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Crucial Conversation Checklist

Were you able to celebrate your favorite women leaders last month? It is so important to look at the things that make leaders stand out… I believe one of the biggest characteristics of leaders is the ability to have crucial conversations…

Let's pause here for a moment. The words "crucial conversation" can feel heavy, serious and difficult. Right? Many of us, including me, have been conditioned to feel the negative impact of these two words. As in "we need to talk right now about what is going wrong".


Let's reframe.


Crucial Conversations = An exchange of one's thoughts, ideas, and feelings to support us in taking decisive action for success.


Yes! I want to be a part of that! When we truly connect to understand the perspective and opinions of others, we have the potential to significantly impact a situation, outcome, and our lives, both personally and professionally.


Most of us are hesitant to deliver any negative feedback to our teams. We worry about what they will think of us and how they will feel. Being open and honest with your team is the best form of kindness. Yes, kindness! Your work relationship with your team will be stronger and you will see faster results. In the end, this is a win for everyone involved.


Crucial conversations require a high level of emotional intelligence, communication skills and preparation. If you’re not familiar with having crucial conversations here are my top six steps to practice and ensure successful outcomes.

  1. Identify the purpose of the conversation. This involves clarifying what needs to be discussed and why. It is important to set clear goals and objectives so that both parties understand the purpose of the discussion.

  2. Prepare for the conversation. Gather relevant information and facts. Make notes on key points related to the situation and the expected outcome. Determine in advance what would make this conversation a win-win. Consider sharing the purpose of the meeting with the other party in advance, allowing them to gather relevant information for the conversation. This preparation will help keep the conversation on track and prevent it from getting derailed.

  3. Create a safe and non-threatening environment. Getting called into 'the bosses' office can set a tone before the discussion even begins. Find a mutually beneficial meeting space. A conference room, an outside picnic table, or even a stand up meeting in the hallway can remove barriers to suport open communication.

  4. Actively listen to the other person’s perspective. When you provide space for the other party to express their thoughts and feelings, it's likely you'll identify a root cause or common denominator. Acknowledging what they say and asking questions to clarify their point of view will create buy-in and engagement on determining the next steps.

  5. Express your own thoughts and feelings clearly and assertively. Use language & tone that is respectful and non-judgmental. The use of “I” statements convey your own perspective, while avoiding blame or accusatory language. State your expectations for the situation vs. the individual. Honesty is the best form of kindness when communicated with tact. Notice how what you say makes you feel as you also notice how it's being received.

  6. Work towards a mutually beneficial solution. Once you've put all the facts on the table, removed blame and have an understanding of the core opportunity, it's time to explore options for how to move forward. Brainstorm a list of possibilities without judging them. You might find the solution actually lies in combining several of the possibilities. Together, consider the long-term implications of your solution. Then decide on 2-3 next steps that you can both (all) commit to, establish timeframes, and schedule your next touchpoint to keep things moving along smoothly.

Having a crucial conversation checklist provides the framework for difficult discussions to be handled effectively and with respect. This will lead to positive outcomes for everyone involved.


What do you think is the most crucial step in having crucial conversations? Are there others you would add to the checklist? I’d love to hear them!


Let’s connect for a virtual coffee & chat about it!



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