How to Have Difficult Conversations

Under extraordinary circumstances of stress, conflict at work is inevitable. Contention needs to be managed not by sweeping it under the rug, but by baring it in the open through honest and transparent conversations.

Avoiding difficult conversations shortchanges your individual and collective success. Having them, on the other hand, can transform your work environment to be positive, respectful and successful.

At the 2020 NextGen Government Training Summit, creator of the Transformational Guidance Training Program, Erica Wexler, explored communication strategies and answered audience questions about navigating difficult conversations. Here are some of the pertinent questions Wexler answered:

The responses have been lightly edited for brevity and clarity.

Q: Has your advice for having transparent conversations changed with the pandemic?

Wexler: Yes and no. In the virtual workspace, they’re still the same strategies because we’re still people. But it has changed because we’re all under so much stress. It’s not just the age of quarantine. It’s also the racial discourse underway. And that’s some of the reasons conflict is coming to the surface. It’s all of the context right now that we are navigating as a society and as an organization.

Q: How do you know when it’s time to have a difficult conversation?

Everyone has a responsibility to get the work done, whether you like someone or not. If it’s starting to impact your ability to get your work done, if it’s starting to impact your ability to sleep at night, or if it’s impacting other people on your team, [ask yourself,] “OK, is this the right time? What’s going on in that person’s context? When am I going to be in the right headspace and have the right bandwidth to be able to have this conversation and show up and really listen?”

Go into their calendar and take a look at the next two weeks. If they are stocked busy for the next two weeks, it may not be the right time to approach them about something personal. You may want to ask [them], “Let me know when a good time is to have this conversation,” and let them come back to you. Sometimes just asking for the conversation might be enough to decrease your stress for the short term.

I would also say be prepared to have an in-the-moment conversation. … First you want to make sure you’re in a good space for it so you can thoughtfully think about how you want to approach the other person.

It’s not an easy “Do it in an hour. Do it in two weeks. Wait three days.” There’s no prescription for that. So pay attention to time and energy, together. 

Q: What is one takeaway to remember about resolving conflict through communication?

If you remember nothing else from today, remember that conflict and communication is about perspective and perception. Going into [the conversation] thinking, “I’m right” is polarizing. Take the mindset of being collaborative, being open and having a curiosity mindset [that] aims to get it right versus being right.

A conversation around honesty and transparency is a lot like an optical illusion, where I know how I’m feeling and I know that this behavior or this action needs to change. [But] I also know that the other person may not realize that the impact they’re having doesn’t match their intention. It’s possible. I’m going to aim to assume good intentions, then work around the reality of it, and realize that that person has a perception or perspective on it that you may not be able to change. Maybe by working together and looking at it as a process, you can show them who you are and they may engage with you differently.