Leadership Communication Skills: Having Difficult Conversations with Your Team

Take a moment to think of a tough conversation that you need to have with someone, be it a family member, friend, boss, or co-worker, but you're holding back.

Hold that thought.

It's human nature to avoid difficult conversations. On one hand, they're complicated, and often times we worry that having them could make matters worse.

Our immediate instinct is to look for a distraction, but a distraction is not a solution.

What Are Leadership Communication Skills?

Leadership communication skills are the abilities leaders use to inform, listen to, and influence their teams. They include active listening, clarity, empathy, and the courage to have difficult conversations. Hard conversations are among the most avoided and most important of these skills, because they build trust and keep small issues from becoming big ones.

Why We Avoid Difficult Conversations

Let's look at some real-life situations.

Avoidance

My husband was seven-years-old when he lost his father. His family never truly grieved the loss together. This caused deep emotional scars that weigh heavily on him.

He's angry with his mother for avoiding talking about it. Yes, as a family, they are not ready to address the elephant in the room. They don't want to hurt each other in the process of bringing up the past.

My childhood best friend is a Project Manager in a top organization. A few years ago his boss became a sponsor on a new change-management initiative. From the start, the scope and deliverable of the project was a red flag, but no one on the team (including my friend) mustered the courage to speak up. They went with the flow.

Fast forward to the project going live, and things went south. Unaccounted working hours, money, reputation, trust, and morale hit rock-bottom. Above all, my friend lost his promotion and his boss was transferred to a different department.

What is the commonality between these two situations? Being willing to engage in a confronting conversation.

Silence

Difficult conversations are no walk in the park. They can leave us feeling anxious, stressed, and desperate for a way out.

The problem, however, is that these conversations are often the most important ones we can have for several reasons.

Facing up to and engaging in hard talks is one of the best ways we refine the core of who we are, become a better version of ourselves, and avoid living in denial.

It can be hard to confront someone about a touchy or uncomfortable topic due to our need for acceptance.

This is what we call Courtesy Bias.

Courtesy Bias is the tendency to give an opinion that is more socially correct than one's real opinion in order to avoid offending anyone.

There are countless resources online on how to navigate difficult conversations, yet most of us still put them off. Understanding what we are avoiding and why is a significant first step in the right direction.

Name What You Are Avoiding

Think back to the prompt from earlier: name a tough conversation that you need to have with someone in your life but you're holding back.

Apply these questions to your situation:

What is the specific conversation I am avoiding?

Why am I avoiding it?

What excuses am I giving?

What is my deeper fear around having this conversation?

Take a moment to write down your answers.

Now that you've identified your blocks in entering into this conversation, let's look at some best practices around engaging in it.

"We all know what it's like to stay silent and comfortable instead of voicing what we believe." Dr. Brené Brown

7 Steps for Having Difficult Conversations at Work

The top golden rule for engaging in difficult conversations at work is to focus on the situation, not the person.

Pushing with your words is like pushing with your hands: if you push, then you will get pushed back.

However, if you listen with respect, then you are significantly more likely to be heard.

According to Fred Kofman, founder and president of the Conscious Business Center, in order to have a productive confrontational conversation you must go through these seven key steps:

1. Listen

Listen quietly, with no interruption. We must be willing to listen to the other party without interrupting. Focus on hearing their side of the situation first. For more on this, see our guide on how to be a better listener.

2. Ask

Inquire openly with sincerity and curiosity. Try out starting your question with, "Do you mean…" to make sure you've heard the other party accurately.

3. Summarize

Let the other person know that you've heard them and understand their perspective.

4. Validate

Acknowledge that what the other person said is reasonable, even if you have a different interpretation. This is how you build psychological safety, so people feel safe to speak up next time.

5. Express

Share your truth. Share your assessment of the situation, examples, reasoning, goals, and suggestions. Be sure to speak in first person and use "I" statements. Avoid using "you", "we", and "it".

6. Negotiate

Engage creatively and try to find a solution that addresses everyone's concerns.

7. Commit

Formalize your agreement with a series of commitments and a timeframe (if needed).

The end goal of every difficult conversation is to understand each other's perspective and find a mutually agreeable solution.

This applies to conversations ranging from confronting your boss to talking with your family about past pains. Strong emotional intelligence makes every one of these steps easier.

Are you ready to have that difficult conversation?

You got this.

Ready to strengthen your leadership communication skills?

Hard conversations get easier with practice and a shared framework. DX Learning helps leaders build clear, caring communication habits, built on the CARE framework.

Explore the DX CARE framework or talk to our team about developing your leaders.

Frequently Asked Questions

What are leadership communication skills?

Leadership communication skills are the abilities leaders use to inform, listen to, and influence their teams. They include active listening, clarity, empathy, asking open questions, and having honest conversations when things get hard. Strong communication builds trust, aligns people around goals, and helps teams speak up before small problems grow.

Why is communication important in leadership?

Communication is important in leadership because it builds trust, aligns people around goals, and helps teams speak up before small problems grow. Leaders who communicate clearly and listen well make it safer to raise concerns, including the hard ones, which leads to better decisions and stronger results.

What are the most important leadership communication skills?

The most important skills are active listening, clear and direct messaging, empathy, asking open-ended questions, and giving and receiving feedback. Leaders also need the courage to have difficult conversations early. Practicing these daily helps people feel heard, understand what is expected, and trust the person leading them.

How do you have a difficult conversation with an employee?

Focus on the situation, not the person. Follow seven steps: listen without interrupting, ask open questions, summarize what you heard, validate their perspective, express your view using "I" statements, negotiate a solution together, and commit to next steps with a timeframe. The goal is mutual understanding and an agreement you both support.

Why do leaders avoid difficult conversations?

Most leaders avoid them because they are uncomfortable and feel risky. We worry the conversation will make things worse, we want to be accepted, and we fear hurting the other person. The cost of silence is usually higher, though. Unspoken issues grow, and teams lose trust, morale, and results.

What is courtesy bias?

Courtesy bias is the tendency to give an opinion that is more socially correct than your real opinion, in order to avoid offending anyone. At work it shows up when people stay quiet about a red flag or soften honest feedback. Leaders can reduce it by listening with respect and making it safe to disagree.

How do you start a difficult conversation at work?

Start by getting clear on what you are avoiding, why, and what you fear. Then open with curiosity rather than blame, and focus on the situation, not the person. Ask a sincere question such as "Do you mean...?" and listen first. People are far more likely to hear you once they feel heard.

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