12 Skills Fundraisers Need for What Comes Next. #2: Grounded Confidence

This is part two of a series highlighting the 12 skills fundraisers need to cultivate in the new year and for what the nonprofit sector and profession of fundraising will ask of us. And what our communities need from us.

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Curiosity opens the door, but curiosity alone doesn’t carry you very far: sooner or later, you have to decide.

You have to choose a direction.You have to recommend a plan.You have to say “yes” to some things and “no” to others.You have to move forward when the information is incomplete and the stakes feel personal.

That moment — the moment when curiosity turns into judgment — is where grounded confidence lives.

Not bravado. Not certainty theater. Not the kind of confidence that arrives loudly and early and wants credit for the meeting.

Grounded confidence is quieter than that, and much harder earned.

Confidence gets weird in fundraising

In fundraising, confidence has an image problem.

Too much confidence and you’re “too salesy.” Too little confidence and you’re “not strategic enough.”I. f you hesitate, you’re unsure.If you decide quickly, you’re reckless.

It’s a narrow corridor to walk, and many fundraisers end up doing the same careful dance: sounding confident while privately second-guessing themselves, or deferring decisions they’re actually qualified to make.

What gets lost in that dance is the most important distinction of all: Confidence is not the same thing as certainty.

Certainty is seductive. Confidence is steadier.

Certainty says:

Grounded confidence says:

Fundraising does not operate in conditions of certainty. It operates in conditions of probability, pattern, behavior, timing, and meaning — all filtered through human beings who are tired, distracted, generous, anxious, hopeful, and inconsistent.

Anyone promising certainty in that environment is either inexperienced or selling something.

Grounded confidence doesn’t deny uncertainty.It accounts for it.

And because it does, it lasts longer than certainty ever does.

Grounded confidence is not a feeling. It’s a relationship.

Here’s the shift that matters most.

Grounded confidence isn’t something you feel about yourself, it’s something you build with yourself over time.

It’s the result of a relationship between:

• experience and reflection

• learning and application

• instinct and evidence

• success and failure

It’s knowing not just what you think, but why you think it — and being willing to revise that thinking when new information emerges.

In other words, grounded confidence is self-trust earned honestly, not declared prematurely.

Why confidence erodes (even in very capable fundraisers)

Many skilled fundraisers quietly lose confidence over time, and it’s rarely because they stopped being good at their jobs.

More often, it’s because:

• success is inconsistently defined

• feedback is delayed or unclear

• outcomes are disconnected from effort

• urgency is constant and reflection is rare

• everyone wants results, but no one wants to talk about tradeoffs

In those conditions, people stop trusting their judgment. They start looking outward for validation: metrics, trends, best practices, benchmarks, consultants, “what everyone else is doing.”

External input is valuable. Outsourcing judgment entirely is not.

Grounded confidence restores balance. It allows fundraisers to integrate information without surrendering agency.

Confidence is shaped by systems, not just people

This is where Systems Thinking quietly matters again.

We tend to talk about confidence as an individual trait, something a person either has or lacks. But in practice, confidence is deeply influenced by the systems people operate within.

Clear goals support confidence. Moving goalposts erode it.

Consistent data builds confidence. Contradictory reporting undermines it.

Aligned leadership strengthens confidence. Mixed messages dissolve it.

In other words, confidence isn’t just about mindset. It’s about environment.

Grounded confidence grows in systems that value learning, clarity, and judgment, not just performance or speed.

That’s not a personal failure; it’s a leadership responsibility.

Professional development isn’t optional here

This is the part we don’t say often enough.

Grounded confidence is not just emotional steadiness. It’s professional formation.

It’s built by:

• understanding fundraising history, not just current tactics

• learning why things work, not just that they do

• revisiting past decisions with curiosity rather than shame

• investing in your thinking, not just your output

Confidence without learning is brittle. Learning without confidence is paralyzing.

The two belong together.

And they take time.

Experience matters. But only if you reflect on it

Experience alone doesn’t produce confidence. Repetition alone doesn’t either.

What matters is the integrated experience of noticing patterns, naming lessons, and updating judgment over time.

Grounded confidence comes from moments like:

• “I’ve seen this cycle before.”

• “Last time we tried that, here’s what actually happened.”

• “This feels familiar — and here’s why.”

That kind of confidence isn’t loud. It’s calm.

And it’s often the most reliable voice in the room.

Grounded confidence changes how you show up

When confidence is grounded, a few things shift:

• You’re less reactive to noise

• You can say “I don’t know — yet” without panic

• You disagree without becoming defensive

• You don’t need every idea to be yours to support it

• You can name tradeoffs honestly

This isn’t about being unflappable. It’s about being anchored.

And anchoring matters — especially when others are looking to you for clarity.

Confidence is what makes invitation possible

Here’s the quiet bridge to what’s coming later in the series.

You cannot offer a meaningful invitation — to donors, boards, or colleagues — if you don’t trust yourself enough to stand behind it.

Invitation requires:

• clarity without coercion

• confidence without control

• openness without collapse

Grounded confidence is what allows you to say:

This is not about having all the answers

Let’s be clear about what grounded confidence is not.

It’s not arrogance or certainty. It’s not pretending uncertainty doesn’t exist.

It’s the willingness to make decisions with uncertainty, informed by experience, learning, and attention.

It’s trusting yourself enough to act and being humble enough to adapt when required.

The skill beneath the skill

If curiosity is the discipline of attention, grounded confidence is the discipline of judgment.

Judgment formed over time. Judgment shaped by systems. Judgment strengthened by reflection.

This is not a soft skill.It’s a leadership skill.

And it’s one of the most important ones fundraisers can develop — especially in times when the ground keeps moving.

Here are five concrete, skill-based ways fundraisers actually develop grounded confidence:

• Review decisions, not just results. After a campaign, meeting, or appeal, ask: What did I decide, based on what information, and would I make the same call again? Confidence grows when you learn to trust (and refine) your judgment, not when outcomes happen to cooperate.

  
  

• Study patterns, not anecdotes.One angry donor or one great win can hijack your confidence. Step back and look for trends over time — in retention, response, behavior, and capacity. Pattern literacy steadies confidence because it replaces reaction with perspective.
  

• Practice saying “I don’t know—yet. ”This isn’t hedging; it’s professional honesty. Naming what you’re still learning keeps you curious and credible, and it prevents the brittle confidence that collapses under pressure.
  

• Invest in understanding why things work, not just how. Read fundraising history. Learn the principles underneath tactics. Ask why a strategy succeeds in one context and fails in another. Confidence deepens when knowledge becomes transferable, not just repeatable.
  

• Make small, intentional decisions and stand behind them.You don’t build confidence by waiting for perfect certainty. You build it by making thoughtful choices, observing the impact, and adjusting without shame. Judgment strengthens through use.
  

If curiosity is how we learn to see clearly, confidence is how we learn to stand where we are and say, “This is the best next step I can see.”