Leading Difficult Conversations to Successful

Recent and current events continue to put a spotlight on how we interact, both personally and professionally.

In these times of continued tension, stress, uncertainty, and volatility, emotions can run high. And while in-person conversations can be difficult enough, virtual conversations can be even more challenging. As leaders and as teams, how do we build our emotional intelligence capabilities and skills to ensure the best outcomes in our daily interactions?

Susan Steinbrecher has been an ECC Affiliate Executive Coach for over 25 years. She is also a 5-time author/co-author with her most recent book Meaningful Alignment: Mastering Emotionally Intelligent Interactions at Work and In Life.As Susan explains, “We know there is a lack of emotional resilience and composure when stress is high. Our job is to educate and provide the skills that help leaders navigate difficult situations and more specifically, conduct difficult conversations to positive, successful outcomes.”

Susan continues, “In one of my favorite HBR (Harvard Business Review) studies, The Making of a Corporate Athlete, Jim Loehr and Tony Schwartz look at the diligent and relentless training of professional athletes that takes place across three distinct stages – preparation, performance, and recovery. They contrast that with the corporate leader, whose regimen is typically event, event, event. Yes, there is preparation, but is it enough? And is there really ever recovery?

Susan offers proven actions on how leaders can build their emotional intelligence to strengthen outcomes across the 3 stages of a conversation – preparation, the conversation itself, and recovery.


To most effectively prepare for a difficult or challenging conversation, leaders should address 5 key areas:

  1. Purpose. As Stephen Covey said, “Begin with the end in mind.” Planning for every business discussion, every business meeting, whether difficult or not, should start with the leader asking, ‘What is my purpose; what do I want to be the outcome?’ In addition to any business objective, include the human objective – to build a relationship(s) of mutual support.
  2. History. Take stock in the current relationship(s). How does it rate on a 1-10 scale? If there has been conflict in the past, understand that both parties will be bringing that conflict, bias, or anxiety to the table, whether consciously or subconsciously. Consider starting the conversation by acknowledging that you have not always been on the same page, but that it’s important to gain consensus going forward.
  3. Alignment. Understand how you are or are not aligned on the objective at hand. What are the key issues or barriers to alignment? And how might it be best to gain that alignment in a collaborative way through this conversation?
  4. Scenario planning. Role plays to anticipate their response. Ask yourself, “If I were in their shoes, how would I respond?” If you don’t know, reach out to colleagues. In the absence of role play, one can be easily blind-sided or triggered, which can quickly derail the conversation and lead to greater dissension.
  5. Mindfulness. Given your purpose and the relationship going into the conversation, think about what else you need to be mindful or conscious of, from business issues to personal issues. For example, a colleague working remotely might come to the conversation with heightened feelings of isolation or anxiety over work/family balance.


The Conversation Itself
Even with thorough preparation, things can quickly go awry if you do not maintain your focus and composure. Think about your conversation in 3 parts:

  1. Purpose. Start the conversation in collaboration by stating the reason for the conversation. Be direct and clear. Use the pronoun we, not I. Suggestions:
    –   Thank you for taking the time to meet
    –   The reason we’re here today …
  2. Discovery. Continue the conversation by asking, listening, and responding. Be empathetic, not defensive. Maintain neutrality to any potential negative emotion otherwise, trust is lost and connection is broken. Be humble. Stay focused and on track by skillfully redirecting any derailers. Acknowledge any past issues or disagreements and express a desire to reconnect and work together to resolve them. Realize this may not be a one-and-done conversation, but that it may take more conversations to move the needle. Suggestions:   Acknowledge & Ask
       –   I realize we have not been on the same page previously. I’m hoping we can …
    –   How are you doing?
    –   What are your thoughts on this project?
    –   What have been your biggest challenges on this project?   Listen & Understand
       –   So let me see if I got that. You said …
    –   Sorry to stop you; I want to make sure I heard you. You said …
    –   Is there anything else I should know?
    –   You’re bringing up an excellent point that deserves attention. Let’s move it to the parking lot where we can give it proper attention at another time.

       –   I’m grateful you shared that.
    –   I can see why you felt that way.
    –   I appreciate your hard work and dedication.
    –   I think we’ve made very good progress through this conversation.

  3. Accountability. Close out the conversation but recap the conversation, share your understanding, and discuss what comes next. Suggestions:
    –   Here’s what I’m understanding …Did I get it right?
    –   Anything else that’s important for me to know?
    –   Here’s what I see as our next steps … Do you agree?

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