Designing an end-of-year meeting for a Design Team – UX Collective

A year-end retrospective package for one-on-one conversations

I know 2018 is coming to an end when Michael Bublé’s Christmas album made its way into our office playlist about a week ago. In the midst of scheduling the final series of 1:1’s with designers on my team, I put together a year-end retrospective package for everyone to fill out prior to our meetings.

The package is intended to serve as a framework of discussion points surrounding each designer’s individual growth and contributions in the past year. In this article, I will detail each page of the package as well as provide a white-labelled, year-agnostic version available for download at the end of the post.


One-on-one’s held throughout the year at regular cadences are crucial because they help team leads keep a constant temperature check on an individual’s current state of mind and, by extension, the overall team’s health.

The last 1:1 at the end of the year holds an even higher level of significance for me because it presents a timely opportunity for self-reflection prior to the holidays, when people tend to set new heights to reach for the next year. I firmly believe that everyone benefits from moments of introspection, but as a manager, I especially encourage my team to build awareness and empathy towards their needs and sentiments because my job is to abstract their awareness and empathy and, in turn, facilitate an environment that promotes professional and creative growth. With such goal in mind, I designed my 1:1’s.

Materials Needed for Each Team Member:

  • Year End Retrospective Package
  • 1 Envelope
  • 1 Pen
  • 1 Black Sharpie
  • 1 Coloured Sharpie or Highlighter
  • 1 Post-It Note

My Team’s Year End Retrospective Package

My team is called the Thundercats! — with no reference to the cartoon 🙂

The first page is a quick summary of the year: what was their happiest team moment, their favourite standup activity, and their most important lesson learned? For my team, we host three standups on a weekly basis and each standup culminates in a quick creative activity (hence the second question).

Next, the growth map allows designers to identify their current and desired level of proficiency in the next year across eight topics, one of which is self-defined. While my assessment of their skillset is important, their own perception of said skills is arguably even more valuable as it demonstrates to me their level of self-awareness and reveals potential areas of discrepancies, if any.

The Finding Fulfillment matrix allows me to understand the factors that make them happy at work. At a fundamental level, what constitutes gratification for them in their day-to-day? Work fulfillment comes in the form of inspiration, growth, respect and feelings of being valued. Where do they see themselves in these dimensions this year and next?

The dimensions that contribute to work fulfillment is elaborated on this page with guiding questions and an area for notes.

The Letter Series is a collection of three letters written to different people. The first letter is addressed to me, their team lead. I ask for honest writing on any topics they wish to reflect upon, including at least one positive note and one item that I can improve on.

The second letter is dedicated to another designer on the team. Topics again are not defined, some suggestions include: What do you appreciate about them? What would you like to learn more about them? After our one-on-one’s, I take this page and personally hand the letter to their teammate.

To ensure that everyone on my team receives a letter, names are distributed at random. In each package, a name is pre-filled on this page and then written again on a post-it note on the cover page. When handing out the package, I ask that everyone makes sure the name on the post-it is not their own.

The third and last letter is written for their future selves. This is a private dialogue between their 2018 and 2019 minds, of which they place inside an envelope when completed. I hold onto their sealed letters and hand them back in six months.

This page encourages reflection on projects completed in the past year and the respective lessons or takeaways learned from each. The rightmost column allows the team to identify their colleagues who have helped them achieve the lessons along the way as a reminder that we are all here to learn from each other.

The last page circles back to the first. They are asked to look ahead into the new year and come up with their most important goal as well as what they are most excited about. The final question is as much a light-hearted end to the retrospective package as it is a personal challenge for myself: what edible treat would they like for their birthday in the new year!

Last but not least, a thank you page to cap the retrospective.


I hope that the design of my year end 1:1’s can inspire you to create a similar dialogue with your team. Or, share this post with your team lead or manager (design-specific or not) to start the conversation! To get started, you may also download a white-labelled, year-agnostic retrospective package here.

Thank you to various inspirations from Margaret Stewart, Nina Mehta, and Year Compass for the package, and Aaron Mohr for our Thundercats team logo.

Cheers to an amazing 2019!

Author: Teresa Man

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