How to Have Difficult Conversations

Aug 28, 2020Business Development, Professional Relationships0 comments

Most people avoid conflict in any way possible. It is particularly troublesome when conflict happens at work. While you do not want to say the wrong thing or appear unprofessional, you do want the issue to be resolved while maintaining your composure. It is essential to take time to consider other perspectives (it may just be miscommunication). It helps to have a few tips tucked away for when you need to have an unpleasant conversation with someone on your team. 


You should not avoid difficult conversations. The longer you delay, the harder they get. You can build up anxiety and make the issue bigger than it really is. Ultimately, in a dynamic workplace, they are going to happen. As Steve Jobs said, “your job is not to be easy on people, but to make them better.” You need to address these situations immediately.


Attempt to steer clear of toxic behaviors. Relationship expert John Gottman calls them “The Four Horsemen of the Apocalypse.” These relationship destroyers are excessive criticism, immediate defensiveness, contempt, and stonewalling. We have all engaged in these behaviors at some point, but there are ways you can work around them. Begin by ensuring everyone involved is willing to be aware of these tendencies and to call them out. 


Have a purpose. Write down three things you want to accomplish and focus on them. If you stay on track with the root of the problem from the beginning, there is less chance the conversation will get away from you. Remember, people do not want to be given a long list of their problems.


Notice your triggers. Emotions tend to run especially high during difficult conversations. When something triggers you, you may want to attack or withdraw. Either way, you are damaging the dialogue and the relationship. Ideally, we would all manage our emotional outbursts and shutdowns–but this does not always happen. When you feel yourself getting worked up, try taking a break, taking deep breaths, or even taking a quick walk to let out some pent-up energy. When you come back, you will have regained your rationality and effectiveness. 


Bring in a facilitator. If the situation at work is particularly contentious, consider finding a facilitator to help you navigate the conversation. Facilitators can help with one-on-one discussions, small team meetings, or help lead entire leadership discussions. Facilitators are helpful because they are third-party individuals who have no agenda other than to help you work through a situation. 


Stick to the facts. Before you begin the conversation, have a clear understanding of the events you are about to discuss. Take responsibility for any part you may have had in creating this issue. Identify what went wrong, the impact, and what can be learned from it.


Always assume the best. Whether you disagree with one of your peers or one of your leaders, remember that most people have the best interests of the team or the organization in mind. When you pause and consider this, you have a stepping stone to move through the conversation productively. Chances are, you have assumed the other person has less-than-good intentions. By shifting your mindset, you can help move the discussion forward positively. 


Be confident and direct. This will help the other person or people in the conversation adopt your energy. If you intentionally approach this as an uncomfortable conversation, it will be. According to Facebook’s Sheryl Sandberg, “feeling confident —or pretending you feel confident— is necessary to reach for opportunities. It’s cliché, but opportunities are rarely offered; they’re seized.” If you ask for a raise or promotion, take the initiative, begin the conversation with confidence, and get to your point quickly. You are never going to get what you want unless you ask.


Be empathetic. Consider what it would be like to be on the receiving end of the conversation. If you see they are struggling with what you are saying, pause so they can gather their thoughts.


Attempt to come up with a solution. The only reason to have a difficult conversation is to reach a resolution. If the solution is not clear from the beginning, work together to come up with one. Listen to their ideas and share yours. Once you come to an agreement, commit to the resolution and make sure there is an action plan moving forward.


Follow up to prevent any fallout. In an ideal world, all conversations would end just how we want them to. Some people have delayed reactions to difficult situations, such as frustration, embarrassment, or resentment after the talk. Check on them occasionally to see how they are doing; this lets them know even after the difficult conversation you still care. 


Conflict, while uncomfortable, can be productive when you approach it in the right way. Always be sure to note and call attention to behaviors that may undermine the discussion. It also helps to stay aware of what upsets you personally, so you do not respond out of anger–and thrive.



For some additional guidance on how you can improve your communication skills, check out our blogs on Asking for Help and Communicating Action


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