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?
- What are the pros and cons of deferring? What are the pros and cons of seizing the moment?
- If I choose to defer, how can I do so gracefully? If I choose to seize the moment, what do I want to bear in mind?
3. Duration
- How much time should I allot for the conversation?
- Is that a realistic assessment, or is that how much time I hope it will take?
- Do either of us have a hard stop at the end of this conversation?
- Do we need to keep track of time? If so, can I share that responsibility with the other person, or is it mine alone?
- How much of a buffer should I leave between the figural "end" of the conversation and the literal moment either of us will need to move on to our next obligation?
- What if the conversation goes much better (or worse) than I expect?
- How good (or bad) will it have to be for me to ignore my schedule in order to continue the conversation?
4. Place
- If we're meeting in person, where should the conversation occur?
- If we're meeting virtually, should it be via video or phone?
- If we're meeting virtually, where should I be located, and where should the other person be located (and can I influence their location)?
- Would a formal setting like an office or a sit-down restaurant provide some useful social constraints, or would it feel too stifling?
- Would an informal setting like a cafe or at home be helpfully relaxing, or would it feel too unbounded?
- If there's a location in which this conversation would normally take place, will that predictability be comforting or stultifying?
- Should it be on my turf, or their turf, or on neutral ground?
- How much privacy will we need?
- Will the presence of other people be helpful or distracting?
- What other environmental factors might be in play?
- Will any visual distractions be in my line of sight or theirs?
- Will ambient noise affect the conversation?
- Will there be any physical discomforts that could make it hard to focus?
- If any of these factors change in the middle of the conversation, what am I prepared to do to deal with them?
5. Space
- If we're meeting in person, how should we be oriented toward each other?
- Should we be across a table, or next to each other, or on adjacent sides?
- Should there even be a table? Should we even be seated?
- What would it be like to hold the conversation while taking a walk together?
- What proximity is optimal, given the relationship and our respective preferences for personal space?
- How close is too close? How far is too far?
- Would I be better served by increasing or decreasing that distance?
- Would it be comforting or inappropriate to touch the other person?
- If it would be comforting, am I prepared to reach out to them?
For Further Reading
Better Conditions for Working Remotely
Intent vs. Impact (When Communication Goes Awry)
How to Deliver Critical Feedback
Make Getting Feedback Less Stressful
Learning to Yield (Navigating Difficult Conversations)
Updated June 2021.
Photo by Didriks.
