Matthew Campobasso believes the legal profession has a control problem. Most lawyers, he says, are incredibly competent, but also incredibly anxious.
“The simplest way I can explain it is to distinguish between competence and control,” Matthew said. “Competence is a skill. It's something that you develop through education, experience, and from making mistakes.”
Matthew learned the difference via his early career as a criminal prosecutor, eleven years as a civil litigator at a Chicago law firm, and seven building in-house legal functions at growth-stage companies. He is currently the Chief Legal Officer of Zone & Co., a financial operations software company. In this conversation, Matthew and GC AI founder Cecilia Ziniti discuss swimming upstream, knowing when to let go, and how AI is affecting legal leadership.
"Letting go isn't lowering the standard,” he said. “You have to choose the standards that actually matter. You're letting go of the illusion of control and focusing on outcomes, which is what great lawyers prioritize."
In addition to his in-house work, Matthew teaches at the University of Illinois-Chicago School of Law, hosts a business podcast, and just released a book called The Case for Letting Go: How to Find Balance in a World That Rewards Burnout.
Stop White-Knucling the Outcome: The Case for Letting Go
The legal profession has created a culture in which catching every risk, spotting every flaw, and controlling every outcome is synonymous with competence. The downside of a legal mistake can mean malpractice, sanctions, reputational damage, or in the worst case, the end of someone's career. The risk of making a mistake is both public and personal in a way that few professions experience.
Matthew’s new book describes the risk of hyperfocusing on perfection: the tighter a lawyer holds onto control, the less effective they become. Most of the attorneys Matthew meets got into the profession because they care deeply about outcomes and believe their involvement makes those outcomes better. While that is usually true, Matthew believes the most important shift a legal leader can make is learning to hold authority without becoming attached to a certain outcome.
"I've spent years white knuckling outcomes that I was really never in charge of in the first place,” Matthew said. “When I stepped back I realized that I did my part, and had no control over the outcome. At that point, you're not managing risk anymore. You're managing your ego.”
Matthew recalls the time a senior executive told him directly that his team was intentionally avoiding the legal department. At the time, he’d been practicing for nearly two decades, and Mathew knew a red flag when he saw one. The two men worked it out, but the moment made an impact.
"You have to learn how to hold authority without pretending to control the outcome,” Matthew said. “With that trust, they come to you. And a big part of being effective as a lawyer is having that steady stream of information. If you're not a place they can bring things to, they sidestep you…and then you're in the dark and the company is taking on risk."
The GC’s job is to be present enough that people feel legal is involved, trusting enough that people feel safe bringing things early rather than hiding them until the last possible moment.
“We cannot risk being the long pole in the tent,” Matthew said. “Even if we're giving good guidance, if the business thinks we're leaving dollars on the table because legal is not keeping pace, people are going to go around legal."
Note from CZ: The anxiety as feature versus bug framing hit me immediately. April Underwood, early product at X, famously said “anxiety is a feature not a bug. It shows up as ultra preparation, considering every possibility, making sure things go smoothly.” Matthew agrees that it's a feature… when you can harness it. It becomes a bug when anxiety has its hands on the steering wheel and you have no agency.
Moving Upstream: Getting Legal Involved Earlier
If the job is to focus on the standards that matter and release the illusion of control over the rest, Matthew believes that the best move a legal leader can make is to get involved as early as possible.
At Zone & Co., the legal team meets with product and engineering beginning with the design phase. On the first meeting of a new product initiative, Legal listens more than they talk, but by the end of the process, they’re contributing equally and solving potential issues in real time.
"We are not a checkpoint at the end,” Matthew said. “We are a voice in the room from day one. Legal may be involved in 5% of that first conversation, but every meeting from that point on, that number multiplies."
Matthew often recommends the book Upstream by Dan Heath, which opens with the story of two fishermen who keep pulling children out of a river. The fifth time, one fisherman starts running upstream to find out who is throwing the children in. Litigation, he says, is pulling children out of a river, while ‘upstream legal’ is running toward the source of the problem.
The practical implication for lawyers is that the earlier Legal is in the room, the less there is to clean up later. Issues that would have arrived as crises show up as conversations. Risks that would have required expensive remediation get wrapped in something fireproof before anyone had to think about them.
"A lot of what we're doing now is future value add versus clean up on aisle three,” he said. “You cover point A to point B in 10 minutes, and then you double back and find the thing you noticed on your journey, and you can pick it up and build a process around it. The first time you think about it is not when it's on fire."
The Leadership Traits that Law School Selects Against
Matthew notes that a handful of personality traits that make great leaders are often the same traits law schools select against. The first is intellectual breadth. Law school and law firms reward deep specialization in order to justify a $2,000 hourly rate. But good in-house leadership requires understanding finance, product, people, and how businesses operate. Schools and law firms train brilliant specialists, put them in generalist roles, then wonder why they struggle.
The second personality trait that leaders need is comfort with ambiguity. Lawyers are trained to find the answer, close the loop, and resolve the question. By contrast, effective leadership requires making the best decision possible with limited information. For lawyers, not knowing the answer often feels like failure.
"Lawyers view 'I don't know' as an acknowledgment that they're ineffective,” Matthew said. “I don't know a lot of other professions like that. Comfort sitting with open questions, making decisions with incomplete information…that's what effective modern leadership looks like."
The third trait great leaders need is emotional inteliigence. This includes the ability to read a room, manage in both directions, give hard feedback with empathy, and build teams who work well together.
"Law school does not teach you any of that,” Matthew laughs. “And actually, if you think about being in a room with a team trying to get to the right outcome, it requires almost the opposite skill on every one of those."
How an Upstream Legal Team Uses AI to Do More
These days, Matthew's team of three lawyers at Zone & Co completes the work of five or six, and legal AI is the primary reason.
With AI handling the research, the drafting, and the first-pass analysis, Matthew and his team have time to handle things they might otherwise have run out of time for, like a compliance gap, an untreated risk, or a contract provision that could become a problem.
“AI is rewriting the operating system of how businesses function, and within businesses, how functions function,” he said. “Legal is very fortunate to sit at the intersection of risk, regulation, product design and commercial strategy, so a GC or CLO that touches those four quadrants has more strategic leverage right now than probably anyone other than a CEO.”
Matthew’s “long pole” problem, or legal becoming a bottleneck, is solved by multiplying the capacity of the team you already have and pointing that capacity upstream, toward the work that prevents problems rather than reacts to them.
Matthew's closing advice to his law students captures his broader philosophy: stop performing someone else's version of success. Get uncomfortable outside the law sooner.
“Ask yourself: did I choose where I am? Or did I just not stop the path that I started on when I felt like something else mattered?" he asks.
The legal leaders who can let go of control, and use tools like GC AI to multiply their team’s capacity, will thrive in the coming decades. Get an edge by testing out the best legal AI on the market, built for in-house legal teams.
