How to Master Difficult Conversations as Leaders

Meet Caroline Milton:

Caroline Milton is working to change the experience of women in business by providing a preventative approach to burnout, building resilient teams, and employing a holistic approach to productivity. With a background in biomedical engineering and supply chain leadership, she has experienced burnout firsthand, and then sought to understand the societal and physiological factors that heighten burnout for women. She now uses her expertise to help equip women to build a toolkit for burnout prevention and to lead organizations through change management that supports productive and resilient teams.

Connect with Caroline Milton

Meet Katie Ervin:

Dr. Katie Ervin is a vision-driven, goal-focused leader with a proven history of innovation and achievement. Throughout her career, she has established a reputation as a transformational leader who is driven by challenge, undeterred by obstacles, and committed to furthering standards of excellence. Efficiency, project management, and organizational change while building trust throughout an organization is a strength.

Connect with Katie Ervin

Meet Ryann Dowdy:

Ryann Dowdy is a community builder and expert in sales. She's built multiple 7-figure businesses of her own - and helped hundreds of women successfully build the 6 and 7-figure businesses of their dreams. Today, as founder of Be in the Room, Ryann's mission is to create a space for women to come together and be fearlessly themselves while empowering the next generation of female leaders.

Connect with Ryann Dowdy (Be in the Room)

Here’s a look inside this episode…

An Overview of Difficult Conversations:

As leaders, we often find ourselves in difficult conversations. Whether we're dealing with a difficult team member or addressing a sensitive issue with a client, these conversations can be challenging. But if we approach them with the intention of listening to learn, rather than listening to respond, we can be much more productive and reach a successful resolution.

Honesty is Kind:

Honest conversations build environments of trust. Leaders may often avoid difficult conversations in fear of hurting people’s feelings. However, it’s always best to be truthful. Honesty creates opportunities for growth, both personally and professionally. When we are honest with others, we create the opportunity for change and progress. Therefore, leaders should strive to be transparent and authentic in their communication to create a foundation of trust with their teams.

Ditch the Script:

When leaders go into a difficult conversation, it is mission critical to be flexible and open. Employees are people – and people just want to be seen, heard, and understood. Those in leadership roles cannot plan a script on how they want the conversation to go - because the other person won't always follow it. Leaders should go into these conversations with the intent to understand and learn, rather than to simply make points. Leaders with a hidden agenda will find it difficult to get any real resolutions from difficult conversations.

Understanding Motivators:

As a leader, it's important to understand not only your own goals and motivations, but also those of your employees. People don't work solely because they want to see you succeed - they also have their own goals and objectives that they're striving to achieve. By taking the time to understand what motivates your employees, you can better support their performance and help them to achieve their goals. Understanding these motivators is key in navigating difficult conversations.

Psychological Safety:

What is psychological safety? It's simply the belief that you can share ideas and speak up without fear of humiliation or punishment. When team members feel like they can't bring their whole true selves to work, it diminishes the quality of work they'll be able to do. People are less creative and less productive they feel the need to put on a mask and hide their true selves in the work environment.

Leaders need to create an environment where people feel a sense of belonging. That means allowing them to bring their whole true selves to work. When people feel like they belong, they're more likely to be loyal and happy – and less likely to have their guard up during difficult conversations.

Self Awareness:

Being a leader doesn't mean you have to be perfect. In fact, the best leaders are self-aware. They know their own strengths and weaknesses, and they're always looking for ways to improve. Great leaders are those who admit to being real and flawed, not someone who pretends to be perfect. Because when leaders fake perfection, they actually end up damaging their team.

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