Five mistakes law firms make when adopting new tech

What are the most common mistakes law firms make when adopting new tech?

Our team at Vineskills has spent a lot of time thinking about the topic. When I polled them in anticipation of writing this, our Slack channel filled up with dozens of responses.

Here are the five most common mistakes that emerged and what to do about them.

Mistake #1: Adopting new technology is not a one-off project.

We often encounter busy teams hoping that transitioning to new technology will happen quickly so they can get back to work. But rolling out new technology like Filevine is not a one-off project with a set completion date. Instead, the most effective teams focus on bite-size, manageable steps that build upon each other. The good news is that this iterative approach not only leads to better outcomes, it also is a great way to engage and motivate people because they’re seeing continuous progress every week.

Mistake #2: Law firms overbuild their technology.

We’ve seen it again and again: a leader is convinced that a new technology with all the bells and whistles will solve all of their problems. But perfect is indeed the enemy of good. We’ve found it’s better to quickly launch something that’s 80% effective and incrementally improve upon it than to wait until everything is perfect. This can be hard for lawyers who have built their careers and reputations on precision and perfection, but embracing early imperfections and continuous improvement will lead to better outcomes.

Mistake #3: People have limiting beliefs about technology and change.

Considering technology as a threat is not only a career-limiting belief in today’s legal profession (see the Thomson Reuters report below for more on this), but it also can put a law firm at a disadvantage compared to its peers. Our team has heard self-limiting beliefs like, “I am not good at computers,” or “There’s no value in using AI.” The teams that struggle the most are the ones that view technology not as a friend but as something to avoid.

Mistake #4: The decision-makers around new technology are missing important context.

A fatal flaw of any tech implementation takes place when the person who is the primary champion or point-person for the new technology doesn’t have the authority to make final decisions. They might know exactly what needs to get built, but they must rely on another decision-maker. Too often, this decision-maker comes in too late in the process and is missing critical context. It’s wise to go slow early to go fast later by identifying the people who are closest to the work and deputizing them to shape how new technology is used.

Mistake #5: Law firms underinvest.

Finally, I’ve seen how law firms commit to a new technology but then underinvest in the time, training, and resources needed to make it effective. This is often a failure of imagination of what’s possible with a platform like Filevine. They want Filevine to help them do what they’ve always done, but just 1% better (when it can actually do so much more). As a result, they get roughly the same outcomes as their old systems, and soon they fall behind their peers (who are rapidly becoming tech companies).

Last Thought

Leading a team through a period of change is one of the most challenging jobs of any leader. I’m reminded of a quotation by Harvard Professor David Shore. He writes, “Managing change is about upsetting people only at a rate that they can tolerate.” His research on navigating the obstacles to effective change management resonates with our experience at Vineskills.

I’d love to hear your thoughts:

  • What is the biggest mistake you made when adopting new technology?

  • Do you have plans to introduce some change into your organization? What do you foresee as the biggest risks?

Helpful Resources

Here are some of my favorite articles I’ve read recently.

  • How to Use Legal Technology to Win More Clients (and Cases). We have seen first-hand how legal technology can help personal injury firms deliver an elevated client experience. This blog from Filevine outlines five ways tech can change client interactions for personal injury firms: 1) Reduce the number of missed leads from missed calls, 2) Automate administrative tasks, 3) Use client data to personalize service, 4) Leverage SMS technology for faster client communication, and 5) Provide real-time access to a client portal. Filevine (7 minutes).

  • The One Question That Can Unlock 1-on-1 Management Meetings. The front-lines of building an organizational culture are one-on-one meetings with your team. I loved this brief article about the one question that can transform one-on-ones to focus on surfacing hidden issues, creating psychological safety, and speaking the truth. MGMT Playbook (2 minutes).

  • Six Essential Lessons on How Leaders Champion Culture. I’ve learned that one of the most important jobs for any leader is to walk the talk and model the cultural behaviors they wish to see on their team. This is not easy; it can feel like you can't mess up. But “do as I say but not as I do” is a recipe for disgruntled employees and a loss of trust. This article features six lessons for leaders who want to champion their organization’s core cultural values. MIT Sloan Management Review (9 minutes).

  • 2025 Report on the State of the U.S. Legal Market. Every January, Thomson Reuters puts out a report on the state of the U.S. Legal Market. One insight stood out to me: While 2024 was a strong year for law firms, they face an upcoming era of rapid change, forcing them to leverage new technologies like AI and rethink their business and operating models. This is worth a read. Thomson Reuters (40 minutes).

Quick Inspiration

Four important questions to continually ask yourself, from acclaimed leadership coach Jerry Colonna.

  • How have I been complicit in creating the conditions I say I don’t want?

  • What am I not saying that needs to be said?

  • What am I saying that’s not being heard?

  • What’s being said that I’m not hearing?

Let’s Connect

We built Vineskills to help law firms more fully leverage the power of Filevine. If your company is looking for Filevine optimization, support, training, or implementation, we’d love to help. You can book a free help call here or just email me at troy@vineskills.com—I’d personally love to hear from you.

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