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Using Roleplay to Prepare Design Managers

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Every so often, a designer gets promoted. If you are lucky, they are someone you have personally trained and developed. Congratulations! You now have a newly-minted design manager on your team. As a new manager, their relationship with the team will most likely change. They are now in charge of delegating design tasks, performance reviews, and leading critique—all things that require a different set of verbal communication and leadership skills.

As the design lead or director, it’s your job to get your manager up and running. If someone is being promoted to a leadership role on your team, I’d like to believe they have shown good instincts and leadership before. They are ready for the next step, but will need to practice within a structure for a while, with your guidance, as they acclimate to the new role. There will be quite a few situations where you cannot be there all the time to guide them, so instead of constantly playing catchup, you can use roleplays as a way to prepare them beforehand.

So, what is the point of roleplay? Do we need to create characters and do some method acting? Nah. None of that. In this context, roleplay asks your design manager to be themselves and to practice language and behaviors. You can then critically analyze their performance together to help them improve as a manager.

There are a few common situations when new design managers will be a bit out of their depth.

  • When they need to lead a design critique session. This may involve leading a team to a new solution, or pushing a designer to look more closely at a part of their work.
  • When they need to delegate design work. This is always a tough one. Lots of designers struggle with delegation, as they may be used to “doing it all myself” and have trouble giving up control of the details.
  • During performance reviews. Yearly reviews are common in larger, more structured companies, and hopefully you have something similar where you work.

I’ll show you the way I usually conduct these role-play sessions, but keep in mind that you should choose methods that you are comfortable leading and that will support your teammate. Not everyone will need this level of support, especially if they have other management experience, but I am confident you’ll be sensitive to people’s skills and abilities.

Plan ahead

Always explain what you will be doing. Book time in your diary in advance, and clearly list out what the session will be about and what it will achieve. I often use some variation of the following email:

As you transition more into a leadership role, it’s my job to help prepare you and ensure you have the tools you need to successfully lead your team. One of the ways we can do that is by practicing some of these common conversations that you will have with your team:

  • offering critique and feedback
  • delegating design work and assigning tasks

I’ve booked 60 minutes in our calendars, and we will use the time to go over some common language, and then practice it together so you get more comfortable. If there are other conversations with your team that you would like to practice, let me know.

These emails have the added benefit of being a template for the new manager to reuse when they do their own training sessions.


I’ll use the example of delegating design work. New managers often struggle with delegation, because of the fear that team members will feel they are being bossy. It’s often a misguided fear, but can have a real effect on how they assign work.

In the session, I start by setting the scenario:

I’m the design manager. I have a large project that I want to assign to you. I’ll ask you to take the project on, give you instructions on what needs doing, and what the deadline is, if at all. You are the designer. Please just react naturally, there is no need to act like someone else.

As I speak, take a mental note of what I say and the words I use. After we are done, we will quickly discuss what happened. Any questions?

We then do the roleplay. I assign the large project, and they respond naturally. Afterward, I ask them to repeat back to me what language I used, and their impressions of it. This is an essential part. You are getting them to say, out loud, the types of language they will need for the next exercise.

This step is a clear example of why you should almost never have two new managers present to each other. Not only will they be confused about what language to use, you risk reinforcing ineffective delegation techniques. Always model the language or management technique first, so they have a pattern to follow.


So, I’ve have set the scenario, and we’ve practiced once, with myself in the lead. After reviewing, we need to switch roles and do it again. Even though I explained the process over email, I still set the scenario and give instructions once more. By repeating this before we practice, I reinforce effective management pattern.

Ok. We are going to switch roles. Now you are the design manager and I’m the designer. You have have a large project that you want to assign to me. Ask me to take it on, give me instructions on what needs doing, and what the deadline is, if at all. Use the language we discussed just now, and what you heard me do the last time.

After we are done, we will discuss how it went. Any questions?

We then do the roleplay again. See how things build up over time? In language teaching, this process is called scaffolding; it allows people to internalize the routines and language they need.


Just as you promised at the very beginning, now you can take a step back. Offer some praise, and offer some constructive feedback to your new design manager. Both are essential!

Ask them to go over what they were comfortable with, what felt awkward coming out, where misunderstandings might arise, and other questions that force critical analysis of their language and actions. Now repeat the cycle! This repeated roleplay allows the design manager to build up a sort of muscle memory of the conversation, making it feel less stressful when they need to have it in the future.

There will be times then the roleplay goes completely off the rails. Don’t be afraid to call a time-out, offer correct language or tips, and then ask them to repeat after you. It’s better to adjust in midstream than wait until the end, when you are really far away from your stated goals.

OK, let’s pause for a second. Your instructions to the designer about a deadline were quite vague, you said, “if you could kinda…” and “maybe try…” and other imprecise phrases when giving them a due date. Let’s try that once more, but this time say, “I’d like you to deliver it by…” instead. How does that sound?

Never think this is just an hour-long session that you book and get out of the way. Training requires that you revisit the conversation, see how your new design manager is getting along with it, and scheduling further practice and review as time goes on. These role-play sessions could even be every month, spread out over a six to eight month period, if that is what it takes to get your teammate comfortable.

Roleplay is but one technique available as you develop your team, but it’s one that I have found successful both as a design manager and a teacher. New managers often have the right instincts and design skills to teach others, but they need a bit of help in learning how to pass those instincts and skills onward. Using roleplay makes them more confident in their actions and team interactions, and gives them accurate, practiced language to use whenever they need to.

8 Reader Comments

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