Walking into the general counsel role at a new company can feel like stepping onto a moving train. New laws, a new business, a new team, and a board with questions you didn’t know were coming. Across Fortune 500 companies, early-tenure departures climbed from 17% in 2022 to 43% in 2025, with external hires accounting for 78% of those exits. The first 90 days are where most of that pressure shows up. Quick wins compound, trust banked early carries through the first crisis, and the 90-day window is when a new GC lays the foundation for the operating model the legal function will run on.
So we asked. For Season 1 of Paragon’s GC Sidebar interview series, CEO Trista Engel sat down with 10 general counsels at companies ranging from Grammarly and Ironclad to Cox Media Group and Collective Health to ask what surprised them most in year one. Their reflections give a working roadmap for new and aspiring GCs and for boards hiring one.
Below, we share what these GCs would tell themselves on day one, the framework that emerges across all 10, and how Paragon’s flexible attorneys can absorb the work that doesn’t need a permanent hire while you build the rest of your plan. For a practical starting point, Paragon also put together The New GC Toolkit, a guide to thriving in the role from day one.
Stepping into the GC role for the first time comes with a steep learning curve, and even the most seasoned attorneys may be caught off guard by what the job actually demands.
The first jolt for many first-time GCs is how little of the day is spent practicing law. Shanti Ariker, Chief Legal Officer at JFrog, put it bluntly: “How much management I do and how little law I actually practice” was the part of the job that surprised her most. The work is following up on details, managing a department, budgeting, and standing in as the voice of the legal team on every topic, including ones far outside your own legal expertise. Her companion observation lands the same way: “You can’t say ‘I’m not a tax lawyer.’ You’re now responsible as the voice of the legal team.”
The implication for the first 90 days is to plan for the management workload from day one. Block out time for one-to-ones with every direct report. Set expectations with the CEO that you’ll spend the first weeks listening before you propose changes. Managing all of that, more than practicing law, is the part of the new general counsel role that catches first-timers off guard.
No senior commercial lawyer or privacy specialist on the team yet?
Paragon’s flexible legal talent can backfill the substantive work so you can focus on leading your team.
Heather Stevenson, General Counsel at Red Cell Partners, named the lesson that gets repeated by almost every successful GC: “Building trust with your internal team, and especially with leadership, is your number one priority. If you don’t have their trust, even excellent legal advice will go ignored.”
Spencer Stuart, the executive search firm, recommends a deliberate “listening tour” across the C-suite, the board, and the legal team in the opening weeks, paired with the discipline to hold judgment until you understand how decisions get made. The order matters. Stevenson again: “If you’ve built that trust, your advice gets listened to. And it also gives you credibility in tougher situations.”
A practical first 90-day move is to schedule introductory meetings with every member of the leadership team, the audit committee chair, the head of finance, and the heads of every function legal support. Spend real time with the sales team in particular, to learn what the company sells, how those deals get bought and closed, and what sets the offering apart. Ask one question in each: what’s the most important thing happening in your part of the business that I should understand? The general rule is to listen twice as much as you speak in the first six weeks.
Jasmine Singh, General Counsel at Ironclad, framed it as a depth shift: “You need to know the company’s direction intimately, not just in a high-level way.” Jennifer Miller, General Counsel at Grammarly, takes it a step further. “I view myself as a business executive with a legal lens,” Miller says, “and the general counsel must lead [strategically], or the business team will just stop including legal.”
In practice, this might be a new GC who reads the last four earnings calls, reviews the strategic plan, sits in on board meetings before issuing any major recommendation, and meets with every product and revenue leader by week six. Reading contracts is necessary. Understanding what the company is actually trying to do with those contracts is the job.
“Crazy is the new normal, and I really think our job is to understand the business.”
— Shu White, Chief Legal Officer and Head of People, Motive
Shu White’s career-defining moment was a data breach at a data security company. “You cannot get through these things without having an incredibly strong team,” she says. “You can make a mistake, be honest about it, talk through how it happened.”
