Maximizing Your Paralegal Skills: Shining in the Side Projects

Legal Technology, Practice Management

As a paralegal, you’re probably quite adept at research. Your current position demands that you be detail-oriented, organized, and efficient. And for those reasons, senior partners at your law firm may have tasked you with working on side projects, such as suggesting ways that the firm can use legal technology to become more efficient.

Or maybe they haven’t asked, but when you see the everyday processes at work in your firm, your gut tells you that the systems are screaming to be optimized. You can feel it in your bones that your competitors are besting you —  not by skills or strategy but with technology.

Either way, there’s an opportunity for you to shine in your paralegal position.

So, where do you start maximizing your paralegal skills?

Approach the challenge by first building a list of needs. Understanding what success looks like to the decision-makers is like giving you the answers to a test before seeing the questions. It gives you the ability to reverse-engineer the process and fill in the gaps.

How do you reverse-engineer a solution?

At its core, every automation solution replaces a repetitive task. When done right, it eliminates human error and accelerates the process of finishing the job. Follow these four steps to successfully build a case for an automated solution in your firm:

Step 1

Start by making your own observations about the tasks that could be automated. Talk to other paralegals, assistants, clerks, and secretaries about repetitive, mistake-prone, and cumbersome tasks. Insights from your colleagues will give you a feel for where the opportunities are so you can speak more specifically with project stakeholders.

Step 2

Informally talk to the project stakeholders about what they’d like to accomplish specifically. Ask each one what success looks like. Expect that answer to differ. Ultimately their responses will get you closer to finding the right solution choices for your firm. Get each stakeholder to put general parameters on the project (time and money). Ask them to identify any priorities. Leaving these questions open-ended will give you a better sense of the overall picture and existing opportunities for short and long-term wins.

Step 3

Compile your feedback. Ideally, you will see overlap between stakeholders. Congratulations! These overlapping results have now become your critical deliverables because you’ve got consensus support. 

Step 4

Review the feedback you initially got from the other paralegals, assistants, clerks, and secretaries. Identify the potential automations that could tactically deliver the goals outlined by the stakeholders. When you can see those possibilities align, then you know you’re on the right track.

“The secret of change is to focus all of your energy, not on fighting the old, but on building the new.” – Socrates

Now it’s time to research solution choices 

Researching business solutions is different than your legal research. For instance, many review sites you may initially uncover may be nothing more than paid promotion sites designed to look like actual, unbiased comparison sites. These sketchy comparison sites can help you identify major players in the space (since they have invested in being on the site), but make sure to vet them from secondary sources supported with third-party reviews, such as Capterra and G2.

Visit legitimate 3rd Party Review Sites.

Once at those sites, use as few words as possible to not overlook potential software choices. For instance, at Capterra, type in “legal” to get:

  • Legal Billing Software
  • Top 20 Legal Billing Software
  • Legal Billing Software Buyers Guide
  • Legal Calendaring Software
  • Legal Case Management Software
  • Top 20 Legal Case Management Software
  • Legal Case Management Software Buyers Guide

At Capterra, you can carefully review the Buyers Guide to see how their top considerations align with the priorities of your stakeholders. For instance, for legal case management software, Capterra notes that integration with existing systems, mobile accessibility, and deployment options are all primary purchase considerations. Integrate that knowledge into your research.

Looking for practice management solution to replace your current systems stack? Download the free, LegalTech Practice Management Buyer’s Guide today. 

Make a list of key players. 

It’s OK if the list is a little longer than expected. You will cull it down soon enough.

Visit their corporate websites. Yes, all of them. 

Once you’ve immersed yourself in the space, you will begin to understand the breadth of your choices, and ideally, the differences between those choices.

Expect to have to cut through the jargon.

Unfortunately, many SaaS (software-as-a-service) companies are guilty of speaking technology language, not a customer-friendly language, in part to hide shortcomings. Use your detective skills to uncover what they’re NOT saying by looking specifically for how they would handle your firm’s specific needs. Consider choices that are built specifically for law firms instead of ones more broadly based. They will always better understand your business as it evolves.

Use this reference to bring tech-talk into plain-speak and help prioritize what may be important for your firm or identify areas for consideration.

Use your network. 

What solutions are your competitors using? Why follow their lead? Because the companies you consider to be competitors are likely similar-sized, with similar business needs. Ask around within your network to see what names bubble to the surface. Look for feedback in LinkedIn groups or through legal associations. If you can engage in conversation, find out what people most like and dislike about their choices. Keep track of the info. It’s not a deal-breaker, but it can give you a viable line of questioning if the software makes it to the consideration phase.

Remember that everyone’s experience is different. 

Never eliminate a solution based on a single opinion. You’re looking for a solution that will work for your firm.

Shorten the list.

It’s time to review your choices. Cull down the list to 3 or so solid candidates. Any more than that makes it too much for your stakeholders to consume. For bonus points, create a list of strengths and weaknesses of each. Make it easy for your superiors to make a decision.

Set the stage. Own the hassle. 

Deployment is always bumpy. It’s like when you upgrade your mobile phone. If you launch it from scratch (without a direct backup), it’s always a hassle. An app crashes. You lose some text messages. Your photos may disappear before they reappear. And the off button isn’t where it used to be.

Your firm’s stakeholders will want it done after hours, so there’s no downtime. Your IT department will want to do testing to make sure it’s secure. No one will want to take the time needed to learn the new system and get onboarded. Instead, they will ask 100 questions about how it works. The bottom line, the transition is a hassle. But the rewards are worth it. Set expectations upfront so that your firm isn’t surprised in the end.

Compile your suggestions into a tidy presentation.

Use this framework to create a short presentation deck for the stakeholders as follows using Andy Raskin’s Strategic Narrative approach:

  1. Name the undeniable shift in the world that creates big stakes and huge urgency—yours will be around automation.
  2. Show that there will be winners and losers—law firms that don’t adapt will be left behind.
  3. Tease the promised land—what this change will help achieve—big picture results for your firm.
  4. Introduce features as magic gifts for overcoming obstacles—focus on stakeholder goals.
  5. Present evidence that you can make the story come true—by investing in one of these short-listed solutions. Then add next steps on how to get it done.


You’ve turned a side project into a working example of how well you understand the big picture goals of the firm. You’ve reverse-engineered the process by getting the stakeholders to tell you what success looks like, and by talking to peers about where the bottlenecks are. Then you assessed the choices to build a viable list of options. Finally, you used a proven presentation framework to present your case.

Let us know how it goes. Of course, we’d love to be in the mix for considerations.

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