Run book 3 of 5
Technical Health scoring, before the workshop
IT scores the technical side first, in sessions organized by support team — so when the business scores Business Fit later, every application lands on the TIME quadrant live.
A note on where scores live: technical scores attach to the application's deployment profile — they're facts about the technology, shared everywhere it's used. Business Fit is scored per portfolio, because the same application can matter differently to different parts of the organization.
1 Plan the scoring sessions Applications are grouped into sessions of 5-12, aligned to the IT support teams that know them.
IT analyst
- Group applications by the IT support team that runs them — each scoring session covers 5 to 12 applications.
- Split anything larger; the rhythm degrades past a dozen apps.
- Flag applications with no clear support team — those need owners before Technical Health can be scored.
- Give each session a target date, sequenced ahead of the business workshops they feed.
Done when: Every application headed for a business workshop belongs to a named session with a date.
2 Score Technical Health with IT Every application in an upcoming workshop has its 14 technical factor scores captured.
The IT team that supports each application · Sessions of 5-12 apps; budget a working session per support team
- Open an application and start its assessment — a full-screen wizard with Business and Technical tabs, one question per screen, running scores in the header.
- Work the Technical tab: 14 factors (T01-T14) covering platform, vendor support, security, resilience, and more — each scored 1-5 against written descriptions, with its weight shown.
- Let the product do the busywork: once an application's hosting type is set, factors that don't apply are auto-scored or skipped ('N auto-scored, N skipped based on hosting type'). Any auto-score can be overridden — with a written reason, so the decision is on record.
- Use Save and Finish Later freely — progress persists per factor.
- Genuinely unknown legacy systems: flag and hold for later rather than guessing.
Done when: Every application in an upcoming Business Fit Workshop has a complete Technical Health score.
Why Technical Health comes first: with it in place, the business watches their application land on the TIME quadrant live as they score. Without it, they score against an empty chart. The live placement is the moment the discipline clicks.
Take the kit with you
The Workshop Kit bundles every handout in this guide — question sets, email templates, the one-pager, and printable run books — plus the full playbook.