Anti-PMO · July 16, 2026
Don't Schedule a Software Kickoff Until Someone Wrote the Request
I've sat through kickoffs that existed only because nobody wanted to write the request. Twenty-eight years later, I still treat a calendar hold as a confession: the story is missing.
I have been invited to kickoffs that had no request. Late nineties. Last year. Same invite: “Let’s get aligned,” which means nobody wrote the week down and the calendar was easier.
A kickoff feels like progress. It photographs well. You leave with owners, a date, and a parking lot. You do not leave with a story a stranger can retell. I have watched forty people spend ninety minutes discovering that the submitter still emails a spreadsheet every Friday. That sentence should have been the meeting.
A calendar hold is not a decision
If the person closest to the work cannot write what happens today, who is stuck, and what better looks like, you do not have a project. You have a rumor with a conference room. I have never seen a kickoff invent those three facts. I have seen kickoffs bury them under a slide titled Next Steps.
Do not schedule the room to extract the paragraph. Send the two missing answers back. The Anti-PMO playbook for software intake is blunt about this: preferred vendors wait. Architecture opinions wait. The go-live date invented in the elevator waits.
Write the week before you invite the building
Use software project intake so the request exists before anyone books an hour. The submitter is the operations lead, the clerk, the person who still runs the workaround. A facilitator is optional. A written week is not.
I remember a 1998 kickoff that produced a charter and no owner for the workaround. We spent the quarter building the charter. The workaround is still there. That is not a cute story. It is the default.
Meet only when a stranger can retell it
When the page is understandable, a meeting can decide a yes, a no, or a not yet. That meeting is short because the argument is on the record. The software delivery management features path is review, questions, estimate, decide. None of those need a séance if the first page already exists.
If you need a kickoff to find the request, you scheduled the wrong event. Cancel it. Ask for the paragraph. I have canceled more kickoffs than I have regretted.