There’s a certain groove that many attorneys fall into over time.
Like most things, it doesn’t happen all at once, it builds gradually. Case by case, deadline by deadline, and system by system.
At the beginning, it’s actually a good thing. You figure out how to get things done. You develop your own way of organizing files, communicating with clients, drafting documents, tracking deadlines. You learn where everything lives and how it moves. And most importantly, you prove to yourself that you can handle pretty much… anything.
This ability is what makes most attorneys successful in the first place: because challenges are just seen as invitations to crush another obstacle and learn something new.
That makes for a very particular (and effective) kind of person. If something needs to get done, you’ll figure it out. If there’s a gap, you’ll fill it. If the system isn’t perfect, you’ll compensate.
Over time, that feels like the ultimate form of control – but, eventually, that control turns into something else.
Too often, the same groove that makes you a powerhouse early on is also what makes it incredibly difficult to let go or change anything later.
It starts to feel like everything works only because you’re the one holding it all together. Then, because you’re the one holding it together, it becomes harder and harder to imagine how someone else could step into any part of it without making it worse or slowing things down.
That’s usually the moment where the idea of getting help starts to feel complicated.
Not in theory. (In theory, it’s obvious. Of course you shouldn’t be doing everything yourself.) But in practice, the question becomes: How would someone else even fit into this?
That’s the question I kept coming back to in my conversation with our Director of Client Services, Amber Horos.
Amber is so much more than our head of customer success – she’s someone who can tell what you need before you even know it. By the time you do, she already has a plan to find the outcome and capitalize on it once you’re there.
What stood out to me when we spoke recently wasn’t just how ILAs are trained or how onboarding works. It was how clearly she sees the point where delegation starts to break down and what practically has to happen for people to do it right.
One of the things that stuck with me was when she said that attorneys often don’t struggle to explain what their work is. They struggle to define what parts of that work need to be shared in the first place.
“Sometimes it’s really easy for the attorney to answer a question,” she said, “but they don’t know off the top of their heads what they actually need to relay.”
That’s such a simple observation, but it explains so much.
When you’ve built your workflow yourself, piece by piece, most of it becomes invisible to you. You’re not thinking about where files are stored or how you move through your CRM or what steps you take between receiving information and producing work. You just do it. It’s embedded.
Until someone else needs the steps laid out so they can help.
Often, this is where things start to feel heavier than they should. Because now, something that felt natural suddenly has to be translated.
The thing is, really effective workflow translation takes time. It takes attention. It takes a level of top-down perspective that most attorneys haven’t needed to create because they’ve been operating inside their own system for years.
So when people talk about onboarding or delegation being difficult, I don’t think it’s because the work is inherently too complicated for anyone else to understand. I think it’s because most firms are trying to hand off work without ever externalizing how that work actually functions.
Amber sees that play out in real time every day. What’s so interesting to me is how much of her role – and everyone’s role at DocketWorks, more broadly – isn’t just about providing someone to do the work. It’s about helping to structure workflow translation.
In our experience, this shows up in small ways that end up making a big difference. Preparing ILAs ahead of time based on the firm’s practice area and the types of tasks they’ll be handling. Walking through systems before they ever log in. Being present in those first few conversations, not just to facilitate introductions, but to ask the kinds of questions that pull information out of the attorney that they might not think to offer on their own.
Our ILAs are all excellent English speakers, so an actual translator isn’t ever needed. But having a “task translator” to interpret the way you’ve always done things and turn it into a system – that’s where you find the difference between trying to explain something once, and never doing it yourself again.
During our call, Amber mentioned that it typically takes between one to three calls to really lay the groundwork.
That number surprised me a little at first, but the more I thought about it, the more it made sense. It’s not that the process is long – it’s that it needs to be intentional. If those first interactions are focused in the right way, the rest of the working relationship stabilizes much faster than most people expect.
The other piece that came up, which I’ve seen in my own work as well, is the instinct to try to offload everything at once.
When you’ve been carrying that much responsibility for that long, there’s a natural desire to just hand it all over. But as Amber put it, that’s another point where things start to break down. “You want to start with a handful and then pause.”
That pause is doing more work than it seems. It creates space for alignment. It allows both sides to understand what “done correctly” actually looks like before adding more complexity. And it builds confidence for everyone that the systems are really working.
Things shift really quickly once that foundation is in place. According to Amber, it typically looks like this:
That progression matters, because it reframes what “getting help” actually looks like. It’s not an instant transformation, but it’s also not this long, drawn-out burden you see in the traditional hiring process that many attorneys assume it will be.
Maybe most importantly, the conversation I had with Amber highlights something I’ve run into in my own work as well. There’s a critical difference between being capable of doing anything and being responsible for doing everything.
For a long time, I operated under the assumption that those two things were the same. If I could do it, I probably should – and if I wanted something done a certain way, the easiest path was to just handle it myself.
But over time, that starts to create its own kind of bottleneck. Not because the work isn’t getting done, but because everything has to pass through the same person to move forward.
To be honest, it starts to take the satisfaction out of the day-to-day and you lose track of what’s important about your work in the first place. That’s when the groove really starts to work against you.
What Amber’s describing – and what DocketWorks is centrally built around – is a way of stepping out of the groove without creating chaos in the process. Not by removing yourself from the work entirely, but by creating the necessary structure around it that decenters you as the only point through which every little thing flows.
Because, at a certain point, the question isn’t about whether you can do everything. Most attorneys already know that they can.
It’s about whether your practice is structured in a way that requires you to.
And if it is, that’s usually not a reflection of whether or not you can delegate – it’s a reflection of the systems you’ve had to build to get this far.
The biggest challenge is realizing that the systems that got you here aren’t always the ones that will carry you forward.
The opportunity is recognizing when the groove you’ve built is no longer serving you – and having the structure in place to step out of it.
Taylor Teachworth works with the team at DocketWorks to share the systems, strategies, and perspectives that shape how today's law firms operate behind the scenes. Through interviews and thought leadership content, she translates the experience of attorneys and legal professionals into clear, practical insights for firms looking to make their practice work for them.