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Sneak Peak in New York City and Chicago: How LexBlog’s AI-Assisted Compass May Elevate Legal Blogging

By Kevin O'Keefe on March 20, 2025
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Next week in New York City at Legalweek, and the following week at ABA TechShow in Chicago, I’ll sit down with law firms and legal professionals to introduce something we’ve been working on at LexBlog: the LexBlog Blogging Compass—an AI-assisted tool designed to help legal professionals maximize the impact of their blogs.

This isn’t AI writing content. We’re testing AI—specifically, a large language model (LLM) trained on legal blogging data—to assist in evaluating, refining, and strengthening how lawyers share their expertise.

And the irony isn’t lost on us—who knew human engagement and authenticity could be improved with an assist from AI?

What Is Compass?

Compass is a blog evaluation tool, combining AI-driven insights and LexBlog personnel expert analysis to measure legal blogs against ten proven criteria for effective blogging.

The goal? To help lawyers and law firms identify what’s working, what’s not, and how to make their blogs more engaging, strategic, and impactful—without losing the personal voice that makes great blogging stand out.

Legal blogging has always been about connection—not just publishing but engaging, building trust, and sparking online citation and conversations. To build a name and grow business.

We believe Compass can help refine those elements, ensuring firms aren’t just posting content but creating meaningful digital engagement that drives business and builds relationships.

If you’re interested in learning more, please let me know—we can meet face to face in New York City or Chicago, or later on, via a video call.

We’d welcome your feedback, LexBlog client or not.

Photo of Kevin O'Keefe Kevin O'Keefe

I am a trial lawyer, turned legal tech entrepreneur, now leading the largest community of legal publishers in the world at LexBlog, Inc.

I am a lawyer of 39 years. Wanting to be a lawyer since I was a kid, I have loved…

I am a trial lawyer, turned legal tech entrepreneur, now leading the largest community of legal publishers in the world at LexBlog, Inc.

I am a lawyer of 39 years. Wanting to be a lawyer since I was a kid, I have loved almost every minute of it.

I practiced as a trial lawyer in rural Wisconsin for 17 years, representing plaintiffs, whether they were injury victims and their family members or small businesses.

In the mid-nineties, I discovered the Internet in the form of AOL. I began helping people by answering questions on AOL message boards and leading AOL’s legal community.

I later started my own listservs and message boards to help people on personal injury, medical malpractice, workers compensation and plaintiff’s employment law matters. Though we were green to technology and the Internet, USA Today said if my firm “didn’t stop what we were doing, we would give lawyers a good name.”

In 1999, I closed my law firm and we moved, as a family of seven, to Seattle to start my first company. Prairielaw.com was a virtual law community of people helping people, a sort of AOL on the law, featuring message boards, articles, chats, listervs and ask-a-lawyer.

Prairielaw.com was sold to LexisNexis, where it was incorporated into Martindale-Hubbell’s lawyers.com.

After a stint as VP of Business Development at LexisNexis, I founded LexBlog out of my garage in 2004 (no affiliation with LexisNexis).

Knowing lawyers get their best work from relationships and a strong word of mouth reputation, and not promoting themselves, I saw blogging as a perfect way for lawyers to build relationships and a reputation.

When I could not find someone to help me with my own blog, I started a company to provide what I needed. Strategy, professional design, platform, coaching, SEO, marketing and free ongoing support.

As a result of the outstanding work of my team of twenty and my blogging, the LexBlog community has grown to a community of over 30,000 legal professionals, world-wide.

Publishing my blog, Real Lawyers, now in its 18th year, I share information, news, and commentary to help legal professionals looking to network online, whether it be via blogging or other social media.

Blogging also enables me to think through my ideas – out loud and in an engaging fashion.

In addition to my blog, I liberally share others’ insight on Twitter. Feel free to engage me there as well on LinkedIn and Facebook.

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  • Posted in:
    Technology and AI
  • Blog:
    Real Lawyers Have Blogs
  • Organization:
    LexBlog
  • Article: View Original Source

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