Handling difficult workplace conversations: 7 tips

Difficult conversations are unavoidable in the working world. Consider this expert advice to overcome the anxiety and handle them productively
99 readers like this.

Does the mere thought of addressing a challenging work situation with one of your employees fill you with anxiety and distract you from other work?

If so, you’re not alone. According to workplace resource firm Bravely, at least 70 percent of employees are avoiding difficult conversations with their boss, colleagues, or direct reports. And workplace health is suffering as a result.

Here are 7 tips for handling difficult conversations at work:

1. Get clear on your objectives

The first step in addressing any difficult work conversation is clarity around what you’d like to achieve from it.

For example, let’s say you need to talk with an employee whose performance is subpar. Are you talking because you want to help them improve their performance, or are you going through the steps so you can transition them out of the organization? Those two scenarios involve two very different conversations, so it’s essential to get clear on what you want to happen at the end of the conversation before you start.

2. Organize your thoughts

Most people who enter difficult conversations without a clear roadmap wind up doing more damage than good. Leaders blurt out things they quickly regret saying, or they find themselves going in circles without an exit plan.

[ Want more insight on developing emotional intelligence? Read also: 4 soft skills leaders will need in 2022. ]

In my book, Can We Talk? Seven Principles for Managing Difficult Conversations at Work, I discuss the need to go into these types of conversations with a well-thought-out outline. I also recommend taking your notes into the meeting to help keep you on course.

3. Practice your lines

How you say something is equally as important as what you say, especially if you’re in senior leadership. The higher up you go in the organization, the higher the expectations are regarding your performance.

Take a few moments and practice your opening lines in front of a mirror. Or, if you’re fortunate enough to have a trusted peer or a coach, ask them to role-play with you until you’re comfortable saying what needs to be said.

4. Listen deeply

Most people are so keen on getting a difficult conversation over with that they charge through the exchange. In doing so, they miss a big opportunity to build a solid relationship with the other person.

If you slow down the conversation and listen deeply to what the other party has to say, you’ll stand a much better chance of moving forward together rather than moving further apart.

5. Get a date on the calendar

The quickest way to stop avoiding a difficult conversation at work is to schedule a date for your meeting. With today’s technology, it’s simple to book an appointment.

The clock starts to tick the moment a get-together is booked on the calendar, which is exactly what is needed to catapult procrastinators into action.

The quickest way to stop avoiding a difficult conversation at work is to schedule a date for your meeting.

6. Expect the unexpected

I’ve coached enough leaders on handling challenging work conversations to know that things don’t always go as planned.

An employee may break down in tears while describing a personal matter that you were not aware of. Or a distraught team member may get up in the middle of the meeting and leave. These things happen, which is why it’s essential to plan for the unexpected. Be prepared to pause and reschedule a difficult conversation, as time for both parties to collect themselves may be what’s needed.

7. End the conversation on the right foot

Before closing out the conversation, it’s always good to confirm the other person’s understanding. Asking someone to tell you their knowledge of what just transpired can be very helpful.

If you’re telling them that they need to be more of a team player and they think you’re talking about improving their tennis game, you’re on different courts. At that point, you can say, “Okay, I probably wasn’t clear enough; let me be specific and tell you exactly what I need you to do.”

Difficult work conversations are inevitable. The sooner you get comfortable with them, the more confident you’ll feel as a leader.

[ Get exercises and approaches that make disparate teams stronger. Read the digital transformation ebook: Transformation Takes Practice. ]

For more than 25 years, Roberta Matuson, president of Matuson Consulting, has helped leaders in highly regarded companies, including General Motors, Takeda, and Microsoft achieve dramatic growth and market leadership through the maximization of talent.