And trust with these partners is built through timely, consistent feedback loops. A quick update after a donor meeting. A shared insight that helps a colleague prepare for their next conversation. A follow-up that closes the loop and reinforces collaboration.

These habits build confidence across the organization and create a culture where donor work feels shared rather than siloed.

Learning With and From Each Othe

Finally, high-performing teams cultivate habits of collective learning. They talk about what’s working. They share what they’re hearing from donors. They reflect on patterns, challenges, and opportunities. They learn with each other and from each other. This is how teams grow stronger through ongoing habits of reflection, curiosity, and shared practice.

A September Mindset

September naturally increases our pace. As we move into the final quarter of the calendar year, donor conversations accelerate, calendars fill, and priorities sharpen. This is exactly the moment when the right habits matter most.

Focusing on these habits now ensures you are doing your most important work; not just the most urgent work. And it lays the foundation for an even stronger 2027, built on consistency, clarity, and authentic connection.

Looking to sharpen your habits? Reach out to discuss a potential coaching partnership with us. 

It’s been nearly ten years since we first introduced the idea of Two Touches through our blog and we continue to be inspired by how many of you have woven this practice into your daily rigor. What began as a simple discipline has become a cornerstone habit for advancement professionals who want to stay grounded in relationships rather than react to urgency.

A decade later, the core truth remains: consistent, intentional outreach builds stronger donor and partner connections. And while the advancement landscape has evolved: new tools, new expectations, new ways of communicating, the need for meaningful, personal touches is just as relevant today.

With that in mind, we’ve refreshed and modernized the concept to reflect what we’re seeing in 2026: more channels, more creativity, and more opportunities to show donors and partners that they matter.

Advancement professionals think about donors and prospects constantly, whether we’re considering next steps in strategy, strengthening outreach to secure a meeting, or collaborating with a partner who has identified a new potential supporter. Yet even when these individuals are top of mind, our actions can tell a different story. We get busy, focus on a handful of urgent items hitting our desk, and suddenly months have passed without meaningful outreach to people we want to draw closer.

This is exactly why I continue to champion the Two Touches practice: a simple, daily discipline that keeps relationships at the center of our work. Beginning each workday with two intentional outreaches to donors, prospects, or organizational partners ensures we start every day with clarity, purpose, and connection.

It’s a small habit with outsized impact.

Why Two Touches Still Matters in 2026

In an era of digital noise, automation, and overflowing inboxes, personal outreach stands out more than ever. Two Touches reinforces the fundamentals of our profession:

• Consistency
• Authenticity
• Thoughtful outreach and stewardship
• Strategic relationship building

When practiced daily, Two Touches strengthens both our discipline and our donor strategies, ensuring we nurture relationships organically.

Touches remain simple, human, and varied, and in 2026, we have even more ways to connect meaningfully:

• A handwritten note celebrating a personal or professional milestone
• A short email sharing an article or update aligned with their interests
• A personalized birthday message that goes beyond “Happy Birthday”
• A link to a news release or campus update that rekindles excitement
• A text message with a photo or brief video from your institution: a performance, a lab breakthrough, a student showcase
• A message celebrating a program achievement or milestone
• A quick voice memo expressing appreciation or sharing a moment of inspiration

Why These Touches Matter

Every strategy relies on a relationship, and every relationship relies on interactions,  both big and small. Moves management is essential, but strategies thrive when they include both active fundraising (moves) and passive fundraising (touches).

Two Touches creates:

• 10 interactions per week
• 40+ per month
• 400+ per year

That’s more than 400 moments where donors, prospects, and partners feel seen, valued, and connected.

Getting Started

Keep a stack of organizational note cards on your desk. Save a folder of articles, links, photos, and updates you can share. Build a habit that reminds donors and partners that you’re thinking of them — not just when you need something, but because the relationship matters.

Who will you reach out to today?

I was recently in an informational interview with someone considering a move into frontline fundraising. We were talking through some of the trends shaping our profession when he shared a question his father had once been asked in an interview many years ago: “How do you deal with ambiguity?”

