Legal Leadership Learnings: 4 General Counsel Insights from Eric D. Greenberg

In today’s corporate legal department landscape, it’s no longer enough for a General Counsel to be a great lawyer. They must also be an adept business leader, relationship builder, and agent of strategic transformation.

On a recent episode of In-House Outliers, the General Counsel of Cox Media Group, Eric D. Greenberg, shared a deeply candid series of insights centered around his journey from Big Law partner to in-house legal leader. His reflections reveal how the role of General Counsel is evolving—and what it takes to thrive in it.

1. Moving In-House Requires a Shift in Mindset

Despite a long and successful career in private practice, Eric acknowledged that moving in-house presented new challenges. Part of that was due to the path Eric took to the GC role—moving straight from law firm partner to General Counsel.

Shifting in-house also gave him an entirely new perspective on business operations. Eric found that managing a legal function required capabilities rarely developed in law firms: operational oversight, budgeting discipline, and team management within a corporate structure. These were skills he had to learn on the job—and he approached that learning curve with humility and curiosity.

One of the first areas that provided him with a wake-up call? The importance of good financial hygiene to the business.

“Accruals were a classic blind spot,” Eric noted. “As outside counsel, I hated them… But now I vividly understand why the company needs to anticipate what legal costs are coming.”

He also used to think that late billing simply meant the client got a free month of financing. But from the in-house perspective, late invoices disrupt financial planning and create friction with the finance team. Understanding the importance of predictable spend—not just delivering the right legal outcomes—was a crucial learning when stepping into the role of GC.

2. Share Your Department’s Philosophy with Your Outside Counsel

Like many legal departments, Cox Media Group inherited a standard set of outside counsel guidelines after being carved out of a larger entity. Initially, Eric saw them as little more than a checklist: invoice submission deadlines, billing format rules, travel expense caps.

But Eric’s Director of Legal Operations, Letitia-Haynes Frasier, proposed a full rewrite—with a different vision. The result was a document that starts not with procedures, but with philosophy.

“We start our guidelines with a section called ‘Philosophy.’ It says: You’re not vendors. You’re fellow legal professionals. And you deserve to be paid fairly for excellent work.”

Eric emphasized that this approach isn’t about being soft on billing; it’s about building mutual trust, and making it clear that great work will be rewarded. He ultimately wants firms to feel invested in the relationship with his legal department—and not like they’re merely locked in a cycle of invoice write-offs. That starts with setting expectations clearly and respectfully—from the very first page.

3. Legal Operations Isn’t Back Office—It’s a Strategic Partner

Eric’s experience working with legal operations leader Letitia Haynes-Frasier offers a textbook example of how legal ops can empower GCs to focus on what they do best.

Early on, Eric admitted he had limited experience with budgets, financial systems, and operational frameworks. Letitia became his thought partner, helping him understand the numbers and enabling more informed leadership.

“Letitia is our ambassador to the future,” Eric remarked. “She goes into the ecosystem, finds what we need, and brings back solutions that move us forward.”

He recounted his initial skepticism toward the value that having Letitia attend CLOC Global Institute (an annual legal operations event that focuses on learning, networking, and legal technology) would provide. But now he carves out time for a dedicated debrief when Letitia returns from CLOC each year, knowing her insights will help guide future planning.

What makes the partnership successful is not just Letitia’s expertise, but Eric’s willingness to delegate, elevate, and treat her role as mission-critical. That dynamic has become a model of what’s possible when legal leaders fully embrace legal ops as a strategic pillar, not just an administrative function.

4. Treat Technology Providers Like Extensions of the In-House Team

General Counsel are routinely required to make strategic decisions regarding how best to deploy the legal department’s resources. Every choice—whether pertaining to hiring, outside counsel engagements, or technology—has ripple effects across the business.

One sometimes-underutilized tool in a GC’s resource-optimization toolbox is leaning on legal technology providers as true partners to the in-house team. By engaging with them proactively, GCs can ensure their teams are getting the full value out of the platforms they’ve invested in.

“When you buy a product and you engage with a partner—like we do with Brightflag,” Eric said, “you’re actually not making a one-time decision. You’re investing in a relationship that’s gonna be hopefully dynamic over time.”

Eric cited the strategic data insights Brightflag’s team regularly shares to ensure his in-house team is maximizing the value received by the platform, as well as Brightflag’s willingness to consider his legal team’s feedback when crafting their product roadmaps.

When legal teams treat technology providers as extensions of their department, they gain more than just software—they gain collaborators who can help solve problems, introduce innovations, and create lasting efficiencies. This approach allows GCs to focus their teams’ energy on high-value strategic work, confident that their technology partners are invested in the department’s long-term success.