Solo lawyers and small legal teams carry a load that does not look like the work in a larger department. You are expected to be an individual contributor and a strategic advisor at the same time. The day-to-day crowds out the strategic, and the strategic crowds out the someday list. AI is one of the few real options for closing that gap, but most of the guidance about it is written for big legal teams with budget, infrastructure, and people to spare. That is not the same problem.
This How to Contract webinar, hosted by Laura Frederick, brought in two lawyers who actually run on the small-team side. Michelle Fleming, Chief Legal Officer of a managed IT services company, has been a legal team of one for roughly 20 years. Ben Kiekel is Senior Counsel at Aptos Labs, where he heads up the commercial legal department for a layer one blockchain company. Both have been using AI in real workflows long enough to have horror stories, working shortcuts, and a useful sense of where the leverage actually lives.
The conversation covered why AI matters more for small teams than large ones, how to find the bottlenecks worth targeting before picking a tool, the workflow habits that catch hallucinations before they catch you, the daily shortcuts that compound, and how to use AI to handle work that would otherwise need a second or third lawyer.
Here are our top ten takeaways from the speakers' comments during the webinar:
Find your bottlenecks before you pick your tools. It is tempting to look at an AI product and ask what it does. The better question is where you are slow. Once you know where the work piles up, you can pick tools that actually solve that problem rather than tools that solve someone else's. This is especially important for solo lawyers, where every hour spent on the wrong tool is an hour not spent on real work.
Use AI for roughly 60 to 70 percent of the work, and reserve your judgment for the rest. That ratio is the actual leverage. AI handles the drafting, the formatting, the first-pass research, and the routine review. You handle the judgment calls, the risk decisions, and the things that only you can do. Trying to push the ratio higher tends to break things. Trying to push it lower means you are not getting the value.
Layer playbooks, personas, and context to compound the effect. A playbook alone is useful. A playbook plus a CFO persona seeded with the actual CFO's bio is significantly better. The output gets reviewed against your standards and through the lens of the person who will approve it. Layering is what turns AI from a faster typewriter into something that actually scales you.
Time-box your AI exploration so it does not eat the workday. Tinkering is how you learn what the tools can do. It is also how you spend three hours fine-tuning an intake form that was not your bottleneck. Set 30 minutes for play and 30 minutes for implementation. Decide upfront what you are trying to automate, augment, or leave alone.
Treat AI like it is out to embarrass you at the worst possible moment. It will randomly switch party names in one clause. It will fabricate entire pages of language and confidently cite to nothing. It will pass its own self-grading checklist on work it failed. The mindset is not paranoia. It is recognizing that the cost of catching errors falls entirely on you, so build the catching into your workflow.
Play models off each other to catch errors. Generating in one tool and reviewing in another works better than asking the same tool to find its own mistakes. Different models tend to be aggressive about flagging flaws in another model's output. Use Claude for drafting where writing quality matters, and run cross-checks through other tools. When a chat goes into a tailspin, kill it and start over with better upstream prompting.
Use AI to extract material issues for early business team conversations. When a 50-page agreement lands hours before a meeting, do not choose between skimming and postponing. Run it through AI, surface the issues the business team will care about, and send those ahead. They start working on the substance while you do the deep review. This protects your review time and creates real, not just perceived, responsiveness.
Build a final sanity check into every contract. Run the final draft through AI with a simple prompt. Check for logic errors, typos, missed section numbers, and broken cross-references. Do not engage with the substance. It is the easiest habit to build and it catches the most embarrassing mistakes, including provisions that were fine earlier in the negotiation but no longer fit the rest of the contract.
Refactor business memos before drafting. Business memos are written for executives, not for legal. They are over-broad where you do not need detail and missing detail where you do. Running the memo through AI to map it to the structure of your form agreement makes the gaps visible immediately. Now you can go back to the business team with specific questions while you start drafting.
Use AI to replace the lawyer you do not have. Solo lawyers are expected to be the GC, the DPO, the ethics hotline, and the regulatory expert on whatever the business needs. AI gets you confident enough in adjacent areas to make a real judgment call about handling work yourself versus sending it out. That judgment call is the value. Use the freed-up capacity to knock things off the someday list that always slides when urgent work crowds out important work.
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