Navigating Tough Conversations, Even When You Don’t Want To

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Your hands start to sweat. Your breathing becomes shallow. Your mind is working in overdrive. Many can relate to feeling this way at some point, especially before a tough conversation. Some can separate emotions from these conversations and handle them with ease, but most… simply can’t do that. Prior to difficult conversations at work, we sit at our desks and let our emotions eat at us.

If you are the one initiating a tough conversation, whether you’re a leader and need to discipline a direct report or you’re a team member and need to tell your boss you’re not happy in your role, you may experience high levels of stress and anxiety prior to the conversation. You might even let the nerves and stress affect you so much that you ultimately avoid the conversation. If this has happened to you, you’re not alone; it’s quite common! According to Bravely, “70 percent of employees are avoiding difficult conversations with their boss, colleagues, and direct reports”.

Why is that number so high? It’s not because the avoidance technique is recommended! It’s because tough conversations are TOUGH. You may fear an uncertain outcome, possible retaliation, or a relational strain. As a professional, your willingness and ability to directly discuss feedback, compensation, behavioral issues, and conflict, is vital for team success. When these tough conversations are avoided, employee engagement, productivity, and trust decrease.

Difficult conversations require thought and preparation yet shouldn’t be approached with a full-fledged plan, as that will be sure to make the conversation more tense and forced than necessary. Instead, simply go in with the intent to produce a better outcome. A better outcome in this situation means “less pain for you, and less pain for the person you’re talking to”.

How can you navigate tough conversations to produce the best outcomes?

Prepare – but not too much

Think about one or two things you want to accomplish in your conversation and stay focused on those.

Schedule the conversation

Nobody wants to be blindsided with a tough conversation. Schedule the conversation ahead of time to allow others to feel more prepared.


The only way you can practice is by making yourself get uncomfortable and have more tough conversations. This doesn’t mean you should be starting drama in your workplace by having unnecessary tough conversations, but don’t shy away when certain conversations need to happen.

Just do it! Don’t wait

Immediately address conflict or issues that arise, and regularly deliver feedback to colleagues when appropriate.

Shift your mindset

Don’t put so much pressure on impending conversations that may be tough. Go in with confidence as if it’s another ordinary conversation, assuming it will go well and be a breeze. The other person will hopefully match your positivity.

Manage your emotions and show empathy

Try your hardest to keep your emotions out of the situation, keeping it professional (without acting like a robot!). There could be strong feelings during the conversation, so be considerate of others’ feelings and give them time to process their emotions.

As a professional at any level, you must initiate and engage in tough conversations. And you have the power to determine how these conversations play out. Take the tips above as a starting point for you to hone your communication and conflict resolution skills.

If you would like to be intentional about growing this area, check out our training that’s coming up → Navigating Conflict & Uncomfortable Conversations at Work

If you want team training to improve conflict resolution, communication, and employee engagement, chat with a CoreCounts Consultant about the options we have for team training!

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