The Annual Compliance Calendar Every Nonprofit Should Know

SPEAKER_00: 0:00

Welcome to the Nonprofit Compliance Brief, where we explain charitable solicitation and multi-state fundraising requirements in clear, practical terms for nonprofit leaders and finance teams. This podcast is produced by Ironwood Registrations.

SPEAKER_01: 0:13

Uh, it’s really wonderful to be here today to dig into this topic.

SPEAKER_00: 0:17

Yeah, and uh I think this is a big one. You know, I was I was reading through a forum for nonprofit finance directors the other day. Just trying to get a pulse on what uh what keeps them up at night. Right. And there was this one comment that really stuck with me.

SPEAKER_01: 0:33

Oh yeah. What did it say?

SPEAKER_00: 0:34

Well, this person described their job uh not as financial management, but as professional firefighting.

SPEAKER_01: 0:41

Wow. Yeah, that that sounds painfully accurate for a lot of folks in this sector.

SPEAKER_00: 0:45

Right. And the biggest source of the heat, the thing that was causing the most burnout. It wasn’t the big strategic decisions.

SPEAKER_01: 0:51

No, of course not.

SPEAKER_00: 0:52

It wasn’t the mission work. It was the compliance paperwork. It was this uh this pervasive feeling that the work simply never ends. Like it feels like a really high-stakes game of whack-a-mole. You know, you smash one deadline in May, you feel good for a minute, maybe you go grab a coffee, and then wham, three more just pop up in June.

SPEAKER_01: 1:11

Aaron Powell And just when you think you’re clear, you get a surprise letter in August from, you know, some state you forgot you were even registered in.

SPEAKER_00: 1:18

Exactly. And that letter always seems to arrive on a Friday afternoon, doesn’t it?

SPEAKER_01: 1:22

Aaron Powell Oh, without fail. Always at 4 30 on a Friday.

SPEAKER_00: 1:25

Aaron Powell Right. So it feels random, it feels chaotic. And frankly, for the people we’re talking to, these are really smart, dedicated professionals.

SPEAKER_01: 1:34

Yeah.

SPEAKER_00: 1:35

It is incredibly stressful to operate in that constant state of reaction.

SPEAKER_01: 1:38

Oh, absolutely.

SPEAKER_00: 1:39

You’re just crouching there waiting for the next shoe to drop.

SPEAKER_01: 1:41

Aaron Powell And that reactive state is well, it’s the enemy of good management. I mean, it burns people out and it completely distracts from the mission. But here’s the thing, and this is really the core mission of our deep dive today based on the annual compliance calendar data we have in front of us. Okay. Those deadlines are not random. They aren’t. No. I mean, they might feel random when you’re in the trenches dodging bullets, but they aren’t.

SPEAKER_00: 2:04

So despite all the chaos, you’re telling me there’s actually a method to the madness.

SPEAKER_01: 2:09

There is absolutely a method. There is a predictable rhythm, like a seasonality to compliance.

SPEAKER_00: 2:14

I like that word, seasonality.

SPEAKER_01: 2:15

Yeah. And the goal today is to help you, the listener, move from that stressful reactive state into a proactive state. We want to show you the underlying mechanic.

SPEAKER_00: 2:25

The gears of the machine.

SPEAKER_01: 2:27

Exactly, the gears. So you can predict exactly when those moles are going to pop up before they even break the surface.

SPEAKER_00: 2:32

Man, I love the sound of that. Moving from chaos to an actual system. So let’s unpack the root cause first.

SPEAKER_01: 2:40

Sure.

SPEAKER_00: 2:40

If there is a system, why does it feel so relentless? Like why does it feel like as soon as we finish one filing, another one just magically lands on the desk?

SPEAKER_01: 2:49

It feels constant because you aren’t dealing with a single entity. You’re dealing with a whole web of distinct sources that all operate on their own independent schedules.

SPEAKER_00: 2:59

So it’s not just quote unquote the government asking for one big report once a year.

SPEAKER_01: 3:04

Precisely. That is the common misconception. You have the IRS, which is the big one everyone knows. Trevor Burrus, Jr. Right.

SPEAKER_00: 3:09

Federal.

SPEAKER_01: 3:10

Right. But then you have state charity regulators. And that’s usually the attorney general’s office, or maybe a specific consumer protection division in a state.

SPEAKER_00: 3:18

Aaron Powell And they’re totally separate from the IRS.

SPEAKER_01: 3:20

Totally separate. Then you have the secretaries of state, often in multiple different states. And on top of all that, you have your own internal governance obligations.

