We might earn a small income when you click on some of our links.

If you work with teams, much of your day is likely spent trying to make sure that relationships at work run smoothly. The hope is that you will be about to navigate your workday in a way that makes it unnecessary to create tension or have difficult conversations. Surely, most of your conversation at work is benign and the work discussions you need to have are usually pretty productive without being stressful, however, there are those conversations that are very difficult to have.

Sometimes these difficult conversations at your work are impossible to avoid. When you do need to address something that could potentially create strife at work, you’ll want to have a strategy to use to approach your coworker with the right attitude and in a way that will potentially leave your relationship as strong as it ever was.  

From telling your boss you’re too sick to come into work to tell a coworker you don’t have time to help them out with a project, here are some Do’s and Don’ts to think about when facing those difficult conversations at work:

1. Don’t Try to Pretend the Conversation Doesn’t Need to Happen

Trying to pretend a pressing work discussion doesn’t need to happen can have a truly deleterious effect on the work environment. It leads to lower morale and a tendency to let issues between coworkers fester. Not addressing a problem head-on may also make the trouble grow and eventually become something larger than it was.

Ultimately, while one may want to think they are sparing the feelings of a co-worker, the desire not to talk about a problem head-on is rooted in cowardice. A great deal can be alleviated by bravely talking through a problem and having the confidence in yourself and your co-worker that it is possible to reach an amicable resolution.

2. Do Put Together a Conversational Strategy

It is very human to attempt to avoid a conversation that may seem painful. Even ruminating on the idea of the discussion might feel distasteful. However, it is crucial to thoroughly think through what you are hoping to accomplish when talking through something troubling at work. The one suggested strategy is to map out three specific goals that you have for the conversation. Also, it’s important to consider what it is you desire as the outcome of this awkward talk.

What would be the ideal? What is the worst-case scenario? How will you begin and what would you like the other person to think on the way out the door?

Perhaps treat the conversation like a performance review and ask how you can make it easier for you both to diffuse an issue while coming up with ways that everything connects in the future.  How you reach this conclusion is what you need to consider when strategizing.

3. Don’t Talk Around Your Topic

Once in the room with the person you’d like to speak with, it can be tempting to deflect the main reason for meeting for a while with pleasantries and chit-chat. Unless the other person is completely oblivious to why they are talking with you, this is a rather transparent ruse and may only have the effect of raising the ire of the person to whom you are speaking. This is the opposite of your intention, so get to what you want to say as quickly as you can. Both sides will appreciate your transparency.

Focus-Difficult Conversations

Photo Credit – Pixabay.com

4. Do Practice Active Listening

Nervousness (or frustration) with a situation might make you eager to talk out all of your points about something right away, letting them tumble out one after another. You might incline to “get out your side of the story” first, before allowing the other person to speak or express their feelings.

However, one of the key parts of an awkward conversation is listening to others and trying to understand their perspective. Some agitated people can be calmed just by talking through their frustration, ad part of the issue might be because they feel like they are not being heard.

Try to listen more than you speak, and do not fear silences. If there are pauses in the conversation, it is not necessarily your job to fill them. It is okay for everyone to take a breath to consider what is being said, particularly if it is rather a difficult thing to hear. Let the conversation breathe when it needs to and don’t be over eager just to get your points across. Also, if a conversation is making someone emotional, do not railroad or ignore their feelings. Give them as much space and understanding as you can.

5. Do Consider Other Perspectives

Using empathy to understand the other person in your conversation is crucial to making an awkward conversation at work come to a positive conclusion. You may feel that it is difficult to spend a moment in the other person’s shoes, but trying to do so is an important exercise toward diffusing a troublesome issue.

Try to demonstrate that you are considering their feelings, but don’t be domineering and try to tell the other person what you think they SHOULD be feeling. Take the conversation as it comes and internalizes their journey as much as your own.

6. Don’t Speak for Anyone but Yourself

There are two tendencies that it is important to curb if you are going to have an amicable discussion with a coworker over a problematic situation.

First, you want to make sure you do not use statements that could be construed as accusatory. This means avoiding saying things that include mentioning the actions they may have taken directly using “you” statements. It is always better to focus on the “I” and talk from your perspective about what you have been hearing or feeling and how you understand a situation.

The second thing to avoid is to try not to talk as though you are representing a group, such as the marketing department, or the shareholders, or your coworkers. This can feel like a domineering action. Even if you DO represent a group, always try to speak from in “I” statements that show how you specifically are feeling.

7. Do Develop a Set of Facts Rather Than Conjectures

In many awkward work conversations, there can be misunderstandings involved. Often people may not have seen the same set of circumstances in the same way. Instead of indulging in conjecture over motivations or thought processes, consider exactly what you know happened and work from there.

Present hearsay as such, by always qualifying it as something you heard that you have not yet verified. By working everything back to incontrovertible evidence you will strengthen the conversation and avoid further misunderstandings.

Difficult Conversations

Create Useful Action StepsDifficult Conversations

Talking through a subject is useful, but not if you haven’t considered how to implement ideas that lead to resolution. Be prepared to talk about several possible ways to resolve an issue and be flexible to include ideas that work for the other person.

Even if you have tentatively resolved a dispute, make sure you take some time to talk about how to avoid this issue in the future. You can also look for systems to put in place to make sure that the next difficult conversation about a similar topic need not be so awkward.

Develop a Pattern of Follow Up

Schedule ways to revisit an issue to make sure that action steps are being worked on and that there is no further difficulty. If tension is still in evidence, go back to your goals and try to adjust to improve a situation. It also might be a good idea to create time for issues to be discussed in a non-work or non-traditional work setting such as on a retreat or lunch hour. This will give people a platform that allows them to speak more freely as an individual, rather than just part of a company.

There are many types of awkward work conversations that surround speaking with your superiors, your fellow employees, or those that work for you. From telling your boss you feel overworked to asking for a well-deserved promotion, it is crucial to develop your conversation skills to follow some of these tips.

The way you handle these kinds of conversations between personality types and within teams can make or break your business. Ideas like sticking with “I” statements and coming into awkward discussions with a plan to get 3 things done, can help you create synergy no matter what disparate personalities you have on your team.  

By coming into a difficult work conversation with a plan to connect with the other person as opposed to an adversarial approach and following the tips above, it is possible to get more from your meeting. Hopefully, by thinking with empathy and considering possible outcomes any problem that comes up can reach a positive resolution.


Written By
Tom Anderson is the editorial director at Haven Life. He is an award-winning journalist whose work has appeared in CNBC.com, Kiplinger’s Personal Finance, Money, Monocle and Wired.

Related Post