5 Tips For Having Difficult Conversations At Work

Luis Congdon

When it comes to having difficult conversations at work, most people are quite uncomfortable and will do their best avoid them. Yet, reports indicate that most people will have some kind of interpersonal challenge with another staff in their career. And while it’s normal for people to avoid having tough conversations, reports show it costs companies billions of dollars each year. 

Learning how to address challenges, upsets, and frustrations at work could save your company millions of dollars and help cut down on sick days, staff disputes, and even boost morale at work. Whether you’re a manager, boss, owner, or team member at your company - avoiding difficult conversations at work can wreak havoc on productivity and satisfaction at the office. 

Learning how to address difficult topics with employees will make a world of difference. This is why today we’d like to give you a step-by-step template for starting difficult workplace conversations with anyone on your team.  

Here are 5 tips to help you start and navigate your way through a difficult conversation in the workplace:

1. Start By Asking To Speak With The Other Person In Private 

Nobody likes to be outed publicly. And no one wants to have a sensitive conversation with others viewing or commenting on the issue. This is why the first step in handling difficult workplace conversations is asking to have a private conversation.  

Whether you’re the boss, a subordinate, or an equal on the team - asking to speak privately helps keep nerves down and will support in keeping the issue private. 

You can do this is by calmly approaching the individual on staff and ask: 

“Would you have a few minutes to chat in private? I’d like to talk for a moment.” 

While it may sound scary to approach someone at work like this, this is the best way to start a difficult workplace conversation. Managers and staff alike can utilize this simple question to get an agreement from anyone on the team to have a private conversation. 

By asking the person if they have some time to chat, you’re giving them the heads up that you need to talk. You’re also preparing them to have a conversation that will pull them away from work and other duties. This question allows them to be prepared and will ensure you’re not speaking with someone who is being pulled by other tasks or immediate needs that their job mandates. 

Now, if the issue is a bigger problem, it’s best to report it to the appropriate person. If for any reason you feel that the issue is serious and should involve someone else, be sure to speak with a superior on your team or another manager. This will protect you and the company. On the other hand, if you feel this is an issue that you can and should handle yourself, follow the outlines here to help you start and successfully have a difficult conversation at work.

2. Utilize A Gentle Start-Up To Voice Your Concern 

Now that you have an agreement to talk privately, it’s time to start the conversation. 

According to research at the Gottman Institute, the first two minutes of a difficult conversation are the most critical minutes of a challenging discussion. The way you start a difficult conversation will most strongly determine its outcome. In other words, how you begin to talk about a problem will most strongly impact the resolution. 

Learning how to begin a difficult conversation in the right way will be your best asset in handling a challenging dialogue at work - and it will impact the resolution in profound ways. 

When you are starting to talk about a problem at work with someone, the best way to start with how you feel. While you may not have liked them in school, researchers and authorities agree that when you start a difficult discussion with an “I feel” statement, it helps move the conversation in a favorable way towards resolution. 

Here are some examples of how you might use a gentle start-up:

  • “I feel concerned because...” 
  • “I feel worried because...” 
  • “I feel frustrated because...” 
  • “I feel concerned because...” 
  • “I feel sad because...” 
  • “I feel agitated because...” 

These statements keep the conversation focused and also opens up the dialogue without blame or judgment. In turn, this helps the receiver understand that there is something concerning or worrying you are a fellow staff member or manager. 

3. Use Specificity & Ask Questions To Improve Communication 

By the time we address an issue with someone, it’s likely there’s more than one thing we’re frustrated or concerned about. That being said, it’s best to focus on one issue at a time. Keep your conversation focused on one issue. 

After you’ve expressed that you’re concerned, worried, or frustrated about an issue - it’s good to follow up by sharing what specific situation has created the cause for concern. 

Maybe your co-worker or staff person has been using vulgar language with clients. Maybe your teammate at work has been showing up late and skipping out on staff meetings. Whatever the situation is, it’s likely that because something has been happening, it’s created an alarm for you and you feel it’s important to discuss the issue with them. This is when you get to tell the other what has explicitly been affecting you. 

If someone who has been showing up late to meetings and cutting out of work early, maybe it’s made you feel worried that this person doesn’t want to be at the company anymore. Or perhaps it’s made you feel troubled because they're usually punctual.

This is where you get to tell them what you’re seeing and why it’s impacting you or the company. 

Here is an example of how you might use this formula:

“Tom, I’ve been worried lately. I’ve noticed you’ve been showing up late to work, late to staff meetings, and that you leave work early.” 

Now it’s a good time to pause. Maybe ask a question about what you’ve noticed.  

It can go something like this:

“Is there something that you’d like to share with me about what is going on?” “Am I wrong in what I’ve noticed or is there something I am missing?” 

Since the goal here is to create a resolution, it’s good to check in to see if they have something to share. Maybe there is some information you don’t know about. Perhaps there is something you can learn during this conversation that will help create clarity and improve communication. 

This dialogue is best managed when it’s a two-way street - where you share and they get to share as well. 

Give them a chance to respond so you can find out more. There’s a chance you’ll learn something that completely changes your response and understanding of the issue. Maybe the staff person will tell you their son has been having lots of problems at school or that their Mom is sick, or maybe you’ll learn you were right about your assumptions. Either way, you won’t know until you take a moment to let the other person respond and share. 

4. Make A Clear Request 

According to communication expert and author of Nonviolent Communication, Marshall Rosenberg, it’s best to handle a difficult conversation with a request. Since there’s an issue, there must also be a desire behind the concern. 

Letting the other person know that you’re worried or upset about something isn’t enough - you must now also let the person know what will help alleviate the issue. 

If the person has been showing up to staff meetings late or has been negative at work - it’s good to find out what has been going on before making your request. 

Once you have more data, likely, you’ll still need to make a request. 

For example, if your staff member has been showing up late and down at work, it’s likely that no matter what you learn - you will still need to ask them for something. But the context and the information you learn from them will help you immensely. That information will then help you formulate a reasonable request.

Some requests that you may ask for can include:

  • Improved communication 
  • A follow-up conversation at a later time 
  • That the fellow employee speak with someone else on the team 
  • That they use some of their vacation or sick leave to take care of the issue 
  • That they adhere to work a performance plan for 30 days 

The list is of what you may ask is endless. If your conversation has opened up a line of communication that helped you understand the issue better, maybe you’ll ask the other person let you know how things are going more often. Or maybe you'll ask for something else.

Whatever caused the problem, the issue is best resolved by asking for something to ensure it doesn’t happen again. 

5. Thank The Individual For Taking Time To Talk 

Now that you’ve both made time to talk - it’s good to end the conversation by thanking the other person for taking the time to meet. Showing appreciation is an effective way to boost employee morale and to acknowledge others at work. Be sure to let them know you value their time and that they took time to meet with you. 

Having difficult conversations at work is not easy for anyone, by letting the other person know you’re thankful for their time you acknowledge that it’s valuable to have met and worked things out. 

Starting a difficult conversation can unpleasant, and ending the conversation can require as much tact as it does to start it. By letting the other person know that you’re glad you spoke and maybe even letting them know something positive about the interaction, you ensure that if there’s a next time you have to talk - it can be received in a positive way. 

While you may not want to have challenging conversations at work, the data is pretty clear that it could cost your company countless time and dollars to not have those discussions. Take some time to study these steps and put them into action - and you may find it helps make staff happier to have open lines of communication.

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