No general counsel learns risk management from a textbook. They learn it from a moment that tested their judgment: a crisis, a bet-the-company deal, a role they weren’t ready for. Ask the best in-house leaders how they came to manage risk the way they do, and they point to an experience that reshaped it, the kind of lesson that never shows up in a job description.
Those lessons matter more as risks multiply. Paragon’s research on how senior legal leaders are rethinking risk, technology, and talent shows AI, regulatory pressure, and lean teams converging at once. The general counsel below, across tech, media, food, and finance, share the career-defining moments that taught them to manage risk, and what each one means for how you build your own approach.
Managing risk isn’t about eliminating it. The general counsel who do it well decide which risks are worth taking and help the business take them safely, a judgment that tends to be forged rather than taught. It’s the throughline across Paragon’s GC Sidebar conversations with in-house leaders.
Mark Kahn, General Counsel at the Oakland Ballers, traces his to a hard stretch earlier in his career:
| “Something that changed my trajectory was when I was at WhatsApp. I failed as a leader, failed to the point where I was demoted, moved back to leading half the team, and then moved into an individual contributor role.”— Mark Kahn, General Counsel, Oakland Ballers |
He spent a couple of years working through it, then rebuilt how he led and, later, a high-performing team at his next company. The lesson stuck: judgment under pressure is the core of the job.
Doe Gregersen, General Counsel at Nav Technologies, frames the goal the same way:
| “Through the years, the most valuable lesson has been realizing that my job isn’t to protect the business from itself.”— Doe Gregersen, General Counsel, Nav Technologies |
A risk management lawyer, in other words, isn’t a gatekeeper. The job is to help the business reach its goals while carrying the right amount of risk, and to know the difference.
In practice, the role covers the legal risks that run across a business: regulatory compliance and data privacy, contract negotiations, intellectual property, and the exposures that roll up into enterprise risk management. The general counsel who handle it well treat it as a repeatable risk management process. They run risk assessments, work to mitigate risk where the stakes are highest, keep the compliance program current, and bring the biggest legal issues to the board of directors, so managing risk supports business strategy instead of slowing it down.
Nothing teaches risk management like a crisis you have to own. Shu White, now Chief Legal Officer and Head of People at Motive, points to a data breach at her previous company, Imperva:
| “When I worked at Imperva before I joined Motive, we had a data breach. We were a data security company that experienced a data breach, and that was really the crisis that made me realize I was ready to be a general counsel.”— Shu White, Chief Legal Officer and Head of People, Motive |
What she took from it wasn’t just an incident-response checklist. Owning the mistake, explaining what changed, and staying honest with customers kept the relationships intact. Crisis management, handled that way, becomes a way to build trust rather than a purely defensive scramble.
Some lessons come from volunteering for more than you’ve handled before. Rishi Varma, Chief Legal and Ethics & Compliance Officer at Cargill, took on one of the largest corporate separations in tech: Hewlett-Packard’s $110 billion split into two companies.
| “I had very little experience with something of that scale, but I raised my hand to lead the legal work.”— Rishi Varma, Chief Legal and Ethics & Compliance Officer, Cargill |
Leading legal on a split that size meant managing enterprise risk across cross-functional teams, solving problems in real time, and communicating with everyone from working groups to the board. Mergers and acquisitions and other bet-the-company events test a general counsel’s risk judgment more than anything, and reaching past your experience is often how that judgment gets built.
The most valuable risk work often goes unseen. Lisa Gorman, Chief Legal Officer at Eventbrite, measures her impact that way:
| “Your best work is often invisible. Your credibility is built on the risks you flag that never happen. Lawsuits that don’t get filed. Disputes that don’t materialize.”— Lisa Gorman, Chief Legal Officer, Eventbrite |
Preventing problems means redesigning the systems that create them, not just reacting when they surface. It also means being honest about which risks deserve attention.
Fabio Bertoni, General Counsel at The New Yorker, treats triage as a core skill:
| “As an in-house lawyer, one of my skills is triaging problems and deciding which ones I don’t need to worry about.”— Fabio Bertoni, General Counsel, The New Yorker |
A general counsel who tries to manage every risk equally manages none of them well. Sound risk assessment is as much about what you consciously set aside as what you escalate.
You can’t weigh a risk you don’t understand, which is why some general counsel credit time spent outside the law. Bita Goldman, Global General Counsel at UNiDAYS, took an operations role early on:
| “Becoming a VP of Operations, where I was managing a warehouse, doing hiring, managing aged inventory, I started to have a business mindset, an entrepreneurial mindset, for how I was going about things.”— Bita Goldman, Global General Counsel, UNiDAYS |
That business acumen changed how she reads risk, tying legal judgment to cost, efficiency, and how the company actually runs.
