1. Buy cast iron skillet
2. Buy a good thermometer
3. Bring steak close to room temperature
4. Liberally salt and pepper both sides
5. Place steak directly on oven rack at 225 degrees until center is around 110 degrees.
6. Meanwhile heat cast iron skillet as hot as possible.
7. Place steak on cast iron skillet. Flip after 30 seconds to 2 minutes.
8. Take off and rest steak for five minutes covered with foil.
9. Add some butter on top of steak.
10. Use cutting board as plate and chef's knife for easy cutting.

Play around with the temperature out of the oven and how long to sear it. I like mine pretty rare, so the sear is just enough to get some browning going.

I usually buy 1" thick ribeyes. Let the steaks come to room temperature after seasoning. Once steaks are room temp, I take a stainless steel pan, and put it on the stove just a little lower than medium high. Throw some Kerrygold in and just as the butter begins to barely turn the slightest tinge of brown, put the steak in. Let the steak sear on one side for about 3-4 minutes. Using tongs (dont pierce the meat), flip meat over and let sear for another 3-4 minutes. Hold steak in tongs and sear the edges for a few seconds. Place steak on a plate and cover in foil, let rest for 5 minutes. Slice the steak against the grain in quarter inch strips.

Your cooking method is probably fine, although I never put fat in the pan before searing beef (and if you're browning it before finishing in the oven, that's what I'd call it.) You want a dry pan to get a good seared seal that will keep the juice inside the steak for maximum tenderness. It's also important for your pan to be hot enough that a drop of water will sizzle and steam.

I enjoy a little butter on the steak once it hits my plate, though.

I'd consider a strip steak to be a relatively tender cut; I can't afford it and usually buy chuck, skirt or blade steak and all of those are probably more tough/gristly than your strip.

Anyhow, prime rib or ribeye might be more tender although the ribeye could also have gristle. I've always liked the gristle myself, but all cuts for all types, right?

If you really like tender meat, you might try a marinade--paleo, of course. :-))

Stop baking your steak. Use the broiler if all you have is an oven. Do it right: http://answers.yahoo.com/question/index?qid=20080107214005AAnKrDC

Season the steak first with salt and pepper.

Cook it using the broiler.

Let it SIT for 5 minutes (steak soaks back up the juice that was forced out of it)(of course this depends on if you put it in a pan type thing instead of a broiler plate).

I rarely cook steak, as I've come to prefer boiling larger pieces of meat on the bone. However, when I want to make a really good steak, this is what I do.

Cook onions in a cast iron skillet with lots of butter and salt until will caramelized
Move onions to the edge of the pan (or a plate if room is limited)
Add more butter to the middle of the pan
Add steak and cook until medium rare, flipping halfway through
Serve topped with caramelized onions

Interesting to see how everyone cooks! Personally:

I take a chunk of pastured butter, do my best to smear on both sides. It won't quite "coat" the meat if both are cold, but you can sorta spread the clumps around and get a thin layer between. Seasoning lately has been minced garlic, fresh chopped oregano leaf, dried tarragon, ground peppercorn and a little bit of salt. I use enough of that, stuck to the butter, to form a bit of a crust when seared.

From there, pan-sear (cast iron on a gas stove top) for a few minutes on each side. Gnaw on with bare hands, growling when one has to chew and tear through ligament. I prefer it a touch bloodier than "rare", basically just seared on the outsides and warm through.

One of my favorite methods: I heat the cast iron pan quite hot, toss in some fat (here I don't prefer butter because it smokes too easily--ghee, lard or bacon grease are good, though), then the steak. Cook until browned on one side, flip, and finish to medium rare. (There's a handy tip for sensing the rareness by gently prodding the steak, then comparing the resistance to the fleshy part of your hand between your thumb and index finger in various states of fist clenching: wide open/relaxed = rare; gently closed = medium/medium rare; tightly clenched = ruined...er..."well." This technique is hard to describe in words, but so easy to demonstrate visually!).

Next comes the fun part. While the steak is resting on the plate, I toss in some finely chopped shallots--a couple tablepoons--and saute until translucent and just beginning to brown. (Leeks or onions would be tasty, but shallots are nice because they contribute their flavor, then get out of the way, all but disappearing into the sauce.) Then a modest pour of dry vermouth, scrape up the yummy browned bits off the bottom of the pan (the "fond"), and simmer to reduce and drive off the alcohol. When it starts to get syrupy, I toss in a couple tablespoons of cold butter, turn off the heat, and whisk the butter around to melt. The cold butter will cause the sauce to thicken. Add salt and pepper as desired, and pour over the steak. A classic (and deceptively easy) French pan sauce. Add mustard if you like, or capers, or nothing else at all. The sauce is delicious any way it turns out--even if it breaks, it will still taste as good as the high-quality grass-fed butter you used!

Strips from Whole Foods should be pretty good cuts. Until you are more used to eating beef, you might consider a medium well cook. With a strip, it won't be as dry as a leaner cut and may not create the chewy sensation you describe. Just a thought. I am a medium rare guy. Another thought would be to find a butcher that has dry aged meat. I always find dry-aged (while more expensive), to slice and chew very easily.

Geeze I ain't seen one y'all talk about chicken-fried-steak or have I dang-gone crossed them stereotypicals again?

It may be that the grade of beef you are buying is not very high, so it will be less tender and fatty. Also, if it hasn't been aged properly, then that will cause problems, too.

The grass fed beef I'm able to buy at my local Whole Foods is some pretty tough stuff.

So, here is a technique to turn lower grade, poorly aged beef into good eats:

http://steamykitchen.com/163-how-to-turn-cheap-choice-steaks-into-gucci-prime-steaks.html

i dry age my steaks. it makes it sooooo much better - you can look it up on through the interweb tubes for the technique. I was nervous at first and slightly grossed out, but all my steaks have turned out great!

I do all beef on the George Foreman. Chucksteak is my favorite steak. Lotta fat. I hate the expensive lean cuts. Try cheekmeat in your slow cooker sometime. Don't overdo it, 8 hours max. Lotta heavenly fat. Fat fat fat.

his is how I make a steak with a great crust and lots of flavor. http://lowcarbcookery.wordpress.com/2012/01/06/how-to-make-a-great-steak/

Choose flank over skirt steak. Season with oregano, salt & pepper. Put some olive oil on a paper towel & wipe down a broiler pan. Pop the pan in the oven & turn on the broiler. Cook 2-4 mins each side (depending on how rare you like). Let rest for 5mins, slice with (not across) the grain. Super cheap & tastes yum every time, promise!