Approach and Strategy to Crucial Conversations

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In “The What and How of Crucial Conversations,” we explored crucial conversation characteristics and the importance of face-to-face communications. In “The Groundwork for Crucial Conversations,”we examined the role organizational culture plays in creating the appropriate environment for crucial conversations. As we continue our breakdown of the ground breaking book, “Crucial Conversations,” we move to how an individual would approach a crucial conversation.

Whether it’s a discussion about a litigation assignment, progression towards partnership, the opportunity to first chair or a performance review, an attorney’s day is full of potential crucial conversations. The list above doesn’t even mention the countless discussions with opposing counsel or perhaps even most impactful, your family.

Here are 4 Keys to Approaching a Crucial Conversation:

1)    Begin with the Right Frame of Mind – It’s always easier to enter a conversation with the right frame of mind than it is to adjust once the conversation begins. Make sure you are in a place emotionally to both have the discussion and manage the possibility of it becoming crucial.

2)    Check Your Motive for the Conversation – My father has a great saying, “You can lie to me all you want, just don’t lie to yourself.” Examine why you want to have the conversation. Is it a power play? Are you seeking clarity on an issue? Are you in search of an apology? Is it a opportunity for advancement? Is the initial topic a subterfuge to a more pressing issue? Why are you having the conversation?

3)    The Goal is NOT to Change the Other Person’s Mind – A common misconception is the conversation is only productive if you change the other person’s mind. This places you in a win/lose posture that can be counterproductive to your preferred outcome. The reality is you may be able to achieve your conversation goal without changing their mind.

4)    The Goal is NOT to Impose your Will – Not that this would happen with attorneys (insert heavy sarcasm), but the allure of battle can be difficult to overcome. However, it’s a necessity to squelch that conquering fire and focus on your reason(s) for having the conversation.

How can you remain focused on the goal, while in the midst of a crucial conversation?

Know What you Want!!

While this seems obvious, it is an often overlooked component. Having a clear understanding of the desired outcome is essential. E.g. – Simply interviewing for an attorney position or negotiating a move to another firm is not clear enough. Salary requirements. Start date. Paralegal (Sole or shared). Billable hours. Office location. Practice group. New revenue goals. Partnership review/ contribution. Know what you want!!

Pitfalls to Avoid

Avoid the Tangential Path – Skilled negotiators will pull you away from the focus of the conversation. They will effectively throw out either red herrings or false choices to move the discussion away from the key points of discussion and down the proverbial rabbit hole.
Avoid Detours Based on Shame, Anger or Self-Defense – Pushing emotional buttons is another means of hi-jacking conversations. It is highly effective, so you have to be prepared to deal with it. Your approach can vary from ignoring having your buttons pushed, to addressing and immediately re-focusing the conversation on your conversation goal(s). There is no “best” approach, since it’s normally highly situational and personal preference based.

Don’t Change the Goal for Pride-Based Reasons: Changing the goal so you can “save face,” “avoid embarrassment,” “be right,” or “win” isn’t usually strong enough to outweigh your initial reason(s) for having the conversation. Remember, know what you want!

Ensuring you have both the right approach and a clear understanding of your desired outcome are invaluable. It can be easy to rush into a discussion not mentally prepared for the potential twists or turns. That’s a mistake. Meanwhile failure to have a clear understanding of what you want, can place you at the mercy of a skilled negotiator. You also may not know when to end a conversation in which you’ve gotten “what you want,” because you don’t know “what you want.”

Next week we’ll discuss what to do when crucial conversations go wrong.


Elliott Robinson, JD is an Executive Coach, Workshop Facilitator & Mediator with Trove, Inc. ( Elliott brings his unique insight to the areas of leadership development, communications and career advancement. Elliott’s writing can be found at:, and his relationship blog, Elliott is the co-host of Blog Talk Radio shows: The Wellness Blueprint ( and Career Impact Radio by Trove, Inc. ( You can follow him on Twitter at: @ERobinsoncoach. You can contact Elliott for information on coaching, workshops or mediation at


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