My First Year as a Team Lead: Lessons, Challenges, and Growth

日本語サマリ

本記事では、BoostDraftのUIチームでソフトウェアエンジニアを務めるJeffが、チームリーダーとしての初めての経験を通じて得た学びや、チームで取り組んだ課題改善のプロセスについて紹介しています。

Jeffは入社から約1年後にUIチームのリーダーに就任。急成長するエンジニアリングチームの中で、業務の内容や負荷が大きく変化し、チームマネジメントやプロジェクト調整など新たな役割に直面しました。

記事では、以下の3つの主要な取り組みを通じて、チーム内の課題にどのように向き合ったかを紹介しています：

・Design Show & Tell：UIの初期段階で社内からフィードバックを集める場を設け、手戻りを削減。
・Bug Bash：機能リリース前にチームでバグを洗い出し、QAの負担を軽減。
・チームミーティングとレトロ：週次の共有と月次の振り返りにより、透明性と心理的安全性を高める。

また、初めてのリーダー経験において学んだことについても語っています。

My First Year as a Team Lead on the UI Team

Hi, I’m Jeff, a software engineer on the UI team at BoostDraft. About a year after I joined the company, I stepped into my first leadership role — leading the UI team. Through this journey, I’ve learned a lot about team dynamics, communication, and how to grow alongside others. In this article, I’ll share how I became a team lead, the challenges I faced, and the changes we made as a team to improve how we work.

Becoming a Team Lead

About a year after I joined BoostDraft, I was appointed as the new UI team leader by then-leader Tsune-San, who was transitioning to lead our new product, Compare. Although I had experience leading large student organizations back in university, this was my first time leading a team in a professional setting.

Thankfully, with Tsune-San’s support and a team full of members with a strong sense of ownership, I didn’t face many obstacles in the early stages of team management.

Challenges

One of the bigger challenges at that time came from the rapid growth of our engineering team — the size doubled within a year. As a result, I had to shift most of my time toward code reviews, team management, and project coordination. This was a huge change from my previous work, which mainly involved completing assigned coding tasks. The change in both workload and job nature was overwhelming at times.

Three Key Initiatives to Tackle Those Challenges

Fortunately, about six months into my new role, a new PDM, Sean, joined the team and offered tremendous help. He supported me in multiple ways — from clarifying priorities across projects, introducing more structured planning processes, to helping streamline communication between teams.

Together, we worked on refining our workflows, which significantly reduced my stress. Today, our team has a much more balanced workload, and we have better visibility into what’s coming in the next few months. I’ve learned so much through this process.

Here are three key initiatives that helped us navigate those changes:

1. Design Show & Tell
   Our UI team works closely with designers to build new interfaces and features. Previously, we often experienced multiple rounds of UI revisions, even after the feature was released.
   With our weekly Design Show & Tell, we invite teammates across the company to hear designers present upcoming features early in the design phase. This helps gather feedback from both engineers and business teams upfront, avoiding costly iterations later.
2. Bug Bash
   As the engineering team scaled up, so did the speed of new feature delivery — and with it, the pressure on QA.
   To help identify issues before features go live and reduce the burden on QA, we introduced Bug Bash sessions. After the first version of a feature is complete, we invite teammates to try it out together. This allows us to uncover potential UI/UX issues and bugs early, ensuring better stability at launch.
3. Team Communication & Retro
   We used to rely heavily on 1-on-1s to check in on each member’s growth and tasks. However, as the team grew, we transitioned to weekly team meetings. This shift helped reduce redundant communication while keeping everyone informed about what others are working on.
   Team members share their weekly progress and challenges, and we also set aside time for technical discussions or decision-making.

At the end of each month, we also hold a Retro, giving everyone a chance to reflect on the past month, identify areas for improvement, and express appreciation. These routines have not only improved transparency but also helped foster a culture where people feel safe to speak up, ask questions, and support one another.

What I’ve Learned So Far

Because this was my first leadership experience, I had many uncertainties in the beginning. To stay grounded, I tried my best to align with our company’s core values as my guiding principles. I encouraged open and honest communication and aimed to create a space where team members felt comfortable asking questions or making mistakes. These values became especially important in a remote work environment.

Lastly, I want to express my deep gratitude to Tsune-San and Sean. They offered me invaluable advice, encouragement, and support when I was just starting out in this role.

I also want to thank every member of the team — thank you for your trust, collaboration, and patience. This journey has been full of learning, and I’m incredibly fortunate to be working alongside a group of people who are willing to grow together.