Date: Friday, 7 Feb 2026 | Duration: 4 hours | Attendees: Div B Designers (5 designers)
With the new division structure in full swing soon, we took a half-day to reset as a design team: reflect on the past year, define who we want to be, and set the foundation for how we work together in 2026.
This document synthesises what came out of the session.
We ran a retrospective covering wins and struggles from the past year. The raw post-its clustered into clear themes.
We grew the team and invested in each other. Two strong new hires joined (Zoey, Vedant). The team made a real effort to welcome everyone. People started mentoring. Designers who came in junior are now operating at senior level. The general sense: we have talented people who are hungry to learn and get better.
We built more autonomy and agency. People felt empowered to shape their own work, figure out their own approach, and make decisions. "Create your own adventure" came up more than once. Decisions that designers pushed hard for are paying off.
We started building foundations. More systematic work around standards, support mechanisms, and discipline (e.g. on FormSG). Design rituals are going well. There's a shift from reactive work towards more intentional, structured practices.
We adopted new tools and explored AI. Claude, AI-assisted coding, and other new tools unlocked new possibilities. There's genuine excitement about what AI can do for the team's work.
We bonded. The hackathon ("Team 10/10, Fun 10/10, Sleep 0/10"), the Japan trip for FormSG team, picnics. These moments of connection matter, and the team feels it.
Team transitions created turbulence. New reporting lines, team changes, joining products where the previous designer was well-loved. Adjusting is a muscle, and it takes time. Several people are still finding their footing.
Isolation showed up in multiple forms. Designers sitting on different sides of the office, feeling disconnected from each other and from the broader team. The CultureAmp results hit hard. Some people felt isolated from other designers, especially early on.
Shipping speed and craft tension. A recurring tension: pushing craft quality vs. just shipping. Design delivery felt slow at times. Eng speed is a constraint. The team is navigating when to hold the bar and when to let go.
Stakeholder and org complexity. Difficult stakeholder relationships, hard prioritising/resourcing decisions, disconnect between vision and what actually gets tracked. Some of this is just the nature of the work, but it wears people down.
Sustainability and career concerns. Workload is heavy. Slumps are hard to navigate. Some designers are unsure about long-term career growth, recognition, and whether this environment is the right fit. There's a desire for more understanding of product constraints and motivations.
Thinking vs. doing imbalance. A candid observation: over-focus on tooling and craft, not enough on problems, framing, user understanding, and quality of thinking. This one is worth sitting with.