My starting point for most people is to get them to reduce 10% of the "bad stuff" and increase 10% of the nutrition. I get them to tell me what they think is "bad" and I help them with alternatives. I do no calorie counting at all - I try to get then to the RDA (or above) for various essential nutrients and then the calories pretty much take care of themselves.
Then keep going - change after change. When someone drinks 3 2-liter bottles of Mountain Dew each day, just getting them to reduce that is a stretch. Water? What's that?
If I can get them to reduce the chemical additives, that's when things start to go better.
Yup - 8 years after losing half my size and I am a cookie eater too. It's hard to make people understand that the new food will be more satisfying that the old, but when it "takes" it's wonderful.