Portfolio Mondays · Stealable one-pager
90-Day Starter Checklist
Install intake, prioritization, and cadence in ninety days, so a project shop starts acting like a portfolio PMO.
From Project Shop to Portfolio PMO: The First 90-Day Map, a Portfolio Mondays episode on Portfolio Intelligence. Watch the episode
The starter checklist
Tick each one when it is real, not when it is planned.
| Done | Item | Notes |
|---|---|---|
| Done? | 1. Baseline the book of work so invisible demand stops running the show. | |
| Done? | 2. Draft intake rules before you accept another hallway yes. | |
| Done? | 3. Run one scored prioritization pass on a limited set, and make a real fund, pause, or kill call. | |
| Done? | 4. Pilot one portfolio review that is not a status dump. | |
| Done? | 5. Calendar the cadence and keep a decision log. | |
| Done? | 6. Let AI draft the templates and scenario packs. You own every tradeoff. |
The 90-day map
Steal the milestones. Adapt the language. Don't paste someone else's org into it.
Days 1-30
Baseline the system
- One view of the book of work: initiatives that consume real capacity, named, owned, roughly sized.
- Draft intake rules: who can submit, minimum info, and what “accepted into the queue” means versus “approved to start.”
- Pick a scoring model stub: the four lenses you will actually score.
- Name who owns the portfolio review. One accountable human.
AI drafts: inventory templates, first-pass intake criteria, demand themes from a messy backlog. You decide: what counts as in the portfolio, who holds the intake gate, what done means for month one.
Days 31-60
Force the first tradeoffs
- Run a scored prioritization pass on a limited set you can finish.
- Stand up a lightweight capacity view. People-weeks or team-slots by month.
- Pilot one portfolio review: mix, capacity, decisions. Time-boxed. End with written decisions.
AI drafts: scenario packs, scoring sheet drafts, cross-item risk and dependency summaries. You decide: what funds, pauses, or is killed, and which capacity assumptions you defend out loud.
Days 61-90
Make it stick
- Harden cadence. Calendar it. Keep a decision log.
- Tighten intake so a yes visibly costs capacity.
- Publish a one-page portfolio operating rhythm.
AI drafts: cadence checklists, “what changed since last review” briefs, decision log cleanup. You decide: the operating model you keep, what you refuse to automate, next quarter's rules.
Ninety days won't finish the rebuild. It gives you a spine: visible demand, a scoring pass you've actually run, and a cadence that reviews the portfolio instead of replaying project status.
Worked example (fictional)
A fictional mid-size delivery organization: solid project managers, a backlog that never shrinks, and leadership asking for “more portfolio thinking.” No special tools. A shared list and a standing review.
| Done | Item | Notes |
|---|---|---|
| Done | 1. Baseline | Single list of named, owned, roughly sized initiatives. Found shadow work and two “small” asks that were not small. |
| Done | 2. Intake rules | Rules drafted. Accepted into the queue does not mean approved to start. |
| Done | 3. Scored pass | Scored a limited slice. One fund, one pause, one kill, all written down. |
| Done | 4. Review pilot | Time-boxed to mix, capacity, and decisions. Ended with written decisions, one of them “defer.” |
| Done | 5. Cadence and log | Monthly review on the calendar. Decision log started. |
| Done | 6. AI drafts, you decide | AI drafted the inventory template and intake criteria. The review owner edited and signed off. |
If month three still feels messy, that's normal. The win is that tradeoffs are visible and somebody owns the gate.
90-Day Starter Checklist · scottpresley.net/tools/90-day-starter-checklist · Portfolio Mondays on Portfolio Intelligence · AI drafts. Humans decide.