I've cooked literally thousands of steaks in restaurants and at home. I've made good ones and a few bad ones. Here are my thoughts and opinions on how to select and cook a good steak and how to avoid a bad one.
The number one rule is to not overcook the steak. I know some people like their steaks medium well to well done. Well, then you're likely to get a steak that's more tough and dry than one cooked medium rare to medium. There just isn't any way around that one. And a lot of people don't fully understand what the difference between the different levels of doneness.
Rare is very red an between warm and hot in the center. Nearly raw but not raw in the center.
Medium rare is still red but it's hot in the center and not quite as red as the rare.
Medium is still slightly red and mostly pink in the center.
Medium well is still slightly pink.
Well done is no longer pink...and no longer good in my opinion. But Well done is the only level that no longer has any pink in it.
The number two rule is to buy high quality beef. These days it's getting harder and harder to find Choice grade of beef. More and more supermarkets are carrying a Select grade of beef. This is because some misguided people think that they want their beef to have less fat in it. Well, that's what you get with Select and you also usually get a dryer and less tender cut of beef too. It varies with the cut and from steak to steak. Select is also a less expensive grade and that's another reason you'll frequently see it in the discount grocery stores. These days I sometimes can't afford choice beef so instead of buying cheap steaks I do without. Why eat cheap steaks? Buy a different cut of beef and cook it another way that suits it. The USDA doesn't grade each individual steak. But just buying something that is labeled, "Choice" doesn't guarantee a great steak. There are better and worse qualities of choice steaks. Buy it, try it, if you don't like it complain to the store and ask for your money back. Most stores are very good about that. If they won't do that then don't go back. Look for a well marbled steak.
Locally we have a discount chain of grocery store and they advertise that they carry Choice meat. Well, it may technically be Choice and it is better than Select grade but it's not as juicy and tender as you can get elsewhere. I've bought from our local Costco quite a bit and they have pretty decent Choice beef. We only have one local, "Meat market" and their beef is really good. Safeway advertises, "Harris Ranch Restaurant Reserve" and it's usually pretty good. But that's really just a marketing gimmick. Raley's has their, "Black Angus" and it's also very good. That name carries a little more weight in the quality department with me. If you can find, "Prime" grade of beef be prepared for a great steak. But also be prepared to spend a lot more. Above all, [u]Don't overcook your steak![u]
Which cut of steak? There are many different cuts you'll see in the stores and some are really better off being used for some other cooking method.
A New York steak is a classic. It's cut from the loin. But if you were to see a whole NY strip roast before it's cut into steaks you'd see that one end has a lot of gristle and connective tissue in the middle. It's only at one end though. When selecting a steak take a look at it. It's common to see a few steaks in the stack that have this connective tissue. Avoid it. The store or restaurant still has to sell these steaks and they still taste good but they have parts that are extra chewy. In the last restaurant where I worked we tried to not sell these and instead used them for employee meals. If we had to sell them we only used them for well done orders. A person who orders a well done steak is used to a dry and chewy steak anyways so it didn't really show up on the plate.

We never had even one complaint about that and lots of repeat customers who liked well done steaks. Like I said, they were used to chewy steaks. At least we used top quality beef so the steaks tasted a good as was possible for a well done steak.
A ribeye steak is another favorite. It's cut from what is commonly called the, "Prime Rib". This steak is very succulent and juicy because it has so much fat in it. Unless you like to eat the fat you'll have more waste with this steak. But the flavor the fat gives the steak is worth it in my opinion. This steak stands up to over-cooking better than any other steak. If you absolutely must order a steak medium well or well done then get the ribeye. It still will be more dry and tough than a properly cooked steak but it will be better than a more lean steak. The ribeye is like the New York steak in that it also has one end that has more connective tissue in it. But it's not quite as bad. I try to avoid it but it's harder to detect than in the New York. Don't confuse the ribeye steak with the cross rib steak. Completely different and the cross rib is very tough.
The filet mignon is another great steak. It is usually extremely tender and delicious. But it's also very lean. It's one steak that absolutely, positively should never be cooked beyond medium. Medium rare is perfect for me. Cooking a medium well or well done filet mignon is like planning a party and pouring all of the champagne into the glasses the night before. Yup, it's still champagne but now it's warm and flat and ruined.
There are two parts to the filet. Theres the tail and the head. The tail is the long part that goes the entire length. The head is the thicker part at one end. They both taste good but the head is typically filled with connective tissue. In my opinion it's best suited to roasting but if someone absolutely has to have a steak cooked past medium then this is the piece for them. It has more internal fat and it stays a little more moist. It will still be chewy because of the connective tissue but at least it won't be quite so dry. The filet needs to have the silver skin cut/peeled off of the outside of it. It's the very thin and very tough sheathing that covers the muscle and it's under the fat that also has to be removed. I worked in a restaurant in the San Francisco Bay Area years ago that served some great burgers for lunch. We ground our own beef and we used a blend of sirloin and all of the fat and muscle trimmings from the filet mignons we used. We sold a lot of filet mignon at night so we had plenty of fat and muscle trimmings for the best tasting burgers I've ever eaten. When trimming and grinding the filet I would usually take out enough for me to have a burger made only from the filet mignon. Oh man was that good! I really miss that place now. Drool, drool.
