Just breathe: Common difficult conversations at work scenarios

No matter what type of company or organization you work at, navigating tough conversations is simply a fact of life. Whether you have to deliver a less-than-flattering performance review or discipline an employee for harassment — knowing how to navigate challenging conversations is an excellent skill for any professional to have.

Yet, that doesn’t mean it’s a skill that’s particularly widespread.

In fact, the evidence suggests that almost all of us (80%) are actively avoiding a scary workplace conversation due to fear.

What’s worse is that the difficult situations and conversations we avoid are often vital and urgent. The fear is so great for some that they take counterproductive measures to avoid having to speak up. The same poll linked above also found that 11% of people will even quit their job to ensure they don’t have to take part in a difficult conversation.

The good news?

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Anyone can learn how to have difficult conversations, and handling them well almost always leads to positive outcomes. Harvard Business Review even found that 94% of employees are in favor of ‘negative feedback’ as it helps them learn how to improve.

If you’ve been struggling with handling difficult conversations at work, you’ve come to the right place. I’ve put together a few common difficult conversations at work scenarios as well as candid tips on how to navigate them successfully. Without further ado, let’s dive in.

Preparation tips for difficult conversations

A big reason why people avoid hard conversations like the plague is the nervousness that they feel beforehand. Well, I’m here to tell you that feeling nervous before having a difficult conversation is perfectly normal.

The remedy?

Ample preparation will help you gain the courage and confidence you need to put your mind at ease and engage in a constructive conversation. Here are a few of the most effective pre-conversation techniques you can employ.

Go over the key points by yourself

You don’t act in a play without rehearsing to exhaustion, and preparing for a challenging work environment conversation is no different.

It would be best if you took the time to sit down by yourself and ask yourself some essential questions, like:

  • What about this conversation is so difficult/uncomfortable for me?

  • Are you worried that the conversation may ruin a particular work relationship or affect the rest of the team?

  • Do you have the right words in mind to communicate how you feel?

Asking questions such as these will help you better understand your own feelings. It may seem obvious, but having an internal conversation like this can be eye-opening. It may even serve as a way to see the issue from the other person’s point of view.

Role play with other team members

Engaging in role play with another team member is a great way to prepare yourself for a difficult conversation. Sit down and have an intense one-on-one with them as if you’re engaging in the actual conversation.

The goal here is to anticipate what the other person may ask as closely as possible. That way, you’ll be prepared to answer the most common questions you think they’ll ask.

Pro tip: Are you scared of them asking you a specific question more than others? If so, focus on that question the most during your role play. By the end of it, you’ll have faced your fear and will have plenty of ways to answer the question.

You can also coordinate with the human resources department to conduct role play — and brush up on company policy.

Choose your words carefully

The words you choose significantly affect how well difficult conversations at work scenarios go. For example, if you have to be the bearer of bad news to an employee about their poor performance, you should think long and hard about your word choice.

Here are two examples to consider:

What not to say:

Jared, I’m sorry to say that your performance this quarter has been nothing short of abysmal. I know you’ve been under a particularly intense time crunch, but your numbers are simply unacceptable. If you fail to improve next quarter, we’ll have to let you go.

This is far too harsh and assigns the blame to Jared. While it briefly acknowledges the pressure he’s been under; the text does not convey any sense of empathy.

When delivering a performance review, it’s crucial to use words that don’t assign blame or elicit negative connotations.

That doesn’t mean that you have to lie and say their performance was good, either. You just need to be a bit more tactful about it. Now let’s take a look at a far better example.

What you should say:

Jared, you had great numbers last quarter, and nobody here doubts your talent. Yet, we can’t say the same for the most recent quarter, as your performance is down by a significant margin.

We know how hard it must have been to deal with the lack of time you had to prepare, but we still feel as if you could have done better. Do you feel that there’s anything holding you back from giving your best effort?

That’s much better; the tone is empathetic and diplomatic, and you made a point to compliment his talent and previous performance. Not only that, but you convey that you’re willing to hear him out and work with him to improve things later.

Come up with a list of action items

Last but not least, you want to stay organized when having a difficult conversation. That’s why I recommend putting together an outline of sorts that contains all the most important action items. It doesn’t have to be anything fancy; a simple bulleted list will suffice. You can even write it on your smartphone so you’ll have quick access to it during the conversation.

