So your grant writer keeps asking annoying questions…

Questions like… “how much further???”

When I onboard a new client, I start asking questions. A lot of questions.

What's the real cost of running this program?
Who's managing it day-to-day?
What happens when the grant money runs out?
Do you have any outcome data from your current programs?
Where will indirect costs come from?
How active is your board?

I can feel the frustration building. They have limited time. They have a great program idea and a rough budget. They just need me to make it sound good on paper, right? They want solutions, not more questions. They’re thinking: Can't you just write the grant?

But here's what I've learned over the years: those questions aren't annoying, they're essential. And when I ask them, it's because I'm trying to set you up for success—not just with this one grant, but with building a sustainable funding strategy.

Good Grant Writers See What Funders See

I recently read an excellent piece by Jennifer Lynch on the Grant Professionals Association blog titled "What Grant Professionals Know That Nobody Wants to Hear." (I am a member of the GPA, a professional association for grant writers.) The author put it perfectly: grant professionals are often the first to spot the structural cracks in an organization's foundation. We see the gaps between what's being promised and what's actually possible. We know when a budget doesn't reflect real costs, when a program lacks defined outcomes, or when an organization is writing in survival mode while trying to sound like it's scaling.

And here's what nonprofit leaders need to understand: funders see it too.

I sit on federal grant review panels, which means I spend hours reading proposals from organizations across the country. I see the good, the bad, and everything in between. When I'm reviewing grants, I'm not just looking at nice writing—I'm looking for evidence that an organization knows what it's doing and can deliver what it promises.

What My Questions Really Mean

When your grant writer asks what seems like an annoying question, here's what they're actually doing:

"What's the real cost of this program?"
Translation: The budget you gave me doesn't include staff time, benefits, rent, utilities, evaluation, or admin support. Funders will notice. Let's build a realistic budget that shows you've thought this through.

"Who's responsible for post-award reporting?"
Translation: I need to know you have the capacity to manage this grant if you get it. Funders care deeply about whether you can deliver and report on outcomes.

"What's your sustainability plan?"
Translation: This funder wants to know you're not going to collapse the minute their money runs out. What's your long-term strategy?

"Can you share outcomes data from your current work?"
Translation: Funders invest in organizations that can demonstrate impact. If you can't show results from what you're already doing, why would they trust you with more money?

These aren't obstacles. They're opportunities to strengthen your proposal—and your organization.

The View From Both Sides

I know this from experience on both sides of the table. When I led Veterans programs at a large local nonprofit, it took me six years to build our grant funding from $750,000 to $2.4 million annually. That growth didn't happen because I learned to write prettier proposals. It happened because I made sure our programs were performing well, our relationships with existing funders were strong, and we could answer every hard question a reviewer might ask.

Now, when I sit on grant review panels, I can immediately spot the difference between organizations that have done this work and those that haven't. The funded proposals have:

• Realistic, detailed budgets that show they understand true program costs

• Clear, measurable outcomes with data to back up their approach

• Strong staffing plans that prove they have capacity to deliver

• Thoughtful sustainability strategies that go beyond "we'll apply for more grants"

• Honest assessments of challenges and how they'll address them

The unfunded proposals? Sometimes they’re poorly written, and sometimes they’re even beautifully written. But all of them are clearly built on shaky foundations.

When Grant Writers Say "Not Yet"

Here's something else Jennifer Lynch said in her article that resonated with me: grant professionals need to be willing to say "not yet" when it matters.

If I tell you that your organization isn't quite ready for a particular grant, I'm not being difficult. I'm being honest. I'm protecting your reputation with funders and ultimately saving you time and energy on an application that won't succeed.

"Not yet" doesn't mean never. It means: let's get your house in order first. Let's build the infrastructure that will support sustainable growth. Let's make sure your next application is strong enough to win.

How to Work Productively With Your Grant Professional

Answer the questions. Even when they feel uncomfortable. Especially when they feel uncomfortable. Those are the exact questions reviewers will be asking.

Be honest about capacity. If you don't have someone to manage the grant post-award, say so. We can help you figure out solutions, but we can't write around a problem we don't know exists.

Invest in infrastructure before chasing funding. Get your outcomes measurement in place. Develop realistic cost allocation systems. Build your program model before you try to scale it.

Trust the process. A grant professional who pushes back on your timeline or asks for more information isn't trying to make your life harder. They're trying to position you for success.

Think partnership, not transaction. The best grant relationships aren't "here's my idea, write it up." They're collaborative processes where the grant professional helps you think strategically about what you're building and how to fund it sustainably.

The Bottom Line

Grant professionals ask hard questions because we've seen what happens when those questions don't get asked. I've watched organizations get funded for programs they couldn't sustain. I've seen the stress, the burnout, the mission drift that happens when you're just chasing money instead of building strategy.

We ask questions because we speak funder language. We know what reviewers are looking for because many of us—like me—are reviewers. We understand that a compelling narrative isn't enough if the foundation is weak.

So when your grant writer starts asking questions, lean in. Those questions are your roadmap to stronger programs, better proposals, and sustainable funding.

The organizations that answer them honestly are the ones that grow.