That single question opened the door to a rich conversation, and, frankly, a truth we don’t talk about nearly enough in advancement: fundraising is a profession built on ambiguity.

For years, we emphasized the importance of confidence: the ability to walk into a room, represent the institution, and speak with clarity and conviction. Over time, that conversation evolved toward courage, especially as fundraisers were asked to initiate deeper, more values‑based conversations with donors. More recently, we’ve elevated curiosity as a defining trait: the willingness to ask better questions, listen deeply, and explore possibility rather than prescribe solutions.

All of these traits still matter. But today, they are no longer enough on their own.

The modern fundraising environment demands something additional, something more dynamic: the ability to be nimble while staying grounded, and agile while staying aligned.

We are navigating:

• Budget cuts that require doing more with less
• Staffing reductions that stretch teams thin
• Growing expectations around dollars raised and donors engaged
• New tools and platforms that change how we work (and how quickly we’re expected to adapt)
• More organizations building frontline teams, increasing competition for both donors and talent

In this landscape, ambiguity isn’t an occasional inconvenience; it’s the daily operating environment. It shows up in ways both subtle and significant, shaping how we plan, how we prioritize, and how we engage donors.

Ambiguity shows up when:

• We’re asked to forecast revenue in a year when positions are frozen, or we have experienced high rates of turnover
• A prospect’s timing, capacity, or philanthropic priorities are unclear
• Leadership sets ambitious goals without yet defining the strategy
• New tools promise efficiency but require time, training, and integration
• Teams are restructured and roles evolve faster than job descriptions
• External forces — economic, political, cultural — influence donor sentiment
• We’re navigating hybrid work, hybrid events, and hybrid expectations

In other words, ambiguity is not a gap in information, it’s the space between what we know and what we need to move forward anyway.

And because this space is widening, fundraisers need a new kind of strength: the ability to stay steady, thoughtful, and proactive even when the path ahead is not fully illuminated.

So how do we grow this muscle? We build it the same way we build any capacity, with intention, practice, and reflection.

• We grow it through curiosity. Asking better questions. Listening for what’s said and unsaid. Staying open rather than rushing to conclusions.
• We grow it through disciplined experimentation. Testing approaches, learning quickly, and adjusting without judgment.
• We grow it through scenario thinking. Planning for multiple possible outcomes rather than anchoring to one.
• We grow it through transparent communication. Naming what’s known, what’s unknown, and what’s next, with teams, with leaders, and with ourselves.
• We grow it through values‑based decision‑making. When the path is unclear, values become the compass.
• We grow it through resilient pacing. Holding urgency and sustainability at the same time, especially when expectations rise and resources shrink.
• We grow it through collaboration. Ambiguity becomes more manageable when it’s shared, when teams think together, problem‑solve together, and support one another.

Ultimately, ambiguity becomes less daunting when we stop treating it as a barrier and start treating it as a condition we are fully capable of navigating. The fundraisers who thrive in this moment are not the ones who wait for clarity — they are the ones who create momentum within uncertainty.

Building a Culture That Can Hold Ambiguity

So, when we return to that original interview question: “How do you deal with ambiguity?” the answer becomes bigger than any one person’s skill set. It becomes a question for all of us, and for the cultures we are building inside our advancement shops.

Because ambiguity is not going away. If anything, it will continue to expand as expectations rise, resources fluctuate, and the landscape grows more complex. The organizations that thrive will be the ones that treat ambiguity not as a threat, but as a shared competency: something we prepare for, talk about, and strengthen together.

Building this muscle at the cultural level means:

• Creating space for curiosity‑driven conversations rather than quick conclusions
• Normalizing learning loops — test, reflect, adjust — instead of expecting perfection
• Encouraging teams to name uncertainty openly, without fear of judgment
• Rewarding adaptability, not just outcomes
• Anchoring decisions in shared values so teams can move forward even when the path is not fully defined
• Supporting one another through change, rather than navigating it in silos

When ambiguity becomes something we navigate together, rather than something each fundraiser must manage alone, we create teams that are more resilient, more innovative, and more grounded in mission. And that’s the real opportunity in front of us.

