Have Difficult Conversations

Have Difficult Conversations is a social and communication skill that opens real doors once you have it. This 90-minute plan is ideal for learners with some foundation — you can complete it wherever you happen to be with the materials listed above, no special background required. The goal is not to leave you with theoretical knowledge but with a tangible, lived experience: by the end of this session, you will navigate challenging conversations with honesty, empathy, and clear outcomes. That concrete outcome is what separates structured plans from casual self-study — you always know what you're working toward and whether you've arrived.

The session moves through 5 carefully ordered steps, covering prepare thoroughly, choose time & place, lead with empathy, and be specific & kind. Each block has a specific time window so you know exactly how long to spend before moving on. The sequencing is intentional: early steps build foundational awareness and muscle memory, while later steps apply those fundamentals under slightly more demanding conditions — the same way a skilled instructor would structure a first lesson. By the time you reach the final step, you will have touched every core element of have difficult conversations at least once.

One thing most beginners miss: Difficult conversations get easier with practice. Starting them is often harder than having them. Keeping that in mind throughout the session will dramatically improve your results. After this 90-minute foundation session, you'll have a clear picture of which aspects of conflict resolution feel natural and which need more deliberate practice. That self-knowledge is the most valuable thing you take away — it turns a one-off session into the start of a genuine learning path.