The point is to have a document nearby containing everything you need to hit on during the conversation. That way, you won’t forget anything crucial — and you’ll be able to maintain a seamless flow. The last thing you want is to get lost and start stammering while you try to gather your thoughts.

Difficult conversations at work scenarios

Proper preparation is a must for engaging in tough conversations at work. By now, you should know how to get ready to have a stern talk with an employee. Now it’s time to put those tips into practice by examining some common examples of difficult conversations.

These are some of the most prevalent scenarios you’ll run into on the job, including:

  • Complaints over compensation/raises

  • Excessive tardiness

  • Poor performance

  • An employee with a bad attitude

You’ll want to know how to navigate each of these tough talks successfully, so let’s take a deeper look at each one.

Compensation complaints

It’s always uncomfortable for managers when employees complain about their pay or that they deserve a raise. Explaining that you simply don’t have the budget for it can make your employees feel undervalued and ignored. At the same time, you can’t cave and give them an unapproved raise, either.

How should you handle this difficult situation?

Here’s how:

Ian, I’m here to discuss why you didn’t receive a raise this quarter. I understand your confusion/frustration, and I’m happy to clarify things for you.

Our company policy states that employee salary raises only occur when the company is doing remarkably well and when the employee plays a significant role in that growth. At the moment, we lack the performance numbers and the budget to hand out a raise. If you’d like to speak with me about how you can contribute to company growth, I’d be happy to schedule a time to meet with you.

That’s a realistic and honest explanation of how raises work, and it’s a great template to use if this difficult conversation at work scenario pops up.

Excessive tardiness

If an employee continuously shows up late, you need to check in with them and ensure they understand the importance of being on time. Of course, that’s easier said than done, as this is another difficult subject to bring up. Yet, it doesn’t have to be if you choose your words carefully.

Here’s a template you can use for an excessively tardy employee:

Andrew, we all enjoy having you on our team, and the work that you contribute is always top-tier. However, there is a specific issue that we need to address today. Your tardiness is a recurring problem that doesn’t seem to be getting better. Is there any reason why you can’t make it to work on time, such as a transportation issue? I’m happy to discuss this with you.

Remember not to assign blame with your words but also not sugarcoat or avoid the issue.

Poor employee performance

If you notice an employee that’s not carrying their weight, it’s better to say something sooner than later. That’s because other employees will soon notice their lack of effort, and it can lead to resentment if you don’t do anything about it. To avoid a dropoff in productivity from all your staff members, take the employee aside for a difficult conversation.

Here’s a template for what you can say:

Jeffrey, when you started at this company, we all knew that the sky was the limit for you. It’s been a joy having you on our team, but we’ve noticed a considerable lack of effort on your part as of late. We’ve noticed that your reports aren’t always complete, and they’re rarely turned in on time.

At our company, we operate as a team, and we all rely on each other to carry our own weight.

We’re concerned, and we want to work with you to improve your performance. Is there anything going on in your life that’s holding you back right now? We’re willing to work with you to get you back on track to success.

As long as you choose your words carefully and maintain eye contact, you shouldn’t have trouble with this conversation.

Negative employee attitudes

Employee morale is a huge factor that affects productivity, so the last thing you need is an employee with a bad attitude that brings everyone else down.

In this type of scenario, it’s necessary to be a bit more straightforward than before. You need to make it clear that negative attitudes won’t be tolerated, especially when they spread to the rest of the team.

Here’s how you can approach the conversation:

Neil, thanks for agreeing to meet with me today. We have an issue with your behavior that we need to address. On (specified date), you mentioned to your coworkers that you hate this company and that all our jobs are meaningless.

That was not productive and directly went against our policy, methodology, and mission. It’s also a clear indicator to me that you do not value your role at this organization. I’d like to be mistaken, so please let me know if you still appreciate your role at our company.

This template is stern and disciplinary without being too harsh.

Concluding thoughts: Difficult conversations at work scenarios

Nobody enjoys engaging in difficult work conversations, which is why they carry the label ‘difficult.’ Yet, they’re a challenge you should always strive to meet, as resolving a difficult conversation will significantly affect your team. Any successful manager or leader needs to know how to navigate difficult conversations at work.