Check Your Calendar
When it's time to sit down and plan my menu for the week (I can't do a month at a time, that's just too much for me), I look at my calendar and figure out what nights there are evening activities, or my husband has a dinner out or is on call. Busy evenings call for a quick meal or crockpot (although my kids aren't fans of the crockpot). I make a hot meal every night as my kids don't get hot lunches at school and my husband is running around so much during the day, there are quite a few days when he doesn't eat anything.
Check Recipes for New Things to Try
Once I know what our week looks like I look through new recipes in my binder (or on Pinterest) to see what I want to try - I try to do one new recipe a week.
Mix It Up
When I first started cooking I made a lot of pasta and chicken as they are cheap and easy. But as versatile as they both are, it gets boring. Now, I try to mix my choices with one chicken, one pasta, one beef or pork, one seafood. Yes that's only 4 meals, see Involve the Family below.
I have a recipe binder with a copy of my "menu" in the front pocket. The menu is the list of recipes I have tried that worked. The inside is divided into two main parts. Recipes to Try in the front (grouped by type) and then Tried and True recipes in the back (again grouped by type). I used to have it reversed, but then would forget to try some new stuff. This way I see new recipes first and am more likely to try them.
Keep Track of What You Ate
Every day I mark on my calendar what we had that night for dinner, this gives me an easy month at a glance of what we have had. Also even though I plan my week, sometimes plans change, so I like to have a true list of what we ate rather than just relying on the menu plan
I try to not repeat meals within a month and that's where tracking meals on the calendar comes in handy. My husband recently suggested that now that we've tracked it for a while just pick a prior week/month and repeat it. Makes sense, but for now I kind of like making a new one each week.
I look at menu and try to find things we haven't had in a while. When I get some ideas, I check the calendar, and if it has been awhile (at least a month), I add it to the plan for that week.
Finally there are some recipes I make that use prepackaged fresh ingredients I don't use much - like mushrooms or asparagus. If I am planning on making one of those meals, I make sure to pick a second meal that uses that ingredient for later in the week. For example if I buy mushrooms for stroganoff one night, I'll use the rest in a stirfry later that week.
Involve the Family
The kids and my husband each get a night every week that they pick the meal. Makes it easier to enforce that everyone eats the same thing for dinner, if they are involved in the decision process.
I go through the weekly circulars for the 3 stores I shop at and see what is on sale of other stuff we may need. They usually arrive in the mail on Wednesday so I go through them before Sunday and make a list of the good specials at each store. Usually it's just staples so this hardly ever changes my menu. I know some people plan their menu based on the circulars but I hardly ever do. I don't plan breakfast and lunch as I don't have time to make a big meal before school, and lunches are pretty basic around here. I don't mind cooking, but I don't love it, so I usually don't make a huge effort for breakfast and lunch.
I use the Our Groceries app for my shopping list. It's not perfect (no way to flag an item you have a coupon for) but it's the best I've found so far.
Once I have the items from our menu plan entered, I add the other things we may need, add what I have coupons for, and head off to the stores. No matter how hard I try I usually have to go to three stores. One that is cheap but doesn't have good produce or meat, another that is more of an ethnic market that has good meat and produce but not always the basics, and finally a third stop at the big chain (with the big prices) for wine and anything I couldn't find at the other two. The whole thing usually takes me a couple of hours on a Sunday, but overall it saves me time as I can go without the kids, so I'm much faster.
I much prefer it to my old way of going to the store daily or trying to figure out at 600pm what to make only to realize I hardly had any ingredients to make anything.
Post the Menu
I post my menu on here, so I have it at a glance and try to add links to any of the recipes I have. Lately I've been using my iPad more in the kitchen. If I'm trying a new recipe that I pinned, I open up the link and put the iPad in my cookbook holder so it doesn't get splattered. Works pretty well so far.