This is actually the hardest part for lawyers transitioning from law firm or government life to in-house counsel roles. Those other experiences train you that being “right” is the most important thing. Being in-house counsel, you learn that outcomes are the most important. https://twitter.com/homsit/status/1343620045398798336

This isn’t to say that in-house counsel need to enable law breaking or non-compliance. It’s about navigating the grey.

Law firm and government lawyers tend to be trained and rewarded for strong arming their audience. But if you do that repeatedly as in-house counsel, you lose your credibility and people try to work around you.

Sean Ruff (now at http://MoFo.com ) had a good saying on this when we were at Square. He talked about having a “hard no.”

We had to enable the business teams, but every now than then use the “hard no” when the teams wanted to do something that was non-compliant.

You had to use your “hard no” judiciously. And it worked best if you had built credibility by suggesting alternative paths to enable the team’s desired outcome.

If you’re a founder or exec and need to hire an in-house lawyer, make sure you ask them about their philosophy on when it’s appropriate to tell a business team “no.” Ask them for examples of when they wanted to say no, but ultimately found a path to yes instead.

Then listen carefully to see if they give you actual examples or philosophical jargon. Don’t hire the lawyer that slings jargon. They won”t get it yet and will be counterproductive to your efforts.