Laura Frederick, Chief Executive Officer of How to Contract, hosted this webinar with Tanya Avila, General Counsel at Marquis, and Chris Crook, General Counsel at CSC Leasing. Tanya has been the first general counsel at five different startups, so she has built this function from nothing more than once and has the data habits to show for it. Chris spent almost 20 years in law, starting as an intellectual property litigator at a large firm and moving in-house at a big company with a proportionally tiny legal team, and he now runs legal alone for a company of about 85 people. One of them has scaled the same problem repeatedly and the other is living the solo version right now, which kept the conversation practical rather than theoretical.
They covered how to triage work when everything looks urgent, when to send work outside to a firm or an alternative legal service provider, how data should drive your next hire, how to build a playbook that stays useful without constant upkeep, why the process has to get fixed before the technology gets bought, and how to keep expectations honest with the business and the C-suite.
Here are our top ten takeaways from the speakers' comments during the webinar:
Triage on purpose instead of by volume. Tanya told us there is no formula for deciding where a small team spends its time, so she runs a set of levers instead. Team capacity comes first, then internal visibility, then complexity and who has the background for it. The visibility lever is the one we tend to underweight. A low dollar contract that the executive team is watching carries a risk that has nothing to do with its terms.
Budget real time for educating the business. Tanya sits with her contract generators at least once a quarter so they understand what her team can and cannot negotiate. She explains the reasoning rather than the rule, which lets them defend a position to a customer without escalating to legal. Chris does the same with his sales and account management teams. Education looks like overhead until you count the escalations it prevents.
Let your own data tell you what to hire. Tanya tracks what her team does and looks back six to 12 months when capacity gets tight. She asks whether the pressure comes from complex redlines, from high volume routine work, or from contract people getting pulled into problems that are not contracts. The answer sometimes points to a process instead of a person. Hiring without that analysis usually means hiring the resume that quiets the loudest complaint.
Plan for continuity when you are the only lawyer. Chris chose a junior attorney over a paralegal or contract manager for his first hire, and continuity drove much of that call. He said plainly that he could get hit by a bus and the company would still need a lawyer who could pick up the work. He expects a contract manager or paralegal to be the hire after that. Both roles matter, and the order you hire them in should follow what breaks first when you are gone.
Consider an alternative legal service provider for routine volume. Tanya has used them and worked for them, and she described pricing built around blocks of hours or projects rather than partner rates. Her last arrangement gave her up to 20 hours a week at a fixed weekly cost, with her playbooks in their hands and the staffing decisions on their side. She would not send them major litigation or a big corporate transaction. The real constraint is that you have to find time to train them, which is the same time you do not have.
Build a playbook that explains the reasoning. Chris had AI draft a playbook from his leases, then fed it every redline he had made since starting and told it to ask why whenever a change did not make sense. What came out captures the risk behind each position instead of just the acceptable language. A junior lawyer working from that can handle a variation nobody anticipated. A bare list of fallbacks leaves them guessing the moment the counterparty goes off script.
Match the playbook to the audience using it. Tanya keeps one playbook and changes the training around it. Contract generators get the explanation of what the language does and why it reads that way. The legal team gets the fallbacks and the business risk behind them. Chris keeps his bottom line positions out of the sales version, because a team that can see the floor tends to get there fast.
Map the process before you shop for tools. Tanya has watched teams spend tens of thousands of dollars on AI and then discover the bottleneck was intake, or a clause renegotiated so often that a template change would have solved it. Chris put it flatly when he said you cannot fix a broken process with tech. Tanya also weighs ease of adoption and favors tools that plug into the customer relationship management system so sellers never leave the software they already work in. Software nobody opens is worse than no software, because you paid for it and still have the problem.
Be transparent with the business about what legal can absorb. Chris called his approach brutal transparency. He shows the business everything sitting in the legal queue and asks them to help set the order, including what moves to the back burner and what goes to outside counsel with a budget attached. That conversation turns a legal capacity problem into a business decision with a price tag. It also means the answer belongs to both of you.
Bring the C-suite evidence about what AI actually does. Chris pointed out that executives hear from every direction that AI will cut legal headcount, and telling them it will not is an argument we lose. He got access to AI tools in a secure environment, built things with them, and came back with specifics about where they helped and where they missed. Tanya chairs a cross-functional governance committee that tests tools and evaluates the results. That way the verdict on a tool comes from the committee rather than from legal appearing to defend its own budget.
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