SPEAKER_00: 3:30

Wow. And I’m guessing none of these agencies sat down in a conference room together to coordinate their calendars and make life easy for nonprofits.

SPEAKER_01: 3:38

Not even a little bit.

SPEAKER_00: 3:40

Shocking.

SPEAKER_01: 3:40

They do not talk to each other. So the result is what the source material calls a rolling calendar.

SPEAKER_00: 3:45

The rolling calendar.

SPEAKER_01: 3:46

Yeah. It isn’t one annual deadline. It’s a cycle that follows the organization year-round. However, and here’s where the insight really clicks there is one variable that dictates almost everything else.

SPEAKER_00: 3:59

Oh. One variable to rule them all.

SPEAKER_01: 4:02

Essentially, yes. The anchor for your entire compliance year is your fiscal year.

SPEAKER_00: 4:07

Okay, your fiscal year.

SPEAKER_01: 4:08

Yeah.

SPEAKER_00: 4:08

That seems sort of obvious on the surface, right? Of course, we report on the fiscal year.

SPEAKER_01: 4:12

Right.

SPEAKER_00: 4:13

But how does that create the domino effect for all these other completely disparate agencies?

SPEAKER_01: 4:19

Aaron Powell Well, nearly all compliance timing begins with the organization’s fiscal year end. The most obvious one is the IRS form 990. The deadline for that is tied directly to when your books close.

SPEAKER_00: 4:31

Okay. Let’s put a concrete example on this for the listeners so they can visualize the timeline in their heads as we go through this.

SPEAKER_01: 4:37

Aaron Powell Sure. Let’s take the most common scenario. If your fiscal year ends on December 31st, that typically creates a May 15th deadline for your IRS form 990.

SPEAKER_00: 4:48

Okay.

SPEAKER_01: 4:48

That’s your anchor date. That is the domino that tips over the rest.

SPEAKER_00: 4:52

Got it. So May 15th, that’s the big red circle on the calendar.

SPEAKER_01: 4:55

Right. But here is the connection people often miss.

SPEAKER_00: 4:58

What’s that?

SPEAKER_01: 4:59

Many state filings and charitable registration renewals rely entirely on that financial reporting cycle. They can’t happen until the financial reporting is ready.

SPEAKER_00: 5:07

Oh, I see.

SPEAKER_01: 5:08

So essentially your compliance calendar really starts with your financial reporting readiness. If that’s delayed, everything downstream gets delayed.

SPEAKER_00: 5:16

That is such a key point. Yeah. If you’re late getting your audit done or your 990 is held up, you aren’t just late with the IRS.

SPEAKER_01: 5:24

No.

SPEAKER_00: 5:25

You’re effectively stalling your license to operate in multiple states.

SPEAKER_01: 5:29

Exactly. It creates this massive traffic jam for the rest of the year. So if we look at this chronologically for a standard calendar year organization, where do you think the work actually begins? Well. Because if the tax form isn’t due until May, people might assume January and February are just quiet months to recover from the holidays.

SPEAKER_00: 5:47

I am going to go out on a limb and assume they are not quiet.

SPEAKER_01: 5:50

You would be correct. They are not. This brings us to the first phase of our calendar walkthrough, which is the early year. Let’s call this the governance phase.

SPEAKER_00: 5:58

Okay. So what exactly is happening in January and February?

SPEAKER_01: 6:01

Usually this is the time for corporate maintenance. Now, this is distinct from fundraising compliance, and that is a distinction that trips up a lot of really sophisticated finance teams.

SPEAKER_00: 6:10

Let’s break that down because I think people definitely use those terms interchangeably. What’s the practical difference between corporate maintenance and fundraising compliance?

SPEAKER_01: 6:20

Think of it like owning a car versus having a driver’s license.

SPEAKER_00: 6:24

Okay.

SPEAKER_01: 6:25

Corporate maintenance is about your legal standing to exist as an entity. That’s owning the car.

SPEAKER_00: 6:30

Right.

SPEAKER_01: 6:31

Fundraising compliance is about your permission to drive it, your permission to ask for money.

SPEAKER_00: 6:36

This is a great analogy.

SPEAKER_01: 6:38

So in the early part of the year, you’re often dealing with the Secretary of State filings, you’re filing annual reports, confirming your registered agents, maybe updating the state on board member changes or officer changes.

SPEAKER_00: 6:49

Right. So this is the we still exist, and here’s our current address stuff.

