Difficult conversations at work: 9 tips + templates

Difficult conversations at work. They’re awkward, sometimes unpleasant and, ultimately, inevitable in any workplace dynamic. You know when you have to talk to Justin about how he keeps showing up 45 minutes late or Ashley because she’s underdelivering on projects? We’ve all been there.

Seventy percent of employees avoid difficult conversations in the workplace, according to a study by career-coaching startup Bravely, this can lower morale and cause a toxic work environment. Facebook COO Sheryl Sandberg encourages her employees to have tough conversations at least once a week. If you’re not having them, you’re not growing, she says.

So, how do we encourage tough conversations and handle them eloquently? We’ll tell you how and check out our infographic below for some quick tips.

Nine tips for handling difficult conversations at work

It’s common for defenses to be high when difficult conversations roll around, so it’s key that you have a plan for when they do. Help make feedback a natural aspect of your organization and frame your thinking so that it’s key to growth and development. Here are a few tips to help make these conversations easier.

1. Don’t avoid it

Difficult conversations can become more difficult the longer you wait. You can also build up anxiety that will make the situation bigger in your mind than it really is. Just like Apple co-founder Steve Jobs said, your job is not to be easy on people. Your job is to make them better. Make feedback a common occurrence, and get in the habit of addressing issues immediately as they arise.

2. Have a purpose

What do you want to get out of the conversation? Write down three things you want to accomplish and focus on them. If you hone in on the root of the problem right away, you lessen the probability of the conversation getting away from you. Remember, we’re all human and no one wants to be approached with a laundry list of issues.

3. Be confident and direct

The person on the other end of the conversation will likely pick up on your energy. If you approach it as an uncomfortable situation—it will be one. According to Facebook’s Sheryl Sandberg, “feeling confident — or pretending you feel confident — is necessary to reach for opportunities. It’s cliche, but opportunities are rarely offered; they’re seized.” If you’re asking for a raise or promotion, take initiative, begin the conversation with confidence and get to your point quickly. You’re never going to get what you want unless you ask.

4. Be open to the other person’s perspective

“Feedback shouldn’t be a monologue,” explains Ask a Manager’s Alison Green, “It should be a discussion, and it’s important to listen to the other person’s perspective. They might tell you something that changes your mind, and you don’t want to be so committed to your initial assessment that you don’t hear it if they do.” Listening to their perspective lets the other person know you’re acknowledging their feelings. Being able to listen and communicate effectively will not only help you resolve the current problem together but will help your relationship long-term.

5. Be empathetic

Think about what it might feel like to be on the receiving end of the conversation. If you see they’re struggling with what you said, pause for a minute so they can gather their thoughts. If they start to get emotional, understand how they must be feeling and reassure them that you’re providing this feedback because of the potential you see in them.

6. Use “I” statements

Starting your sentence with “I” instead of “You” avoids put-downs, promotes positive communication and fosters enthusiasm to find a solution. It’s a huge part of what differentiates constructive and critical feedback. We’ve provided some examples of how to do this in the section below.

7. Stick to the facts

Before your conversation, have a clear idea of what happened. Take responsibility for your part in the situation and focus on the facts. Identify where either person went wrong and discuss the impact of this conversation on each of you, the team and the organization as a whole. Not every conversation is going to go your way and not everyone is going to agree with your point of view. Try not to let your feelings get in the way of a resolution.

8. Come up with a solution

The goal of having this conversation is to reach a resolution. If the solution isn’t clear from the beginning, work together to come up with one that you both agree on. Listen to their ideas if they have any and bring some of yours to the table as well. For example, if you’re telling an employee they didn’t get a raise, explain why and offer solutions on how they can improve. Once you’re in agreement, commit to the resolution and make sure there is an action plan going forward.

9. Follow up to prevent fallout

In a perfect world, all of the conversations we have would end the way we want them to. However, that’s not the case. Some people have delayed reactions to bad news and may experience feelings of frustration, embarrassment or resentment after leaving the conversation. Be aware of this and check up on the other person periodically to make sure they’re doing okay. If there seems to be some tension, schedule time for an offsite get together that doesn’t revolve around work talk — like grabbing a cup of coffee — where you meet as individuals and not colleagues.

Nine difficult work conversations + templates

Uncomfortable work conversations arise in a wide range of situations and can occur among coworkers, your managers or people you supervise. While letting someone go or asking for a raise are both difficult conversations to have, what about the ones that are just plain awkward? From addressing employee concerns about promotion decisions to telling your boss you feel overworked, below are nine uncomfortable conversations and tips on how to handle them.

Employee to supervisor

employee talking to supervisor

1. When you don’t agree with your boss’s decision.

Disagreeing with someone in a respectful and non-condescending way is tough — especially when that someone is your boss. If you feel strongly enough about your opinion, you should speak your mind. Any good boss will respect your confidence and may even reward you in the end. Just make sure to keep the conversation positive, focus on results and respect the final decision. Here’s an example:

“I wanted to talk to you about the recent strategy you put in place. I think it is a great idea, however, I worry the rest of the team will feel overworked and this may lower morale over time. If we do [EXAMPLE OF ALTERNATE APPROACH] instead it may get the same results, while keeping employees happy. I wanted to bring this to your attention because I know how important company culture is to you. However, I will ultimately respect whatever decision you decide to make.”

