Roleplaying Difficult Conversations

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As a manager, I had no idea how to handle my first disruptive teammate. The work environment was becoming less and less psychologically safe; the rest of the team had started to work from home more to avoid being yelled at by her. But she rarely acted out when I was around, so I found myself struggling to give this teammate feedback.

I tried to have a “hard talk” with her about her behavior, but it went sideways. I would leave our one-on-ones unsure if anything that I said had landed. Her bad behavior continued, and finally I talked with some more experienced managers about what I should do.

What helped me move forward was practicing the difficult conversations that I needed to have with my teammate. One of the other managers would play the role of my teammate, and I would practice giving the feedback. They played the role so well that I found myself at an impasse, or teary, or angry—but these managers had excellent feedback for me each time.

“Don’t say ‘always’ or ‘never’—it’s a trap.”

“Remember to put the ball back in her court, and make it clear what the next steps are.”

“Don’t list out every specific example; keep the conversation focused on how the behavior needs to change. Otherwise the talk could get derailed about the specifics of each and every example.”

Sometimes the managers would play my role, and I would play the part of my teammate, so I could see how they would approach the feedback differently. I learned a ton about how to create space and keep the conversation moving forward by watching them roleplay.

Over time, practicing the feedback helped me to hone the words that I needed to say, and avoid the potential traps my teammate would create. But more importantly, it made me much less scared when I had the real conversation, because I had already practiced what it felt like to be punched in the face with these emotions. Of course there were surprises in the conversation (you can’t prepare for every single potential!), but I was able to handle it much more productively having practiced.

Practicing difficult conversations and feedback helps you be a better manager, but the real reason you should do it is to fully support the person on the receiving end. It’s your job to help them be successful! Below, I’ve outlined some ways that you can bring difficult conversations practice into your workplace, to help your coworkers receive the helpful, specific and actionable feedback they deserve. Enjoy!

Lara

Roleplay giving feedback

Pick one person to practice giving real life feedback. Pick another person to pretend to be the recipient of the feedback, and pick a third person to observe the practice session.

The feedback-giver should instruct the recipient on how they should play the part. Will the real-life recipient get defensive? Shut down? Cry? Something else? The practice recipient should play the part, but shouldn’t go over the top—try to make it as realistic as possible, to help the feedback-giver get some good practice.

The observer should write down notes as they practice. What worked well? What went sideways? What should they try next time? What should they avoid doing? The observer’s goal should be to give solid feedback to the feedback-giver, to help them deliver excellent (actionable, specific, productive) feedback in real life.

Hold a “difficult conversations showcase”

Grab a conference room for an hour and invite all the managers in your organization. Ask six folks to practice giving/receiving feedback at the front of the room, so that the rest of the managers can see different styles and approaches to giving feedback in your group. In each example pair, one person will play the manager role, and the other will play their direct report.

Create fake scenarios (or use the ones below!) and share one with each pair so they can practice without using real-life information. Give them up to 6 minutes for each practice conversation, then call time. After each one, debrief with the whole group:

This is great for performance review season, so people can learn from their peers about different approaches (and pitfalls to avoid!) when having difficult conversations with their direct reports.

Practice scenarios

Manager: Your direct report has told you they think they deserve a promotion, but you don’t think they’re ready, because they haven’t consistently been performing at a more senior level.

Direct report: You’ve checked off all of the boxes on what it means to be senior. You did exactly what the career ladder says the work is of a senior person. It’s time for you to get a promotion.


Manager: Your direct report has asked for an enormous raise. However, you do not believe they’re ready for a compensation increase, as it would put them out of band (and much higher than their peers who are much more effective in their roles).

Direct Report: You have a job offer from another company for a lot more money. You’d like to stay at this company if they can match the other offer.


Manager: You heard from a lot of peer feedback that your direct report is being a jerk in meetings. They’re interrupting others, derailing conversations, and causing the team health to disintegrate. You need to deliver this feedback to your report.

Direct Report: You’re ready for a promotion. You say what needs to be said, you speak truth to power, you’ve made a huge impact on how much the team has been able to ship.


Manager: Your direct report is hesitant to ship incremental improvements to the user experience. They debate ad nauseam each project, and you’ve heard from the rest of the team that this person is slowing them down.

Direct Report: You believe this company doesn’t spend enough time on quality. You agree with your team’s priorities, but you want to make sure you’re not shipping a low quality or partial experience for our users.

Lara Hogan

I’m an author, public speaker, and coach for managers and leaders across the tech industry. Previously VP of Engineering at Kickstarter, and Engineering Director at Etsy.

I champion management as a practice within the tech industry, and celebrating career achievements with donuts.