This Week in HeyCounsel (May 28, 2026)

The gap between early-adopter enthusiasm and practical utility of AI; how members are preparing contract playbooks from scratch; an event about AI notetakers and the practice of law.

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Weekly Community Digest

May 28, 2026

29

Client
Opps

28

Questions
Answered

5

Upcoming
Events

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⚡ This Week in 30 Seconds

15 new client opportunities this week. England & Wales estate administration, legal malpractice, trademark strategy, SaaS contracts, LLC-to-debt conversion, and more. See all  Members
A member posted an honest take: they can't figure out how to make Claude genuinely useful. Daily limits hit before anything substantial gets done. 6 replies covered the gap between AI hype and real-world utility. See this week's Community Spotlight. Read the thread  Members
The Claude Cowork Teams subscription question got practical. Members worked through the data privacy implications and at least one creative workaround for solos who need the DPA protections but don't need all the seats. Read the thread  Members
Next Event: What should lawyers consider when using AI notetakers? Practical guidance on privilege, client consent, engagement letter language, and tool selection. RSVP here
 

🔥 Community Spotlight

The Honest AI Post

A member posted something this week that a lot of people are probably thinking but not saying: they legitimately don't understand how to use Claude in any useful way for their practice. It helps with polishing and brainstorming, but anything more complex either doesn't work or hits the daily usage limit before they've done anything substantial. They tried building an expense tracker. It kept losing pieces. By the time they asked it to fix the third thing, they were at their limit. The conclusion: it would have been faster to do it manually.

Six replies followed -- and they were good ones. Members talked about the gap between early-adopter enthusiasm and practical utility, why the ROI depends heavily on what you're asking it to do and your tolerance for setup time, and the honest reality that off-the-shelf AI still requires real investment before it pays off. One member said you're "much closer to normal than you may realize." Another pointed to pre-built skills as a way to get value faster without the learning curve. Worth reading if you're trying to calibrate where AI actually fits in your practice right now.

Read the thread →  Members

 

💬 Threads of the Week

When Your Client Wants More Than Legal Help →

An FGC asked about the practical and ethical considerations of taking on CAO/COO-type executive work alongside legal work for a startup client. The thread is a useful checklist: what malpractice and E&O insurance covers (and doesn't), how your entity type may restrict non-legal services, why you need to keep legal and non-lawyer work separate to protect privilege, and what engagement letters should say when you're wearing both hats. Multiple members have done this -- the tradeoffs are real but manageable if you structure it right.  Members

How Members Build Their Contract Playbooks →

A member asked how others go about preparing contract playbooks from scratch. The community covered the practical approach: start with your standard templates, add fallback language for the clauses that always get negotiated, and refine over time. A format that came up as a favorite -- a simple chart with the clause, fallback 1, and fallback 2, plus notes on the tradeoffs for each position. AI is now in the mix for first passes.  Members

Ethics Counsel for the AI Era →

A member asked for referrals to external ethics counsel who can handle the questions that are coming up right now -- AI notetaker disclaimers in engagement letters, internal AI acceptable use policies, conflict check frameworks. Bar guidance is still catching up. Members offered referrals and a few stepped up to help directly. If you're trying to get ahead of the ethics issues that come with building an AI-native practice, this thread has a useful shortlist.  Members

Claude Cowork Teams Plan: What Do You Get, and What Do You Do with Extra Seats? →

A member asked about upgrading to Claude Cowork's Teams plan primarily for the DPA and no-training-on-your-data guarantees. The thread got specific: the primary account owner can export all chat data, users can't see each other's chats by default, and extra seats are a real consideration for solos who don't need a full team. At least one member shared a creative approach they're already running to put those seats to work without waste.  Members

All threads above are members only.

 

🏆 Community Win

A member posted this week that they've been struggling with focus and motivation working solo -- and asked if anyone wanted to co-work virtually as an accountability partner. By the time replies rolled in, the conversation had shifted to organizing a standing "Flow Club" -- a virtual co-working channel where members can drop in, post their intentions, and work alongside each other in real time.

Multiple members stepped up. The community organized itself around a real need, in a single thread, in a single day. That's what this place is for.

Apply to join HeyCounsel →

 

🚀 New Client Opportunities

A small sample of this week's opportunities -- members get access to the full list, plus the ability to submit proposals.

1. England & Wales Estate Administration for US Beneficiary with International Tax Issues →
2. Legal Malpractice Attorney Needed -- CA-Licensed or Pro Hac Vice in MN →
3. Trademark Strategy, Feasibility, and Cost Analysis for Brand Portfolio →
4. Commercial Contracts Counsel for Georgia B2B SaaS Startup →
5. LLC Equity-to-Debt Conversion and Promissory Note -- Tight Deadline →
6. New York Subsidiary LLC Formation and DBA Filing →
7. Defense Contracting & Export Controls (ITAR/EAR) Co-Counsel for Interim fGC Engagement →

See all opportunities →  Members

Want access? Apply to join
 

📅 Upcoming Events

JUN
9

AI Notetakers and Your Law Practice

What should lawyers consider when using AI notetakers? Practical guidance on privilege, client consent, engagement letter language, and tool selection.

Register →
JUN
17

Build Your Firm Website with Claude Code

A hands-on session walking through how to build and launch a professional firm website using Claude Code. No prior coding experience required.

Register →
JUN
18

Biz Dev Q&A with Megan Senese and K. Adam Bloom

A focused Q&A on business development strategies for independent practitioners -- what's working, what's changed, and how to build a sustainable client pipeline.

Register →
JUN
29

Contract Attorneys, Co-Counsel, and Of-Counsel Arrangements

A practical session on structuring co-counsel, contract attorney, and of-counsel relationships -- fee arrangements, ethics considerations, and how HC members are making it work.

Register →

Full calendar →

 

⚖️ Why Join HeyCounsel?

HeyCounsel is a vetted private community for solo and small firm lawyers. The idea is straightforward: independent practitioners deserve the same resources, relationships, and opportunities that large firms take for granted. Here's what membership includes:

✔️  New client opportunities and member referrals
✔️  Best practices for building AI-native firms
✔️  Relationships in a private Slack community of vetted peers
✔️  Exclusive discounts on tech & services, including Spellbook, GC AI, and more
✔️  Hundreds of member-contributed templates
✔️  Free CLEs, educational programming, and mastermind groups
✔️  Private demos, hackathons, and in-person events
Apply to Join HeyCounsel →
 

Have a great week,
Brian

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