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How to Have Difficult Conversations as a Leader

Imagine you’re sitting at your desk, staring at the clock. The meeting is in 10 minutes, but still, you don’t feel ready. You’ve rehearsed the conversation in your head 100 times, but your stomach is still in knots. 

Today, you need to talk to a team member about their performance. It’s not just a regular chat but a tough conversation you’ve dreaded for weeks. You know it needs to happen, but you’re worried about how it will go. 

Will they get defensive? Will the discussion strain your relationship? 

As a leader, having these difficult conversations is part of the job, but it doesn’t make them any easier. With the right approach, you can turn these challenging moments into opportunities for growth and understanding. Let’s talk about how. 


Some key factors that keep us from engaging in difficult conversations, or handling them as we’d like to, are our personalities, experiences, and culture. These factors impact how we approach difficult conversations, how others approach them, and how we all handle them when we’re in the middle of one. 

Personality: 

Everyone has a unique personality that affects how they perceive and respond to difficult situations. While some are naturally passive, others tend to be direct and assertive. No personality is better, each style simply means we need to be aware of our tendencies and what is needed in various situations.

Experiences: 

Past experiences shape how we view current issues and how we engage in conflict. If we grew up engaging in healthy conflict we will be well-versed in addressing issues, while honoring people. If conflict was avoided or seen as harmful, we often lack the skills needed to engage in difficult conversations. Someone who has had negative experiences may be more defensive or sensitive. For example, if an employee faced harsh criticism from a previous employer, they might be more apprehensive during feedback conversations. 

Culture

Cultural backgrounds influence how people communicate and handle conflict. What is acceptable in one culture might not be in another. For example, in some cultures, direct confrontation is seen as disrespectful, while in others, it is expected.

In addition to our personality, experiences, and culture, we all have triggers that can make difficult conversations harder. As a leader, you need to understand your triggers to stay calm and collected in high-stakes conversations:

  • Truth Triggers: When what you believe is true gets challenged.
  • Relationship Triggers: When trust or psychological safety is perceived to be broken. If you feel an employee has betrayed your trust, addressing the issue can be challenging.
  • Identity Triggers: When your sense of self is challenged. If your leadership abilities are questioned, it can hit close to home and make the conversation more difficult.

Common Stumbling Blocks to Difficult Conversations 

Stay composed and confident through difficult conversations by planning for and navigating common stumbling blocks that get many derailed. 

The Timing of Difficult Conversations is Important 

Don’t delay difficult conversations. The longer you wait, the higher the stakes and emotions. Address the issue as soon as possible.

Starting the Conversation

Begin with kindness and clarity. Say something like, “I’m going to share this in a kind way and I’m going to be 100% clear on the issue at hand.” This sets the tone for a respectful and straightforward discussion.

People First Focus: Let the person know you care about them. For example, start by saying, “I value your contributions to the team.”

Doing it Live and in Person:

Face-to-face conversations are often the best way to handle difficult issues. They allow for better communication and understanding through body language and tone of voice.

Staying on Topic: 

It’s easy to get sidetracked. Focus on the main issue. If the conversation is about missed deadlines, don’t bring up unrelated personal or professional issues.

Delivering with Clarity: 

Be clear and concise. Address one item at a time and be kind. Use simple language and avoid jargon.Quick and Clear Ending: Keep the conversation short and to the point. Summarize the main points and outline the next steps.


Now that you understand the foundation of how to have difficult conversations, it’s time to learn how to implement these steps.

In this FREE guide, “How to Have Difficult Conversations Well: A Leader’s Guide to Getting It Right When Relationships and Results Are On The Line”, you’ll receive the coaching to learn HOW to implement and succeed in these tough conversations.

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Difficult conversations are part of leadership. By being kind, clear, and supportive, you can navigate these talks successfully. Use these steps to resolve issues AND maintain relationships for future success. Be proactive, address issues promptly, and always follow up.


Remember, you might need a little extra support. Our coaches are here to help you see your blind spots and create the action steps you need. If you are ready to build a leadership plan to get your organization to succeed, get started with an executive coach today.

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