Strategies for Handling Difficult Work Conversations


Difficult conversations cropping up at work is very common. It’s something we all face all the time. So, whether it’s about telling a client the project is delayed or informing a vendor his product is sub-standard – all are an inevitable part of managing the work environment. As an entrepreneur, how should you prepare for this kind of conversation? And, how can you manage the verbal interaction so that it goes smoothly?

Identify your objective

Think about what exactly do you want to get out of the conversation? What is the desired outcome? What are the non-negotiables? What are the new options that you want to achieve by the end of the conversation? Once the objective is clear, you can also plan how you will close the conversation. Don’t end without clearly expressed action items. What can you both agree to do to overcome potential obstacles?

There must be a clear purpose. Write down any two or three things you want to accomplish and focus on them. If you pinpoint the root of the problem initially, you lessen the probability of the conversation getting out of hand.

Clarity is important

Be clear about the issue. When a problem crops up, and a conversation is required, what do you do? To prepare for the conversation, you need to ask yourself two important questions: What behavior is causing the problem? What is the impact that the behavior is having on you, the team or the organization? You need to find clarity for yourself so you can articulate the issue distinctly. Otherwise, you risk going off on a tangent during the conversation. Lack of focus on the central issue will take the conversation off track and it will also sabotage your intentions!

Be confident and direct

If you are confident, positive, and direct, the person on the other end of the conversation will likely pick up on your energy. If you approach it as an uncomfortable situation, it will remain one. Feeling confident is necessary to open up opportunities. Begin the conversation with confidence and get to your point quickly. You’re never going to get what you want unless you ask.

Be open to the other person’s perspective

It should be a conversation, that’s two-way. It’s important to listen to the other person’s perspective, for they may present a perspective that changes your mind. Listening to their perspective lets the other person know you’re acknowledging their feelings. Being able to listen and communicate effectively will help you resolve the current problem together. It will also help your relationship on a long-term basis.

Be empathetic

Think about the other person – what it might feel like to be on the receiving end of the conversation? If you see they’re finding the going difficult and are struggling with what you said, pause for a minute so they can gather their thoughts. If they start to get emotional, understand how they must be feeling. Then you need to reassure them that you’re providing this feedback because of the potential you see in them!!

Stick to the facts

Before your conversation, have a clear idea of what had happened and what the current situation is like. Take responsibility for your part in the situation and focus on the facts. Identify where any of the people involved went wrong and discuss the impact of this conversation. Remember it will not always happen that every conversation will go your way and not everyone is going to agree with your point of view. Try not to let your personal feelings get in the way of a final resolution to the problem.

Always come up with a solution

It must be clear – the goal of having this conversation is to reach a solution. If the solution isn’t clear from the beginning, then work together to come up with one that you both agree on. Share your ideas and also be open to listening to their ideas if they have any. Once both of you agree, then commit to the solution discussed and make sure there is an action plan going forward.

Follow up is required

It’s never a perfect world – all of the conversations we have do not always end the way we want them to. Some people have delayed reactions to bad news; some may experience frustration, embarrassment, or resentment after the conversation. Keep an eye on this. If there seems to be some tension, spend some quality time, like grabbing a cup of coffee – where you meet as individuals and not colleagues.

Ultimately, dealing with the issue at hand will lead to better results in the long run. Your team members will really respect you and appreciate you more for dealing with the situation head-on. 

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