Hit and miss? maybe not
Your bosses tip of tickling the boost pump does have a basis in sound science.
As you probably know or do now from the previous threads. When a hot fuel injected engine sits it is often possible for the fuel contained within the 1/8 stainless steel fuel lines from the flow divider to the fuel injector nozzles to vapourise or boil off. You then have nothing but basically air in those lines.
Lycoming and TCM have somewhat different fuel metering systems and if you have the time, Aircraft Fuel Metering Systems by Aviation Maintenance Foundation Inc. is worth a read and explains the various systems well. You often find this range of publications in the various pilot shops and they are quite cheap. i digress.
The idea of selecting ICO (idle cut off) and full throttle and boost pump on, allows cooler fuel to be pumped into the body of the flow divider but it doesn't go to the injector lines due ICO being selected. From here it returns to the fuel tanks via the vapour vent line attached to the flow divider. The 60 seconds allows enough time for the cooler fuel to replace the small amount of fuel in the divider and remove some of the heat in the body of the divider.
So when you do finally introduce fuel to the injector lines (by coming out of ICO) it is hopefully cool enough to last sufficient time in the lines to get you started before it to vapourises.
Or maybe not. Here is where your bosses tip comes in. The engine fires but then starts to die, you've just struck some air in the line and a quick flick of the boost pump sends a rush all be it small rush of fuel up the injector line and hopefully you catch it before it dies.
Hope this gives you some insight, but please don't take my scribblings as a definitive description of this small part of the system. Grab a tech manual sometime. You might also find the principals of the air bleed injector different to what many would tell you.
Best of Luck
M