Coaching for Difficult Conversations

What is a Difficult Conversation?

A difficult conversation can be either anticipated or unanticipated and be on the phone or in person. It is a conversation in which:

  • One or both individuals care very much about the outcome
  • One or both individuals are risking something in conducting the conversation (personal and/or professional)
  • One or both individuals know the what, may also know the why. But given the unpredictable nature of communication, may be less confident about the how

What’s Involved in Coaching and Training for Difficult Conversations?

Coaching and training helps individuals master difficult conversations by planning for what they can know even better and preparing for the unpredictable aspect of conversation, the part that they can’t really know until they are in the midst of it.

  • If it’s a phone conversation, the focus is on mastering the ability to read the situation without the benefit of visual information. Emphasis is on advanced active listening skills, enhanced empathy and self-inventory before and after the conversation.
  • If the conversation is in person, the focus is on mastering non-verbal communication (from oneself and the other person) to create as constructive a conversation as possible. Emphasis is on using active listening skills, somatic and non-verbal awareness and communication and self-inventory before and after.

There are numerous books and resources on the Internet with best practices and techniques, however in my experience – personally and as a coach, the most reliable indicator of an effective communicator is trust. Therefore, every detail of my coaching and trainings are designed with integrity-based trust as the goal.

Each person has different strengths and weaknesses when it comes to communication, therefore, when it comes to the specific kind of support needed to set him or her up for success, a tailored strategy is called for, whether individual coaching or group training.

Coaching and trainings are designed to provide supplementary support to professionals who have to conduct difficult conversations in the course of their work and responsibilities. They are not meant to replace core training programs, but to provide additional support and insight into how to prepare for, conduct and debrief after conversations that are highly sensitive in nature but extremely important to do well.

While there are likely specific procedures to follow in terms of what to communicate and what not to communicate for liability reasons (for example) there will always be unknown variables in live conversations on the phone or in person. How does the individual prepare for and handle the unpredictable aspect of a difficult conversation in a way that results in the best possible outcome? Coachings and trainings address this challenge by providing exercises and processes that bridge the areas of professionalism, empathy and leadership.

While it’s true that you can’t plan for every possible scenario, there is a way to prepare oneself for the intrinsically unpredictable aspect of difficult conversations that can shift the quality of a conversation from bad to better, or good to excellent with even the most difficult situations.

How to work with me?

If you have an individual or team whose responsibilities involve conducting difficult conversations and they are high stakes conversations, please contact me. I’d love nothing more than to help them be even more effective and experience greater fulfillment in the process.

To learn about my credentials, story and philosophy, go here.


“I worked with Robin as part of an ongoing initiative to further improve the process of communicating with families about organ and tissue donation immediately after the death of their family member.  Given the extremely sensitive and important nature of the situation, this required a consultant with the highest degree of professionalism and empathic skills. Robin has a unique ability to identify the key areas of strength and challenges in a conversation and develop a specific plan of improvement. Her feedback and suggestions were absolutely on target and have resulted in consistently exceptional service to our donor families.”

Lisa Stocks, Executive Director at Lifesharing