New GCs are often told a crisis will come. What surprises them is how soon, and how often. Building incident response muscle in the first 90 days means knowing where the playbooks live, who the outside specialists are, and which board committee gets the first call. If those answers aren’t immediately clear, that’s the first project.
Eric Greenberg, General Counsel at Cox Media Group, named the structural shift: “We’re moving away from a model where someone calls legal only when there’s a legal issue, and toward one where the GC is at the table, helping map company strategy.”
That shift happens by force of habit, not invitation. Andrew Epstein, formerly General Counsel at Demandbase and now leading legal at ElevenLabs, frames the work it takes: “How do you push yourself to be innovative as a member of the team to help fight that perception, or that misconception, that legal isn’t able to do those things?” Epstein adds that the framing matters more than the legal opinion itself: “You have to be able to frame a key initiative in a way that’s impactful to the listener, and makes sense to them.”
For the first 90 days, that means saying yes to invitations that don’t have an obvious legal angle. Sit in on product reviews. Join the M&A pipeline meeting. Build a habit of speaking last and connecting the legal point to the business decision the room is actually trying to make. The C-suite stakeholders watching will start to bring legal into conversations earlier, which is the actual goal.
The legal department is now an AI department, whether you planned for it or not. According to FTI Consulting’s General Counsel Report, 44% of GCs say their legal teams now use generative AI, up from 28% in 2024 and 20% in 2023. The catch: 85% of general counsel said they lack the preparation needed to handle generative AI risks, and 75% of legal departments lack a technology roadmap.
Eunice Buhler, General Counsel at G2, captures the upside of handing routine legal work to technology: “Now that job can be completely done through AI and other technologies. Now it’s our time to shine as lawyers by applying our judgment and experience.” Heather Stevenson at Red Cell Partners adds the realistic counterweight: “Now it’s also which tools, which AI, and how do you make sure the tools you choose aren’t just shiny objects, but actually help you get more done?”
The first 90-day move: pick one workflow (typically a piece of contract lifecycle management or document review) and run a small AI pilot with clear success metrics. Document the policy that goes with it, even if it’s a one-page draft.
Michael Stein, General Counsel at Gambling.com Group, named the gap between what the role looks like in a job posting and what it looks like in practice. “In a small company, in my opinion, it’s pretty much all hands on deck for anything that comes up. Sometimes that means helping HR collect computers from former employees who won’t respond.”
Even at larger companies, new GCs find themselves owning the regulatory question no one else wants, fielding the inbound from investors, or stepping in on a vendor negotiation because the timing of an executive change left a hole. The instinct to draw the box tightly around legal will fail. The better play is to set a working principle for what you’ll own personally, what you’ll route to your team members, and what you’ll triage with flexible legal talent for the duration of the surge.
Ron Bell, Chief Legal & Administrative Officer at Collective Health, didn’t pull the punch: “The biggest challenge is easy, complexity. Complexity and ambiguity. It’s never been harder to be a lawyer, definitely never been harder to be a GC. A big part of being a GC now is being a navigator of ambiguity.”
Bell’s prioritization rule is the part new GCs should write down: “You don’t have to win every battle. You just have to know which battles matter.” For the first 90 days, that translates to a written, ranked list of the three legal risks most likely to define the next 12 months for the legal function, and a willingness to defer everything else until those three are moving.
Eric Greenberg’s proudest accomplishment at Cox Media Group reframes how legal can show up: “We used legal as a kind of R&D lab, researching legal claims, policy issues, public affairs strategies, and deployed that in a composite approach. We weren’t just playing the game the bigger party created, we changed the game entirely.” That isn’t standard advice for a new GC. It’s also exactly what boards and CEOs increasingly say they want.
The first 90-day move is more modest: identify one process inside the legal function that everyone tolerates and no one defends, and commit to a 60-day improvement project on it. The improvement itself matters less than what it signals to the rest of the company.
Jennifer Miller at Grammarly closes with a portable rule for any in-house lawyer. “A person should always be either learning or earning. If it ceases to be true, that’s when it’s time to seriously think about moving on.”
