I know some brothers who have asked their bosses to take their lunch break slightly later to read jummah and have been allowed to do so, but personally I find it very uncomfortable to approach my boss t. What should I do?
You should do the same. you shouldnt feel uncomfortable, what about feeling uncomfortable by not performing salaatul jumuaah and missing out and not pleasing Allaah? Im thinking everyone feels rather 'uncomfortable' approaching their boss, but i guess we have to make the effort insha'Allaah.
Once you approach him also put your trust in Allaah to make it easy for you.
Many brothers in my work place perform Jummah and they have spoken to their relevant managers and have even said that they would willing work an extra hour to make up for this.
There is also a jewish colleague who observes the sabbath and he leaves early afternoon on friday.