8 minute read

Manager’s Guide: How to Handle Difficult Conversations at Work

You’re waiting to begin a 1-1 with your direct report. There’s a knot in your stomach that grows as the time ticks closer to the meeting. This is the last thing you want to be doing right now.

You’re about to have a difficult conversation.

As managers, difficult conversations are part of the job. You’ll find yourself delivering bad news both up and down, dealing with poor performance, letting team members go, and more.

Unfortunately, most managers aren’t trained in how to have difficult conversations at work. 

So they—and you—are left to do some digging on your own. Which is what’s brought you here.

In this article, you’ll learn:

  • a framework for handling difficult conversations, no matter what they are
  • what to do when the conversation isn’t received well
  • how to have difficult conversations with your manager
  • the cost of handling difficult conversations poorly

But first, let’s all get on the same page with what difficult conversations are and why we find them so challenging.

Difficult conversations explained: what are they and why are they so challenging?

Difficult conversations, challenging conversations, tough conversations. What are they?

The authors of Difficult Conversations define them as ‘anything you find hard to talk about’. 

One of the most telling characteristics of whether a conversation is difficult or not is if you fear the outcomes of having that conversation. 

It just so happens that work life is full of them. And people really do dread them.

In fact, a 2015 study by the Chartered Management Institute found that 57% of its 2,000 respondents said they ‘would do almost anything’ to avoid a difficult conversation. 

52% said they would rather put up with a negative situation at work than have to talk about it. 

That reluctance comes down to fear: 

  • fear of emotional responses
  • fear of confrontation
  • fear of the unknown
  • fear of communicating the point wrong 

Managers however have to face those fears head on. Handling tough conversations is in the job description.

The steps we’ve outlined below will help you do so effectively and hopefully make having those difficult conversations a little easier. Then you can have a successful conversation that reaches a desired outcome—whatever that outcome is.

How to have difficult conversations: Steps you can follow for every difficult conversation you have

Difficult conversations are one of the most stressful parts of people management. But they can be managed. 

Here are the steps you should take with every difficult work conversation:

  • Set aside a specific time
  • Prepare your talking points
  • Follow the 3 Cs of communication
  • Listen actively
  • Acknowledge their feelings
  • Focus on solutions, not blame
  • Lay out next steps

Now, let’s break each step down so that you can implement them properly.

Set aside a specific time to have the conversation

Difficult conversations are challenging for both parties involved. They can be wrought with emotion and sometimes the other party can feel like they’re being attacked (even when that’s not the case).

For that reason, they require privacy, focus, and a disturbance-free environment.

As Matthew Ramirez of Rephrase puts it, “It’s important to have sensitive discussions in a secluded environment. Ensure that the conversation is held between two individuals only, with no interruptions or disturbances.”

That's why one to one meetings are the ideal setting. 

Why? Because they're already scheduled, occur regularly, and provide a private and confidential environment. 

What you don’t want to do is use finding the ‘right time’ as an excuse to put off the conversation indefinitely.

So while you don’t want to bring up a difficult conversation spur of the moment when emotions are charged, you also don’t want to put it off.

Prepare your talking points

Preparing your talking points is more than just a step in the process; it's a strategy to ensure clarity and balance in a difficult conversation. 

By focusing on facts and not feelings, you can articulate your concerns without letting emotions take over. 

However, your own feelings might be at the core of the issue, like feeling undermined or unappreciated. When that’s the case, preparation helps you communicate these emotions in a neutral way.

You can use your one-on-one agenda (grab our one on one meeting template here) to prepare for the conversation. 

You can keep your talking points in a private document but add the topic itself to your shared 1-1 agenda. This gives your direct report a heads-up on what's coming.

If you’re a Waggle user, you can populate your meeting agenda from the Manager’s Dashboard and keep track of past conversations too.

Josh Miller, an HR Manager and Founder of Smart So Tech, shared his advice on preparing for a difficult conversation:

Ultimately, preparation sets the stage for a productive dialogue and builds your confidence in handling the conversation effectively.

Stick to the 3 Cs of effective communication: clear, concise, consistent

When it comes to difficult conversations you want to avoid ambiguity or confusion. That’s where the 3 Cs of communication come in. The conversation should be clear, concise, and consistent.

