
Last week, Evan Glaser and Jon Lasley from Alongside AI joined us for a presentation on AI-ifying your law firm. Full recording here. They walked through four ready-to-use "skills" (basically text-based instruction sets) that plug into Claude Cowork and handle things like triaging new client inquiries, writing status updates, reviving stale relationships, and drafting content for LinkedIn and newsletters. They shared all of their skills with our members via a downloadable file that you can copy here. More on these skills (and how to sign up for their first workshop cohort) below.
🚨 What’s happening to our “This Week in HeyCounsel” weekly digest? Our newsletter is changing for the better. Instead of the weekly digest, we’ll be sharing hard-earned learnings from our community in a thoughtful, human-written format (like this edition).
So how do I get my digest? HeyCounsel members can get a weekly digest directly from Claude via our MCP Connector. Just add our connector and ask Claude for a weekly digest, and you’ll get a personalized overview of everything that happened inside our community.
And now, the skills from our conversation…
The Intake skill: It’s time to turn a Friday-at-5pm inquiry into a five-minute review instead of a 45-minute administrative burden. When a potential client emails you, the skill reads the inquiry, runs a conflict check against your contacts and matters, scopes the work using your rate card, fills in your engagement letter template, and drafts a reply email in your voice. The output sits as a Gmail (or Outlook) draft with the engagement letter attached. You review it on your phone during your commute home and hit send. The AI owns the middle (reading, structuring, drafting), and you own the end (judgment, accuracy, tone).
The Status Update skill. This one writes client-ready updates from your raw matter notes. You run it for one client or for all active clients at once. It reads the matter file, translates shorthand into clear language, and drafts one email per client in your inbox. It follows your conventions (Evan's default: where things stand, what's next, what I need from you) and deliberately omits internal strategy notes, like your negotiation floor or settlement targets. Light editing takes a minute or two per client. Evan showed a batch run across four active matters where the AI flagged which updates had an ask, which were FYI only, and which should be skipped.
The Relationship Engine skill. This one picks five people to reach out to each week based on a score it assigns contacts in your system. It reads your CRM, roster, or even an Excel sheet, and scores each contact on two axes: how long since your last real touch (weighted by relationship type, so a quiet referral source scores higher than a one-off past client) and whether there's a concrete reason to reach out now (buying a business, opening a second location). It picks exactly five, writes an opener for each one that references something specific, and drops five drafts in your inbox. Running this every Monday morning at scale gets you to hundreds of outreach touches per year.
The Content Pipeline skill. This one takes a bit of proactiveness. It reads a de-identified client-question or topic log (something you’d set up in Notion, Google Drive, Granola transcripts, or any note-taking tool), picks recurring evergreen questions, anonymizes client details, and drafts both a newsletter section and a shorter LinkedIn post in your voice. Evan showed an example built around the question "Do I really need a contract for a $5,000 project?" The skill scored it using a star system and explained why it chose that question over others.
The free starter kit with all four skills plus the customization skill is available here.
📆 HeyCounsel’s Upcoming Events
Wed, Aug 5 → The Fractional GC Practice: How to Structure, Price, and Protect an Advisory Book — nbi-sems.com/products/102686
Tue, Aug 11 → Selling and Acquiring Law Firms: A panel — luma.com/heycou-8pj5
Thu, Aug 13 → Setting up marketing automations to listen for signals: A demo with Osmaura — luma.com/heycou-q4bw
More from our conversation with Alongside AI…
Your AI system is only as useful as the information you connect it to. The most important step is integrating your AI agent into the systems where your business data already lives: Clio, Lawmatics, Practice Panther, Gmail, Outlook, Slack, Teams, Google Drive, SharePoint. The database doesn't need to be fancy. An Excel sheet works. A Notion table works. The key concept is making your business "queryable," meaning an AI system can search and read it. If you don't have a formalized system for something like conflict checking, you can build one from scratch with AI help.
You can schedule skills to run automatically instead of typing slash commands every time. Claude Cowork has a scheduling feature where you set a skill to run on a cadence. Relationship Engine every Monday at 8am. Status updates every Friday afternoon. Content Pipeline every Wednesday. The intake skill doesn't fit scheduling because it's reactive (someone submits an inquiry, you respond), but the other three are built for it.
Free tiers of AI tools are dangerous for law firms because your data may train the model. Evan recommends paid business or enterprise tiers where your data stays private. Beyond that, Claude Cowork lets you set granular permissions for each integration. Read-only access can be set to "always allow," while write access (drafting emails, creating files) can require your approval each time. Anonymizing client data before feeding it to any AI system is a good default habit.
Quick hitters from the session:
Start with one skill, get it working end to end, and expand from there rather than trying all four at once.
The Skill Creator skill (built by Anthropic) interviews you about your problem and writes a custom skill for you in plain English.
A "database" for conflict checking can be as simple as an Excel spreadsheet or a Notion table.
Use the Customization skill (included in the free starter kit) to adapt the four demo skills to your specific tools and preferences without manual editing.
Set Claude Cowork's permissions so read-only actions are always allowed but write actions require your approval.
⭐ The AI-Native Bootcamp. Interested in a 4-week bootcamp with Alongside AI and HeyCounsel? We’re launching an intensive, hands-on experience for 8-10 willing and able law firm owners to transform their practice to an AI-heavy operation. Reach out to [email protected] or reply to this email to hear more.
Thanks for reading! See you next week 🤙
- Brian Scherer, Co-Founder & CEO