12 Skills Fundraisers Need for What Comes Next. #3: Discernment

The Problem Isn’t a Lack of Advice

Fundraising doesn't suffer from a lack of advice.

We're drowning in it.

"You should be doing more digital."

"You should stop doing mail."

"You should shorten your letters."

"You should personalize everything."

"You should follow this expert, adopt that framework, use this tool, ignore that one."

If you work in fundraising long enough, you eventually develop what I call the should-heads — that crowded mental space where every confident voice sounds authoritative, every recommendation feels urgent, and every decision starts to feel like a test you didn’t know you were taking.

Discernment is the skill that lets you step out of that noise.

Not by rejecting expertise. Not by ignoring best practices. And definitely not by deciding you know better than everyone else.

Discernment is something far more disciplined than that.

Discernment Is Not Instinct

(And it’s not obedience either)

Discernment is not instinct dressed up in nicer clothes. Sometimes intuition is worth listening to; sometimes it’s just stress wearing a trench coat.

Discernment doesn’t dismiss intuition, but it doesn’t hand it the steering wheel either.

Discernment is the skill of integrating multiple sources of information at once.

Experience.

Data.

Research.

Context.

Values.

Constraints.

Consequences.

Ethics.

And then choosing responsibly.

Not because you know the right answer, but because you know how to choose between multiple informed options.

Because real experts understand context and nuance. They know when principles bend, and they know how far to bend them before the break (and what happens when they do break.) They know when adaptation is required.

For fellow Gen X-ers who remember Air Supply, "They know all the rules and they know how to break 'em and they always know the name of the game." (i.e. Making Donor Love Out of Nothing At All - I digress.)

A lack of discernment means you know the rules, but not yet when - or how - to apply them.

Best Practices Are Not Commandments

Best practices are not commandments.They are distilled learning, not universal law.

Discernment is what keeps knowledge from becoming brittle.

It’s the ability to say: That’s generally true, but not here. That works in this context, but not with these donors. That principle holds, but the expression needs to change.

Without discernment, knowledge becomes rigid. With it, knowledge becomes responsive.

This is especially important in fundraising, where context matters more than correctness.

(Another digression, but just to be exquisitely clear - discernment is also not "but we're/our donors are different!" Are they? Are you? Really. SO different that no 'best practice applies to you? Discernment is also about finding that balance.)

Discernment Is a Systems Skill

Discernment is also a systems skill.

It asks not just, “Will this work?” But, “What will this set in motion?”

How will this affect trust? Dignity? Workload? Sustainability? The donor relationship six months from now?

When Confidence Outpaces Experience

There’s another reason discernment matters right now — and it’s not comfortable to name, but it needs to be said.

Not everyone offering advice in fundraising has earned the authority they project.

We live in a moment where visibility is easily mistaken for expertise. Where a large following, a slick brand, or a confident tone can stand in for experience, context, or accountability.

This is how tactics get sold without theory. How shortcuts get marketed as strategy. How “tricks” get passed off as wisdom.

The problem is advice that has never had to live with consequences. Experts in fundraising who've never sat across the table from donor, sweated over a grant application, lost sleep over a gala or gone home with papercuts after getting the mailing out on time.

Discernment is what allows fundraisers to ask:

• Where did this idea come from?

• Under what conditions did it actually work?

• What system was it part of?

• What tradeoffs did it require?

• And who bears the cost if it fails?

• Is this necessary technology or another Bright Shiny Object?

  
  

Without those questions, flashy advice spreads faster than thoughtful practice — and organizations pay the price.

Discernment is not cynicism. It’s respect for complexity.

And it’s how fundraisers protect both their donors and their missions from confidence that hasn’t yet been tested by reality.

Discernment Is an Ethical Skill

Discernment is also an ethical skill.

It’s not about choosing what’s most effective at all costs.

It’s about choosing what’s right, given the information in front of you.

Sometimes that means choosing the slower path. Sometimes the less flashy option. Sometimes restraint instead of optimization.

And sometimes making the unpopular, unsupported position and standing your ground with, yep, Grounded Confidence.

Yes, your Board Chair is the ultimate authority for the organization. (Kind of - governance is a different blog post for another day). But unless they come from nonprofits and fundraising, they're not experts in what you do. Discernment will tell you when you need to push back on leadership based on your knowledge, skills, expertise, and research.

How Fundraisers Develop Discernment

(On purpose)

So how do fundraisers actually develop discernment?

By studying principles, not just prescriptions.

By asking, “Under what conditions would this be true?”

By holding multiple truths without rushing to collapse the tension.

By naming tradeoffs honestly.

By debriefing decisions, not just outcomes.

Discernment isn’t knowing everything.

It’s knowing how to choose.