How to Have Difficult Conversations

In every sector, there are times you need to speak with a coworker or supervisor about an issue. Here's how to ensure you get your point across—and your problem solved

By Jessie Cook, Local 68 steward and Local 68 Board member

Let’s be honest: there are some topics that are painful to bring up, but need to be brought up, especially at work.

I recall a situation where a supervisor was not so subtly trying to get a worker fired, harassing them in person and by text and telling them they were “getting paid too much and should be more appreciative.” Eventually someone in a leadership position noticed, talked to the worker, and a formal complaint was filed.

Due to the severity of and length of time this had been going on (more than six months), the supervisor was immediately dismissed. Of course, had the worker been properly informed about how to have a difficult conversation, this would not have carried on for so long.

There are three main things to remember when approaching a difficult conversation:

- Choose your words
- Choose your audience
- Choose your timing

Let’s dive a bit deeper into what choosing each of these factors means.

Words: Before losing it on someone in a heated conversation, one of the main things you first need to determine is the purpose of the discussion. This can vary, but below are some common conversations that can threaten to become unprofessional.

- Was there an incident, such as on-site bullying?
- Are you asking for a raise?
- Were you or someone else feeling uncomfortable because of another’s actions?
- Was someone not pulling their weight or doing their job?
- Do you need a different task or to work with another crew?
- Were instructions not clear?
- Were you feeling uncomfortable with a task?
- Do you need time off?
- Is safety an issue?

So many “difficult conversations” could be simplified by getting to the root of the purpose without emotions involved in the conversation.

If you’re feeling angry, offended, upset, scared, or excited about a situation, take a second to breathe, think it through, and choose your words before speaking. Don’t be afraid to write down what you want to say or have notes to keep the conversation on topic. Let the logical part of your brain come into play before speaking and don’t allow emotions to spin your words into an unproductive conversation.

Audience: Much like with the words you choose, you need to take into consideration who you are speaking to before beginning to talk. Is it a coworker? Or do you need to speak to a supervisor about more serious matters, such as health and safety?

Selecting the right audience alleviates the chance of getting on the “gossip train.” Also, think about the order of command. Going directly to the top of the hierarchy by going to a supervisor with a minor issue may ruffle some feathers. Also, it goes without saying that if all you do is complain about the issue to everyone except the person who could help resolve the matter, you will certainly annoy all those involved.

Timing: This ties into both previous steps. Your timing is of great importance when deciding how to deliver information.

For example, you wouldn’t ask your boss for a raise in the middle of a critical lift or morning meeting, or another time when they have a million other things on the go at once. Workplaces are busy, and people often forget serious conversations when they are not focused.

When it comes to more urgent issues, like workplace violence or harassment, a detailed log should always be kept of the issues and incidents. Maybe you aren’t ready to go to your supervisor after a small altercation but keeping a record of the individuals involved (including witnesses, if applicable), what was said/done, and when and where it happened (date, time, and place). That way, if it persists and more issues arise, there is documentation—and you never know if someone else has had similar issues! Of course, if supervision doesn’t take you seriously, go to your CLAC steward or representative.

If you take these steps into consideration before you have that difficult conversation you’ve been dreading, it will go much more smoothly and will result in a constructive and proactive conversation, leading to the best possible outcome.

Jessie Cook has been in the heavy civil construction industry as an equipment operator for seven years. She is passionate about workplace development, safety, and the fair treatment of all, particularly for young women in the trades. She looks forward to her new adventure of motherhood and being able to stay at home with her dog and horse. For more tips from Jessie, follow her on Instagram at @clac_jessie.