Why Projects Fail and Where You’re Probably Losing Money
- Apr 15
- 4 min read
At Hairpin, we work with a lot of organizations that have strong ideas, thoughtful strategy, and a real desire to grow.
I've had multiple people frustratedly ask me why nonprofits run so inefficiently. I used to say that it's because they don't have enough money to pay for top-quality talent in the way that a Fortune 100 company could. And while I know there is some truth to this, I have learned that talent is rarely the core problem.
The actual issue is much more pervasive and fortunately much more solvable.
The work just doesn’t get finished!
Projects start. Conversations happen. Everyone agrees on the direction and gets excited. And then a few weeks later, no one is quite sure where something stands or who is actually moving it forward.
This isn’t a talent issue. Honestly, it’s not even a time issue.
It’s a systems and accountability issue.
Where things start to slip
This is usually not as dramatic as an employee sitting on TikTok instead of doing their job.
Instead, an idea comes up in a meeting and never gets formally tracked.
Once in awhile, none of this feels like a big deal because we are so busy working on our missions.
But stack a few weeks of that together and multiple initiatives and then you start to see it.
That’s when teams say things like, “We’re so busy, but nothing is really moving!”
The cost no one is tracking
This is where it starts to matter more than people expect.
Not having a clear system doesn’t just slow things down. It affects how well your organization actually delivers on what it promises.
You see it in fundraising. But you also see it in programs.
A grant gets awarded, but the work behind it is loosely structured.
Staff are already stretched thin, so the program gets built on the fly.
Reporting becomes reactive instead of intentional.
The end result feels rushed, the funder feels completely underwhelmed, and all the good intentions in the world can’t make a difference in that funder’s desire to award you ever again.
That has real implications. Not just for outcomes, but for how donors experience your organization and whether they come back or move their dollars to a different organization.
And then there are the more visible operational gaps:
Staff spend time constantly revisiting conversations instead of executing them
Work gets duplicated, or quietly dropped
It’s not chaos. It’s just constant friction. And it adds up fast!
At some point, a real system becomes necessary
Here’s the part most organizations resist a little too long.
You can get by for a while using notes, email threads, or a shared document.
But once you have multiple priorities, multiple people, and real expectations tied to funding or service delivery, that approach breaks.
There is no single place where work lives. No clear ownership. No visibility into what is actually moving.
That’s where a project management system becomes essential.
Not nice to have; rather, necessary.
What a project management system actually does
A good system is not about being organized for the sake of it.
It does a few very practical things:
It gives every project a clear home
It forces ownership and accountability so nothing sits in abyss of “we”
It makes the next step visible at all times
When those are in place, execution improves quickly.
If you’re not sure whether this applies to you, try this:
List out everything your team is actively working on right now. Then ask three questions for each item:
Who owns this?
What happens next?
When is that happening?
If the answers aren’t obvious, or if the answers vary depending on who you ask, you’re already feeling the gap a system would solve.
What this looks like in practice
Last year we worked with a team that had three of their own annual giving and cause marketing campaigns planned and nothing was formally tracked so they just never got completed. Within two weeks of implementing a project management system, all three were back on schedule.
No joke. It was THAT simple.
Nothing about their strategy changed.
Instead, they just made the work visible and held each other accountable.
The tool matters less than the shift, but it still matters
There are plenty of tools that work: ClickUp, Trello, Asana.
I’m the typical technology nerd who geeks out hard on great apps. And I would argue an app helps a lot, but even without using some fancy too. The specific platform is not the hard part.
The hard part is moving from “we talk about work” to “we track and manage work in a shared system.”
This is what gets things unstuck!
What a project management system actually does
When teams adopt a real system, things start to feel and respond different quickly.
Projects move without constant follow-up.
Programs are built with more intention, not last-minute effort.
Campaigns launch when they are actually supposed to.
And your strategy starts… well, working.
What a project management system actually does
Most organizations are not short on ideas.
They are short on structured execution.
And at a certain point, that requires more than good intentions. It requires a system.
If things feel slower than they should, or like work keeps getting stuck halfway, it’s worth looking at how your work is being managed.
Because in most cases, that’s the difference between having a mission and actually delivering on it.
I’ll be honest: I hate fluff. The goal of this newsletter is simple: to give you insights that are actually useful in your day-to-day operations. Through our work at Hairpin, we’ve seen firsthand the challenges teams face around fundraising, data management and growing thier missions, and we want to share what we’re learning along the way.
Each month, we’ll highlight topics, ideas, and practical solutions that can help you strengthen your fundraising, make better systems, and ultimately increase your impact. If there are specific topics you’d like us to cover, I’d love to hear from you. And even if you don’t have anything in mind, feel free to reach out and say hi.
Thank you for being here, and I hope you enjoy. Here is to your next million!
Austin Pierce
Founder & Principal Consultant
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