5 Tips for Handling Difficult Conversations at Work Like a Pro

Difficult Conversations at Work

Most business owners don’t love dealing with difficult conversations at work. But whether you’re encouraging an employee to improve their performance, asking a vendor for a payment extension, or giving bad news to a customer, having difficult conversations is bound to happen.

When difficult conversations come up, you need to be ready to handle them with grace, professionalism, and respect. Learn how to handle difficult conversations at work to keep your business running smoothly.

Examples of difficult conversations at work

Difficult conversations at work can take any form. Although the bulk of your tough conversations might be with employees, you can also have difficult conversations with customers or clients, vendors, investors, lenders, and independent contractors.

According to a Harvard Business Review (HBR) survey, some difficult conversations include negotiating a raise, handling a difficult personality, and apologizing for a mistake.

Some other difficult conversations you might have at work are:

  • Turning down an employee’s idea
  • Encouraging an employee to improve their performance
  • Resolving conflict between two or more employees
  • Terminating a position
  • Telling investors your business is losing money
  • Asking vendors for new invoice payment terms
  • Letting customers know there is a problem with their orders
  • Talking with frustrated customers

The kinds of difficult conversations you can have at work are endless. But, the same basic tips for handling conversations are the same.

Tips for managing difficult conversations

Here are five tips that can help you have difficult conversations with employees, customers, and whomever else you encounter in business.

difficult conversations at work

1. Don’t avoid having the conversation

You might hate conflict, but putting it off will only make matters worse. The longer you put off having the difficult conversation, the bigger the problem will become. Once you realize there’s a problem, set up a meeting and address it.

Let’s say your employee continually misses deadlines. You need to talk to them about their performance before your business bottom line suffers. And, putting it off might make the conversation much more difficult. The employee might get defensive and wonder why you didn’t bring this up sooner.

Or, let’s say you have a long-term customer who is angry with a change in your business. If you avoid hearing them out and having the difficult conversation, you could end up with lost business.

2. Nail down the purpose of the conversation

Approximately 80% of participants in the HBR survey said they were likely to prepare for a difficult work conversation before having it.

Before you actually have a difficult conversation, be prepared. Hone in on the heart of the problem so that the conversation doesn’t get off track.

Knowing why the conversation needs to take place can help you develop goals. For example, if an employee is making far fewer sales than every other employee, the purpose of your meeting might be to assess their strategy, come up with a new one, and increase their sales by X percent.

If you don’t know the purpose of the conversation, why are you having it? And if you aren’t focused on the actual problem, you and the person on the other end will start dragging in other problems.

Having a purpose for the conversation might also help you to stick to the facts instead of getting carried away with your emotions. Prepare the points you want to talk about and gather any applicable documentation beforehand.

3. Be willing to listen

During the conversation, you need to be respectful of the other person. Instead of dominating the entire talk, you need to listen to what they have to say.

Whether the other person is responsible for the problem or you are, listening to them helps you see things from their point of view. The HBR survey found that 81% of participants would acknowledge there are multiple ways to view the situation, which is necessary for coming to a solution.

If you take a step back and realize you don’t need to be talking the whole time, you can truly understand what the other person is saying and get to the root of the issue. Verify that you understand what the person is saying to show that you are listening.

Listening can help smooth over ruffled feathers and show the person that you care about what they’re saying. And, it can help you remain calm, humble, and polite. This can make for a more effective, less stressful talk.

4. Come up with solutions

A difficult conversation shouldn’t just be a time to air your grievances. It also needs to be constructive. Otherwise, what’s the point?

In some cases, you might need to determine a plan beforehand. Or, you can work with the other person during the difficult conversation to develop actionable solutions.

Coming up with solutions goes hand-in-hand with establishing a purpose for the meeting. If you have a list of possible solutions, you can keep the conversation on track, show that the problem can be improved, and have both parties part with a plan going forward.

5. Review the issue

Managing difficult conversations at work effectively doesn’t end when the talk is over—you need to take action afterward, too.

Follow-up with the individual to make sure they are satisfied with the outcome of the meeting (unless you fired an employee).

If the solution required action on their part, ask them how it is coming along. If the solution required action on your part, detail what you have done.

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