Steps to Manage Difficult Conversations at Work

There are plenty of difficult conversations that need to be had at work on regular basis. Whether it’s approaching your boss about that raise you need or having a hard talk with a coworker about their behavior, it’s important to approach those moments with confidence. Building up anxiety about those conversations won’t help either you or the person you have to talk to. Handling them appropriately can improve the atmosphere of communication in the working environment.

Practical advice to steer clear of office gossip on our blog post Steer Clear of the Water Cooler: How to Avoid the Rumor Mill.

Step One: Choose Your Time

There’s no truly “good” time to have an awkward conversation, but timing still matters! When you know you’re going to have a difficult conversation, think through the best time for it. If you know your boss is stressed about a big project, for example, it’s not the best time to go with a minor issue. If you have to make a difficult point to a coworker or to an employee who works under you, it may be more useful to do so at the end of the day so that they can go home and think about it. If necessary, go ahead and schedule a meeting for your difficult conversation so that you know you’ll be uninterrupted.

Step Two: Plan What You Want to Say

You’ve done great work for the company, including participating in many tasks outside your job description. In spite of that, it’s been over two years since your last raise–and you’re starting to feel the pinch. Perhaps you need to let a coworker know that specific habit has become a big problem, and you have evidence that you need to add to the discussion. Make sure you take the time to plan out what you’re saying in this conversation. You can’t script out every moment, after all, you have no idea how the other person is going to respond. Yet, you can make sure that you’ve thought through what needs to be said and how you want to say it for a more effective conversation.

Step Three: Listen

When you’re having a difficult conversation, make sure you don’t rush through what you have to say. Instead, take the time to listen to what the other party has to say genuinely. They might have some very valid points to make–or they may disagree with some of your arguments. Listen carefully to what they have to say, rather than formulating your response as they talk. In many cases, it may change the entire shape of the conversation. Taking the time to listen also lets the other person know that they’re essential to the discussion and that you care about what they have to say.

Step Four: Approach Conversations with Confidence

There’s a reason why this is important to you–and you’ve clearly taken the time to think it through. Make sure you convey that confidence during your discussion. Whether you’re trying to handle conflict or make a difficult request, your confidence could make the difference and approach a solid, productive conversation. At the same time, be open to changing your perspective if necessary. In many cases, the other party may have valid points that can help transform your opinion and make it easier to deal with ongoing challenges.

Practical advice to steer clear of office gossip on our blog post Steer Clear of the Water Cooler: How to Avoid the Rumor Mill.

You may also like

managing your tech team

6 Best Practices for Managing Your Tech Team

Numbers to Information

From Numbers to Information


PMBOK Key Concepts