1. If the junior dev is really that critical for a large project for some bizarre reason (fix that next time), tell Gary he's critical to that and say you can realloc ppl to cover or do this task under a 1hr time limit if it's urgent (if exceeds then kill the task). 2. Say to Gary next time let me know directly rather than dm someone on the team so you can route it to the right person (buys trust, covers team). 3. Renewal of BigCo is important to the biz. You should have some room to accommodate requests like these without being a stone to adhoc requests. It will not buy you or your team favour at all. Remember, this is a startup!