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10 Tips for Holding Difficult Conversations at Work


Whether you’re relaying bad news to an employee or addressing a workplace incident, managing difficult conversations is as uncomfortable as it is inevitable. 

Most people try to avoid conflict as much as possible, but that isn't as easy for employers. Putting off a challenging conversation may protect feelings, but it can also lead to poor performance, continued workplace conflict, and degradation in company culture.

And according to McKinsey, toxic behavior is currently the No. 1 driver of negative workplace outcomes, ranging from anxiety and burnout to intent to leave. 

So how can employers prepare for and better manage difficult interpersonal dynamics?

Challenging Conversations in the Workplace

Every manager has had at least one bad experience with a hard conversation at work, leading to lingering feelings of dread and, consequently, avoidance. 

Some common examples of difficult discussions might include:

  • Addressing negative feedback
  • Owning up to a mistake
  • Providing feedback to a direct report
  • Discussing redundancies and terminations
  • Reporting a colleague’s misconduct
  • Investigating inappropriate behavior
  • Mediating disputes and conflict resolution
  • Establishing boundaries with a colleague
  • Asking a manager or superior for a raise or promotion

From this list, it’s clear that these problems don’t resolve themselves. The longer a manager procrastinates a tough talk, the more resentment can build up and the more difficult it becomes to have a productive and healthy conversation.

Why Have Difficult Conversations in the First Place?

When managers ignore or otherwise fail to address a difficult situation head-on, it can have ripple effects across the organization, creating an environment where employees are afraid to speak up or reach out for help. 

For instance, avoiding a discussion with a direct report about a behavior or performance issue could result in the employee continuing the same pattern of mistakes. Not only can this lead to misunderstandings and a general lack of clarity, but without intervention, these problems could result in termination if they get bad enough.

In other words, there is no getting around a difficult conversation—only through it. By creating a psychologically safe environment to have these discussions, employers can:

Allow Employees to Feel Heard and Valued

Everyone deserves respect. Having tough conversations at work shows employees that their leaders respect them enough to hear them out and listen to their feelings and experiences. 

This open dialogue can further validate their feelings and help them feel heard and recognized at work, thereby cultivating a supportive environment that values every person’s perspective. As a result, employees feel more motivated and committed, leading to improved collaboration and overall job satisfaction.

Encourage Honesty, Transparency, and Healthy Communication

Challenging topics or issues are bound to arise in the workplace. But when they do, addressing them directly can lead to conflict resolution and a better understanding for everyone. 

That doesn’t mean managers should become the end-all-be-all arbiter. Instead, they should encourage their employees to speak and listen with an open mind while modeling this behavior at the same time. This transparent communication empowers employees to express their concerns and hear different perspectives as they work toward mutually beneficial solutions.

Recognize Uncomfortable Workplace Issues

Engaging in challenging conversations often compels managers and employees to confront uncomfortable and often overlooked issues. These discussions can shed light on ineffective processes or sensitive topics, such as discrimination or harassment. 

Listening to and addressing these concerns is essential to demonstrate an organization's commitment to taking accountability and creating a healthy and inclusive work environment. This immediate conflict resolution also allows for timely interventions and corrective measures that positively impact company culture, employee morale, and overall collaboration.

Improve Work Environment and Company Culture

Having difficult discussions in the workplace is about more than just allowing employees to speak their minds. 

A truly successful conversation is about achieving understanding first, and a mutually desired outcome second. When both parties are able to communicate openly about their feelings and work toward a common goal or solution, it promotes excellent collaboration skills and strengthens the work community. 

The result? Companies benefit from a robust culture of constructive feedback and active listening.

10 Tips for Managing Difficult Workplace Conversations

While the benefits of having a difficult yet productive conversation in the workplace are profound, managing one is no simple task. 

In addition to maintaining professionalism with employees, managers must also contend with their own nerves and potential tension or conflict. So what can they do to prepare for their next tough conversation?

Here are 10 tips to help employers navigate difficult discussions in the workplace:

1. Don’t Procrastinate a Tough Conversation

The first tip is simple, yet it’s often the greatest hurdle to overcome—don’t avoid the conversation

Avoidance is all too common, leaving room for anxiety or resentment to fester and even more challenging conversations to arise later down the line. Effective managers tackle these difficult situations head-first, whether it’s an underwhelming performance review or an HR issue. 

2. Plan Your Talking Points, But Don’t Write a Speech

Before diving into the conversation, however, it’s important to take a step back and plan out an approach. On a basic level, that means clarifying the purpose and objectives of the discussion and gathering necessary information or materials. 

Going beyond this standard prep work, managers can also consider how the other person will react to the conversation and prepare responses. But a meaningful conversation should feel organic, so it’s best to prepare talking points rather than a full script.

3. Focus on the Facts of the Situation

Approaching the anticipated discussion, managers will likely be pulling together the facts of the situation, whether it was a behavioral incident, performance issue, or dispute. In any case, it’s crucial to separate truth from personal feelings and look at the case objectively. 

While this might require using supporting data or evidence, it shouldn’t be presented in a confrontational manner. Managers should also be mindful of their tone, as sticking too much to the facts could come across as cold and detached. 

4. Consider the Other Person’s Perspective

As managers continue to examine all angles of a situation to facilitate a meaningful conversation, one essential element to consider is the other person’s perspective. 

Stepping into the employee or colleague’s shoes and acknowledging the issue from their viewpoint can lead to a more collaborative, constructive conversation. Not only does it show that managers care about their employees, but it also expands their own perspective on the matter—promoting a mutual understanding that better facilitates resolution.

5. Create a Comfortable Environment

The final step before the actual conversation is to foster a comfortable, open environment for all employees. 

Building trust and mutual respect takes time and effort. That’s why it’s crucial for managers to have regular meetings where they can check in with employees and have candid discussions about anything that comes up. 

This recurring feedback exchange makes addressing issues that arise much easier and less awkward.

6. Be Confident But Empathetic

Depending on the severity of the topic, difficult workplace conversations can seriously strain relationships with colleagues. 

Approaching the discussion with empathy, respect, and compassion is crucial—but that doesn’t mean managers should add their feelings into the mix. Instead of saying something like, “This is really hard to do,” managers should remain objective to avoid the conversation becoming too personal.

7. Remember to Listen

Active listening is another critical skill for managing difficult conversations. Managers should give employees the space to share their thoughts and feelings without interrupting them. 

One way to do this is by slowing down the conversation and pausing a moment before responding to truly process what the other person said. To reach a mutual understanding, both parties should engage in this practice.

8. Discuss Possible Solutions

Outside of redundancy or termination conversations, there’s almost always a way for employers and employees to find a solution together. 

While managers may come prepared with a list of action items for the end of the meeting, they should also use the discussion to build on these, working with the other person to uncover the most productive resolution possible.

9. Don’t Forget Yourself

Even in a successful conversation, emotions can still run high. That’s why it’s important for managers to be aware of how their feelings can play into a discussion. 

Maintaining a calm, professional demeanor is critical, so if the conversation becomes heated, it might be wise to take a deep breath or a short break.

10. Reflect on the Conversation

Finally, once the hard part is over, managers should learn whatever they can from the discussion by asking questions like, “What went well?” and, “What could be improved next time?” Reflecting on each meeting provides an opportunity for growth and improvement that only improves effective communication in future conversations. 

Leveraging Effective Communication to Boost Employee Mental Health

As employers continue to learn from difficult conversations and work toward bettering themselves and their companies, these efforts help to create an environment in which employees are free to be themselves and thrive in the workplace.

Looking for more conflict resolution tips? Read about 11 more ways leaders can use communication to improve employee mental health.

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