In our final episode of GC Sidebar Season One, Ron Bell, Chief Legal and Administrative Officer at Collective Health, joins host Trista Engel for a sharp conversation about leading through complexity, prioritization, and the kind of leadership that scales beyond authority.
From navigating ambiguity across privacy, AI, and global change to choosing the battles that truly matter (his “Tolstoy test”), Ron shares how GCs can move businesses forward without clinging to control. He reflects on a career from Chicago litigator to 18 years at Yahoo (culminating as GC) and on to Collective Health, and proposes his tongue-in-cheek Universal Reply All Prevention Act of 2025.
Trista Engel: Hi, I’m Trista Engle, CEO of Paragon Legal, and welcome to GC Sidebar, a short and sharp conversation series with today’s most forward-thinking general counsel.
In just four questions, we cover the legal industry, leadership, careers, and a little fun.
Today I’m joined by Ron Bell, Chief Legal and Administrative Officer at Collective Health, a company that helps employers simplify and personalize the way they offer health benefits through a single integrated platform, making healthcare less confusing and more human.
Ron began his legal career as a litigator in Chicago before transitioning to in-house roles at Apple and Yahoo. He spent 18 years at Yahoo, serving in various legal capacities and ultimately stepping into his first general counsel role. In 2017, he joined Collective Health as CLO.
Ron’s impressive career has been driven by his ability to create opportunities for himself that excite him, all of which seem to have been successful, except for an early aspiration to be a Supreme Court reporter.
Ron, I’m excited to have you here. Thanks so much for joining me.
Ron Bell: Thanks for having me.
Trista: What’s the biggest challenge facing GCs and in-house legal teams today?
Ron: The biggest challenge is easy, complexity. Complexity and ambiguity.
In the last 10 years, between the pandemic, global expansion, changes in privacy law, introduction of AI, electoral conflict, and shifts in the federal government, it’s never been harder to be a lawyer. And it’s definitely never been harder to be a GC, because you’re advising businesses on what to do when even the authorities and regulators often disagree with each other.
A big part of being a GC now is not just issue-spotting or laying out what the law says, it’s being a navigator of ambiguity. You’re leading across functions, sometimes across borders, and isolating the long-term risks and challenges for the business. And you’re doing that at a time when different GCs might give different answers.
Trista: That’s a great point. In a profession that often looks to precedent, we’re living in unprecedented times, and have been for years now, which requires being nimble and able to adapt.
Ron: 100%.
Trista: What’s the most valuable lesson you’ve learned as a GC?
Ron: You don’t have to win every battle. You just have to know which battles matter.
I often use this framework, if something goes wrong, would it make for a good plot in a Tolstoy novel? If it would, it matters. It requires our time.
If it’s something minor, maybe it upsets someone or we lose a small amount of money, it might be something we can let go. Obviously, we want to address everything we can and be responsible, but we have to keep calibrating and asking: Does this matter? Will it move the business forward? Is it about actual legal compliance? Is it business-critical?
Trista: Great point. And going back to complexity, that really comes with the need for prioritization.
What’s the best career advice you’ve received or given?
Ron: Don’t confuse control with leadership. And don’t confuse leadership with authority.
The best leaders, whether GCs or otherwise, don’t cling to doing everything themselves. They empower, delegate, hire, coach, even when it’s messy or slower at first, because they know that over time, if you’re the busiest or smartest person in the room, you’re probably doing someone else’s job and robbing them, and the company, of growth.
Leadership isn’t about avoiding decisions, of course you still make them. But it’s about knowing your stakeholders, the board, CEO, executive team, investors, regulators, and understanding what each prioritizes. Then you synthesize that for the team and come up with a course of action.
Trista: I love both of those points and how they connect. One of the hardest transitions is moving from being an individual contributor to a leader with authority, and learning how to get buy-in.
Ron: Exactly. The sooner you learn that, the more impactful and sustainable your career becomes.
Trista: If you could write a law that all companies had to follow, what would it be?
Ron: I’d be a big proponent of the Universal Reply All Prevention Act of 2025, which says any email to more than 15 people must have a persistent warning when you hit “Reply All.” Something that makes you really think: Do I need to do this? Because every unnecessary reply takes up people’s time and attention.
Trista: I’d vote for that law. Even fewer than 15, I’d like a pop-up for each name asking, “Does this person really need to be on this email?”
Ron: Exactly.
Trista: Bonus question, who’s your favorite fictional lawyer?
Ron: I have two. First, Atticus Finch from To Kill a Mockingbird, ethical, principled, takes tough cases, speaks truth to power, balances being a lawyer and a parent, and he’s fearless.
Second, Vinny from My Cousin Vinny. Easy to dismiss because he’s funny, but he’s methodical, investigates, uses experts well, and wins tough cases. In a way, he makes the law more accessible.
Trista: I don’t think I’ve ever heard Atticus Finch and My Cousin Vinny mentioned together, but I love it.
Ron, thank you for sharing your thoughtful answers.
Ron: Thanks for having me.
Trista: That’s a wrap on today’s GC Sidebar. Catch more great conversations on our website at paragonlegal.com. Thanks for tuning in.
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