Kenji has convinced me that it’s not worth trying to get a good sear on ground meat in chili and bolognese. In his recipes the ground beef is cooked with the chili paste, garlic, and onions (or with other stuff in the ragu). The lost maillard flavors can be recovered with soy sauce, fish sauce, marmite, and MSG.

So to answer your question, during. Kind of, since it gets flavored by the other stuff.

I think the only wrong answer is before, because that will give the meat a sausage consistency. I don’t want rubbery beef in my chili.

Also well done on asking a chili question that doesn’t start a war about beans.

My chili powder (Alton Brown recipe and other stuff) goes into the pan with a little hot fat just before I brown the meat. This way it can borrow a truck from curry and fry the spices a minute before they come in contact with the meat.

Try stewing steak instead of ground beef… I won’t go back

During. Not sure if it makes a difference in the final product, but I want to make sure it tastes good before I toss it in with the rest of the chili.

I season right when it goes into the pot (salt and pepper), and then I do two “dumps” of the other seasonings - one towards the beginning prior to adding liquids, and another towards the end of cooking.

Right before it goes into the pan/pot. You want to at least use salt at this point to keep moisture in the meat while cooking and allowing it to brown better before you start tossing in everything else.

Before: cumin, garlic, paprika. After: everything else, including salt.

Those three when browned are delicious, the others either burn easily (like oregano) or are liquid (like my pepper sauce).

I don’t use ground meat for chili, typically I will use a braising cut. For that, I salt it, and let it air dry for a bit, then sear it. When it’s nicely browned, I’ll pull the meat out, throw in onions to deglaze the pan, then garlic, any spices that could use a toasting (like cumin), and some tomato paste.

Finally I pour in my chile puree, which in my opinion is a non-negotiable part of what make chili, chili. That’s just a combo of a few different types of dried chiles that I’ve toasted, soaked in liquid like chicken stock, blended, and passed through a sieve. Then I slice up the meat, and put it back in.

If I were to use ground beef, I would basically just do the same thing, but I’d skip the salting part and just do it all after I add the liquid. It’s hard to get good color on ground beef if you have a big hunk of it, especially if any moisture is pulled out of it. Sometimes if I need to brown a bunch of ground beef, I’ll do it in batches, basically cooking each chunk like a separate “burger”. If I’m lazy, I’ll do however much can fit in a single layer well spaced, then just toss the rest in after. I’d rather have half of the meat well browned than all of it “grey”.

When searing meat and adding spice in a more or less “dry way”, for taco meat or chili or some curries, I sear the meat to nearly where I want it, then add the dry spices to toast on lower heat before “deglazing” with water/stock/whatever else makes sense. You can also just toast the spices separately, but some toasting is nice either way and I think this is convenient.

Generally salting early is good for anything you want to get any kind of browning on, it’s just that the meat and any other additions might also be salty, so you don’t always get to. Spices will give a better flavor over time, like a “rub”, but you can’t necessarily sear meat with spices on it. Things are usually tradeoffs.

(Just noticed this post is 4 days old, my bad :p)