Annual Planning in Six Weeks (Not Six Months)

TL;DR

The step-by-step calendar, template pack, and facilitation notes for a 50-person offsite.

Who this is for

Founders and operators at $1M–$50M revenue companies engaging a fractional operations leader. Use this as the artifact you scope against in week one.

The play

1. Week 1 — Diagnose. Interview the exec team, pull the last four quarters of data, and produce a one-page current-state assessment.
2. Week 2 — Design. Draft the target-state artifact (dashboard, model, cadence, playbook) with named owners and refresh intervals.
3. Week 3 — Roll out. Ship v1 to the leadership team, capture objections, and set a two-week review to iterate before locking it in.
4. Week 4 — Handoff. Document the operating rhythm, assign the in-house owner, and set a 30-day check-in.

What good looks like

• The artifact is used weekly by the exec team without prompting from the fractional leader.
• One in-house owner is named and trained on maintenance.
• Success metric is instrumented and reviewed monthly.

Common mistakes

• Over-designing v1. Ship the 60% version in week two; iteration beats polish.
• No named in-house owner. If the fractional leader is the only one who touches it, it dies when they roll off.
• Skipping the socialization step. The exec team has to hear the plan twice before they'll act on it.

Next step

Post a private mandate on RecruitFractional to receive a vetted shortlist of fractional operations operators within 72 hours.