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Legal Dilemma

Joseph Grenny

Joseph Grenny is coauthor of four bestselling books, Change Anything, Crucial Conversations, Crucial Confrontations, and Influencer.


Crucial Confrontations

QDear Crucial Skills,

I am a corporate lawyer. I have been trying to tell our VP of Legal Affairs that I believe the company is at serious risk for litigation on an issue. Each time I do she cuts me off without listening and argues that we’re fine. I see major holes in her counterarguments and don’t believe they would stand up in court. This particular issue is a specific area of expertise of mine. The VP–while very smart–has no real background in this particular area. Mainly I just want her to listen to and consider my points. If after listening she still thinks she is right, I am fine with her making the final judgment.

This is especially risky because she has a short fuse and both yells at and fires people who disagree with her. How do I get her to listen on this important issue that I’ve already unsuccessfully approached her on several times?


Gag Order

A Dear Gag Order,

It’s interesting to me how often our answers are embedded in our questions–particularly when it comes to crucial conversations. Other people (like me) look smarter than they deserve when they do little more than play back what you just told them. I believe that may be the case with your question. You ask the question, “How do I get her to listen to us on this important issue that I’ve already unsuccessfully approached her on several times?” My first piece of advice is to have a conversation with her about precisely that. Don’t talk to her about this issue. Talk to her about your inability to talk to her about the issue.

If you ever find yourself having the same conversation twice, odds are you’re having the wrong conversation. If your real concern is how the conversation is going, then that’s what you should be talking about. Now, with that said, it’s important to ensure that she feels safe when you do talk. Otherwise she’ll likely attribute bad motive to you (you’re doing this because you’re arrogant, or gunning for her job, or whatever) and then she’ll feel totally justified in yelling at you or firing you. Not a good outcome. In the critical first 30 seconds–what we call the “Hazardous Half Minute”–of this crucial conversation, you must do three things:

1. Make it safe. Help her know that you respect her and that you care about her best interests.

2. Describe the gap. Describe factually what has happened compared to what you expect to have happen. Be sure to avoid hot, judgmental, emotional words that would damage safety.

3. Make it motivating. Help her understand the natural consequences of her not engaging with you on this topic–obviously emphasizing consequences she’ll care about.

Here is a possible script just for illustration. Your choice of actual words will best be informed by your best guess at what makes her feel unsafe when others challenge her and what consequences motivate her the most.

“Ms. Finch (for fun let’s pretend she’s Atticus’ daughter), I have a concern I’d like to discuss if that’s okay. I want you to know my whole reason for raising it is to be sure I’m doing the job I was hired for, and to be loyal to you in every best sense of the word. Can I take a minute to share my concern? (Make it safe–clarify your intentions and respect). Here’s the concern: On three occasions I’ve attempted to describe some legal risks I see on issue X. On each occasion you’ve disagreed so quickly that I have not been able to do justice to my argument (Describe the gap). Here’s my concern–I don’t think you want me to check my brain at the door. And yet that’s what I’ve felt tempted to do. I’m also absolutely sure that you care a great deal about this company–and hope you see me having the same value. I know you wouldn’t lay low if you saw a big risk–and I suspect you’d see me as delinquent if I did the same (Make it motivating–give her a reason to listen to you and describe motivating natural consequences of not listening). May I have five minutes to make my argument? After that, I’d like to have you shoot holes in it–and give me permission to do the same with your points if that’s okay?”

Now–I don’t know that this is the right script. But so long as your VP has some good motives somewhere inside her, I think I’ve accurately described your objective. In the first 30 seconds, you must Make It Safe, Describe the Gap, and Make It Motivating for her to listen to you. Once you get started–particularly if she’s an impatient person and begins to cut you off again–you’ll need to hold her to the agreement she just made. Very politely remind her of her commitment to your five minute speech–and continue on. Then be sure to be true to your commitment to listen to her counterarguments and support her final decision.

I especially loved your question because your attitude is 100 percent right. Organizations are not democracies. We don’t all get to vote about the final decisions. But we do have an obligation to speak up when we have important meaning to contribute. You clearly do–and I wish you the best in discharging your responsibilities!

Warm regards,


Joseph Grenny

“If I haven’t challenged you, I haven’t helped you.” Joseph Grenny is a New York Times bestselling author, keynote speaker, and leading social scientist for business performance. His work has been translated into twenty-eight languages, is available in thirty-six countries, and has generated results for three hundred of the Fortune 500.

The ideas expressed in this article are based on the skills and principles taught in Crucial Accountability. Learn more about Crucial Accountability.

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One thought on “Legal Dilemma

  1. Is there any chance that “Gag Order” should go above the VPs head to express his concerns? Or that he should at least document his concerns and provide them to her as a record that he did his job. Whlie it is very importantto have the difficult discussion, it seems to me that when a legal issue is involved, it makes sense to make your case to as many people as possible.

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