Can WitnessWork remind me to plan next week?

Yes. Go to Preferences → Plans, turn on Remind Me to Plan Next Week, then choose Remind On and Remind At (Saturday at 6:00 PM unless you change them). At that time, if the following week has no plans yet, you get one reminder inviting you to plan it. Weeks follow your Start of Week setting. Any plan in that week, including a recurring plan, means no reminder, and adding one later clears a reminder you've already received. If you've marked every day as an off day under Availability, you aren't reminded. Tapping the reminder opens the Schedule at that week's month, where you can tap a day to plan it or use the Assistant's suggestions when you have an hour goal. The reminder is also listed in the Home bell until that week ends, even if system notifications are off. It's available for every publisher role. Turning it on asks for notification permission, or opens your device settings if you've declined before. Reminders are worked out on your device from your own plans and aren't sent anywhere. Each device schedules up to two weeks ahead, so open WitnessWork at least every two weeks to keep them coming, and if you plan on another device, open WitnessWork on this one so it can cancel the reminder. On Android, the system may deliver a reminder a few minutes late to save battery. If reminders don't arrive, check that notifications are allowed for WitnessWork in your device settings (on Android, including its Reminders category) and that Focus or Do Not Disturb isn't silencing them. If they still don't arrive, report the problem from the Help Center without including names or other private details.