SPEAKER_01: 6:53

Exactly. It’s maintaining the corporate shell. And it’s vital because if you lose your good standing with the Secretary of State, if you get administratively dissolved, it jeopardizes everything else.

SPEAKER_00: 7:05

Right. Because you can’t register to fundraise if you don’t legally exist.

SPEAKER_01: 7:08

Exactly. But again, this is completely separate from the charity regulators who care about your actual donations.

SPEAKER_00: 7:14

Okay, so January and February are for housekeeping, getting the corporate house in order. Then the snow melts, the birds start chirping, we hit spring, and the tone changes.

SPEAKER_01: 7:26

Yes. In the nonprofit world, spring means one thing: IRS reporting season.

SPEAKER_00: 7:31

The main event.

SPEAKER_01: 7:31

The main event. For a December 31st fiscal year end, spring is dominated by preparing the Form 990, finalizing the financial statements, and getting all those supporting schedules together.

SPEAKER_00: 7:42

And based on the source material we reviewed for this deep dive, this really seems to be the make or break moment for the rest of the year.

SPEAKER_01: 7:49

Oh, it really is. This period drives almost all other compliance activity.

SPEAKER_00: 7:53

Because of the downstream effect.

SPEAKER_01: 7:55

Right. Because the states, those charity regulators we mentioned earlier, they rely on these IRS filings for their renewal reviews. They want to see the 990. They want to see the audit.

SPEAKER_00: 8:04

So if you’re messy in the spring.

SPEAKER_01: 8:06

You are guaranteed to have a chaotic summer and fall. If the spring filings are late or if they have errors, it disrupts the entire flow of the year. You can’t renew your license to solicit in many states without that 990 attached.

SPEAKER_00: 8:18

That is a crucial insight. The 990 isn’t just a federal tax form to keep the IRS happy. It’s effectively the passport you need to enter the state renewal season.

SPEAKER_01: 8:28

Precisely.

SPEAKER_00: 8:33

We hit that May deadline. We wipe the sweat off our brow. The team wants to take a break. Can we go to the beach now? I mean, it is summer, after all.

SPEAKER_01: 8:42

Well, you can go to the beach, but you better have good Wi-Fi and maybe a waterproof laptop.

SPEAKER_00: 8:46

Oh boy.

SPEAKER_01: 8:47

Because once the IRS forms are filed, the charitable registration renewals begin appearing.

SPEAKER_00: 8:52

The shift.

SPEAKER_01: 8:53

Yes. The shift from federal to state. States have varying renewal cycles, but many of them align their deadlines shortly after the IRS filing is complete. They know you just finished your taxes, so they say, okay, send us the data.

SPEAKER_00: 9:06

And this is where it gets complicated for organizations that are growing, right?

SPEAKER_01: 9:10

Yeah.

SPEAKER_00: 9:10

Because not every state has the same deadline.

SPEAKER_01: 9:12

No.

SPEAKER_00: 9:13

It’s not like everyone just magically agrees on June 15th.

SPEAKER_01: 9:16

Right. Right. I mean, if you’re only registered in one state, it’s pretty simple. But if you’re fundraising nationally, you might have these staggered deadlines. Some are due four and a half months after the fiscal year ends, some are due six months after. Some allow extensions, some don’t.

SPEAKER_00: 9:31

And this brings up a major theme from the research that I really want to highlight for you listening. There is a very clear correlation between success and complexity here.

SPEAKER_01: 9:40

That’s right. And it’s an important point. Compliance tends to expand alongside fundraising growth, and organizations that review requirements periodically avoid most problems.

SPEAKER_00: 9:50

That is a really powerful statement. Can you unpack that a bit? Why does growth specifically trigger this compliance trap?

SPEAKER_01: 9:58

Just think about the mechanics of growth. As you grow, you find donors in new states. You register in those states to be legal. Now you have more deadlines in the summer window. Right. If you aren’t reviewing those requirements periodically, you just get caught off guard. You might think, oh, I just have the usual three renewals like last year, but suddenly, because of your growth, you actually have 10.

SPEAKER_00: 10:19

Wow. So summer is really about managing that complexity. It’s about taking the work you did in the spring and systematically distributing it to all the different jurisdictions that require it.

SPEAKER_01: 10:28

Yes. And coordination is absolutely key here. You need to make sure the right documents get to the right states at the right time. You are essentially syndicating your financial data across the country.

SPEAKER_00: 10:38

Okay. So we navigate the summer renewals, we push through, we’re moving into fall. The leaves are turning. Pumpkin spice lattes are back. And interestingly, the data calls this period the peak.