Ji-Hyun Park, Global Head of Legal at Intercom, stretched in a different direction, rotating into compliance and litigation:
| “If I hadn’t taken that opportunity, I probably would be in a different place right now. So that really changed my trajectory.”— Ji-Hyun Park, Global Head of Legal, Intercom |
Moving into an unfamiliar practice area showed her how compliance risk builds up when a company scales quickly, the kind of exposure that’s easy to overlook until it becomes a real problem.
Risk management rarely offers a clean answer, so the skill is deciding well without one. Alisha Cieslak, former Chief Legal and Risk Officer at Gordon Food Service, had to unlearn a lawyer’s instinct:
| “I’ve also learned to let go of perfectionism, which can be difficult for lawyers. Often, the need for perfection comes from fear or insecurity. But as you gain experience and sharpen your judgment, you learn how to make decisions and navigate uncertainty in a way that builds trust with leadership.”— Alisha Cieslak, former Chief Legal and Risk Officer, Gordon Food Service |
Comfort with uncertainty often comes from being pushed into it.
Jenn Wall, General Counsel at Intrinsic, found hers when a product was shut down:
| “Then Google Glass was shut down. That could have been a setback, but in retrospect it was the moment that really allowed me to become a generalist.”— Jenn Wall, General Counsel, Intrinsic |
Saying yes to whatever legal work came next gave her the range to spot risk across the whole business, not just one corner of it.
The newest entry on every general counsel’s risk register is AI, and 88% of legal leaders say they’re already contending with its disruption. Used well, it clears routine work so lawyers spend more of their time on judgment. Eunice Buhler, General Counsel at G2, sees that judgment as the control that keeps AI in check:
| “This is a time where judgment … is more critical than ever, because a lot of the basic tasks of a legal department can and should be completed using technology tools.”— Eunice Buhler, General Counsel, G2 |
The risk isn’t the technology itself; it’s leaning on it without the human oversight to check its work. Managing AI risk means putting the tools on the routine tasks and keeping a lawyer’s judgment on everything that carries real consequence.
The lessons above point to a repeatable way to handle risk: match each type to the right approach and the right resource. Deciding what your team owns and what it routes out is part of making the business case for flexible talent versus outside counsel, and it tends to line up like this.
| Risk Management as a General Counsel | ||
|---|---|---|
| Risk domain | How leading GCs approach it | Where outside counsel or flexible talent fits |
| Crisis and incident response | Own the response, keep customers informed, fix the root cause | Outside counsel for high-stakes exposure; flexible talent for surge capacity |
| Enterprise and M&A risk | Lead cross-functionally and keep senior judgment close | Outside counsel for deal strategy; flexible talent for diligence and execution |
| Preventive and structural risk | Run risk assessments and risk scoring, then redesign the systems that create problems | In-house ownership |
| Regulatory and compliance risk | Run the compliance program, track evolving rules, and stay ahead of regulatory oversight | Flexible talent for high-volume work like multi-state licensing research |
| AI and technology risk | Apply judgment as the control and vet tools before adopting them | Legal operations; flexible talent for implementation |
| Governance and board risk | Own corporate governance and brief the board of directors on the biggest exposures | In-house senior judgment; outside counsel for securities and disclosure work |
| Operational and business risk | Build business fluency to weigh trade-offs in context | In-house ownership |
The general counsel who manage risk best share one habit: they treat every hard moment as a lesson and let it sharpen their judgment. A demotion becomes a leadership philosophy. A data breach becomes a crisis playbook. A deal you weren’t ready for becomes the range to handle the next one. Managing risk, in the end, is less about avoiding it than about learning from it faster than it can catch you off guard.
When risk work stretches your team past its capacity, Paragon’s flexible legal talent adds experienced coverage for the regulatory, deal, and specialized work that risk management demands.
A risk management lawyer, usually the general counsel or a member of the legal team, identifies the legal risks a company faces, decides which ones matter most, and gives the business the legal advice and legal oversight to manage them rather than avoid them entirely. The work spans crisis management, regulatory compliance, contract negotiations, and advising the board of directors.
A general counsel manages risk with a repeatable risk management process: run risk assessments to map the company’s legal risks, prioritize the ones with the biggest potential impact, and match each to the right resource, whether that’s the in-house team, outside counsel, flexible legal talent, or technology. A sound risk management strategy is proactive, working to mitigate risk and prevent problems rather than only reacting to them, so risk decisions support the business strategy.
Use outside counsel for bet-the-company, high-judgment matters like major litigation or complex deals. Use flexible legal talent for overflow, specialized projects, and high-volume regulatory work, such as multi-state licensing research, that a lean in-house team can’t easily absorb.
A general counsel oversees the full range of legal risks a company faces, including regulatory compliance, data privacy, contract negotiations, intellectual property, employment, and litigation. Part of the job is spotting which legal issues and legal matters carry the most exposure and giving the business clear legal guidance on how to handle them.
Employee Portal
Apply