🌟 Editor's Note
Welcome to Multihat. A newsletter for legal professionals who wear a lot of hats. Multihat is a publication for Conxtrued, a free, open source prompt library for legal professionals.
I am one of your hosts, Caroline, and let me tell you how this newsletter will work. First, I may adjust the template below depending on feedback (I love feedback, good or bad). Second, I will focus on prompting, news and legaltech tools. For the legaltech tools, they will be tools I find online or try myself, but this will never be an endorsement for any of them. Third, and finally, I like to write with a sense of wry humor, please keep that in mind.
🗓️ Upcoming AI Conferences for Legal Professionals
If you received your AIGP certification, then this conference is a good way to get your continuing education credits.
Dates: September 18-19, 2025
Location: Boston, MA
It looks like it might be focused on law firms, but it explores how to use AI in your practice.
Dates: November 19-20, 2025
Location: New York
🚀 The AI Legal Update
Winning the Race: America’s AI Action Plan
Where did it come from? It came from Executive Order 14179 signed on January 23, 2025
The focus: Limiting regulation of AI to propel innovation
Why should you care? It favors states that limit AI regulation, which means we may see a slow down in states passing laws on this topic
🦄 LegalTech AI Tools
LegalOn Technologies: Contract Review for In House Teams
I was introduced to this company via a webinar with 177 of my legal colleagues. Considering I have seen webinars get 3 attendees, this was pretty impressive and shows the legal community interest.
The Founder(s): According to Crunchbase, the founders are Nozomi Tsunoda and Masataka Ogasawara, who are former corporate lawyers from Japan. The current CEO is Daniel Lewis who was hired in late 2022 to help with the company’s expansion. It appears that Daniel Lewis did go to law school, but never practiced law, and has been a legal technologist for most of his career.
Key Innovation: Workflow automation for in-house legal ticketing, contract review and internal collaboration.
Funding: $50M Series E round, in July 2025.
🔥 Prompting Courses for Legal Professionals
If you are looking for how to prompt…
GCAI offers prompting for lawyers regularly.
Sterling Miller wrote a blog post on the topic.
🏆 Prompt of the Month
And the Award Goes To!
Marc Mandel
🌉 Background: General Counsel of EXOS. Check out his LinkedIn.
👑 Prompt: IP Risk Assessment of AI Provider ToS
Vibe Lawyering
If you have been “vibe lawyering” like me, then you might also hate it when your work starts to become a marketing cliche. But here we are.
I don’t really think vibe lawyering is a thing that is any different than what lawyers have been doing for decades, taking a template and word smithing it.
The cool thing about vibe lawyering with a chatbot or legaltech tool is that you can converse with the document. For example, the other day I was working on the cyber breach notification section of a contract. Usually these provisions are burdensome on the vendor, but one specific bit of text is impractical. It states, “if vendor suspects or confirms unauthorized access of the products, vendor shall immediately provide notice to customer. Such notice shall contain the date the breach occurred, details of the breach, etc.…”
It is impractical because if a vendor suspects a breach, are they able to provide a notice with details, what was accessed, etc.? No. Probably not.
So, I prompted my custom GPT that I built (with all the US state privacy laws) with the following, “I don’t like the “suspects” language that triggers a notification requirement that may 1. delay the vendor from actually investigating and confirming the breach and 2. require details that the vendor does not have and may never have because their suspicions turned out to be false. Please adjust the language highlighting your deletions and bolding your additions.”
This worked pretty well in that it broke apart suspected breaches notifications from actual breach notifications. Apparently this is vibe lawyering.
About your author? I am a corporate securities attorney originally trained at Gunderson Dettmer as a “startup lawyer” until I went in-house as a General Counsel at two tech startups, Sailthru (2011-2015) and Clarifai (2015-2018). Clarifai is an AI company and gave me the confidence and the expertise to start my own AI tech company, so now I know the ins and outs. Currently, I am a partner at Outside GC where I focus on AI, cybersecurity, privacy, M&A, corporate/ securities and every other hat you can wear as a general purpose lawyer. I have been practicing for 25 years and licensed in CA and NY.
See you later!