If we can build cultures that embrace ambiguity, with curiosity, courage, and nimble alignment, we will not only strengthen our teams, but we will also strengthen our impact. We will be better partners to our donors, better stewards of our missions, and better leaders for the communities we serve.

In the end, the question isn’t just How do you deal with ambiguity? It’s How do we build a culture that can hold it, and grow because of it? Because when we do, we are all better for it.

The most effective gift officers are not the ones who know everything; they’re the ones who are curious. Curiosity is what opens doors, deepens conversations, and builds trust. It’s what allows a fundraiser to say, “Tell me more about what matters to you,” instead of rushing to provide information that may or may not be relevant.

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January gave me a gift I didn’t quite expect.

I stepped away for an extended holiday — no client commitments, no meetings, no flight delays or deadlines. Just space. But it wasn’t simply a vacation; it was a social experiment for me. Over the past few years, I’ve watched the boundaries between my work life, volunteer life and my play life blur into something unrecognizable. I love what I do, but I could feel the constant hum of “always on” creeping into every corner of my day.

So, I tried something bold (at least for me): I took my work email off my phone.

Not muted. Not tucked into a folder. Gone.

And here’s what surprised me most, something inside me fell back into place.

Without the ping of an incoming message dictating my attention, I found myself making intentional decisions about when to work and when to relax and enjoy. If I chose to open my laptop, it was because I meant to; not because a notification hijacked my focus. When I worked, I was sharper. When I rested, the time was truly restorative. The mental static quieted. My shoulders dropped. My mind unclenched. My creativity felt more alive.

Three weeks back into the office, and I still haven’t reinstalled email on my phone. There have been a few minor inconveniences. Moments when I had to wait to find contact information or recognize that a few hours to respond would be just fine. But the wins have far outweighed the challenges. I feel more grounded, more present, and more in control of my own attention than I have in some time.

And it’s made me think about our profession more broadly.

We are seeing unprecedented levels of burnout, exhaustion, and reactive behavior. Too many of us are living in a cycle of responding rather than leading, reacting rather than choosing. We’re moving fast, but not always with purpose. And when everything feels urgent, nothing truly gets the space it deserves.

Intentionality is not a luxury. It’s a restorative practice.

It’s the difference between being pulled through your day or walking through it with clarity. It’s the difference between exhaustion and energy, between noise and meaning. And it doesn’t require a sabbatical or a plane ticket, just a willingness to pause and ask:

What do I want to give my attention to right now? What deserves my time, and what simply distracts me?

Maybe for you it’s turning off notifications. Maybe it’s blocking time for deep work. Maybe it’s reclaiming your lunch hour or choosing one evening a week that belongs entirely to you. Maybe it’s saying no to something that drains you, or yes to something that fills you back up and brings you more joy in your role.

Intentionality isn’t about doing less; it’s about doing what matters with more presence and less noise.

As we settle into February, a month that often feels like a sprint after January’s re-entry, I encourage you to consider where a bit of intentionality might restore you. Where could you create a boundary that protects your energy? Where could you design your day rather than react to it? Where could you choose, rather than be pulled?

I didn’t expect the simple change of removing email from my phone to shift so much. But it did. And it reminded me that small acts of intentionality can create big openings for clarity, calm, and purpose.

 

If you’ve ever watched “Friends,” you’ll remember Ross’s infamous attempt to move a couch up the stairs. With Chandler and Rachel struggling to maneuver, Ross keeps shouting one word: “Pivot!” It’s a hilarious scene, but also a surprisingly apt metaphor for fundraising today.

As we close out 2025 and look toward 2026, the ability to pivot: to adjust, to be nimble, to change direction without losing sight of the goal, is one of the most critical skills for gift officers and advancement teams.

Why Pivoting Matters in Advancement Work

Our industry continues to shift. Donor expectations evolve, technology reshapes engagement, and economic realities influence giving patterns. Yet many of us remain in our comfort zones, relying on approaches that worked one, five or ten years ago.

Building relationships that lead to generosity requires more nimbleness than ever:

• Pivoting strategies when donor interests shift.
• Pivoting outreach approach and platforms when initial outreach goes unanswered.
• Pivoting conversations when a prospect responds differently than expected.
• Pivoting priorities when organizational needs change mid-year.

