Navigating Difficult Conversations: 7 Tips For Success

Successfully navigating difficult conversations is an essential leadership skill. Done well, and you will create a high-functioning and competent team that respects you, respects each other and enjoys working together. However, avoiding or mishandling difficult conversations will lead to a mediocre team lacking trust and struggling to meet performance expectations.

If you find yourself managing a dysfunctional team, it is 100% your responsibility, as the leader, to have the conversations needed to fix any issues. This may feel like tough love, but leadership is about effectively communicating and solving problems. Your ability to handle difficult discussions will mean success or failure for your team. It’s not on the team to fix this – it’s on you – the leader.

If you’ve ever avoided having an uncomfortable conversation, I have good news. First, you’re not alone – nearly everyone feels uneasy about tackling challenging topics. Second, anyone can do it if willing. It doesn’t matter your IQ or educational background. All it takes to have a difficult conversation is doing it.

Why We Avoid Difficult Conversations

Most people would rather not be uncomfortable, even if a particular conversation must take place. One poll found that one in four people have been putting off an awkward convo for at least six months.   Fifty percent avoid the other person at all costs, and an incredible 11 percent quit their jobs to avoid a difficult conversation!

Although it’s usually easier to face the issue, people often fear rejection, retribution, and misunderstandings—no wonder 50 percent of managers cite difficult discussions as their top challenge.

Avoiding these conversations can lead to disengagement, lack of motivation, and employee turnover. Luckily, you have it in you. All it takes is trying. Learn the steps, practice, and reap the rewards of fiercely leading your team.

Top 4 Examples of Difficult Workplace Conversations

Here are the most common difficult conversations you might have at work.

1. Performance Reviews

As a leader, you’ll likely be giving a negative performance review here are there. Despite being highly uncomfortable, giving honest performance reviews is essential to having a well-performing team. Allowing an underperforming person to stay in a role that’s not right for them is the quickest way to lose the entire team’s respect and motivation.

A negative performance review should come after plenty of training, coaching, and feedback to the employee. Suppose this is the first negative performance review you’ve given an employee. In that case, it makes sense to agree to a plan of action and approach it with a solution-oriented mindset to focus on helping the other person improve.

2. Giving feedback

Many people feel uneasy about giving feedback to employees or peers. Still, it’s the only way to ensure the person knows your expectations and has an opportunity to fix the issue.

According to the incredibly successful book, The One Minute Manager, immediately give negative feedback and be specific about what the person did wrong. End the feedback conversation by reaffirming the person’s value on the team, but not of their performance in this situation. They should know that the performance didn’t meet expectations but that you still value them as a team member.

3. Exposing Bias or Discrimination

If you witness or experience injustice or bad behavior in the workplace, you likely need to have a difficult conversation. It’s crucial to address these events to prevent them from happening again or escalating.

The best thing to do is to reach out to your designated HR contact and talk through any observation or evidence of bias or discrimination.

4. Charged Convo with the Boss

There will be occasions when you need to have a difficult conversation with your boss. You may be asking for a pay raise, additional responsibility, a promotion, or addressing a workplace issue. If you ever find yourself in a charged exchange with your manager, stay composed, respectful, and choose your words wisely.

Clarify your point of view, but avoid turning it into a major fight by thinking before you speak, never lifting your tone, and hearing what the boss has to say.

How to Approach Challenging Conversations

Put Yourself in Their Shoes

Before and during the discussion, consider what the other person may think and feel. Try to understand how it may feel for them to be in this situation. Instead of being hung up on your viewpoint, hear what the other person says, and do your best to understand their perspective. Consider how they feel about having this conversation and what drives their objectives and expectations.

Identify the Ideal Outcome but Be Flexible

Avoid holding on to strict expectations and be ready for compromises. Consider the ideal outcome, but prepare for something different. Keep in mind that the priority is to come to a mutual understanding and leave the discussion without resentment and unsolved points.

If you’re having a difficult performance review or feedback discussion, the other person may not agree with you. But a good outcome is that they understand the issues you see, and you have a plan for moving forward.

Listen Actively

Think before you state your opinion and take time to listen. People often focus on what they’ll say and disregard the other person.  Understand where they’re coming from and address their concerns in your response.

Active listening includes observing verbal and non-verbal messaging, asking clarifying questions, and giving the other person your full attention.

Protect Yourself Emotionally

Although that might be easier to say than to do, ensure that the conversation doesn’t emotionally drain you. Take a break if you need it, and do your part in preventing the discussion from escalating into a fight.

Moreover, you don’t have to find a solution right off the bat. Sometimes it’s enough to open a dialogue and disrupt the status quo. That makes it more likely to reach a conclusion the next time you discuss the issue.

Stand Your Ground but Avoid Being Defensive

People often become defensive and miss the point of the conversation. Do your best not to transfer the blame or focus on conflict instead of resolution.

Stand up for yourself and state your point, but avoid playing the victim card or ignoring your responsibility.

Be Empathetic

Remember that we’re all human. Each of us struggles with insecurities, worries, strengths, and weaknesses. Be kind and try to come from a place of wanting to do what’s best for everyone.

Seek Solutions Together

Consider a solution that works for both sides. Work together on finding the best conclusion and talk about what happens next.

If it’s impossible to agree on a solution right away, determine a time again where you can meet again.

Have the Conversation

Difficult conversations are stressful for everyone, and most people would rather avoid them. Yet, that won’t make the issue disappear and will likely cause more pain over the long term.

Focus on finding a satisfying conclusion for both sides and turn it into an open and honest dialogue. You may even turn an unpleasant discussion into a stronger relationship by respectfully addressing issues.

You’ve likely got a difficult conversation you need to have in some area of your life. Take the essential steps to prepare for the discussion and determine the ideal outcome. Commit to doing it soon.

Regardless of whether the other person agrees with you or if you ultimately achieve your goal, you will feel lighter having had the conversation and more confidence in tackling the next one!

Keep going on your professional development journey. Check out these unconventional development ideas to keep your career moving in the right direction.

About the author

Nina Sheridan is a seasoned author at, a blog renowned for its insightful exploration of the increasingly interconnected worlds of business, technology, and lifestyle. With a keen eye for the dynamic interplay between these sectors, Nina brings a wealth of knowledge and experience to her writing. Her expertise lies in dissecting complex topics and presenting them in an accessible, engaging manner that resonates with a diverse audience.