What you will have at the end
The open question stops being an open question. It becomes a one-paragraph draft decision, a date, and a reminder that brings it back on that date.
1. Connect
Nothing. This needs no connector. It works in whichever channel you already talk to June in.
2. Tell June the decision
One message:
I need to decide whether we drop the Starter plan. By Friday.
June writes the bad first draft: a decision, the reasoning, what you lose. It is meant to be wrong in useful ways. Editing a wrong answer is faster than producing a right one from nothing.
3. Choose the mandate
Ask for the reminder in the same thread:
Remind me Friday at 10:00 Berlin time to decide, and put the draft in the reminder.
June brings the decision back up on the date. It may not decide for you, and it never marks a decision done. That stays yours.
4. First run
The draft arrives within the conversation. On Friday the reminder brings it back to the thread, whether or not you decided sooner; if you did, ask June to remove the reminder.
5. Adjust
If Friday comes and goes, say "push to Tuesday" and the reminder moves. It comes back on whatever date you last set, with the draft in it.