There is that well-known moment in every fundraiser's year where the pressure to "start asking" becomes very loud.
The fiscal year is ticking. Leadership wants results. The pipeline needs to move.
And so you have the urge to reach out to donors before, if you are being honest with yourself, you are truly ready to.
I say this gently: starting the ask process before the foundation is in place does not speed things up. It often sets you back.
At Kittiwake, I talk with clients about their readiness realities. We map where they see themselves and where they actually are. The conversations are frank, but they are always productive, because once you know where the gaps are, you can make a real plan and real progress.
I wanted to share a little of that process with you, so you can do the same.
It starts with a simple question: what does readiness actually look like?
Start with your organization.
Before you approach anyone for a major or planned gift, sit with some honest questions.
Is your leadership stable and trusted?
Can you explain the bigger vision behind the organization, the problem you’re solving, and how you’re going about it?
Can you clearly articulate where a gift will go, why it matters right now, and how it connects to what they care about?
And do you have the infrastructure to steward a donor over the long haul, not just process their paperwork and move on?
Planned giving especially requires this. A donor who names your organization in their will is not closing a transaction. They are making a decision rooted in deep trust, and they will be watching how you take care of them for years to come.
If your organization cannot sustain that relationship with consistency and care, the ask is premature. Full stop.
Then look inward.
Do you genuinely know this person? Not just their capacity, but what keeps them up at night, what they are proud of, what they want their legacy to mean?
If the answer is "not really," you are still in cultivation. And that’s okay. It’s where the real work happens anyway.
Knowing when someone is ready is its own kind of skill.
It’s rarely announced. It shows up quietly: in the questions they start asking about impact, in the way they talk about the future, in how they begin to refer to your organization as "we" rather than "you."
When someone starts leaning in, you will feel it. That is the spark. And your job is not to manufacture that moment; it’s to meet it.
Planned giving and major gifts are not a conversation you have once.
They are the result of a relationship that has been tended carefully, sometimes over years.
When both sides are truly ready, the ask does not feel like an ask at all. It feels like the next natural step.
And that is exactly where you want to be.
Best wishes,
Sarah
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