What do we talk about at a Product Ops team workshop?

Sharing the What, Why, and How of the User & Product Operation group's workshop

The end-of-quarter hustle

The end of the quarter at DelightRoom is incredibly busy. For about a week or two, every team thinks and discusses fiercely to prepare for the company-wide end-of-quarter workshop (quarterly review & planning). It's also a period for a final sprint to squeeze out a little more performance and get closer to our goals before the quarter closes. If the company were a person, it feels like it enters 두뇌 풀가동 모드 at the end of every quarter.

The end of Q1 2022 was just as intense as any other quarter. Especially with more teams onboarding new people, it felt like we talked and synced our thoughts even more fiercely than usual. In our User & Product Operation (UPO) group, we had two new teammates join over the last two quarters. As a result, roles and responsibilities (R&R) were reorganized and the team's OKRs evolved, making us feel the need to intensively discuss our direction and actual work plans. And so! Adding another scoop of intensity to this busy season, the UPO group went on a team workshop.

I'm writing this to document such a productive day, and hoping it helps someone out there grappling with similar concerns. Let me share why we went on this workshop, how we structured it, and what we learned from it.

A hidden wish: Going on a team workshop

When you're running day in and day out with work, there comes a time when you lose your breath. Sprint after sprint, quarter after quarter... as you run endlessly like this, you start wanting to calmly look back and ask, am I doing well, and am I truly having fun right now?

Especially as the team grew, it became harder to check if we were all running well together. Although we tightly sync on our plans while setting team OKRs, we're so busy setting goals and deciding on metrics that we lack the time to look into each other's situations, thoughts, and feelings. Maybe that's why, even after spending hours discussing and refining OKRs, the thought of "Ah, I want to talk more..." kept lingering in my head. But wondering "Would it be okay when everyone is so busy?", I just kept this wish to myself.

Then, during a meeting where we were wrapping up our Q2 OKR planning, I threw out the idea: "Shall we go on a workshop to do a retrospective and deeply discuss what we'll do next?" Thankfully, both June and Fo must have felt the same way, as they responded even more enthusiastically than I did. On a Thursday with one week left in March, we quickly set the date for the following Monday.
Strike while the iron is hot—once we made up our minds, we shouted Go! 😎

The Why, What, and How of the workshop

01 Why are we going on a workshop?

When we gathered everyone's thoughts on "What are we trying to do at the workshop?", our biggest goal narrowed down to one thing.

Preparing the UPO group to "do well" in Q2 2022

To be more specific, it was this:

• Team direction level: What direction have we been running in + what direction should each of us run to achieve the goals set in our OKRs?

• Concrete work level: Let's extract concrete Key Initiatives and PBI ideas that align with our direction.

02 What will we do at the workshop?

Now we had to design the program. It wasn't about planning everything rigidly to fit perfectly, but we shouldn't waste our precious time and energy. So, before drafting a schedule right away, I wrote down the thirsts I had felt while team building.

🎉 Our team worked hard & did well this quarter, and I want to celebrate together

We do have sprint retrospectives, but I wanted us to acknowledge and rejoice in what we did well over the entire quarter. Compared to what we achieved this quarter, the metrics we set in our OKRs didn't rise significantly. It was hard to see immediate results in the metrics since we were still in the foundation-laying phase, and due to unexpected variables, we couldn't execute our plans as much as we wanted.
However, even though both of them had joined recently, they found great problems and even created solutions at an incredible pace of growth, so I wanted to celebrate and thank them.

🖼️ ️️️As R&R became more clearly defined and expanded, I wanted to align the pictures each role was aiming for

There are currently three main roles in the UPO group. A role that listens to and talks with customers, a role that verifies product quality, and a role that localizes in-product copy. If initially one person juggled multiple roles or divided them up a bit, now the R&R is clearly separated. Because of this, the blind spots regarding each other's work were gradually increasing.

Fortunately, we sync often—daily, weekly, bi-weekly, and quarterly—but I wanted to have an honest talk about whether we are enjoying the work, and if there are any worries or lingering concerns, no matter how small. Since we're one team, I believed we needed to share these thoughts and ponder them together to build a solid collaborative structure.

🎯 I wanted to close the gap between OKRs and extracting the actual work we would do

After clearly setting our direction through goal setting at the end of the quarter, we'd been deciding what to do next week through bi-weekly PBI Grooming. In other words, to achieve the goals defined by our OKRs, we defined and refined the important tasks we thought of through these grooming meetings.
The bummer, though, was that while I wanted to invest concentrated time into extracting PBIs to paint the big picture, getting bogged down in daily work meant we ended up mostly talking about whatever came to mind at the moment. The tasks we chose certainly had a big impact, but we lacked the time to take a bird's-eye view of what other tasks might be out there.

So, by allocating more time than usual, we decided to flesh out our KRs step by step and ideate on where to start digging into the problems.

03 And thus, the program was born

After sorting out our own needs like above, we thought about what kind of program could satisfy each need.

