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Thank you Shannon for being a wonderful team lead

when Work >>> Life 😅

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Unless something is literally illegal for you to agree to, as counsel you shouldn’t be in a position to even be seen as potentially “blocking” any deals. Your feedback should be expressed as “here are the risks and potential ramifications and things you should consider.” Hopefully your business has a structure in place where there are separate stakeholders who can take your advice and conduct the cost-benefit analysis to determine whether the deal is worth moving forward with.
C1, in that situation, where you’re concerned about later being blamed for any fallout from the bad deal, I’d generally phrase my feedback as serving as a risk analysis of the deal (rather than acceptance) and explain to the commercial folks that whether or not to accept that risk is not a legal issue. It’s their own fault (or the company’s fault) if that’s seen as you functioning as a “blocker”
I have learned to advise and let them make their business decisions, even when I advise against it. I watched this blow up spectacularly on a Senior Director who was pushing through a $3mil contract despite multiple cya emails from me stating that I did not recommend they proceed. The CEO lit her up, asked me what happened, and I shared the receipts with him clearly showing that I’d already counseled her against doing the things he was lighting her up for. I looked great, she took the L.
She came to me after and said “I thought that the fact that you didn’t stop me meant that you were aligned.” And I was like “No, I sent you multiple clear-as-day red-flag emails telling you my position, when I send you something in writing, that is my position.”
They can’t have it both ways - Legal can’t be not allowed to say “no” one day/be a roadblock if they do, and then be the final arbiter who has to make the decision the next. But the business wants to have it both ways so they can avoid accountability.
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If you build up a trusted relationship with your sales/business leadership, then they will learn to trust when you say no, it's for good reason. Have you taken the time to discuss with that individual why they feel that way, to get examples and explain what the potential risks could be if those deals aren't negotiated carefully? Help them understand that all deals move a lot quicker as well when sales and legal are on the same side and if they are also properly championing a deal, and give examples of that as well. Instead of "how can I get approval for this" approach it from the perspective of "how can we approach this hurdle together".