Legal Ops Roundtable: Tips for a Successful Technology Implementation

Adam Friedman | April 28, 2022 | Articles

Implementing new technology can be a daunting task for an overburdened legal department already focused on meeting the legal needs of the core business. Between siloed attorneys, busy schedules, and a bias toward maintaining the status quo, legal ops leaders need to be driven, focused, and communicative in leading the charge to adopt new technology.

On Apr 21, 2022, SimpleLegal participated in LINK’s April roundtable hosted by Stephanie Corey (CEO, UpLevel Ops) and featuring Lyndsey Cain from the New York Times and Jamie Ingles from Stripe, where they discussed their best practices for effective change management. Here are our takeaways from the discussion.

Start with “Why?”

When implementing new technology it’s important to make sure you and your colleagues start by answering four essential questions:.

  • Why are we implementing changes?
  • What are the pain points?
  • What are we trying to solve?
  • Why are we solving it?

Clearly communicate why the change is happening, what your colleagues can expect, what the desired outcome is, and why it will be better than the status quo. Explaining the “why” is instrumental to getting buy-in from colleagues and defending your initiative from detractors.

Plan Ahead + Know Your Goals + Give Yourself Time

My dad always taught me nothing ever goes to plan and always assume things take longer than expected. My dad may have had some cynical insights, but he was never caught flat footed by life.

When it comes to change management, dad’s insights ring true. Implementing new software doesn’t just happen. It isn’t checking boxes. Successful change management means detailed planning: knowing the players, knowing what resources you need, knowing what a successful outcome looks like, and making sure you build in enough time!

Always assume things will take longer than you expect. When setting your implementation schedule, you should consider adding a time buffer into each phase of implementation, so you can account for unforeseen delays. It’s a lot easier to finish your implementation early than to explain why your solution is being delivered late.

Develop Internal Champions

Oftentimes a solution will impact multiple stakeholders: IT; Accounting; Procurement, etc. Once you’ve identified that you’d like to implement a new solution, make yourself an expert on the solution and educate your colleagues on how this new solution will positively impact their lives at work. Get your colleagues excited about eliminating manual data entry, about eliminating the need to track down open invoices, or about those extra 5 hours a week they’ll now have to spend with their kids. Sell the dream of what life will look like after implementation so you have allies in pushing the initiative forward.

(Over) Communicate

No change management initiative failed because too many people were informed! Don’t assume people know what you are up to or that they are staying on top of new initiatives… assume they aren’t. Make sure you let everyone who will be impacted by the change know that change is coming… scream it from every rooftop! Remind your colleagues in every email signature or newsletter… let them know every way you can, in whatever channel, so that there are no surprises and everyone is aware of and expecting the new solution.


Implementing a new solution is different every time and nothing will ever go perfectly. But, if you can learn to live with uncertainty and you remember the steps above, you will get through your next technology implementation and be stronger for it.

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