How to Handle Difficult Business Conversations Without Losing Your Sanity

Photo by Michał Parzuchowski on Unsplash

Difficult business conversations are bound to happen in any workplace whether it is with employees, clients, investors, lenders or vendors. These conversations may arise from many scenarios such as when you are addressing difficult someone with a problematic personality, or when negotiating a promotion. Other times like when a colleague has delayed a needed report, missed a deadline, or when you have to tell an employee that their job is at risk of being terminated.

Difficult business conversations are associated with intense and complex emotions, unforeseen reactions, vulnerability and fear of losing control of the parties involved. No business owner loves to deal with these kinds of conversations, and as a result, most of them tend to delay their intervention in the hopes that the issue will disappear. Avoiding handling these difficult conversations only leads to poor performance of the individuals involved and might result in low turnover to the broader organization in the long run.

Having these types of talks is something that everyone dreads, but unfortunately, they need to be dealt with at the earliest stage possible. Like in the gym, if you want to have a perfect appearance, you have to work hard. This article outlines 5 ways of maximizing your ability to handle difficult business conversations;

1. Prepare yourself and the other person for the discussion

Determine why the conversation must take place and knowing what you wish to achieve at the end. Having a purpose and a goal for the talk helps you to focus on what the issue is, have the facts at hand and to put any other irrelevant conversations at bay. Write down these problems, topics and relevant information you wish to raise during the discussion because you can forget them or raise unplanned issues if the meeting gets heated. When you are ready for the conversation, it is crucial that you also hint the general idea of the impending exchange to the other party so that they can prepare themselves in advance too.

2. Be unbiased and focus on the facts

Since difficult conversations arouse complex emotions, it is challenging to remain objective when having them. Your feelings about the situation, how to start it or the attitude you have towards the employees involved shouldn’t be a barrier for you to act professionally or put your needs above the organization’s goals. Do not let your personal biases or prejudice cloud your judgment. Try to remain positive amid the uncomfortable conversation, and you will be able to deal with the situation professionally. Take a deep breath to calm yourself to put your emotions off the table and base your facts on the presented evidence. Ensure that you keep an open-mind while handling the situation. You may even question your beliefs and assumptions at some point to remain objective on the issue.

3. Listen to the other party

When you have opened up the conversation, diffuse tension by presenting the matter clearly, letting the other party know that they will have time to express their side of the story and your desire to solve the case. Listen actively to their viewpoint. Do not interrupt them. If they say something that catches you by surprise, take time to reflect. Communicate your views with generosity, respect, integrity, and truth. You can ask them questions so that you can understand their point of view better.

4. Take care of the reactions

It is not unexpected for the other person to feel angry or upset about the outcome of the discussion. The important thing is to handle the person with care during that situation. Put yourself in their shoes and figure out what you would want to hear if you are in the same position. Do not tell them that their actions are silly, irrational or dramatic but instead be compassionate. Show empathy and give the person a break to compose themselves.

5. Find a solution and maintain a follow-up

At this point, you have shared all the information and expressed your opinions. It is time to be constructive and come up with actionable and amicable solutions. You shouldn’t coerce the other person to accept your decision or point of view, and instead, you should find a middle ground where a solution will be fair for all the involved parties and agree on what needs to change. It is also advisable to maintain a follow up even after the conversation is over to ensure the outcome was fair to the individual and they are taking actions to change.


Ability to handle difficult business conversations is essential for any business owner or manager. It is not an easy thing, but with practice, it becomes much less difficult to master it. Arrange a face to face meeting as soon as possible and confront the situation with empathy and in a constructive way so that you can attain a win-win solution.