What I learned about lawyers after I stopped being one.

Law firm clients have started keeping score. In Thomson Reuters’ 2026 Future of Professionals report for law firm leaders, 77% of clients said AI-enabled quality improvements from outside counsel are essential. Only 3% to 6% said most of the firms they use are delivering. Seventy-one percent of in-house legal professionals expect firms to change how they charge as AI use grows, yet only 28% of firms say they have changed their pricing at all. The report frames this as a technology gap. From a buyer’s perspective, I see something else: the gap clients feel most is in the work AI cannot do.

Twenty years ago, I was a partner in the health care and health policy practice at a large firm. I have not billed an hour since. Instead, I’ve built companies in some of the most heavily regulated corners of the economy, including medical devices, digital health, medical diagnostics, and pharmacy, and have paid for a great deal of legal work along the way.

The gap between a lawyer and a principal is wider than most law firm partners believe. It is not the distance between a lawyer and a layperson. I still read the statutes and the regs. It is the distance between someone who produces legal work and someone who must decide, on a Tuesday, whether to spend $60,000 on a legal analysis or on a new salesperson.

Since then, a handful of lawyers have become genuinely indispensable to me. What they have in common is worth describing precisely because the pattern is learnable; it is not what most client-service training teaches, and the firms that already understand it are quietly winning the founder market.

One example: selling a venture-backed medtech company to a foreign market leader. The deal involved more than a dozen patents and nearly as many purchase, licensing, and co-development agreements, all tied to onerous engineering metrics and regulatory hurdles. The acquirer had a wide array of in-house and outside counsel, both at home and abroad. Our side had one lawyer. It took a year to close, and we weren’t billed until closing, an unrequested courtesy. Unsurprisingly, that lawyer now ranks among the nation’s top life sciences attorneys.

They answered the question I actually asked.

The lawyers who earned the most of my business shared one instinct: they gave me an answer.

Not a survey of the authorities. Not a range. An answer, with the reasoning attached and the risk priced. “Here is what I would do. Here is the chance I am wrong. Here is what being wrong costs you.” That formulation is worth more to a founder than any amount of additional research because it is the only form in which legal advice becomes usable.

The reason is structural, and it is easy to miss from inside a firm. Client-service training is built around the in-house buyer, a lawyer embedded in a company whose job is to absorb outside counsel’s work and translate it for the business. That buyer values carefulness and is well served by it. A memo that lands on “it depends” is useful to a general counsel.

The founder has no translation layer. I am the translation layer, and I also run the deals, sign the contracts, and live with the outcome. The best lawyers recognized this and adjusted what they delivered without being asked. They were not less rigorous. They understood that the rigor had to be spent getting to a recommendation rather than documenting the space around one.

The same instinct shows up in how the best firms introduce themselves to founders. The strongest pitches I have ever received reflected a deep understanding of the issues facing an early-stage CEO rather than the general counsel of a large enterprise. No office map, no practice group inventory. I am buying two or three specific people, and the firms that lead with those people and offer creative solutions consistently win the meeting.

They were available, and that told me everything.

A pattern I did not expect has held for two decades with almost no exceptions: the best lawyers are the reachable ones.

They take the call. They answer within the hour, even if the answer is “give me until tomorrow.” I assumed this meant they were less in demand. The opposite is true. They have seen the issue before; they know within minutes whether it is difficult or routine, and that fluency buys them the time to be accessible. Expertise creates availability.

In the founder market, availability is part of the substance. In a 340B drug-pricing contract negotiation or a provider transaction, the decision window is often measured in days, and advice that arrives after it closes has zero value, regardless of quality. The lawyers who understand this deliver a good answer on Thursday and refine it later. I call them first the next time.

They understood my objectives, and they knew what the market was.

Two related habits, and both are about recall rather than research.

The first is holding the company’s objectives, not just the matter’s. Founders run several things at once, and the same contract can be a revenue play in one quarter and a tactical option in the next. The counsel who mattered most to me could open a call already knowing what we were trying to accomplish and how this piece fit with the rest of the business. That is what makes a relationship compound: I stop paying for ramp-up and start paying for judgment.

The second is knowing what the market is in the moment. When I ask mid-negotiation whether a three-year exclusivity with a twelve-month tail is standard for this kind of arrangement, the valuable answer comes back in that same conversation. Market knowledge comes from scores of deals, and I pay a premium for it.

