How To Prepare For A Difficult Client Feedback Session

My trick for successfully managing a difficult conversation? A conversation map. This is a skill that Guillaume Wiatr taught me more than a decade ago. I've probably butchered his initial training on it but it's a skill that I continue to revisit and refine for myself. Every time I need to address something important with a team member or client, I open a google doc and map out a few key points: 1. What is my goal for this conversation? This is important: Do I want to learn something? Do I need to communicate boundaries? Are there next steps that need to be addressed? I write it down. 2. Then I map out my opening statement and try to keep it to 3ish sentences. This practice helps me avoid small talk at the beginning of the conversation, which can sometimes derail me. It also forces me to find the clearest and briefest way to get to the point. 3. I identify 2-3 questions I have for the other person. I find that difficult conversations often require us to step back from our assumptions/view and to learn something. So, I balance my opening statement against a few questions that seek feedback and understanding. This step can help me adjust my strategy half way through a difficult conversation and is usually THE piece that allows us both to leave the conversation, feeling good about it. 4. I consider their pushback/questions and how I might respond. 5. If possible, I share it with someone else to see if I'm being clear, fair, and productive with my map. 6. "Bonus" points: If the difficult conversation needs to be documented, you've already got your paper trail. Often times, my map won't take more than 1/2 a page. But even something this small can offer a lot of value. And, in case you're wondering...no....I don't usually deploy the oreo cookie approach. Similar to my comments on small talk, I think the compliment sandwich muddies the waters and offers the potential for sidelining the true purpose. I believe it's better to simply approach difficult conversations with empathy, clarity and openness.

When I simulate stakeholder conversations using GenAI, I explicitly tell the AI what puts me in defensive mode and ask it to use those to try and trigger me more. Most people practice handling various objections: What if they question our timeline? What if they question this data point? However, it's when we are triggered that we struggle most: What if they interrupt me repeatedly? What if they dismiss my expertise? Here's how to prep on "hard mode" with GenAI: 1. Identify your specific defensive triggers (we all have them!) 2. Tell the AI: "Here's what tends to put me in defensive mode... please include that type of trigger in the simulation." 4. Practice responding calmly to your exact trigger points 5. Get coaching notes from the AI with suggestions on better ways to handle the trigger. Remember: You know the data and the research. Often, it's when we get defensive or triggered that we aren't able to come up with clear, confident responses. Practice your triggers.