SPEAKER_01: 10:52

Yes. Fall is often the busiest compliance period of the entire year.

SPEAKER_00: 10:57

Wait, really? Really? I would have thought spring with the IRS deadline was the busiest. Why does fall take the crown?

SPEAKER_01: 11:03

It’s the convergence. Remember, many states synchronize their filings with the physical reporting cycles, but they often have extension periods or due dates that land in the fall, specifically around November 15th for calendar year filers. So you get this massive clustering of renewals right toward year end.

SPEAKER_00: 11:20

What exactly are they asking for in the fall? Is it brand new data?

SPEAKER_01: 11:24

No, it’s usually the same data, but packaged for different regulators, updated financial statements, the IRS filings you completed earlier, officer certifications, and sometimes additional disclosures specific to certain states like California or New York.

SPEAKER_00: 11:37

And here’s the irony that always gets me. When is the most important time for fundraising?

SPEAKER_01: 11:43

Year end, the last quarter, giving Tuesday. That is the ultimate sprint.

SPEAKER_00: 11:48

Exactly. So right when the development team is screaming, we need to focus on the annual appeal, we need to focus on revenue, the finance team is completely buried in the peak compliance season.

SPEAKER_01: 12:01

It is a massive structural conflict. The administrative burden hits exactly when the organization needs to focus on revenue.

SPEAKER_00: 12:08

And this is where that reactive versus proactive mindset we talked about earlier is just critical.

SPEAKER_01: 12:13

It’s essential. If you’re reacting in the fall, you are taking resources away from fundraising. You’re pulling the executive director into compliance meetings to sign forms when they really should be out at donor lunches. If you planned for it, compliance is just a background process running quietly while the main stage is focused on the mission.

SPEAKER_00: 12:31

That is a huge motivation to get this right. You want the compliance to be invisible so the mission can be visible.

SPEAKER_01: 12:39

Exactly. Perfectly said.

SPEAKER_00: 12:40

So we survive the fall crunch.

SPEAKER_01: 12:43

Barely.

SPEAKER_00: 12:43

Barely.

SPEAKER_01: 12:44

Yeah.

SPEAKER_00: 12:44

We hit the end of the year. Is December just a time to rest?

SPEAKER_01: 12:48

Well, hopefully there’s a little bit of rest involved, but strategically, year end is the preparation phase for the next cycle.

SPEAKER_00: 12:56

So instead of just filing, we’re actually evaluating.

SPEAKER_01: 12:58

Yes. This is the time to look at the big picture. You should be reviewing your donor geography. Where did the money actually come from this year?

SPEAKER_00: 13:07

Okay.

SPEAKER_01: 13:07

Did we get a bunch of new donors in a state where we aren’t currently registered?

SPEAKER_00: 13:11

Oh, that’s a really good catch. Because if you accidentally raised, say,$50,000 in Florida because a campaign went viral, you need to know that before you file your next report.

SPEAKER_01: 13:21

Exactly. You cannot just copy paste last year’s list. You should also look at fundraising expansion plans. Is the team planning a big digital campaign next year? That might trigger new registration requirements. You should look at organizational changes, new officers, new addresses, and a really big one-up coming audit thresholds.

SPEAKER_00: 13:43

Okay, stop there. What do you mean by audit thresholds?

SPEAKER_01: 13:46

So this is a technical nuance that trips people up constantly. Some states require an independent audit once your revenue hits a certain level. Okay. For example, maybe you didn’t need an audit last year because you’re under the cap. But if you had a great fundraising year, you might have just tripped that wire.

SPEAKER_00: 14:03

You need to know that in December.

SPEAKER_01: 14:04

You have to know it now. You do not want to find out in May that you needed an audit when you’re scrambling to file your 990. That is a total disaster scenario because audits take significant time.

SPEAKER_00: 14:15

So proactive review here prevents massive surprises in the next cycle. It basically resets the clock.

SPEAKER_01: 14:20

It closes the loop. The cycle ends, but it also begins again right there.

SPEAKER_00: 14:24

This walkthrough makes it so clear that this really isn’t random. It’s a machine. But even with a map, people still get lost. What are the common mistakes you see? Where do otherwise smart people go wrong in this?

SPEAKER_01: 14:37

The biggest pitfall we see is silos.

SPEAKER_00: 14:40

Like tracking deadlines in totally separate departments.

SPEAKER_01: 14:43

Exactly. It happens all the time. Legal has the Secretary of State deadlines because they handle the corporate stuff. Finance has the IRS deadline because it’s tax. And development has the state charity renewals because it’s fundraising.