Just like Ross’ couch, the goal is the same: get it up the stairs. But the path to success often requires adjusting angles, trying new approaches, being willing to laugh, while also finding the joy in our work.

Practical Ways to Pivot as a Gift Officer

• Reframe asks (invitations): If a donor hesitates on a major gift, pivot to impact, what they hope to accomplish, a multi-year pledge or a planned gift conversation.
• Adapt your gratitude approach: How donors see gratitude is shifting, have you asked how someone wants to be thanked, acknowledged or recognized? Do you know their preferred way to communicate with your organization?
• Leverage data: Intuition is important, but do not make decisions for your donors. Utilize donor analytics that reveal giving patterns and engagement opportunities.
• Stay curious: Pivot from “we’ve always done it this way” to “what if we tried this?”

Nimbleness isn’t about abandoning strategy; it’s about adjusting tactics to keep momentum alive.

Pivoting in Personal Life

As many shops reduce hours between now and year-end, I encourage you to think about how you pivot yourself personally. Where can you shift focus from work to family, friends, fur babies, or simply restorative personal time?

Just as nimbleness fuels professional success, it also fuels joy and renewal. Taking time to pivot toward what matters most outside of work ensures that when 2026 begins, you’ll return with energy, passion, and clarity. I will spend some of that time with a few of my favorite people, and there is a good chance that will include some “Friends” binging!

Holiday Message

As we wrap up this year, I want to thank you for the important work you do in building relationships, advancing missions, and strengthening communities. May this holiday season bring you moments of rest, laughter, and connection. And may 2026 be a year where you pivot with confidence, toward opportunities, toward growth, and toward joy.

November has long been a season of gratitude in our industry when advancement professionals pause to recognize the generosity of our donors, the strength of our partnerships, and the importance of the missions we serve

But gratitude is more than a sentiment we express; it is a practice we cultivate. And one of the most powerful ways to bring gratitude to life is through the questions we ask.

In our trainings, we’ve been engaging more deeply with natural stakeholders: physicians, providers, academic leaders, and nonprofit executives. These conversations often begin with donor motivations; but we encourage our partners to go further, to explore gratitude and impact directly.

We suggest asking:

• How has our organization expressed gratitude for your giving?
• How should we demonstrate appreciation for your generosity?
• Do you feel your gifts are making an impact?

These questions transform gratitude from a simple “thank you” into a dialogue. They help us understand not only how donors value their giving, but also how they envision their legacy and impact. In turn, they open doors to future opportunities and deeper alignment between donor intent and organizational mission.

Probing questions like these are not just tools to support discussions, they are expressions of respect. They signal that we are listening, that we care about the donor’s experience, and that we want our gratitude to be authentic and meaningful.

As you shape your own donor strategies, consider how gratitude-centered questions might strengthen your approach. Gratitude is not static; it evolves across communities and generations. Taking time to understand these shifts ensures that our expressions of thanks remain relevant, intentional and authentic.

As we celebrate National Philanthropy Day, we are feeling gratitude. At KDD Philanthropy, we are profoundly grateful for the ways we partner with you and for the lessons we continue to learn together. Gratitude is not only something we say, but also something we practice, every day, in collaboration with you.

In today’s increasingly polarized climate, fundraisers are often on the front lines of conversations that reflect deeply held personal values. These moments can be complex, sometimes uncomfortable, and they can challenge our instincts to respond, react, or retreat. But as professionals in Advancement, we must learn to wear what we call a “Teflon coat.”

This is not about being indifferent or disengaged. It’s about cultivating the ability to let certain comments slide off; not because they don’t matter, but because they’re not about us, personally. They’re often a donor’s way of expressing identity, values, or worldview. And our role is not to judge or absorb, but to listen, learn, and discern alignment with the mission we represent.

We represent institutions, not ourselves.

When a donor shares a viewpoint that doesn’t reflect our own, it’s easy to feel caught off guard or even offended. But it’s important to remember we are not speaking on behalf of our personal beliefs. We are representing the values, goals, and vision of the organization we serve.

