"Evil Employer in Edmonton" writes in:
When will I know I'm ready for henchmen? How do I hire them? What should I do to retain them?
Henchmen are only as loyal as their economic situations. This is the basic truth of hiring help as a villain, and it cuts both ways: people too poor to go anywhere else will be desperate and fickle, but they are unlikely to stab you in the back because they can't. Conversely, henchmen making $200 an hour (American) for fairly easy work will stay loyal through a lot of crap.
Here's some numbers for you. A soldier's pay is anywhere from $15K to $20K a year, but they get a shit ton of benefits - housing, education, and medical. A private military contractor can make $150K to $250K a year, depending on skills. If you can comfortably sustain that sort of cash flow, henchmen are for you.
There are three major venues for hiring henchmen:
Organized crime. Let's just be clear about what I mean here. You are not going to be poaching made men, no way, no how. You aren't approaching the Mob's soldiers with a better offer. No, you are going to the caporegime you work with to make an offer to the boss. If "the caporegime you work with" does not immediately conjure up a name from memory, you are not ready for this.
Cops, mercenaries and PMCs. You can advertise (discreetly!). Avoid "Soldier of Fortune" - it's for adventure story writers. Former members of the French Foreign Legion are a possibility (when in doubt, ask to see a French passport).
Street thugs. This is usually the bottom of the barrel, but if you're on the outs with the local Mob and can't crack the military or law enforcement nut, go here. Find a local gang, offer them money, and explain your program to them. They will be unreliable and territorial, but if you treat their boss as a peer, you can often pump up their ego long enough to get them along for a caper.
Retention is difficult. In general, you want to cultivate loyalty. Fear works best. Cash works reliably. I suggest you get a copy of Machiavelli's "The Prince" and read it carefully.
One trick I've found, especially for unreliable bangers, is to get them into some sort of dangerous situation mid-caper. Then, make sure you are the only one who can get them out. Do so in some flashy, spectacular fashion. You want to shock them into a feeling of admiration, obligation, or at least fear.
The most reliable henchmen will already have gone through some sort of military or law enforcement program, and will want cash. Pay these guys like clockwork. The more thoroughly you make use of them, the more of your secrets they will learn, and the more damage they can do. Never treat them as expendable.