Difficult Conversations

There are a few points I hit like a broken record when coaching, and one of them is speaking directly. From the outside looking in, I can identify information, feedback, or expectations that, if clarified, would ease things for both my clients and their colleagues. In my mind’s eye, these conversations act like Liquid Plumber on a clogged drain, making the work flow

My job in these moments is to help my clients clarify their essential question or feedback and prepare to address it. I ask,  “What would happen if you asked that question directly?” or “What would occur if you offered that feedback?” and…“How would you feel about initiating that conversation?”

Often, once I draw to attention to a missing communication, my clients are off and running. They leave determined to have an important conversation, and they typically return with good news. “I talked to X about Y,” they report. "I feel so much better.” More often than not, the suggestion is all they need.

Sometimes, however, the situation is more complex. The missing communication may have complicated nuance or emotional weight. It may have been avoided for too long, making things tense and awkward. In these cases, folks need more preparation, and I coach them through it.

Although you can’t engineer human interactions, you can be intentional around message and tone.

To support this, I developed a model with four steps: assess, plan, rehearse, and exit. I lay it out below with coaching questions and techniques. Please use and share them freely.

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Honor the stakes. Why does this conversation matter? What do you stand to gain, and what do you fear losing? Beyond material outcomes, what are the emotional stakes?

Examine complexities. What makes this conversation difficult? With what other issues is the subject tangled? Where do you have a clear point of view or solutions, and what aspects are you still processing? 


Define success. What is the most important thing for you to communicate or ask? What is your goal for this conversation?  What would you consider a good outcome, or a good range of outcomes?

Outline talking points. How exactly will you say what you need to say? What words will you use to broach difficult topics? What potential objections can you identify, and how will you respond? How will you keep the conversation focused if it threatens to stray?

Embrace key phrases to support a good tone. What will you say to signal your candor? How will you communicate that you care about the other person and their point of view? How will you respond if your conversation partner becomes emotional, or if you become emotional?


Rehearse sensitive points in private. Practice—in the mirror, and, if you can, in role play with a trusted third party. Record yourself practicing, listen, and refine. (I know. It sounds painful, but it works.)

Practice general conversation skills in public. For anything that isn’t sensitive or private, practice in real life. Find opportunities in other, lower-stakes conversations to test your plan and key phrases for keeping a good conversational tone. The idea is to feel more relaxed and natural when applying these skills in future stressful moments.


Have a graceful exit plan. What will you say to wrap the conversation quickly, if needed? How will you be polite and compassionate in the moment, without getting stuck? Practice this too.

Know when to use it. What will be red flags that the conversation is becoming unproductive? What might you observe in your conversation partner? What are your own internal cues? (You might notice your heart rate increasing, sweaty palms, difficulty thinking, or heat on your face, beyond simple “nerves.”)

Difficult conversations are…well, difficult. However, you will get better and more efficient at them over time. Eventually, you will become confident in a compressed version of this process, as communications happen in real time. (Pro-level!) In the meantime, lean on a coach or a wise colleague/friend to get ahead of the conversation looming large in your mind. 

You’ve got this.