Make your First Ask -- a Connection Ask!

Tom Iselin
May 30, 2021
4 min read

Updated: 2 days ago

This blog and video is reminder that the first "Ask" you should make has nothing to do with asking for money!

https://youtu.be/TkDFTvUmKdQ

Make your First Ask -- a Connection Ask!

Why You Should Never Ask a First-Time Donor for Money

Imagine this: you’re the director of fundraising for a local soup kitchen. A board member gives you the name of a friend who might be a potential donor. You pick up the phone, introduce yourself… and during the very first conversation, you ask for $5,000.

How would you feel if someone did that to you?

Probably irritated. Maybe offended. Definitely uncomfortable.

Yet this is exactly what many fundraisers are told—or pressured—to do: call the names on the list and “go get the money.” It’s a terrible strategy. Not only does it feel pushy and disrespectful, it damages trust and kills long-term potential.

There’s a far better, far more effective way.

Why Asking Too Soon Is a Relationship Killer

When you ask a first-time donor for a large gift before any relationship exists, you’re essentially saying:

“You’re a cash machine. I want what’s in your wallet, not what’s in your heart.”

Donors pick up on this instantly.

This behavior:

Irritates donors
Breaks trust
Makes the organization look tone-deaf
Lowers the chance of future gifts
Damages the donor experience
Triggers the “run away” reflex

The size and frequency of donations are directly tied to the quality of the relationship you build.And like any relationship—with friends, colleagues, partners—it takes time.

A Better Approach: Make a Non-Monetary Ask First

Instead of opening the relationship with “Can you give us money?”, start with something far more effective:

A connection ask.

This means inviting the donor to:

Observe your programming
Take a tour of your site
Volunteer for a day
Attend a performance
Join you at a friendraising event
Watch your mission in action

None of these require asking for money.All of them create emotional connection.

A donor who sees your work, meets your team, and experiences your mission firsthand is more likely to:

Understand your impact
Care about your outcomes
Feel inspired
Trust your leadership
Become personally invested

It’s the difference between someone reading a brochure and someone standing in your kitchen watching hungry families eat because of your work.

Experiences build belief.Belief builds generosity.

Why Non-Monetary Asks Reduce Pressure (For Everyone)

Non-monetary asks take the fear out of the first meeting—for both you and the donor.

For you, the fundraiser:

No anxiety about “the big ask”
No pressure to close a gift
No awkwardness

For the donor:

No fear of being cornered
No feeling of obligation
No discomfort or pressure
No surprise “hard sell”

This creates a relaxed environment where real relationships can grow.Trust organically builds.Credibility rises.And donors feel respected—not hunted.

This Shows Donors You Care About Them (Not Just Their Money)

When you start with connection, donors feel seen, heard, and valued for who they are—not just what they can give.

They get to:

Learn your story
Experience your mission
Meet your people
Feel your passion
Understand your work on a personal level

And most importantly, it shows them that you care about:

Their interests
Their comfort
Their process
Their reasons for giving
Their desire to make a difference

That’s how you create loyal, generous donors.

When You Finally Make the Ask, They Say “Yes” More Often

Once a donor has seen your work, felt your mission, and built a relationship with you, they are far more receptive when you eventually ask for a financial gift.

This strategy leads to:

Larger gifts
More consistent giving
Higher donor retention
Stronger donor satisfaction
Increased referrals

Donors appreciate—and remember—that you didn’t push.They talk about the positive experience.They tell their friends.Your reputation grows.

Contrast that with the organization down the street that pushes hard early on.Donors know the difference.

The Takeaway: Start With Connection, Not Cash

The next time you’re asked to solicit first-time donors:

Don’t ask for money
Don’t lead with pressure
Don’t treat donors like ATM machines

Instead:

Make a non-monetary ask first.Invite connection.Build trust.Engage emotionally.Then ask.

It works. Every time.

About the Author

Tom Iselin is recognized as one of America’s leading authorities on high-performance nonprofits. He has built nine sector-leading nonprofits and two software companies, written six books, sits on multiple boards, and has been rated one of America’s Best Board Retreat and Strategic Planning Facilitators. His work on nonprofit strategy, board leadership, and culture has been featured on CNN, Nightline, and in Newsweek.

Tom is the president of First Things First, a firm specializing in board retreats, strategic planning services, fundraising strategy, and executive coaching for nonprofit CEOs.

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If you’re looking for a board retreat facilitator or strategic planning facilitator who has been in the trenches and understands real-world nonprofit challenges, Tom can help your board gain clarity, build alignment, and create an actionable plan that improves performance and impact. His sessions propel organizations to the next level of performance and impact . . . and they're fun!

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