When Repetition Gets Cheap, the Pyramid Breaks

Future of Law Newsletter — Issue #10

March 2026 (5-min read)

When Repetition Gets Cheap, the Pyramid Breaks

By Brett Colvin, CEO of Goodlawyer

Not long ago, AI in legal felt like a novelty. Now it’s changing the math.

Not because the tools are perfect, but because the cost of producing legal work is collapsing. The repeatable work that once justified time, headcount, and hierarchy is getting cheap.

The liability isn’t.

It lands with the person who signs—the name on the filing when something goes wrong. That’s what most AI commentary misses: the constraint isn’t capability. It’s accountability.

AI already does real work: first drafts, redlines, diligence summaries, research. It kills blank-page time. But it doesn’t take the meeting with the regulator. It doesn’t sit across from the board. It doesn’t get examined under oath. Responsibility stays with the senior lawyer who signs off on the outcome.

A deal turns overnight. The AI-driven first draft is “good” until it isn’t. One defined term shifts. One indemnity exception doesn’t track. One “close enough” clause becomes the clause everyone fights about.

Nobody sues the tool. They sue the company.

And then they ask: Who approved this? Why wasn’t it escalated?

The most valuable lawyer isn’t the one who uses AI the most.

It’s the one who knows where it must stop.'

The metrics have changed

GCs are being asked to run legal like an operating function, not a priesthood. The scorecard now looks like every other department’s: cycle time to close, spend per deal, and headcount efficiency.

You’re expected to move faster without adding people, defend every rate increase, and explain spend in plain English. If you can’t explain the invoice in one sentence, you’re not buying expertise—you’re buying layers.

For decades, legal careers were built on volume: you learned by doing and advanced by pushing more paper. When repetition gets cheap, ladders built on volume start to crack. The premium shifts to orchestration and ownership: steering the model, catching misses, escalating early, and signing off when it counts.

Drafts accelerate. Accountability doesn’t.

The pyramid breaks

Large firms run on leverage. Partners sell judgment, juniors do the work, and the meter keeps running. Associates aren’t overhead. They’re profit.

AI makes junior time less scarce—and less billable. When a client can get a solid first pass in minutes, they stop paying for three rounds of drafting and layered review.

As drafting and review get automated, revenue and headcount decouple. Some firms will bolt AI onto the old structure. That buys time. It doesn’t fix the economics.

So pricing changes. Fixed fees normalize. Thinner teams compete. And if legal doesn’t redesign allocation intentionally, finance will do it for them.

Routine shrinks. Signature risk doesn’t. So decision power concentrates with the people who sign.

What this unlocks

This shift doesn’t have to make the loneliest jobs in the company lonelier. The best CEOs and GCs build for concentrated accountability: clear decision rights, tight escalation paths, and seasoned judgment close to risk. They use AI to compress noise, not outsource responsibility.

In practice, that means fewer lawyers doing repetitive work and more experienced lawyers embedded where decisions get made. They shape workflows, catch misses, and keep things moving.

Goodlawyer is built for that world: senior lawyers close to risk, AI in the background, fewer handoffs, faster decisions.

The winners won’t be the teams that automate the most. They’ll be the teams that know exactly what can’t be automated—and build around that edge.

Brett Colvin
CEO, Goodlawyer

The Making of a Key(stone) Decision Maker

By Zak Biggs

Peter Piliounis spoke with Zak Biggs about leading lawyers, burnout, and his journey from Biglaw to being a Fractional GC, with a stop at Cambridge.

ZB: Give us the quick career rundown — the greatest hits.

PP: I spent a few years at Bennett Jones, then moved to Clifford Chance in London. Then I did a Master of Laws at Cambridge — probably one of the best years of my life — and taught law for a year.

I worked in-house in the UK, then came back to Canada and eventually joined TransCanada (now TC Energy). I was there for 13+ years, then decided it was time to do something different. I tried a few things before becoming a Fractional GC.

ZB: How did your time as Director, Legal at TransCanada shape you as a leader?

PP: The biggest shift was learning how to lead lawyers. Lawyers value autonomy. You point them in the general direction and let them figure it out. If you give them ownership and space, they’ll usually surprise you in a good way.

ZB: What were you working on during those in-house years?

PP: A lot of new project development and joint ventures. I was involved in the original Keystone pipeline — from a whiteboard concept, to entering into long-term contracts, to converting an underused gas pipeline into oil service, and then having the project built. That kind of work is fascinating because I wasn’t just analyzing risk. I was helping shape something tangible from the ground up.

ZB: So why leave a senior in-house role?

PP: Burnout, if I’m honest. And I was doing less actual legal work than I used to. I missed it.

Fractional practice appealed because of the flexibility and the variety. I can choose the kinds of clients I work with and the type of work I take on. If I want to go for a bike ride in the middle of the day, I can — as long as the client's needs are met.

ZB: As a Fractional GC, you partner closely with executive teams, rather than slotting into an established legal team. What do you enjoy about working that way?

PP: I prefer the variety. In a big legal department, you’re often doing one narrow type of work. I’m also comfortable making the call. I’ll assess and outline the risk as green, yellow, or red — and explain how to mitigate it. I like helping the executive team move forward with clarity.

ZB: You did your LLM at Cambridge. What’s your best memory?

PP: I enjoyed being back in school and teaching law afterward. But what has stuck with me was playing “ice hockey,” as they call it, for the university team. We ended up winning the varsity match against Oxford. That was a highlight.

ZB: You’ve described your current work setup as “pretty cushy.” What do you mean?

PP: I work less than full-time by choice. On a per-hour basis, the compensation is comparable to what I made in-house. I just choose to work fewer hours.

I get flexibility, variety, meaningful work — and a life I actually enjoy. I often have other lawyers ask me, “How can I get the same?” I tell them, "Goodlawyer."

Connect with Peter on LinkedIn. To practice like Peter, visit our For Lawyers page.

Cohere's In-House Team Thrives with Goodlawyer

Brett and Zak flew to Toronto with one goal: film this video with Goodlawyer’s biggest customer.

Our latest vlog follows their mission to meet Kosta Starostin, VP Legal at Cohere — Canada’s largest AI company.

Watch the video.

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