1. The company policy: of the company has a no-remote policy this will be very difficult. If the company has a limited-remote policy, it’s already much easier, it means asking for additional remote days on top of existing policy and provides you an opportunity to show that you are productive working remote
2. Your productivity and mutual trust: on the individual level I like to believe everybody can be productive remote. On the aggregate it didn’t work that way though. Some people would use the remote time for personal matters and chalk up a day with limited output to ‘I was doing research’, others would have twice the output they had at the office. It’s difficult to know up front where someone will fall on that scale. If you can show with 1-2 days remote that you can be productive, it’s a huge help in this decision
3. Spill-over effects. If others in your team are (possibly) not productive remote it might be difficult to give you a full remote opportunity. Others will expect the same privileges and it might be easier to limit it for everybody rather than explaining individuals that I dont trust them remote yet.
4. Interactions: if the office has a weekly townhall, or if we have a quarterly long-term planning session, can you join these, or do we need to setup video and mics for that? It helps if you can be in person on these moments (even if you’re not convinced they’re always useful)