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.
