The Future of Law Starts in the Group Chat

Future of Law Newsletter — Issue #6

November 2025 (5-min read)

The Future of Law Starts

in the Group Chat.

By Brett Colvin, CEO of Goodlawyer

Every GC I Know

Law used to run on hierarchy. It started in law school during OCIs, when the “cool” (smartest?) kids got scooped by Big Firms before they even knew what the Rule Against Perpetuities was — or why they should care. From there, the path was linear: you summered, articled, got hired, then waited your turn.

In Biglaw, hierarchy shaped everything — who got promoted and how work moved. Tasks went down. Decisions went up. Associates drafted. Seniors reviewed. Partners approved. Control was the point, but it came at the cost of speed, agility, and impact.

Now law runs on connection. Every GC I know is in a group chat with their team, their law-school friends, and their peers at other companies. What started as Slack threads and WhatsApp groups has become the new campus for in-house lawyers — where late-night DMs turn into friendships, answers arrive in seconds, and confidence grows through connection.

Firms built hierarchies. GCs build trust. And if you’re in-house, you can feel it — the center of gravity has shifted.

The New Rules

Law once rewarded control: knowing every answer, closing every loop, being the smartest person in the room. That worked when information moved slowly and status moved fast. But the room changed.

Information now moves too quickly to hoard. The advantage isn’t knowing — it’s accessing. Modern in-house lawyers compete on speed, clarity, and trust. Inside these digital circles, they’re rewriting the playbook in real time — sharing scars, testing ideas, and building confidence together.

AI didn’t just make drafting faster; it broke the scarcity model of legal intelligence. Research, contracts, and risk analysis are now instant commodities in an open market for knowledge.

When knowledge becomes abundant, its value drops. What rises are the things that can’t be automated: judgment, empathy, and context.

That’s the paradox: the smarter the machines get, the more human lawyers must be.

What Comes Next

The best GCs already see it. They’re building a new operating system for legal work — powered by AI, data, and trust — and proving value through impact, not hours. The walls are coming down, and conversations are moving faster than firms ever could.

We see it every day inside the Goodlawyer Slack — lawyers connecting, sharing wins and lessons.

On November 20, more than 2,000 lawyers will gather for the Future of Law Summit to explore how AI, community, and leadership are reshaping what it means to practice.

Because what’s next won’t be built by institutions. It will be built by lawyers — one DM, one question, one act of generosity at a time.

The future of law starts in the chat.

Brett Colvin
CEO, Goodlawyer

Telling Your CEO They're Wrong – And Other Ways to Build Trust as a GC

By Zak Biggs

After 18 years as General Counsel at MNP, Charmaine Toms, K.C. knows how to speak truth to power. Three weeks in, she told her then-CEO his plan was “all wrong” — and still landed a seat at the exec table. She sat down with Zak Biggs to talk trust, budgets, and what comes next.

ZB: What move helped you earn your seat at the table?

CT: Three weeks in, I walked into the then-CEO’s office and said, “That whiteboard plan you drew for Legal is all wrong.” It was a bold move, but I trusted my legal knowledge and my belief that the business needed something different, which I presented. That moment set the tone – that I’d speak hard truths, but always with a solution.

ZB: What do you think is the key to a good GC/CEO relationship?

CT: Trust, hands down. You need to know each other as people, not just titles. Go for lunch, ask about their family, and remember their kids’ names. Connection beyond the work builds the trust you need to tell hard truths and know you have each other’s backs.

ZB: What’s your take on GCs reporting to the CFO instead of the CEO?

CT: If the GC doesn’t report to the CEO, that’s a red flag for me. It tells me Legal isn’t seen as strategic and puts them a step behind the real decision-making. To be effective, I think you need a direct line to the CEO, full stop.

ZB: What advice do you have on getting legal budget approval?

CT: Start by showing you run a tight ship. I was careful with every dollar — whether it was meal expenses or managing external counsel. I always stayed in the trenches, questioned the legal bills, and kept scope in check. That built trust with the CEO and CFO. So when I asked for more budget or a new hire, they knew I wasn’t padding — I was planning. Most years, the question was “Are you sure that’s enough?”

ZB: You chose to retire earlier than most lawyers — why and what’s next?

CT: After an amazing career, I wanted to step aside at the right time and make space for the next generation. I am loving my freedom, but am still connected to the legal world and trying to help leave the profession better than I found it.

I’m mentoring, going for coffees, and chairing the Future of Law Awards — which I’m proud to be part of, because in-house lawyers deserve a lot more recognition than they currently get. I can’t wait to see that change, be part of the Awards and attend the Future of Law Summit later this month!

Connect with Charmaine on LinkedIn and register for the Future of Law Summit here.

LEGAL EVENTS

Future of Law Summit (Virtual, Nov. 20)

You already know it’s the biggest (and most entertaining) virtual legal event of the year! Join 2,000+ lawyers coming together to reimagine the future of our profession. We overheard Josh Weinberger rehearsing his closing keynote — that man has gravitas.

Invite your lawyer friends by copy/pasting the following:

Hey! Are you signed up for the Future of Law Summit hosted by Goodlawyer on Nov 20? It’s free and virtual with 2,000+ lawyers exploring AI, community, and leadership. 3.25 hrs of CPD. Check it out: https://summit.goodlawyer.ca/

Future of Law Awards (Toronto, Nov. 20)

Announcing the finalists for the GC of the Year Award... 🥁

Congratulations to Alice, Farah, Niamh, Craig and Jennifer!