In regulated health care, this extends to the operating model, and it is where the best counsel separate themselves. They can describe, unprompted, how the money moves: who bills, who is reimbursed, at what rate, on what timeline, and where the margin sits. In this sector, that knowledge is a precondition for the legal analysis, and the lawyers who have it produce structures that are both defensible and actually operable, the only kind worth paying for.

They priced the decision, not the document.

Legal spend competes with a hire, additional marketing, a build, or a market entry. The firms that present a fee in those terms stand out immediately because they answer the question I am actually asking: not “is this a fair rate for this work,” but “is this the best use of the next $75,000 in the business?”

The counsel who understand propose a scoped, staged first phase that determines whether the deal is even worth pursuing before anyone commits to the full engagement. They put a number on it. And when the answer can be reached without them, they say so. The very best are willing to tie part of the fee to the deal signing or the round closing.

They argued with me.

The best legal work I have bought did not arrive solely as a recommendation. It arrived as an argument.

There are almost always several structures that yield an acceptable answer, and the one we start with is rarely the one we should finish with. What I want is a counterparty in the thinking and the analysis. Someone willing to say, “that works, but here is a second path, and here is what each does to your economics,” and then willing to have the version we land on look nothing like what either of us walked in with.

That takes real confidence because I am going to push. I will war-game downstream consequences that are hard to see from outside the business: what a covenant does to a hiring plan, how a structure reads to a future acquirer, and which concession costs nothing today but everything in eighteen months. The lawyers I have kept around the longest treat that pressure as the point of the exercise. Those conversations produce better structures than either of us would reach alone, and they are the most valuable services I buy.

They brought me ideas, but also knew when to hold them.

The counsel I value most brings things forward unprompted. A structure they saw work elsewhere, a regulatory shift that opens a door, or an observation that what we are building could be sold in two ways instead of one. Some of the best moves my companies have made began as an aside from a lawyer who was not asked.

The ones who are exceptional at it also size up the room. They know the difference between when an idea is a gift and when it is a distraction — the day a deal is cratering, the week we are heads-down on diligence, and the call when I need a decision, not a horizon. They hold the idea and bring it back the following week, when it lands as insight rather than as a pitch. That timing instinct is the difference between counsel who feel like a partner and counsel who feel like a vendor.

They let the principals do the deal first.

This last one is a discipline on my side of the table, but the best lawyers reinforce it.

Nothing goes to counsel until the principals agree on the business terms: price, scope, term, who does what, and what happens if it does not work. Documents are a poor medium for reaching agreement and an excellent one for recording it. Before drafting, the strongest counsel ask whether the principals are actually aligned, and they send me back to the table if we are not. That question has saved me months. The times I skipped this step, I paid for it twice: once in drafting and again in renegotiation.

From there, the role is a shield rather than a sword: protect the terms the principals reached, catch what I missed, and occasionally be the reason a position cannot move—counsel who work that way close deals.

The line has moved, and it moved toward them.

The biggest change in the buyer’s chair over the past three years has nothing to do with law firm strategy. I was never a transactional lawyer, but I can now handle a meaningful share of what I used to pay associates for, including first-pass contract review, statutory research, multistate regulatory summaries, and document assembly. Every founder I know is doing the same. Not well enough to bet the company, but well enough to know roughly what the answer is before I call.

This is good news for the lawyers described above because it moves the line to exactly where their value already sits. Judgment under real uncertainty. How a specific regulator has responded in the past. The willingness to argue a structure to the ground. A name and a license attached to a recommendation. All of that is worth more now than it was five years ago, and no large language model can yet provide any of it. Clients have already figured out where the line is. The firms whose value sits on the right side of it are in a better position than they may realize.

What I would tell my former colleagues

If I could send one message back down the hall to the practice I left, it would be this: what your best clients want from you is also the most interesting part of the job.

It is the decision rather than the document. The number rather than the range. The business as it actually operates. Being reachable, willing to argue, knowing the market without looking it up, and delivering it all within the window when it can still change an outcome. In my experience, that is the highest form of lawyering, and the people who practice that way are why I respect good lawyers more now than I did when I was one.

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Douglas McCormack is founder and managing partner of Acumen Partners, a Washington, D.C. investment and advisory firm. He previously was a partner in the health care and health policy practice of a large law firm.