🎉 Our team worked hard & did well this quarter, and I want to celebrate together
→ Let's run a retrospective on the past quarter, but make gratitude and celebration the core focus!

🖼️ As R&R became more clearly defined and expanded, I wanted to align the pictures each role was aiming for
→ Let's draw up an ideal of what each person considers to be a perfect & fun way of working!
→ To clearly recognize the realistic constraints we face right now, let's conduct a Pre-Mortem!

🎯 I wanted to close the gap between OKRs and extracting the actual work we would do
→ Let's flesh them out in the order of Objective > Key Result > Key Initiative > PBI, (Top-down)
→ Conversely, let's create Key Initiatives from PBI ideas and connect them to Key Results! (Bottom-up)

…

Hmm. We had roughly set the agenda, but I felt it lacked organic flow as to "why" we were doing each program. It's not like the workshop couldn't proceed without an organic flow 🙂, but since we were dedicating the long hours of an entire day for three people!, I wanted every hour to feel meaningful in the grand scheme of things.

After some short but intense brainstorming, I drew up a picture like the one below.

과거 Look back on the past quarter to acknowledge each other and find areas for improvement,
미래 - 이상 Sync on the ideal goals our team ultimately wants,
미래 - 현실 Share anticipated challenges for the next quarter to identify what we want to avoid, and
현재 Acknowledge the gap between our ideal goals and the outcomes we want to avoid, finding ways to narrow that gap.

After some short but solid contemplation, the program was complete! We all headed out on Monday morning feeling reassured and spent a fruitful 6 hours at a nice coffee shop. It was pretty exhausting as we used a lot of physical and mental energy, but we felt proud to have discussed things deeply with one mind. 😎

Realizations left by our first workshop

Perhaps because it was our first workshop, we gained precious lessons in areas we hadn't thought much about before. As expected, organizing lessons and making them your own is the fun part after finishing something, right? Let me tell you what I felt.

Talking about 1 thing 10 times is different from talking about 10 things connected all at once

• Of course, there is an efficiency to breaking things down and having 10 separate conversations, but since every piece of our team's work is closely connected, discussing them all at once yielded a lot of insights. Workshops take a lot of resources, so it'd be hard to use this method frequently, but I thought taking this kind of time once a quarter would be highly valuable.

• For example, on the topic of "How do we respond to user-reported bugs?", we usually split the discussion into interacting with users, investigating internally, sharing with other teams, and following up on the resolution process. This method was good for pinpointing problems, but it left the big picture feeling vague. However, discussing it as a whole with the workshop as an opportunity allowed us to paint the flow we ultimately want, making us feel the importance of what each part means. It even led to scalable discussions.

Goals and metrics are important, but you shouldn't miss out on praise and recognition

• It's such an obvious thing, but it's a lesson deeply etched into my mind once again. We're understanding phenomena and judging success through data, but ultimately, behind the data the team manages are the team members, right? I thought I should recognize and celebrate more of the important trials and errors, precious achievements, and sense of responsibility that aren't fully captured by data alone. When I praised myself for doing a good job, it fired me up to do even better.

Let's also talk often about our individual goals and desires

• When you clearly set R&R and start running, there's very little time to talk about what the other person and you yourself ultimately want. The day is short enough just getting the immediate work done. But since DelightRoom holds "joy" as a core value, I felt we needed to know when each of us finds joy and what we dream of.

• When we actually talked about this topic, I saw 무엇을 하고 싶은 누구누구 rather than 어떤 역할로서의 누구누구. In other words, we were able to deeply understand each other's communication styles, preferred ways of working, and goals. I gained the confidence that we could better understand each other and drive successful collaboration in the future.

Balance, it's all about balance!

• The word "balance" was mentioned quite a few times during this workshop. Future ideals vs. outcomes to avoid, making decisions on the fly vs. setting a plan and executing it, high-level goals vs. concrete PBIs, top-down discussion methods vs. bottom-up discussion methods, etc. Once again, I realized that there is no single right answer for anything.

• Honestly, when you work, you naturally lean a bit toward a familiar method or a method each person thinks is right, but I felt that we need to give each other feedback and always maintain flexibility so we can strike a good balance. Empathizing with this together allowed me to let go of the pressure to find a definitive answer.

A fun team dinner, and what's next

After pouring our energy out for over 6 hours, the three of us wrapped up the workshop with delicious pork belly. We ate to our hearts' content! Until our bellies burst! And we chatted excitedly as a reward for our hard work. We laughed so much that my jaw was sore when I got home.

Thanks to having such a productive team workshop, a few days later we were able to attend the company-wide workshop having sent off Q1 with zero regrets, brimming with confidence for the next quarter. I made up my mind to run an even better program in an even more comfortable environment and have fun doing it again next quarter!

I don't know how lucky I am to be able to work joyfully with good people. It made me pledge to become a good person, a good coworker, and a good lead in return. It was a quarter filled with gratitude for June and Fo who joined me. We'll work happily in the newly started Q2 as well. Please look forward to the infinite growth of our UPO group and DelightRoom! 🚀