Years ago, one of my first projects as a paralegal was reorganizing the shared drive for a legal department. It took me the better part of three months, gave me more migraines than I’d care to admit, and taught me far more than I expected about organization, growing businesses, and people.

At the time, I thought I was organizing files. Looking back, I don’t think that’s what I was doing at all. I’ve been thinking about that project a lot lately. I can’t quite put my finger on why it keeps coming back to me, but every time I work with a business that’s struggling with organization, I find myself remembering those three months and everything they taught me.

I knew coming into the job that it would be difficult. Within six weeks the department had grown from one attorney to four, plus me. The attorney overseeing my work told me my first task would be organization. I clapped my hands and said, “I love organizing. Let’s do this.” What I didn’t realize was just how much of a mess everything had become.

Growth is tough. It’s tough for children as they learn to walk, talk, tie their shoes, and figure out who they are. It’s tough for parents when those same children grow up, move out, and suddenly the house is quiet again. Businesses aren’t any different. A one-person department works one way. A five-person department works another. Somewhere in the middle, there are always growing pains while everyone figures out what works and what doesn’t.

That legal department was no exception. One attorney had been there for about ten years. Then, almost overnight, there were four attorneys trying to work together. They all had different ideas, different experiences, and different ways of approaching things. That’s exactly why the project landed on my desk instead of theirs. They were busy reviewing contracts, answering regulatory requests, and doing the work only attorneys could do. I was a paralegal. I had the time to dig into the mess while they kept everything else moving.

And honestly, what I dealt with wasn’t really that terrible in the long run. Did it take three months? Absolutely. Did I get migraines? So. Many. Migraines. 

Most of my days looked exactly the same. Open the shared drive. Open my project spreadsheet. Figure out where I’d left off. Open another folder. Document every file. Then another folder. Then another. Somewhere in between there would be an attorney asking me to pull documents together for a regulatory request, write a quick case brief, track someone down for signatures, or help with whatever else had landed on their desk that day. Then I’d go right back to the spreadsheet.

At first, I thought I was organizing files. Eventually I realized I wasn’t even close. I was trying to understand them first. I’d open one folder and find a document. Then I’d open another folder and find the exact same document. Then I’d find another version with a slightly different name. Sometimes it had been filed under the client. Sometimes under the department. Sometimes under a regulator. Sometimes it lived in all three places. After a while I stopped trying to decide where anything belonged because I couldn’t even tell what I was looking at anymore.

That’s when I started documenting everything. Every folder. Every document. Every file name. Every last thing on that shared drive went into a spreadsheet. I even noted the last time each document had been opened because I needed to understand what I was dealing with before I started making decisions. It probably sounds a little excessive, but I couldn’t start unraveling the threads until I understood where they all led.

And that’s exactly what it felt like. Unraveling threads. Every time I pulled on one, I’d uncover three more. Some days I felt like I wasn’t making any progress at all. But little by little, patterns started to appear. Once I could sort and filter the spreadsheet, I realized something that surprised me. What we were working with wasn’t actually that bad. It just needed someone willing to step back and see the whole picture before deciding how everything should fit together.

When I finally finished my analysis, I put together a proposal for how the shared drive should be organized going forward. Not just the folders. Everything. Every historical document was renamed using the new naming convention because I didn’t want there to be an old system and a new system living side by side. I wanted one system that everyone understood. When I presented it to the General Counsel, she smiled and said it was exactly what she’d been hoping I’d come up with when she handed me the project. I’ll admit, that felt pretty good.

The attorney who’d been there for ten years had to adjust. That was expected. The newer attorneys picked it up quickly, and before long all of us were working the same way. Documents were named consistently. Files were where everyone expected them to be. Track Changes was turned on whenever documents left the department so nothing came back with silent edits. Discovery requests became easier because we knew exactly where to look. Everything simply worked.

The biggest thing I learned from that project had nothing to do with file names or folder structures. It was that nobody had created that mess on purpose. The more time I spent digging through those files, the less frustrated I became with the attorney who’d built the original system. I actually found myself wondering what those ten years had looked like for her. Was she overwhelmed? Was she simply trying to get through another busy day? I don’t know. What I do know is that everything she did probably made perfect sense at the time because she was the only one using it. She didn’t have to think about whether someone else could find a document while she was on vacation or out sick. She just needed a place to save it so she could keep moving. There wasn’t any malicious intent. There rarely is.

I think about that every time someone apologizes for the way their books look, the state of their files, or the pile of receipts they’ve been avoiding for months. When I tell you I don’t judge your systems, I mean it. You had a reason for doing things the way you did.

Maybe it worked when your business was smaller. Maybe it worked when you were the only employee. Maybe it worked when you had five clients instead of fifty. Or maybe you were simply overwhelmed and trying to make it through one more day. You made one quick decision because you didn’t have time to think about it. Then you made that same decision again tomorrow. And the day after that. Before long, it wasn’t a shortcut anymore.

It was the system. Sometimes we get trapped in that mindset of, “But I’ve always done it this way.”

I understand that because, at one point, that way probably worked. Businesses grow. People grow. The systems that got us where we are aren’t always the systems that will carry us forward. Sometimes we’re simply too close to see that ourselves, and that’s okay. Sometimes all we need is the willingness to step back and look at the whole picture. Sometimes we need another set of eyes to help us see what we’ve stopped noticing.

Sometimes I wonder if that attorney ever realized how much she taught me. Not about file organization or naming conventions, but about giving people grace. The more time I spent digging through those files, the less I saw a messy shared drive and the more I saw someone who had simply been doing the best she could with the department she had at the time. Nothing she did was malicious. It all made sense to her because, for ten years, it only had to make sense to her.

Honestly…I see that a lot. Not just in legal departments. In bookkeeping. In filing systems. In businesses that have simply outgrown the systems that once worked.

That’s why I don’t judge.When someone apologizes for their books or the state of their files before we even get started, I’m usually not looking at laziness or failure. I’m looking at growth. Sometimes all people need is someone willing to help them unravel the threads.