TL;DR — Quarterly planning at T-Square is a two-day ritual: review last quarter, set themes for next quarter, pick the explicit “no” list, share publicly. The list of what we are not doing is as important as the list of what we are.
Planning rituals can be theatre or they can be useful. The useful version is shorter, more honest, and produces a document the team actually re-reads during the quarter. Here is how we do it.
The two-day ritual
- Day 1 morning — last quarter review with the team. What shipped, what slipped, why. Honest version, not the polished version.
- Day 1 afternoon — open brainstorm. Everything anyone wants to ship next quarter. No filtering yet.
- Day 2 morning — themes. Cluster the brainstorm into 3-5 themes. Each theme has a one-sentence outcome.
- Day 2 afternoon — the no list. Explicit list of items from the brainstorm that we are NOT doing. With one-line reasons.
The artifacts
- Quarterly plan document — themes + outcomes + the no list, three pages max
- Public version — sanitized for clients and prospects, published on the blog (this is one)
- Internal kanban — themes broken into tickets, owned by individuals
- Mid-quarter check-in — calendar event at week 6 to re-baseline
Q3 2026 themes (the actual plan)
- Blink AI public API — design done in Q2, ship in Q3
- Nexia Academy reporting layer — expanded per-tenant analytics
- Multi-region Postgres pilot — Hetzner-based DR for one client
- Mobile localization tooling — internal tool that unblocks two client projects
- Content pipeline — sustain blog cadence, 2-3 posts per week
The Q3 no list
- Second native macOS product — interesting, not now
- Custom UI component library — sounds fun, low leverage
- Internal AI agent for ops — premature, our ops is not painful enough
- Public mobile SDK — not enough customer demand to justify
The discipline
The plan is wrong by week 6. Update it then. Keep it short enough that updating it is cheap. Long plans rot because nobody wants to rewrite them.
Frequently asked questions
How long do you plan ahead?
One quarter in detail, two quarters in themes, four quarters in direction. Past one quarter, plans are wrong; the discipline is to write them anyway so you have a baseline to update.
What is the hardest part of planning?
Saying no. Every quarter we get more good ideas than we can ship. The list of what we are NOT doing is as important as the list of what we ARE doing.
Working on something similar?
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