At Stackline, quarterly planning was a ritual. All-hands kickoff, department OKRs, cross-functional dependency mapping, mid-quarter check-in, retro, repeat. It looked responsible. It felt like running a real company.

It also consumed roughly six weeks of calendar time per year across leadership — and produced documents that were outdated by week five.

We killed it. Not planning itself — quarterly planning as a company-wide event.

The hidden cost of the cycle

I timed it once. Q3 planning involved:

  • 12 hours of leadership pre-work
  • Two full-day offsites
  • Department sessions (4 teams × 3 hours)
  • A “final alignment” meeting that existed because we didn’t trust the first one

That’s before individual contributors translated OKRs into Jira tickets they’d reprioritize anyway.

6 weeks
Estimated leadership + IC time spent on quarterly planning cycles per year

What we do instead

Rolling 6-week priorities. Each team publishes three priorities for the next six weeks — not twelve objectives with key results nested three levels deep. Three. If everything is priority, nothing is.

Monthly metric review, not quarterly. Revenue, churn, activation, burn. One hour, whole leadership team, numbers on a screen. Decisions same day.

Annual direction, quarterly checkpoints. We still set annual themes — “expand mid-market,” “reduce support load” — but we don’t re-derive them every 90 days.

Most quarterly plans are fiction by week six. Admit that and plan accordingly.

6-week priority template (one page per team)

  1. Priority 1 — outcome + owner + done-when
  2. Priority 2 — same
  3. Priority 3 — same
  4. Explicit not-doing list

Pushback we got

“Investors expect quarterly rigor.” Our investors expect us to hit numbers. We report monthly. Nobody asked for OKR PDFs.

“Teams need goals.” They need clarity on what to ship this month, not a cascade from a objective that says “delight customers.”

Results after four cycles

Ship velocity up — hard to attribute cleanly, but sprint completion improved 30%. Morale improved in eng surveys; planning fatigue was a real theme in exit interviews before.

We didn’t become chaotic. We became less performative. There’s a difference.

If your planning process exists mostly to produce artifacts, cut the artifacts. Keep the decisions.