I could be projecting, but it sounds like your team member has ADHD. My work set up an automated system that emails people between 9-10am if they forgot to log

I could be projecting, but it sounds like your team member has ADHD. My work set up an automated system that emails people between 9-10am if they forgot to log their time the day before. You get dinged if and only if it gets to the second reminder at 11. As someone with ADHD I only distinguish two times: now and not now. Having a reminder that means "do it now" took me overnight from terrible timesheet compliance to near perfect. It's not an automated reminder that happens every day at that time like an alarm clock. That would get tuned out / filtered out very quickly. The key is it's a novel message that I only see if I screwed up by forgetting the day before. And it's easy to forget because the ADHD brain is like a CPU with only one register, and the register spill circuit for service interrupt / return from interrupt is faulty. In order to impersonate a functioning human being I tie certain things I need to do each day (like filling out my timesheet) to certain other events during the day. But if the routine gets broken or I get interrupted in the midst of doing the thing - the mind state that held what I was supposed to be doing is just gone.