Miller’s framing is useful in general terms because it cuts both ways for a new GC. The first 90 days should be packed with learning. By the end of year one, the trajectory should also be earning, in influence, in scope, and in the seat you hold at the leadership team table. If neither is moving, the role isn’t the right fit, and the data on early-tenure GC departures suggests plenty of seasoned in-house leaders have made the same call.
Across the 10 GCs, a working framework emerges. Use it as a starting point and adjust to your company stage, board structure, and team size.
 Days 1 to 30: Listening Tour Schedule 30-minute conversations with every member of the executive team, every direct report, the chair of the audit committee, and the heads of the three functions you’ll work with most. Ask each one variations of the same three questions: what’s working, what isn’t, and what should I make sure I don’t miss. | Days 31 to 60: Diagnose and Prioritize By week six, you should have the three issues that will define the legal functions’ next year. Common candidates: a regulatory transition, a tech and AI policy gap, a contracting backlog that’s slowing the business, or a team-structure mismatch that needs a hire or two. Document the working operating model with your CEO and align on what the legal department is being asked to deliver in year one. | Days 61 to 90: Commit and Act Deliver one quick win. Publish your team’s first AI and tech use policy, even if it’s a draft. Present a 12-month plan to the CEO and the audit committee that names the three priorities, the resources needed, and the dependencies you’ll need from the business. Decide which work stays in-house, which goes to outside counsel, and which is handled by interim or flexible attorneys for the duration of the build. |
New GCs often inherit a legal department that’s understaffed, behind on a project, or stretched across more work than the headcount supports. Hiring permanent attorneys in your first 90 days is rarely the right move; you don’t yet know the long-term shape of the team. Interim and flexible attorneys are the bridge.
The most common use cases for a new GC in year one:
| Backfill during the listening phase A senior commercial or privacy attorney covers the day-to-day work for 90 to 180 days while you assess team needs and finalize the org chart. | Project-based work outside your team’s depth A specialist handles a privacy program build, an M&A diligence sprint, or a litigation discovery wave without a permanent hire. |
| Coverage during planned absences A flexible attorney with relevant in-house experience holds a key seat while a team member is out. | Surge support for overflow and quarter- or year-end spikes Extra hands on board materials, governance work, and committee minutes during overflow periods and quarter-end or year-end spikes. |
Across all of these, the value to a new GC isn’t just the work getting done. It’s the option value of waiting to make the permanent hire until you actually know what shape the legal function needs to be.
The general counsel role in 2026 is broader than legal. It’s part navigator, part operator, part communicator, and very part lawyer. The 10 GCs in Paragon’s GC Sidebar series are blunt about how much of year one is spent learning to hold all of that at once, and they’re equally clear that the first 90 days are when the foundation gets set or doesn’t. If you’re stepping into the role, or hiring someone who is, the move that pays off most is creating room to listen, to learn the business, and to build the team and outside counsel network deliberately rather than reactively.
When you need extra capacity to make that room, Paragon’s flexible attorneys can step in for the project, the surge, or the bridge until the right permanent hire is ready, or even needed at all. Reach out and request an attorney from Paragon today.
New general counsels have no shortage of questions heading into their first 90 days, and the answers often shape how the rest of the role unfolds.
The first 90 days as general counsel should focus on a listening tour with leadership, a diagnosis of the legal function’s three biggest priorities, and one or two quick wins delivered. Save permanent hires and large structural changes until you’ve completed the assessment.
Most general counsels describe feeling settled around six to nine months, after the first board cycle and the first year-end close. With many GCs being in the role for under five years, a learning curve is the norm.
A direct reporting line to the CEO is widely viewed as the standard for senior GC roles because it preserves the independence and access the position requires. Reporting to the CFO can work for smaller companies but tends to limit the GC’s seat at the leadership team and board.
Build board credibility by asking for early one-on-one time with the audit committee chair and lead independent director, by keeping board materials short and direct and framed as an executive briefing rather than legal analysis, and by delivering one substantive improvement to the board’s legal or governance experience in the first six months.
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