Behavior & Culture, Leadership | May 08, 2025

Navigating Difficult Conversations: Strategies for Constructive Communication

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  • Navigating Difficult Conversations: Strategies for Constructive Communication

Leading difficult conversations at work when you’re a manager can be a minefield—first, because you, as we all do, have biases and make assumptions, and second, because identifying those biases takes time and dedication.

So, we’ll give you a head start in learning to communicate constructively. We’ll tell you about the fundamental strategies and list a few sentences and words to avoid when handling difficult conversations with team members.

Key takeaways:

  • Certain words and expressions tend to make others feel angry or offended.
  • Phrases that express judgment, cause defensiveness, or take the focus away from improvement are not constructive.
  • Start difficult conversations from a place of understanding and respect.
  • It’s OK to define goals for difficult conversations, but it’s not OK to leave the other person’s feelings, reasons, and worries on one side.
  • Listen actively with genuine interest and full attention.

Why difficult conversations matter for leaders and managers

One of the reasons why dealing with difficult conversations is so important for leaders is conflict resolution. Managing difficult conversations with empathy, fairness, and honesty—all elements of emotional intelligence—prevents conflicts from occurring and de-escalates the ones that emerge. Besides, leaders wouldn’t be effective relationship managers if they couldn’t talk their team members out of conflict in the workplace.

Leading difficult conversations constructively is essential to move teams, projects, and entire organizations forward. By not turning their back on tough chats, positive leaders contribute to keeping personnel satisfied with their roles and the work environment, which translates to employee engagement. And you know what having engaged employees means? It means you retain top talent within the company and remain competitive in the market.

Constructive communication inspires, guides, and motivates. Sure, mistakes and failures can’t be left ignored—but evolving matters more, and effectively managing difficult conversations at work points employees in that direction.

Strategies for constructive communication 

Here’s an example of a tough work conversation: You, as a team leader, got the results of your team members’ annual performance review—one of them performed poorly, and you must deliver the news one-on-one. Following are the crucial steps to communicate the bad outcome constructively.

Establish clear goals

When communicating a difficult situation to an employee—such as their poor performance—and if the end goal is to move the needle, there’s no point in sugarcoating what happened. Most importantly, there’s no point in emphasizing how bad the situation is.

More than scrutinizing why their performance fell short of expectations, you want underperforming staff to improve their performance. So, before having any tough conversation in the workplace, define the goals for the talk, and keep those goals in mind while chatting. 

Remember: Don’t spend too much time on problems—instead, focus on solutions.

Lead with empathy

Effective leaders and constructive communicators are empathetic. They take others’ feelings, motivations, and concerns into consideration. 

That doesn’t mean they’ll overlook the mistakes and failures of personnel, low revenue, or the launch of a competitor product, and it surely doesn’t mean they won’t act on those things. But it does mean they’ll initiate difficult conversations from a place of understanding. 

And that’s how difficult conversations can be handled successfully by positive leaders—with mutual understanding and genuine consideration for each other’s points of view. Without that, it’d be hard for employees to listen to their managers and feel inspired to improve.

Listen actively

If you’re leading difficult conversations with empathy, you’re already off to getting whatever situation you’re dealing with back on track—whether that’s a team member’s poor performance, a headcount reduction, or budget cuts. But empathy with active listening takes you further.

When you focus your full attention on what employees are saying and nod, react with micro facial expressions, ask questions, and paraphrase, you show genuine interest in their motives, feelings, and worries. But you must have that genuine interest because employees can tell whether you genuinely respect them or not.

Don’t forget to put your phone away in a place you can’t reach while chatting; otherwise, you won’t fully engage in the conversation, and you won’t get anywhere.

5 words and phrases to avoid in difficult conversations

With the right strategies in mind, you’re less prone to making an employee feel angry or offended. But strategies without implementation are useless, so below is a list of terms and expressions to avoid when leading difficult conversations.

1. “You should”

Giving instructions to a team, a department, or a company is something you must do at times. But if you start a one-on-one conversation with this expression, you’re setting off an unproductive conversation. You’ll come off as judgmental even if that’s not the case—and no one likes being judged. 

Your team member will most likely get defensive and focus on what went wrong rather than listen to your advice and learn how to improve. 

Failure isn’t the message—improvement is. So, instead of saying, “You should” do this or that, say, “How about” doing this or that or “Let’s” do this or that, and explain why.

2. “That doesn’t make sense”

to you—but it might make sense to your employee.

Ask them to walk you through their rationale and go from there. Sometimes, it’s more effective to consider the team member’s perspective as valid and discuss it until you get to the point you need to address than starting off by suggesting they’re wrong.

3. “Obviously”

Don’t ever assume you’re right and everyone else is wrong. There might be other valid standpoints, and you’ll lose your team’s trust. 

They’ll start to see you as an authoritarian—or at least someone who thinks they’re smarter. And that, along with other factors that make work environments toxic, is a strong reason for leaving a job.

So, instead of saying “obviously,” say, “from my perspective,” explain the perspective to your team member, and start a discussion about your viewpoint. Of course, you’ll come to the point of taking action, but considering multiple perspectives is not only wise but can also unfold valid arguments you hadn’t thought of.

4. “You always”

This is a statement of exaggeration, and it’ll set the tone for the entire conversation. The employee will feel compelled to fight you off throughout the discussion, and guess what? 

You’ll sound anything but credible, and the employee will focus on how many times the situation occurred as opposed to the causes and, above all, the efforts they must make to guarantee it won’t happen again.

5. “It’s not personal”

…but it usually is—it is personal for the employee, and you’ll make them angry if you say it’s not.

The message underlying this expression is that you don’t care about the impact of your corrective measures on your team member’s job and, quite frankly, their personal life.

The right thing to do is to acknowledge the negative effect of those measures or just not to say, “This isn’t personal” in the first place.

Taking the next step in mastering leadership communication

We want to take part in your journey of leading difficult conversations at work. That’s why we’d love for you to look over our leadership eLearning courses. They cover all the leadership skills to advance your career—including effective communication, conflict resolution, and emotional intelligence. Plus, you can take them any time, anywhere, from any device you wish.

Andrew Fayad

Andrew Fayad

Andrew Fayad is a managing partner at Positive Leader and the co-founder of ELM Learning, a leader in learning and talent development since 2013.