Table Setting by Didriks dinnerseries 6960369650 EDIT

We know it's going to be a difficult conversation because we keep putting it off. We know it's going to be difficult because we feel unsettled when we think about it. We know it's going to be difficult because we're not sure it's going to end well. What can we do to make it easier and increase the likelihood of success?

I regularly help clients prepare for a difficult conversation: firing an employee, sharing critical feedback with a colleague, resisting an unreasonable superior, having a heart-to-heart with a friend who's struggling. And I believe they're well-served by what I call setting the table: considering all the tactical steps and logistical factors that might help (or hinder) their efforts. I see five aspects to difficult conversations, and within each one there are a number of questions we can ask in order to prepare. I'm not suggesting that you need to answer all of the questions below, and you may lack the ability to determine some of the answers. But we can become so distracted by the challenge of a difficult conversation that we fail to consider the many ways in which we might prepare, and it's often helpful to simply pause and remind ourselves of our options before we take action.

1. Relationship

• Who is this person to me, and who am I to them?
• What is our status relative to each other, both formally and informally?
• What authority or influence do I have over them?
• What authority or influence do they have over me?
• How will these factors affect my invitation (or my request or my command) to speak with this person?
• Are we engaged in an ongoing dialogue, or will this conversation be something new for us?
• How will that affect their response to the conversation?
• How do I want this conversation to impact the relationship? Deepen it? Challenge it? End it?

2. Timing

• When should the conversation occur? What time of day? What day of the week?
• Am I rushing things to get it over with?
• Am I dragging my feet in the hope that the issue will be resolved before I need to deal with it?
• What will I and the other person be doing immediately before and immediately after the conversation?
• What timing will allow both myself and the other person to be in the best possible frame of mind for this conversation?
• What if the other person initiates the conversation before I expect it to occur?