A Leader’s Guide to Having Difficult Conversations


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In this episode of the Sales Leadership Awakening Podcast, host Steven Rosen and Colleen Stanley delve into mastering difficult conversations, stressing preparation and agreement on the next steps. They highlight vital emotional intelligence skills essential for navigating these dialogues effectively. Practical strategies for delivering constructive feedback and fostering growth are shared, emphasizing the importance of stating intentions and fostering psychological safety.

“If this is an important discussion that we want to help someone get better on our team, taking the time to think it through, to prepare what you want to say, how you want to say it, if you have a coach or if you have a colleague that you can role play it through and see how it sounds, you’re going to get much better results.” – Steven Rosen

Key Takeaways:

  • Preparation is vital to having successful, difficult conversations. Thinking through what you want to say and how you want to say it can lead to better outcomes.
  • Emotional regulation is an essential skill for sales managers to develop. Managing your emotions during difficult conversations can help prevent them from escalating into arguments.
  • Empathy is crucial in difficult conversations. Understanding and acknowledging the other person’s thoughts and feelings can help create a more productive and respectful dialogue.
  • Stating intentions before giving feedback can help create psychological safety and ensure the feedback is received constructively.
  • Focusing on feedback and coaching when onboarding new employees can set the expectation that difficult conversations are a normal part of the company culture.
The interactive podbook below contains videos, audio, articles, summaries, transcripts, and YouTube shorts from this podcast episode.

Full Episode Article:

Title: “A Leader’s Guide to Having Difficult Conversations”

Byline: By sales leadership and coaching experts Colleen Stanley and Steven Rosen


Having difficult conversations is a challenge that many people shy away from. Over 50% of individuals avoid these conversations simply because they find them uncomfortable. This is true even for high drivers, who are often assumed to be comfortable with difficult conversations. However, mastering the art of having these conversations is essential for effective sales leadership.

In a recent episode of the Sales Leadership Awakening Podcast, hosts Steven Rosen and Colleen Stanley discussed strategies for having difficult conversations and shared insights on bridging the gap between knowing what to do and doing it. They emphasized the importance of preparation, emotional intelligence, and constructive feedback in navigating these challenging discussions.

Preparing for Difficult Conversations

One of the critical factors in successfully navigating difficult conversations is preparation. The more you prepare, the better the conversation is likely to go. This includes understanding the issue, seeking to understand the other person’s perspective, and formulating a plan of action for change.

Rosen suggests a five-step framework for preparing for difficult conversations: First, prepare for the conversation by understanding the issue and seeking to understand the other person’s perspective. Second, agree on the next steps and ensure a plan is in place for change. Third, invert the traditional approach by having the individual send their plan of action to the manager, which increases commitment and accountability. Fourth, follow up on the plan of action to ensure progress and provide ongoing support. Fifth, reflect on the conversation and learn from it to improve future interactions.

By following this framework, sales leaders can confidently approach difficult conversations and increase the likelihood of positive outcomes.

The Role of Emotional Intelligence

Emotional intelligence plays a crucial role in navigating difficult conversations. Sales managers must develop two critical emotional intelligence skills: emotional regulation and empathy.

Emotional regulation is the ability to manage one’s own emotions during a difficult conversation. Sales managers must remain calm and composed, even in the face of resistance or defensiveness from the other person. By staying emotionally stable, sales managers can focus on finding a solution rather than getting caught up in the need to be right.

Empathy is another essential skill for having difficult conversations. It involves understanding and acknowledging the other person’s thoughts and feelings, even if they are not explicitly expressed. By demonstrating empathy, sales managers can create a safe and supportive environment for the conversation, which increases the likelihood of a positive outcome.

Constructive Feedback for Growth

Giving constructive feedback is critical in difficult conversations. The goal of feedback should be to facilitate growth and improvement rather than make the other person feel like a ton of bricks have been dropped on them.

One strategy for ensuring constructive feedback is to focus on the underlying issue rather than the presenting problem. Often, the presenting problem is not the real problem, and addressing the root cause can lead to more meaningful change. By examining the hiring process and incorporating feedback into the onboarding process, sales leaders can set the stage for a culture of growth and improvement from the start.

Another important aspect of giving feedback is stating your intention. You create a sense of psychological safety and trust by clearly communicating that you intend to help the individual improve and make their life easier. This can make the difficult conversation feel less threatening and increase the likelihood of a positive response.

Bridging the Gap: Belief Systems and Preparation

Examining your belief system to bridge the gap between knowing that difficult conversations are necessary and having them is essential. Do you believe that sharing is caring? Can coaching genuinely transform people? By aligning your beliefs with the importance of difficult conversations, you will be more motivated to do the hard work of leadership.

Additionally, preparation is vital to successfully navigating difficult conversations. Taking the time to think through what you want to say and how you want to say it, and even role-playing the conversation, can significantly affect the outcome. Practice makes perfect, and by preparing thoroughly, you can confidently approach difficult conversations and increase the likelihood of a positive outcome.


Mastering the art of difficult conversations is essential for effective sales leadership. By following a framework for preparation, developing emotional intelligence skills, and giving constructive feedback, sales leaders can confidently navigate these challenging discussions and achieve positive outcomes. By examining their belief systems and investing time in preparation, sales leaders can bridge the gap between knowing what to do and having difficult conversations. Remember, difficult conversations are an opportunity for growth and improvement for both the individual and the team.

Republished with author's permission from original post.

Colleen Stanley
Colleen Stanley is president of SalesLeadership, Inc. a business development consulting firm specializing in sales and sales management training. The company provides programs in prospecting, referral strategies, consultative sales training, sales management training, emotional intelligence and hiring/selection. She is the author of two books, Emotional Intelligence For Sales Success, now published in six languages, and author of Growing Great Sales Teams.


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