Once upon a time, your stuffy, conservative boss was considered a counterculture beatnik, smoking funny cigarettes and quoting Allen Ginsberg while trying to hitch a ride to San Francisco.
In short: he was cool.
When you're ready to talk bonus, grab him and head for the time capsule that is Beat Hotel, the new brasserie and live music venue now open in Harvard Square.
Watch as your boss's brow instantly un-furrows, and his perma-scowl cracks. At this sibling to South End jazz haunt The Beehive, you're greeted by bright, seductive flowers and nymphs twisting playfully along the walls that will have you feeling appropriately psychedelic without the aid of any funny fungi.
Don't let him go back to scribbling sort-of-profound stanzas in his moleskin notebook. Keep him focused on the value you bring to the organization, such as how you already know to order the salmon tartare and filet mignon paired with a Soursop Fresca (bluecoat gin, lime, agave and soursop nectar with soda).
Keep "free love" out of your negotiations, unless you're on a double date. In that case, we're pretty sure Kerouac and co. would be totally supportive of you cozying up in a booth taking in a jazz trio as part of the nightly live music card.
Just remember: it's snaps, not claps.