Dimitri Mastrocola, Partner – In-house Counsel Recruiting, Board Services at Major Lindsey & Africa explains how understanding your company’s values and expectations is key to hiring in-house legal leaders who truly thrive.
They hired a brilliant AmLaw 10 lawyer as Deputy GC.
Harvard law grad. Technically sharp.
Fifteen months later, that lawyer was gone.
Not because they weren’t smart.
Not because they lacked legal skill.
They just didn’t fit.
I watched it happen.
Slow sidelining.
Lost influence.
Quiet exit.
The issue wasn’t competence.
It was cultural misalignment.
I’ve seen it play out dozens of times – silent breakdowns no résumé could have predicted.
“Even great in-house lawyers miss the mark when their instincts don’t match how the business really works.”
It shows up in small but telling ways:
• A lawyer who overanalyses inside a business that makes decisions fast
• A cautious advisor in a company that’s comfortable in legal grey zones
• A blunt communicator in an environment where nuanced messaging matters
Even great in-house lawyers miss the mark when their instincts don’t match how the business really works.
After two decades recruiting GCs and senior legal leaders, I’ve noticed what separates strong hiring teams from struggling ones. The best dig deeper than legal skills. They look for alignment.
Here are four areas they focus on:
Decision timing
Do you reward speed or depth?
Risk Tolerance
Do you want edge-pushers or play-it-safe advisors?
Communication style
Do your execs value directness or diplomacy?
Unwritten rules
What behaviours actually earn trust, influence, and advancement?
You won’t find those answers on a résumé.
Try asking:
“You’re asked for a legal opinion with limited context and just six hours to respond. What do you do?”
The answer shows how a candidate thinks, communicates, and operates under pressure.
Also, get your business leaders involved early.
When there’s a shared understanding of what success looks like, hiring becomes a lot less risky.
About the author:
Dimitri Mastrocola is a Partner at Major, Lindsey & Africa in New York and widely regarded as one of the pre-eminent executive legal search consultants on Wall Street and beyond. His search practice is focused on general counsel, in-house counsel and chief compliance officer placements for national and international corporations (private and public, across all industries), diversified financial services firms, asset management firms, alternative asset managers (including hedge funds, private equity firms, sovereign wealth firms and family offices), corporate and investment banks, broker-dealers, proprietary trading firms, commercial banks, non-bank lenders and insurance companies. Dimitri has expertise placing general counsel, CCOs and their teams within PE- and VC-backed portfolio companies in all industry verticals. He also works with for-profit organisations to diversify their boards of directors. For more details, please click here.
Dimitri Mastrocola
Email: dmastrocola@mlaglobal.com
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