These principles ensure you’re understood. They also possess the power to turn a tough conversation into opportunities for growth.

But, allow us to caveat that point with this one: every conversation and every employee requires a unique approach, tailored to the issue at hand. You can’t approach these conversations with a blanket framework and expect the same results every time. 

Sudhir Khatwani, Founder at The Money Mongers, shares real-world examples of how difficult conversations can be approached differently. 

His first example is about a direct report who struggled with time management:

His second required a different approach and even involved HR:

Sudhir’s examples serve as reminders that every situation is unique and that some difficult conversations require mediation. You may need to have an internal conversation with senior leadership or HR before having the conversation with your team member.

→ Looking to build the behaviors and communication skills of a great manager? Check out our article: How to be a good manager. ←

Listen actively

Ever found yourself just waiting for your turn to speak? Eager to share your own perspective after someone else has shared theirs? 

In a difficult conversation, that approach won't cut it. You have to listen to the other person’s perspective fully. This conversation isn’t meant to be ‘won’, it’s meant to be resolved.

It's not just hearing the other person’s words; it's about getting to the heart of what's being said.

Why does this matter? Because it shows respect. It builds trust. And it can uncover the real issue that needs solving.

A difficult conversation between a manager and direct report should be just that—a conversation, not a lecture.

When your difficult conversation involves delivering criticism, sharing bad news, or bringing up a situation where your team member might be in the wrong, you need to hear their side of the story and their concerns. 

Acknowledge their feelings

You've listened actively, but now comes another crucial step: acknowledging their feelings.

Think about a time when you felt misunderstood. Were you frustrated? Did you become defensive?

When you’re the recipient of a difficult conversation, these are natural reactions. 

But imagine if in those situations, you felt heard and understood. 

Acknowledging feelings isn't about agreeing or taking sides. It's about recognizing the emotions at play.

Maybe your team member is feeling frustrated, overlooked, or even scared. By acknowledging these feelings, you're building a bridge, not a wall.

Focus on solutions, not blame

Difficult conversations can quickly become a blame game.

But that’s not helpful and can breed resentment between you and your team members. 

You’re the manager so you have to take the lead on finding solutions.

Ask, "What can we do to resolve this?" rather than "Whose fault is this?"

Here's why this matters:

  • Blame isolates; solutions unite. By looking for answers together, you're improving the relationship.
  • Blame stagnates; solutions innovate. Finding ways to move forward encourages creativity and growth.
  • Blame demotivates; solutions inspire. Working towards a common goal can turn a negative situation into a positive learning experience.

So next time you're faced with a difficult conversation, remember to steer clear of the blame. Focus on what you can control and how you can improve the situation together.

Lay out next steps

The difficult conversation has been had. So what comes next?

Moving on. How do you do that? You make a plan.

Here's why this part is so crucial:

  • It turns talk into action. You've identified the problem and found a solution. Now, it's time to make it happen. Waggle can help—the platform documents action items and assigns them for you, nudging whoever is responsible to complete them on time.
  • It sets clear expectations. By outlining what needs to be done, who's responsible, and when it should be completed, you're removing ambiguity.
  • It builds accountability. Clear next steps mean that everyone knows their role in the resolution.

Not every difficult conversation is about delivering negative feedback or talking through interpersonal conflict but even those require next steps. 

Here’s an example:

You’ve just told your team member that there will be redundancies in the company. Their role isn’t at risk but the team size will shrink and the next few months will be really intense as you both work to compensate for the loss of that talent with your own efforts. 

Once you talk through everything, you’ll need to lay out a plan of action.

How are you going to protect your team members from burnout? Are there conversations that need to be had about compensation for new responsibilities? 

Here’s how you lay out effective next steps:

  • Be specific: "We'll improve communication" is good, but "We'll have a weekly check-in" is better.
  • Set deadlines: A goal without a timeline is just a wish. Make sure to set achievable deadlines.
  • Follow up: Schedule a time to revisit the issue and assess progress.

As you navigate challenging conversations, see next steps as the roadmap that takes you from the problem to the solution.

What to do if the conversation is received poorly

Even with the best preparation and intentions, not all difficult conversations go smoothly. 