This distinction is critical. It allows us to stay grounded, professional, and focused on the larger purpose of our work: building relationships that advance impact and fuel generosity.

When we approach listening as a strategic tool, we will have better outcomes. Donor comments, especially those that feel polarizing, are often windows into what matters most to them. Instead of reacting, we can ask ourselves:

• What is this donor trying to tell me about their values?
• How does this align (or not) with our institution’s mission?
• Is there a path forward that honors both perspectives?

By approaching these moments with curiosity rather than defensiveness, we position ourselves as thoughtful partners and trusted guides.

As our industry continues to evolve, so must our approach to donor engagement. Professional fundraisers are not just relationship builders, they are strategic listeners, cultural interpreters, and mission advocates. Wearing our “Teflon coat” doesn’t mean ignoring difficult conversations; it means choosing when and how to engage with intention.

Assume best intent. Most donors are not trying to offend or provoke. They’re sharing what matters to them. When we assume best intent, we create space for dialogue, understanding, and, sometimes, transformation. And when a donor’s values do not align with our organizations, we can still honor the conversation while making informed decisions about fit and partnership.

Let’s all lead with purpose and passion. That means showing up with empathy, professionalism, and clarity — even when the conversation is complex. As you continue to navigate through a busy and hectic fall fundraising season, remember your Teflon coat. It’s not armor — it’s wisdom.

January may be the time for new year’s resolutions, but advancement professionals know July 1 is often when the fundraising clock starts over — and when we make our own resolutions about how we will approach the new fiscal year.

The need for one resolution became clear to me after several clients in recent coaching calls shared their challenges in working with internal partners.

From faculty to program leaders to hospital CEOs and more, we know these partners are essential to our work. We also know that, sometimes, our attempts to work with these partners fall flat: They may be “too busy,” not comfortable in this space, unconvinced of the value of philanthropy and the advancement team or have any other perception that undermines this effort.

But consider what a bought-in partner can bring to our work: They make prospects feel seen and valued. They set a vision and the path to get there. They have seats at important tables where philanthropy needs to be represented. Your internal partners can truly be the key to reaching philanthropic goals — and you can’t afford to let these relationships falter.

Over the course of my career, I’ve come to identify five non-negotiable elements of partnerships that work:

• Educate yourself. No one wants to have a partner who doesn’t take the time to learn the area they’re representing, the dynamics of the institution, etc. By attending classes or presentations, reading material related to the field (e.g., “Chronicle of Higher Education”), asking questions about their work and their passions and more, you don’t just learn. You build credibility and you demonstrate that you care — two absolute essentials to partnerships that work.
• Set clear expectations for both parties — and live up to yours. How will you and your partner work together? What will you provide and what will they be asked to do? Outline expectations clearly from the beginning and always meet your own, and you will remove any uncertainty or misunderstanding. And every bit as important, you will demonstrate that you are the leader in your area of expertise.
• Use time wisely. No one wants to be in a meeting that “could have been an email,” so make sure yours don’t fall into this category. Come prepared with a full agenda but use some time each meeting build rapport too. However, using time wisely isn’t limited to meetings. Staff your partner so that their efforts for advancement are as simple as possible: Draft the email you want them to send a donor; provide talking points about a fundraising initiative before they pitch it to the CEO; etc.
• Be authentic. Your colleagues become your partners once you build a relationship based on trust, and trust does not exist without authenticity. This is easy to know in principle, but harder to put into practice. For example, authenticity requires opening a conversation about challenges you and the partner may be having as you work together. It may be reflected when you provide feedback about a prospect visit you both completed. It also shows up when we are vulnerable, sharing our passions, opinions and concerns. This step may be the scariest, but it’s also the most rewarding.
• Celebrate! Find things to celebrate: a good meeting, an introduction to a key prospect, a smaller gift that starts a relationship, and so on. No one wants to be part of something joyless. So, bring the joy, and share it!

Together, these actions add up to so much more than the sum of their parts. They create trust. There is nothing more foundational, more game-changing, than a mutually-trusting relationship with your internal partners. Once there is trust, the true partnership begins.