how do you handle internal stakeholders that like to play devils advocate and attempt to guess at what the counsel will say to redlines? they would sometimes also share our convos directly with opposing counsel without my sign off

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I once had to escalate to our head of legal because they were not only interfering with my job but sharing internal emails with the other side (a vendor). It was very obvious and a systemic issue with that team. She had a nice long talk with that group explaining why it was inappropriate.

When it happens, I tell the stakeholder it’s great to be prepared for counterpoints but our job includes doing what’s best for our company, and if the other side has problems with what we are saying they should be the ones to bring it up. For sharing things outside the company I not only mark internal emails with “internal only” all caps but also remind them that our discussions should be private unless we decide TOGETHER they can say something to the other side. It’s annoying and fees like babysitting grown adults but most people get it the first time (and the ones that don’t got a talking to from our head of legal).

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gotcha, the same thing is happening but the person also shares what I share with them on Teams as well to the Vendor…

I wouldn't tell them anything and would exclude them from the email chain. Just say you've got it from here and you'll let them know if you have any questions.

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Then maybe confine your responses to redlines and in-doc comments and just use them to pass those back and forth?

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Give them a wet willy

Easy fix. Commissions drop a few % points based on how many redlines there are to your standard contracts.

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