So what do you do if things take a turn for the worse?

  • Stay calm: Keep your emotions in check and maintain a professional demeanor.
  • Listen and acknowledge: Maybe there's a misunderstanding. Listen to their concerns and acknowledge their feelings.
  • Seek support if needed: If things escalate, don't hesitate to involve HR or another mediator.
  • Plan a follow up: Sometimes, a cooling-off period is needed. Schedule a time to revisit the issue.

A poor reaction doesn't mean failure; it's just another challenge to navigate. You've got this!

Managing up—Having tough conversations with your manager

While this guide has focused on navigating difficult conversations with your direct reports, let's not overlook another challenge: managing up. 

Yes, sometimes those tough talks are with your manager.

The truth is, the same rules apply. You still need to prepare, be clear, listen, and focus on a solution.

The biggest difference is that in these situations you’re probably communicating a fault or mistake you’ve made that they need to be aware of. Or you’re communicating constructive feedback.

There’s always an added stress when managing up because the person is ‘above you’ in hierarchy. Hopefully your company has a healthy work culture based on trust and transparency—one where psychological safety has been established.

The cost of mishandling difficult conversations

Mishandling or avoiding difficult conversations isn't just a minor misstep; it can have serious consequences.

And they do get mishandled, largely due to lack of training. 

Here are some of the most common consequences of poorly handled difficult conversations:

Conflicts from disagreements: 

When disagreements are left unresolved, they can escalate into major conflicts that disrupt the entire team. It may even impact employee engagement and employee retention.

Team dysfunction from clashes: 

Differences in personalities and poor communication can create a dysfunctional team environment, hindering collaboration and progress.

Project failure from silence: 

If team members hold back their ideas or concerns, projects can veer off course and ultimately fail.

Morale and culture impact: 

Failing to hold individuals accountable for inappropriate behavior or poor performance can erode team morale and create a toxic culture.

Did you know that managers have as much impact on people's mental health as their spouse (both 69%)? 

Keep that in mind when preparing how you’ll approach and respond to difficult conversations at work.

Want to learn how to motivate your team and keep morale high? Check out our article: How to Motivate Your Team (in Good Times and Bad)

Missed opportunities for improvement: 

If performance issues aren't addressed promptly, team members lose the chance to correct their course. This can lead to serious consequences, even dismissal.

Frustration from unequal burden: 

Avoiding a conversation with a team member who isn't pulling their weight lets the entire team down and fosters resentment.

Personal stress from avoidance: 

And don't forget about yourself. Continually putting off difficult conversations adds to your stress. You have enough responsibilities without the added weight of unresolved issues.

Again, that CMI study revealed that 66% of 2,000 workers felt stressed or anxious about an upcoming difficult conversation, and 11% even suffered from nightmares or poor sleep. 

Your fear of having the conversation only prolongs the agony and intensifies the negative emotions. As much as it hurts, you just have to get it over with so that you can move toward a solution sooner.

Join Waggle today. 

Examples of difficult conversations at work

Whether you're a seasoned manager or stepping into a leadership role for the first time, understanding the types of conversations you might face can help you turn a difficult conversation into a successful conversation.  

Here are some examples:

  • Performance issues: Addressing a team member's underperformance or behavioral problems.
  • Salary negotiations: Discussing pay raises, bonuses, or compensation expectations.
  • Layoffs or terminations: Communicating job cuts or letting an employee go.
  • Conflict resolution: Mediating disputes between team members or departments.
  • Feedback on sensitive topics: Providing constructive criticism on personal habits or behaviors that affect the workplace.
  • Project failures or delays: Discussing setbacks or failures in a project and finding ways to move forward.
  • Personal issues affecting work: Talking about personal problems that might be impacting an employee's performance.

Navigating difficult conversations, while never easy, can be made easier. 

By understanding the common scenarios, employing strategies like those outlined in this guide, and having a tool like Waggle on your side, you can navigate difficult conversations with confidence and empathy.

Waggle is an AI co-pilot for remote and hybrid teams, automating management admin, delivering timely nudges and coaching in real-time to help you lead and support your team effectively, every day.

Put management best-practice into practice by getting early access to Waggle—the AI co-pilot for managers. 

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