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A quick note before we dive in: today's Deep Dive is written by my friend Kyle Robisch, Founder and Partner at Latitude Legal, and I think his perspective is one you’ll really value.

Kyle works in flex legal talent, which means he spends his days talking to GCs. As a client, as a resource, as a sounding board. That gives him a perspective I can't offer on my own. My path to GC was a winding one, and I love talking about the lessons I picked up along the way. But what makes Kyle's piece special is that rather than drawing from one career story, he’s drawing from hundreds of them. Each path is unique, like mine, but the takeaways are universal.

With that, I'll hand it over to Kyle.

I talk to a lot of general counsel. A lot. In many ways, it’s my job. As a partner at a flex legal talent company, my job is helping legal departments get more work done, more efficiently, more quickly. So, I spend hours each week talking to legal department leaders about the work they’re doing, their pain points, and how we can get them help when they need it most. Tally it up, and over the past year, I’ve spoken with hundreds of GCs in legal departments of all shapes and sizes. Fortune 100 companies to single lawyer startups and everything in between.

Through those conversations, I’ve learned a lot about effective general counseling and how the most successful GCs got there. I’ve also spoken with countless in-house lawyers who are interested in getting to the GC seat, whether now or later.

There is a myth that becoming GC is just about accumulating enough legal reps. More deals. Bigger matters. Higher-stakes calls. But if I’ve learned anything, it’s that the job isn’t “more law.” It’s more judgment, more leadership, more ownership, and more relationship building.

For us lawyers, that can feel counterintuitive. Shouldn’t being GC be more about technical skills than soft skills like judgment and EQ? To be clear, it’s both. You need to be a good lawyer to be a great GC. But solid legal skills are only half the battle.

If you’re serious about the big chair, here are the five takeaways I’d keep front and center.

It’s lonely at the top. The buck stops with you. And that’s exactly why you can’t try to do it alone.

The GC role can be isolating if you let it be. You’re the escalation point. You’re the one who gets the late-night call when something breaks. You’re expected to have clarity when others have anxiety.

But here’s the reality: the best GCs build infrastructure around themselves long before they “need” it.

That includes:

Contrary to the conventional wisdom, asking for help isn’t weakness. Just the opposite, it’s sound judgment. It’s recognizing that the cost of being wrong—alone—is higher than the cost of being humble. If you want to be GC, start building your own “personal board of directors” now. The stronger your ecosystem, the better your decisions.

If you’re waiting for a perfectly linear career path to GC, you’ll be waiting a long time.

Many of the strongest GCs I know didn’t climb a straight ladder. They zigged. They zagged. They took roles that didn’t “make sense” on paper.

They worked in sales. They spent time in accounting or finance. They operated inside product teams. Some were founders. I’m not just talking about GCs who spent time as AGC or corporate counsel supporting those business teams. (Although that’s great too.)

I’m talking about GCs who spent time out of the law entirely, in those roles they now advise as general counsel. I’m also talking about GCs who leaned into industry and title pivots, to upskill or gain new subject matter expertise.

And all of that made them better GCs. Why? Because they’ve sat in the seats they now advise.

A GC who’s sat in finance understands the real life impact of P&L.

A GC who’s sold understands their sales teams’ incentives, quotas, and goals.

A GC who’s built something understands operational friction.

That empathy translates directly into credibility. Business partners don’t want abstract legal commentary. They want counsel from someone who understands the stakes because they’ve felt them.

So if you’re considering a pivot—new industry, new function, even a stretch role that’s more business than legal—don’t default to fear.

Ask instead:

The answer is probably a resounding “yes.”

Yes, technical skill matters. But as you move toward GC, your value shifts. Early in your career, you’re rewarded for spotting issues. As GC, you’re paid to decide what to do about them.
The higher you go, the messier the inputs become. Facts are incomplete. Timelines are compressed. Everyone wants certainty; no one has time for it.
Strong GC candidates develop three instincts:

If you’re aiming for the role, start practicing now. In meetings, don’t stop at analysis. Push yourself to land the plane.
Translate risk into business terms—dollars, customer impact, time to market. Understand how your CFO thinks about exposure. Learn how your CEO processes uncertainty.
The law is the baseline. Judgment is the differentiator.

The best GCs own it. They own the decision. They own the recommendation. They own the consequences.

Don’t get me wrong, they aren’t reckless. They’re not casual about risk. But they are willing to take a position. At some point, there is no additional memo that will make the call easier. There’s no extra footnote that eliminates ambiguity. The organization needs direction.

And that’s where the “figure it out” muscle kicks in. Great GCs own the problems they’re given, making their team’s problems their own. They roll up their sleeves and figure it out, even—and especially—when there isn’t a clear cut legal or business answer.

They absorb the ambiguity, synthesize it, and move. They don’t hide beyond caveats and “maybes.”

This doesn’t mean you always get it right. It means you’re willing to decide.
If you want to build this muscle, start small.

Ownership compounds. The more you demonstrate it, the more you’re trusted with it.

A surprising number of lawyers think effective general counseling is about wielding authority. Yet in reality, it means mastering influence. You’ll advise executives who don’t report to you, guide teams through change, and say “no” in ways that preserve relationships. The upshot? The best GCs build credibility so that when they do draw a line, it matters.

That requires communication and EQ as core skills. Can you translate legal risk into strategic tradeoffs? Can you align a room without overpowering it? Can you help a team see around corners without sounding like the Department of Doom?

If you disappeared for two weeks, would the business say, “We miss their contracts,” or would it say, “We miss their judgment”? Aim for the second.

Leadership at the GC level isn’t about being the smartest person (or lawyer) in the room. It’s about being the calmest, clearest thinker in the room when stakes are high.

In short, there isn’t one path to the GC seat. But there are consistent patterns:

If you’re aiming for GC, don’t wait for the title to start acting like one.

Take the calls no one wants. Frame the options others avoid. Make the recommendation when the room goes quiet. Build the relationships that make hard conversations easier.
That’s how you become GC.

Thanks so much to Kyle for taking the time to share his perspective with you. You can connect with him on Linkedin or by email at [email protected].

This is the first time I’ve had a guest writer, and I’d love to know what you think. Do you appreciate hearing from someone with a different perspective? Prefer to just hear from me?

Hit reply and let me know. I read every message.