The sirloin is another popular cut. It's typically served in trendy chain restaurants like Appleby's. It's a very flavorful steak but for me the tenderness is hit or miss. I've never worked in the kind of restaurant that would serve a sirloin steak so my only experience is cooking it at home or eating it a few times when dining out. This is one steak that you really should buy only with the choice stamp on it. And even then it's hit or miss. A few weeks ago Safeway had their, "Harris Ranch Restaurant Reserve" sirloin steaks on sale for only $3.00 a pound. That was a heck of a buy so I bought a package of them for my family. I was pleasantly surprised that they were really juicy, flavorful, and very tender. Great steaks! Earlier this week I saw they had the same steaks on sale again. This time I bought 2 packages thinking we would eat one now and freeze the other one for later. I cooked one package of them on the grill but I found that they weren't as juicy or tender as the first ones I bought. They were still good but not great. Fortunately they were only $3.00 a pound. Wednesday night I decided to use the other package of sirloin steaks cut up into strips for the Thai Mussuman curry that I made. It was great for that and a much better use than cooked as a steak.
The flank steak is an unusual cut and isn't your typical grilling steak served with baked potato. It's very flavorful but in my opinion it's really only good if you grill it medium rare and then slice it thinly across the grain. It's great when marinated too. It also is great for homemade beef jerky but that's another story. I worked in a restaurant in Portland, Or., and the owner refused to serve hamburgers. (He was somewhat of a food snob.) But customers still sometimes wanted something like a burger for lunch so his consession was to serve marinated flank steaks. We made a spicy, sort-of-Asian marinade, grilled them and sliced them thin across the grain. We served them on some awesome toasted buttermilk bread that we made in the restaurant. We made our own mayonaise and served it with the typical lettuce, onion and tomato. It was an excellent substitute for a hamburger.
Chuck steaks, top and bottom round steaks, eye of round steaks, tri-tip steaks, flat iron steaks, etc...While they may be flavorful they are rarely very tender. In my opinion they are best when marinated and then not overcooked. After cooking you should let them, "Rest" until they are still warm but not hot. Then slice them across the grain and serve them in thin strips. The resting period will help keep more of the juices from draining out when you slice them. Some of these are also good when you, "Cube" or tenderize them with a meat hammer or if they do it with a machine at the butcher shop. Chicken fried steak is awesome but you need to make sure you get a piece that doesn't have any fat veins or connective tissue running through it. Swiss steak is another delicious use for tenderized steaks. I haven't made that for a while...I'll have to do that soon.
Whether you fry your steak in a hot cast iron pan, broil it in your oven, or broil it on your grill, make sure you use high heat. The hottest you can get it. If your steak is getting too dark on the outside and it's not done on the inside you can then either turn it down or move it to a cooler area on the grill. But I've rarely had this problem unless it was a very thick steak. When cooking really thick filet mignon steaks at the last restaurant were I worked I would cook them most of the way on the grill and then if necessary, (medium or medium well, or worse) I would set it in the oven to finish it. Keep in mind that a steak will continue to cook after it's removed from the heat.
Another thing, don't keep messing with the steak. You shouldn't have to flip it more than one time. I usually throw it on the grill, rotate it once to give it that criss-cross pattern, then flip it. I may or may not rotate it again depending on the steak and how fast it cooks. People always say not to use forks on their meat when cooking it. Yeah, I guess. But honestly, I've never found much use for a BBQ fork anyway even if the holes in the meat didn't matter. Buy yourself a good sturdy set of long aluminum or stainless steel tongs from a kitchen supply house. Look in the phone book, you'll probably find one in your area. Also a good long spatula is handy sometimes too. but I only use those for things like fish or smaller pieces of chicken.
Some people also seem to like using thermometers when cooking steaks. I've never used one and I don't find them very accurate anyway. How far into the steak do you put it? Is it really only half way in? I say to feel it with your fingers. The more you cook it the more firm it gets. It takes practice and you may over or undercook a few steaks but I feel the best way to learn is by trying it. You're better off undercooking a steak than overcooking it. You can always cook it a little longer.
When you're first learning I think that making a small cut into the steak, (Only one time towards the end of cooking!) and checking to see how it's coming is ok. I know, I know. It will let the juices out. Well, you won't have to do this very often once you learn to judge the doneness by feel and you won't dry it out as much as some people claim. I haven't had to do this for years but it sure helped me learn. I've seen this done in restaurants for really thick steaks. You do it on the side that goes done onto the plate and nobody will ever know. They just know that their steak is perfectly cooked. Remember, it keeps cooking after you remove it from the heat.
I've seen that some people try to cook a steak by sticking to a timeline. Every steak cooks a little differently. Even steaks the same thickness will cook a little differently. With all of the variables of heat, thickness, cut, etc. I can't imagine how this can be a reliable method of cooking a steak. Learn to cook by feel and you'll have more consistent results.
I don't marinate a
good steak because I feel it just hides the flavor of the meat. That's not to say that I don't like some flavoring on the outside. But if you marinate it the internal meat takes on another flavor. To each their own though. It's a matter of personal preference I guess. I just add salt and freshly ground black pepper to a steak before I cook it. I do sometimes like a good sauce after it's cooked. I will post an after-grilling marinade from my grandmother in-law, (From Sicily) but I'll post that recipe separately. I have marinated some cheaper cuts of beef for grilling with great results but I usually end up slicing that meat up instead of serving it as a whole steak.
So, buy Choice or better grade of steak. About 1" to 1 1/2" thick is best. Use high heat and don't flip the steaks over and over again. Take it off before it's fully cooked to your liking. Try to get used to eating your steaks cooked less than medium well or well done. Learn to cook without a thermometer. Use lots of butter on that baked potato!
Bruce