First, understand the simplest form of the expression:
こんな風に
like this
When you are teaching Origami, you would say:
Fold it like this.
こんな風におります。
So, the expression by itself does not speak to health, appearance, folding, or flavor. Quite simply, "like this". So it depends on what follows.
夏には、こんな風に 着飾ります。
In summer, you can dress it up LIKE THIS.
Now, let's make the statement above a question.
夏には、どんな風に着飾りますか?
How do you dress in Summer?
Notice how it became simply "How".
Now, let's get back to your original.
山田さんはどんな風にしていましたか。
This is a conjugation of する(do) in progressive tense.
So, in the end it's quite literally:
How was Yamada doing?
Since it does not specify what it is about, it could be anything.