Do You HAVE to ASK?
Do You HAVE to ASK?
“I didn’t even have to ask!”
You may have heard someone say this — and thought, “Wow! That’s great!”
You may have even seen this praised as a goal in fundraising.
But here’s the better question:
Is that really the best outcome for your donor and your organization?
(Warning: a little tough love ahead.)
Let’s unpack this. The key question is not whether you had to ask — it’s why didn’t you?
Four Possible Scenarios:
- You were uncomfortable asking.
If you’re honest, you intended to ask… but the words didn’t come. Your inner voice said, “It’s too much” or “It’s not the right time.” That’s fear — and it can lead to silence, or worse, nervous rambling.
- You didn’t know exactly what to ask for.
You understand the big picture of your organization’s needs, but you’re unclear about specific giving options to present. I call these your Vibrant Options for Giving (VOGs) — created by connecting your strategic plan and operating budget with the question:
“What could be funded with private gifts?”
This gives you a variety of meaningful opportunities to explore with each donor — aligning their comfort and interests with your mission.
- Your donor was already eager and engaged.
You’ve nurtured a strong, ongoing relationship. At some point, your conversation naturally turns to what they’d like to do this year. There’s no formal ask — it’s more about clarifying where their enthusiasm and interest lie.
- Your donor always steps up for new projects.
You know this giver well — she thrives on making an impact, now. She sees a need and acts, often generously (and usually six figures!).
In these four scenarios, the first two are red flags.
The answer? A clearly written 3-sentence Ask (grab the free worksheet here: marcyheim.com/askworksheet) — and practice!
Also, in scenario #2, your leadership may be contributing to the confusion by failing to define priorities clearly. You can’t make a confident ask if you don’t know what you’re raising money for.
We engage with strangers and invite them to become benefactors.
Yes, we are asking for money — but that’s only part of it.
The deeper truth is: we’re helping people give in a way that brings them joy.
The journey from stranger to benefactor is about discovering what inspires their generosity. You listen. You ask questions. You invite them to co-create the impact. You offer real experiences — a tour, a meeting with the CEO, and a chance to see the mission in action.
Some steps are universal. Others are unique. But all of them are intentional — designed to deepen the relationship between your donor and the good their giving makes possible.
And along the way? Clear, confident asks make it easy to say yes.
You have a heart for our county fair.
You understand how generosity helps the fair thrive for the kids and community.
Would you consider meeting to explore ways giving to the fair would be meaningful for you?”
When the giving goal (your VOG!) is clearly defined, the ask becomes simple:
You’ve been helping provide an Academy experience for worthy students for years.
You understand that cost keeps some kids from experiencing our loving, Christian environment.
Would you consider a gift of $50,000 to establish the Smith Scholarship Endowment and support an Academy Worthy Student forever?”
Start with your best guess about what your donor might want to do.
Write the ask. Test it through experiences that show impact.
Spring is a great time to start planning your asks. By fall, you’ll have clarity.
In the meantime, enjoy the relationship. Stay curious. Test ideas. Writing the ask sets an intention — and that’s powerful.
So be bold. Stretch your thinking. And take action, even if it’s scary.
When you and your donor arrive together at the right gift, it’s worth the risk — the uncertainty — the slight missteps along the way.
Because in the end, it’s not about the money.
It’s about what the money does.
And when you help create that kind of impact — that kind of joy — for your donor and your mission?
Invest in Joy™