SPEAKER_00: 14:57

And they aren’t talking to each other.

SPEAKER_01: 14:58

They aren’t talking. So if one drops the ball.

SPEAKER_00: 15:01

The others don’t know until it’s too late.

SPEAKER_01: 15:02

Right. The second huge mistake is relying on individual memory or what we call tribal knowledge.

SPEAKER_00: 15:09

Aaron Powell Uh, the Susan factor.

SPEAKER_01: 15:11

Right. Oh, Susan always handles the Pennsylvania renewal in August. Well, what if Susan leaves? What if Susan gets sick?

SPEAKER_00: 15:16

What if Susan just forgets because she’s swamped with the audit?

SPEAKER_01: 15:19

Aaron Ross Powell Exactly. Relying on human memory instead of real systems is just dangerous. Another common one is confusing those corporate filings we talked about in January with the charitable registrations. People think, oh, I filed my annual report with the Secretary of State, so I am completely good to fundraise.

SPEAKER_00: 15:36

And as we establish, that is definitely not the case. One is existence, the other is permission.

SPEAKER_01: 15:42

Correct. And finally, the wait and see approach. Only addressing renewals when a notice actually arrives in the mail.

SPEAKER_00: 15:48

Aaron Powell, which feels like the very definition of that whack-a-mole stress we started with.

SPEAKER_01: 15:53

It is. Notices get lost, they get mailed to old addresses. If you wait for the notice, you’re likely already late, and now you’re paying late fees.

SPEAKER_00: 16:00

Okay, so let’s talk solutions. How do we build a system that actually works? How do we stop the firefighting?

SPEAKER_01: 16:07

It starts with a centralized deadline tracker. It doesn’t have to be fancy software, though that obviously helps. Even a simple shared spreadsheet is better than nothing. But it has to be central and it has to be accessible to everyone involved. Legal, finance, and development.

SPEAKER_00: 16:22

A single source of truth.

SPEAKER_01: 16:24

A single source of truth. And you need clear internal ownership. Who is responsible for which line on that spreadsheet? Is it the CFO? Is it the development director? An external firm.

SPEAKER_00: 16:36

Right. And I really like the idea of aligning this with other regular business rhythms.

SPEAKER_01: 16:40

Yes. Align compliance reviews with your budgeting process or your board meetings. Make it part of the regular operational discussion, not just some annoying side project. And conduct an annual compliance check-in, just like you do a performance review for staff, do a performance review for your compliance status.

SPEAKER_00: 16:57

Aaron Powell The takeaway here really seems to be that most issues arise from coordination gaps.

SPEAKER_01: 17:02

Yeah.

SPEAKER_00: 17:03

Not necessarily because the regulations themselves are impossible to understand.

SPEAKER_01: 17:07

That is spot on. It is rarely the complexity of the law that gets people in trouble, it is the complexity of their own internal lack of coordination.

SPEAKER_00: 17:15

So let’s bring this all together. What is the big picture here for you listening who is maybe feeling a little overwhelmed by all these dates and requirements?

SPEAKER_01: 17:22

The big picture is that nonprofit compliance is not random. It follows a predictable seasonal pattern tightly tied to your financial reporting. It’s a rhythm.

SPEAKER_00: 17:32

And once you hear the beat, you can dance to it.

SPEAKER_01: 17:34

Exactly. By understanding this rhythm, deadlines become manageable. They stop being emergencies and just become standard tasks. Planning turns a major source of stress into a stable operational process.

SPEAKER_00: 17:47

And that ties back to a really interesting thought about culture. I’ll just throw this out there for you to mull over. When you view compliance as a cycle rather than just a checklist, it fundamentally changes the culture of the finance team.

SPEAKER_01: 18:01

Absolutely.

SPEAKER_00: 18:02

It stops being about just getting it over with and starts being about maintaining a healthy ecosystem for the organization to thrive in.

SPEAKER_01: 18:08

That’s it. It’s about building a foundation that supports the mission rather than a burden that detracts from it. When the foundation is solid, you can build as high as you want.

SPEAKER_00: 18:17

Well, I certainly feel less stressed just talking about it. It’s amazing how much clearer things look when you lay them out on a timeline like that.

SPEAKER_01: 18:24

It really does make a difference. It puts you back in the driver’s seat.

SPEAKER_00: 18:27

If you found this discussion helpful, you can find additional compliance guides and visual resources at ironwoodregistrations.com. Thanks for listening.