September 17, 2020    |    By

Being the boss comes with many privileges, but it also comes with many hard responsibilities. One of these responsibilities is having difficult conversations. Difficult conversations most often concern employees who are not performing as expected. But employees aren’t the only ones you may have to face. You might need to tell investors in your business that you are losing money. It can often happen when the company is new but can also occur at any time. Let’s take a closer look at how you can handle these difficult conversations in a way that makes it easier for everyone involved.

Difficult Conversations at Work – Examples

What types of difficult conversations are you most likely to face in the workplace? The following are just a sample of the most common ones:

  • Negative feedback on performance – Nobody likes to hear they are not doing a satisfactory job. People may react in anger, go on the defensive, and even cry. You must take the time to address poor conduct, however, and do this in a way that creates an atmosphere of change.

  • Terminating an employee – Firing someone may be one of the most challenging things you need to do as an employer. Reasons vary, and sometimes you can’t help but make the decision even though the person may not have done anything wrong, such as when the business is failing. How can you fire someone in a way that eases things for both of you?

  • Resolving conflicts in the workplace – People differ. The more people you have working for you, the higher the chances of having a dispute arise between two or more employees. Getting control of this situation before it grows to an unmanageable size is essential.

  • Telling investors that the business is losing money is stressful at best. People get frustrated, and even angry when you tell them they are losing money. Your investors trusted in you when they invested in your business. Telling them that the company is losing money is one of the most challenging things you will have to do. You already feel bad, and their reactions may make it worse. Speaking up is, however, necessary.

Prepare for the Conversation

Before you speak with the person or persons that you need to talk with, take the time to prepare for the conversation, make a list of all the points you need to cover and think about how you can address these points directly, yet fairly. Consider the various scenarios that could arise and prepare for how you will handle those reactions. Preparation will help relieve some of the stress involved in an awkward conversation.

Things To Note

Keep a couple of things in mind regarding all problematic conversations. While each talk will have different variables, taking care of the static stuff will allow you to better approach the situation.

Keep It Confidential

Keep the conversation private. Only those who are directly involved in the situation should attend the meeting. Bringing in additional people is disrespectful and unprofessional. Breaking confidentiality also puts the other party immediately on the defensive as they will feel that you are ganging up on them.

Be Consistent

Make it a point to hold all employees to the same standards. Bringing up Joe’s constant absences won’t go over so well if Sally is allowed to be late several times a week without being confronted. When the rules stay consistent, and they apply to everyone, then your conversation will have less room for argument and will appear fairer.

During the Conversation

You have prepared, and the time has come to have an awkward conversation. The party or parties involved have entered your office and are waiting expectantly to hear what you have to say. Employing the following guidelines will help things go smoother.

Be Specific & Direct

The best thing you can do is be direct. Don’t waste time on small talk but instead get to the point as soon as possible. Be honest. Don’t add extra details or keep the other person guessing with veiled hints. State your case from the start in a calm, even manner. Once you have covered the gist of what you need to say, turn the floor over to the other person.

Listen To What The Other Party Has To Say

A conversation consists of two sides. Once you have said what you want to say, give the other person a chance to talk. Curb any urge to interrupt. Allow the person to speak. Attempt to understand what the other person is trying to say. Acknowledge their viewpoint and repeat things back to them in your own words if that helps you understand fully. Do not make quick judgments. Take time to think about what they had to say before you continue. Maybe they have presented you with some knowledge of which you were previously unaware. Empathy doesn’t mean you believe every sob story that others convey. Simply listen, examine, and then decide.

Be Respectful

Respect comes across in many ways. The first show of respect is closing your office door to keep the conversation private. During the discussion, refrain from taking phone calls or answering knocks on your door unless they are an emergency.

Don’t curse or use any kind of foul language. Do not call names or in any way attack the other individual. Keep your voice soft and even. You may find many emotions swirling around inside, but don’t allow them to show during this conversation. Remain a picture of calm professionalism.

Be Empathetic

Put yourself in the other person’s shoes. Try to consider what they are feeling and attempt to allow them to process whatever emotion arises, as long as safety isn’t an issue. As stated earlier, people will respond differently to the same situation. Allow that first wave of emotion to subside before continuing.

Take into account the person you are speaking to when you choose your words. Do everything possible to help them understand your point of view. If they can fully understand where you are coming from, it will be easier to move forward from this point together.

Offer Solutions

In many cases, the conversation will be about an issue that can be solved. Once both sides have had a chance to state their case and process the information, it is time to work together to try and find a solution. At the time you made your preparation, you may have considered some possibilities. Speak with the person and make it be more cooperative than an order. In this way, progress will be made quicker. In the cases where there is no solution, such as firing an employee for something directly against the company policy, remain calm but firm. Offer what help you can in the way of a reference, but don’t allow emotion to sway your decision if you know it is correct.

After the Conversation

Once the conversation is over, take the time to review how it went. Are there things you could have done differently? If so, make a note to do so in any difficult future decisions. Take note of anything surrounding the situation that you may have learned during the conversation. Maybe you learned of a circumstance that you had not considered, and it will help you view a future incident by someone else in a different light. Every situation gives you a chance to learn, grow, and improve.

Remember to Act Professionally

You will face dozens of hard conversations throughout your business life. Each one will differ in many aspects. One thing to keep in mind for each one is to remain professional at all times. You are the leader in your business, and that translates into being the leader of these conversations. Let the other party be able to follow your lead by remaining calm and professional, keeping the content about the problem, and not an attack on character. Remain fair and respectful at all times. Everyone will benefit from this approach.


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This blog post is intended for informational purposes only and does not constitute legal advice. No attorney-client relationship is created between the author and reader of this blog post, and its content should not be relied upon as legal advice. Readers are urged to consult legal counsel when seeking legal advice.