2. When you feel overworked.

It’s OK to admit it. Sometimes we feel overwhelmed at work and simply have too much to do. But, how do you tell your boss you have too much on your plate without coming off as lazy or not a team player? It’s important to be honest, avoid complaining and offer solutions to help. Your boss may have no idea bandwidth is an issue and you could be doing him or her a huge favor. Here’s an example:

“I’ve had some trouble handling the number of things on my plate right now. Would you be OK with me delegating [TASK] and [TASK] to [name] as they are taking up most of my time? Our new intern said she had some availability and I would love to get her trained up on the process.”

3. When you’re sick.  

Don’t feel the need to apologize in these situations. We’re all allowed to be sick sometimes. Make your note short and sweet about why you need to take the day off. Here’s an example:

“Unfortunately, I woke up feeling too sick to come into the office today. I am going to take a paid sick day to rest up and get better. However, I plan on checking my email periodically throughout the day in case anything urgent comes up. Please let me know if you have any questions. I hope to be back in the office tomorrow!”

Supervisor to employee

supervisor talking to employee

1. When a personality clashes with the team. 

Not everyone is going to get along in the workplace and when this happens, it tends to create an uncomfortable work environment. If the employees can’t seem to work it out themselves, pull both aside privately. Make sure to listen to both sides, determine the real issue and find a solution. Here’s a couple of ways to start that conversation:

“I understand there is an issue between you and [EMPLOYEE NAME]. I wanted to pull you aside to make sure this wasn’t affecting your work and those around you. I have scheduled some time for you and [EMPLOYEE NAME] to grab coffee together outside. I think it would be good for you to connect as individuals and not as coworkers.”

2. When an employee doesn’t meet expectations but has a positive attitude.

It’s hard to tell someone you genuinely like that they aren’t performing well. However, positive attitude or not, employee performance affects the whole organization, so it’s important to discuss it in a professional manner. For this conversation, we recommend addressing the problem, offering ways to help and providing reassurance. Here’s an example:

“As your manager, it’s my job to point out the areas you need to improve on. This ensures that you’re constantly growing your skillset as well as your professionalism. Right now, I would like you to focus on improving your [AREA THEY NEED WORK IN]. To help, I would love to set up some training sessions to get you on the right track.”

3. When an employee disagrees with a promotion or compensation decision.

When there are opportunities for advancement, it’s natural for colleagues to become competitive. If you’ve promoted someone over others, jealousy may ensue and if it starts to be a problem, address it right away. Make sure to be empathetic, but also stand by your decision. Here’s an example:

“As you know, [EMPLOYEE NAME] got promoted on Wednesday. I wanted to have a chat with you because I know you expressed interest in the opportunity. The reason I chose to promote [EMPLOYEE NAME] is because they have consistently hit client goals month over month. They also excel in [SKILL] and [SKILL] which are some areas I feel you could improve on. I realize you’re looking for upward mobility in the company and just because this opportunity didn’t work out doesn’t mean there won’t be other ones that come up. I am prepared to help you get there and would like to set you up for success with future opportunities.”

Employee to employee

1. How to ask for help. 

Sometimes that big project you’ve been working on proves more challenging than expected and you need an extra hand. Employees may avoid asking for help because they don’t want to be perceived as incompetent or annoying. Reaching out for help when you need it is not shameful — it’s smart. Be honest with what you can handle and ask others for help when you’re feeling swamped. Here’s an example:

“Hey, I started working on [PROJECT], but I’m getting stuck on [WHERE YOU NEED HELP] and it’s due this Friday. I saw that you have previously done [RELATED PROJECT] and senior leadership was very happy with the outcome. Could I schedule some time with you to brainstorm potential approaches?”

2. Saying no. 

Say your coworker asks for your help on a project you don’t have time for, or they ask for help on an assignment you have very little knowledge (or interest) in. It’s OK to say no. Especially if you don’t have the time. However, a lot of us struggle with saying no in the workplace. Most of us want to be liked and well-respected, but you have to be wary of those who might take advantage of you. Here’s an example of how to say no:

“ I would love to help, however, I am currently at capacity because of a few projects. If this is something that can be started next week, I’d be happy to assist then. In the case that I get my projects done early, I will let you know.”

3. Dealing with a distracting co-worker. 

Sitting next to Chatty Cathy may be entertaining at first, but if the distraction begins to inhibit your work, it’s time to have a conversation. Especially, if the sound of their voice carries throughout the office. Gently pull your colleague aside and have a genuine conversation. Make sure to keep their feelings in mind and remain respectful throughout. Here’s how:

“I’ve really loved getting to know you, but I found that sometimes I fall behind in work because of our conversations. Maybe we can schedule some time to get coffee once a week?” 

According to mindfulness teacher and executive coach Kim Nicol, people leave managers, not companies. Encouraging your employees or coworkers to own difficult work conversations is challenging. Nicol’s tip: lead by example. When it comes to uncomfortable conversations like asking your coworkers salary or saying no to a fellow employee, communication is key in any work environment. If you’re open, hopefully the rest of your team will be.

For more tips and stats on difficult work conversations, check out our infographic below.

Tips for tackling tough conversations at work

Haven Life Insurance Agency offers this as educational information only and does not endorse any companies, individuals or strategies discussed here. Haven Life is an online life insurance agency offering term life insurance issued by Massachusetts Mutual Life Insurance Company.

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