The six month speed bump is just one bit of great information I got from Andrew Spittle’s advice on scaling support teams, based on his tenure as Automattic’s head of support (Note, I’m inserting my own paragraph breaks for the sake of readability):
Here’s one way that collective 6-month speed bump plays out. When people join their first distributed company they love the seemingly boundless freedom. They love their work, love working from home, love the schedule flexibility and dive in whole hog.
Pretty soon, though, they realize that they’ve lost all discipline in setting work aside. They find they let pings interrupt them at all hours. They find themselves working 60-hour weeks. They find that they have no quiet time.
When you have many people simultaneously hitting this inflection point it can be expressed as an issue with company expectations or with the team itself. You have to take a step back, though, and realize that this is a growth process everyone goes through.
You have to help each person realize that, in part, the problem is one of individual expectations, workflows, and discipline. If instead you restructure the entire team in response to this pain point you ultimately withhold from people a learning experience that helps them build sustainable and healthy individual remote work habits.