From Outside Counsel to the Inside Seat: What Changed Everything
My first management team meeting as a General Counsel, I was humbled by how little I really knew.
I had fantastic mentors.
Worked at respected firms.
Litigator turned corporate and M&A attorney
I read all the books.
Took all the finance CLEs.
But still—there was a gap that I didn’t even know existed.
I was a 6th-year lawyer, hired by a client to be their GC.
That day in the boardroom, I was surrounded by people I had known for years as outside counsel.
Now I was on the inside.
And what I heard made my heart sink.
They were talking about legal as:
- Pure cost.
- A necessary evil.
- The department of no.
- Ways to work around it.
No one was talking about how it could be strategic.
No one was talking about how legal helped drive growth or shape outcomes.
I had worked so hard to be useful and to “win” and be the very best drafter –
But inside the room, I realized I had been optimizing for the wrong things.
I realized from that vantage point that the thrill of “winning” a motion didn’t correlate to whether the business saw a “win.”
The perfect draft didn’t always move the company forward.
And discovery? Well, I’d already suspected much of that wasn’t the point.
Thinking of everything that could possibly go wrong and creating the perfect contract – might not matter if no one will sign it.
That AHA was a pivot point.
I started asking different questions:
* Why is this project even on the table?
* What options do we have and how can legal help?
* Maybe legal writes bullet points for the business team instead of firing off a letter that will cause a breakdown in the negotiations.
Since then, I’ve worked with lawyers who want that same seat at the table and most lawyers we talk to want that relationship with their clients.
And here’s the hard truth:
Most were never taught how to think like that.
We were trained to issue-spot.
To win.
To prove our value with the amount of effort.
But not how to prioritize
Or project manage.
Or how to determine the right price.
Many come by it very naturally, but even then the system isn’t designed to reward finding the easy way.
That’s what we teach inside the ADVANCE Bootcamp: Pricing Ed.
Because when legal is aligned with strategy, it’s not a cost—
It’s a competitive advantage.
And if you want clients to treat you like a strategic advisor—
You need a business model that doesn’t get in the way.
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