9 Difficult Work Conversations and How to Handle Them

When interacting with differing personality types at work some tension can arise. However, it is often important to have multiple perspectives on one project. You may find that integrating a team of personality types at work will be more efficient and outcomes are ultimately more useful and comprehensive. 

That said, you may encounter ways that opposing personality types clash, leading to awkward situations and the need to navigate difficult conversations. If you can work through these difficulties strategically, you should find your team is strengthened and your goals become more achievable. It’s not all plain sailing, however, and there are a number of potential pitfalls. Treat internal strife incorrectly and you run the risk of harming morale or having team members that refuse to work together. 

With that in mind, it is imperative to prepare yourself beforehand to handle some typical difficult work conversations. 

It’s useful to arrange these conversations in terms of company hierarchy of:

• Employee to supervisor
• Supervisor to employee
• Employee to employee

Difficult employee-to-supervisor conversations

Handling awkward conversations with your boss can be particularly tricky. Obviously, you do not want to put your job in jeopardy or be disrespectful, but sometimes it’s imperative to speak up. More often than not, you’ll be surprised to find that a superior respects someone who judiciously speaks their mind and has a specific opinion. 

1. Disagreements with a decision

If you find you do not fully agree on a decision, it is likely worth connecting about the question instead of just letting it be, particularly if the decision is something that makes you uncomfortable, or that you feel perhaps could create a larger issue if left unchecked. 

It is always better to speak to something promptly, rather than try to ignore something or let it fester. In addition, keeping the conversation geared toward a positive outcome is the best way to proceed, while considering end goals. 

If your superior requests something that seems not feasible to deliver, for example, you might respond with something like:

“I was hoping to speak with you about the recent ask. While I would very much like to be able to provide you with the deliverables you are hoping for, I fear that it may derail some progress of the team which will not allow us to perform current tasks as effectively. If I could suggest an alternate approach, [suggestion] may allow us to accomplish what you are looking for more expediently.  

I hope it’s alright to connect with you about this as I know how concerned you are about both the morale of the team and our ability to do our best and most productive work. That said, of course I respect whatever your decision may be, and will follow whatever directive you think is correct.”

2. Having to say no to something due to overwork

One of the most difficult conversations workers face is having to say no (or at least not right now) to an authority figure because of overwork. Introverted personality types may have particular difficulty with this. However, there is nothing to be ashamed of when asking for some time to prioritize other projects. You might say something to the effect of: 

 “While I very much would like to work on [TASK] I have had to prioritize [other TASK] which needs to be delivered very soon. Are you comfortable with my delegating [TASK] to [another employee] as it would be an excellent experience for them.” 

3. Dealing with illness

When you are feeling ill, it’s easy to try to push through at work, because you feel as though your boss will judge your absence harshly. However, it’s most likely that a superior will be sympathetic and won’t want you to come to work sick either, with the possibility of spreading your illness to others on the team. There is no reason not to be honest and forward about illness or needing a personal day. Do not apologize or beat around the bush. 

Here’s an example of how to address this situation: 

“I’m afraid that I woke up feeling ill and will not be able to come to work today. I should still be available by phone and via email if there is anything urgent, but otherwise I am going to take today as a sick day to recover. My hope is to be back in the office tomorrow.”

Difficult supervisor-to-employee conversations

1. If two team members are not getting along

When team members with opposing personality types clash it can be toxic for an office or project. The important thing is to get them on the same footing and try to introduce personal empathy, so that they see each other as individuals rather than as people who make opposing work-related decisions. 

A way to address this might be:

“So, it’s come to my attention that there is some disagreement between you and [OTHER EMPLOYEE]. While I know you’d never consciously let this affect your work, it’s part of my job to make sure our team works cooperatively. I’d like the two of you to sit down after work or for lunch to connect on terms outside of the office. In fact, at the upcoming company retreat, I’ve assigned some time for you two to connect on a specific project that I think will employ both of your strengths.”

2. Connecting with an employee who isn’t reaching goals but is very enthusiastic

Some employees need to be guided in a certain direction in order to improve their skills in the way you would like. Often they are very dedicated, but don’t seem to be reaching up to expectations, usually because they are stuck in a strategy that isn’t working or haven’t had a chance to train in a particular skill set. If you give this kind of employee a lifeline and some training, you may find they become one of your best workers. You might make suggestions and meet with them regularly to be a part of their growth process. Addressing them you might say: 

“I truly appreciate all of your hard work and I hope you recognize how much I rely on your growing level of responsibility as I know you recognize that you could use a little help in [skill]. I’d love to connect with you on ways to improve. It would be great if you would be available to meet and to schedule some training sessions that I think will be very well worth your time. While it might be some time investment in the short-term, I am very sure it will pay huge dividends in the long run.”

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

Picking someone for promotion sometimes comes with the price of making other team members feel as though they have been deliberately looked over. Being as transparent as possible with the selection process as well as what another employee can do to find comparable promotion can alleviate some of the tension associated with this. 

“I’m sure you know that we have chosen [EMPLOYEE] to take on the available opportunity. I know that you were very interested and it was a difficult decision. Ultimately, it was my decision to go with [EMPLOYEE] because of their seniority and that their work level has been consistently high. Also, they have demonstrated the capability to apply leadership and have excellent rapport with clients. I understand that this may be frustrating and know that you are seeking ways to have greater responsibility in the company. There are other positions on the horizon, to which you will likely be very well suited, and it is my hope that we can work on any skills or materials you may need to be successful in taking up the next opportunity that comes along.”

Difficult employee-to-employee conversations

1. Asking for assistance

One of the most awkward conversations to have with a coworker is when you need help. However, most peers are very happy to demonstrate their expertise and to guide you if you need it. You might inquire: 

“Recently, I noticed that you were very successful when it came to [PROJECT]. I’m working on something similar and could really use some advice. Would you be open to sharing your process at all and would you have any time this week to connect about it?” 

2. Telling someone you are too busy

You want to be open to taking on any work that others need, but sometimes you need to say no. It is a much better strategy to try to say no or to delegate, rather than to say you are able to do something and then simply not deliver on that promise. Instead of ghosting on a project it might be better to say something like: 

“Unfortunately, I don’t have enough bandwidth to help with this right now. Is it something that can wait until next week when I’ve finished a couple of larger projects? If so, I can definitely help out then and if I can do anything earlier than that, I’ll keep you in the loop.”

3. Feedback to a talkative friend

Sometimes, some of your best extroverted friends at work can put you behind in your projects because they love to sit and chat about things in their lives. While you don’t want to offend a friend, you also don’t want to put your job in danger because you are not getting work done. It’s a delicate situation that you’ll want to handle carefully.   

“Hey, I’m working on a particularly rough project or two this week, it’s just overwhelming, and I really need to buckle down and concentrate. If you have a sec, instead of chatting at our desks, can we schedule lunches and some time outside of work to talk.”

The way you handle these kinds of conversations between personality types and within teams can make or break your business. Other ideas like sticking with “I” statements and coming into awkward discussions with a plan to get three things done, can also help you create synergy no matter what disparate personalities you have on your team.