Stay Ahead of Your Prospects: Proactive Beats Reactive Every Time
Another of Jerry’s rules is a favorite among campaign veterans:
“Do not let the tail wag the dog.”
He is talking about a common trap: reacting to prospects and circumstances instead of leading the process. His advice is practical – think two to three weeks ahead when you are in a campaign.
In today’s hyper‑busy fundraising world, that kind of proactive mindset can be the difference between a calm, confident effort and a constant scramble.
What “tail‑wagging” looks like in real life
Most of us have been here:
A major prospect is ready to talk, but your materials are not fully baked yet.
Leadership wants to see progress, but you are still waiting on internal approvals and project descriptions.
You find yourself saying, “Let me get back to you on that” far more often than you would like.
When prospects sense that you are always catching up, not leading, it undercuts confidence. It also makes their concerns and timing feel like emergencies instead of planned steps.
Jerry’s point is not that you should have all the answers. He is clear that no one does. His point is that you should not be perpetually surprised by questions and needs that were predictable.
Thinking a few weeks ahead in a campaign
In a campaign or major initiative, thinking two to three weeks ahead might include:
Knowing which prospects you hope to see in that window – and making sure case materials and internal approvals are ready before you call.
Anticipating likely questions: “How will this project be sustained?” “What about operating costs?” “How does this fit into your long‑term plan?” Preparing clear, honest answers in advance.
Coordinating internal players – program staff, finance, leadership – so you are not scrambling to schedule key people or pull numbers at the last minute.
It is about moving from reaction to readiness.
Proactive posture in everyday work
Outside of formal campaigns, you can still apply this rule to your weekly rhythm:
Portfolio planning. At the start of each week, identify your top 5–10 donor moves and what each one needs from you next. Do not wait for them to nudge you.
Pre‑visit briefings. Before important meetings, check in with colleagues who know the donor or program well so you are not blindsided by internal issues or history.
Calendar discipline. Protect time for planning. If every hour is booked with meetings, you will not have the mental space to think ahead.
Proactivity is not about controlling everything. It is about reducing the number of avoidable surprises.
Anticipating concerns builds trust
Jerry advises development officers to anticipate prospects’ concerns. That is as relevant as ever.
If a donor raises a hard question and you can say, “That is a great question – we have been thinking a lot about that,” and then offer a thoughtful answer, a few things happen:
You signal that you take their perspective seriously.
You communicate that this campaign or project is not being made up on the fly.
You open the door to a more honest, strategic conversation.
When donors feel that you and your organization are thinking ahead, they are more willing to invest in your future.
Because they see that you are already living there.