How to Navigate Difficult Conversations at Work

Career Advice / December 7, 2020

Research data curated by Fast Company reveals that almost one-third of professionals admit that they’d rather work an extra six hours a week than enlist help from their bosses or colleagues. It’s mostly because of stress, challenges with co-workers or managers, staying on top of new projects, and the fear of making mistakes.

Admitting that you need help is one thing, but hashing it out with someone you work with is an entirely different story. Many of us try to avoid having conversations about delicate subjects, but there are times when it can no longer be avoided. It’s usually when you find yourself needing a promotion, admitting that you made an error, revealing that you’re moving to a different company, or telling your boss that their management style isn’t working for you.

Having these types of conversations are always hard because emotions are usually involved, but they must happen if you want to resolve issues that may be hindering you from doing your best work.

To help you navigate challenging conversations in the workplace, here are some tips that you can follow:

Figure out what’s at stake

Before anything else, you must first recognize what you want to get out of the conversation. Discern whether you want understanding, resolution, or a compromise. If you manage to get to the root of the issue you want to raise, you’re reducing the chances of the conversation getting away from you. Additionally, it’s also important to pay attention to any blame or judgments that you may hold.

Mindful suggests that you think about what parts of the conversation for you are logistical and which parts are relational. And most importantly, you also have to consider if your goals are indeed realistic. Do you and the other party have the ability to handle the conversation in the way you’d like? Is it even the right time to have a raw and honest conversation? Is the other person capable of resolving the issue, or are you handing them a problem they cannot solve? Ask these things to yourself before embarking on a discussion so as not to waste anyone’s time — including yours.

Draw boundaries on acceptable topics

If you’re an employer, you have the responsibility to facilitate meaningful discussions in the workplace. Dustin York, a professor leading Maryville University’s online communications program and a consultant for Barack Obama’s 2008 U.S. presidential campaign, explains that leaders have a crucial role in encouraging respectful dialogue. They’re in a position to set boundaries on what topics can and cannot be discussed in the workplace, and one example that York gave is political talk.

He suggests that leaders send a company-wide note with guidelines about discussing political news in the work setting, so people have something to refer to when they feel the need to discuss controversial topics amongst themselves. If at all possible, it’s also worth inviting trained facilitators to lead a discussion about having difficult conversations at work to equip employees with better communication skills.

Create an agenda, but don’t write a script

Difficult conversations aren’t something you want to have in the spur of the moment. But you don’t want to come unprepared, either. Sometimes, emotions may get in the way in the middle of the discussion, and it might make you forget some of your main points, so it’s best to have an agenda listing your main talking points without writing a full-blown script. Doing the latter will only be a waste of time since you can’t exactly anticipate how the other party is going to react.

However, if you’re keen on planning it out even further, the best course of action is to think of the questions the other person might ask and have your answers prepared. For instance, if you’re asking for a raise, you can probably already foresee that your manager will ask you why you deserve to have one. It would be best if you wrote down your contributions beforehand, perhaps a list of things you’ve done where you have provided value to your organization. This way, you’ll be less flustered when you’re finally talking to your superior, and you’ll be better equipped to emphasize your worthiness for a raise.

Show empathy

There’s no overstating how important empathy is when it comes to difficult conversations. As previously pointed out by Deb Ward, you should take the time to consider how the other party might be feeling. Try putting yourself in their shoes and imagining what it takes to resolve the issue from their point of view. You should also focus on what you’re hearing instead of what you’re saying since your genuine attention will encourage the other party to elaborate. You have to keep in mind that the narrative you have in your head might be completely misguided.

Author Joel Garfinkle points out that difficult conversations actually don’t require much talk, especially if you’re one that has been approached. He notes that instead, you should focus on listening, reflecting, and observing. When you practice active listening, it makes it easier to handle difficult conversations well because you’re giving the other person the opportunity to express themselves. And when they know and feel that they are being heard, it will boost their morale and encourage more collaboration.