One really important thing to remember, especially when shooting outdoors, is to factor in the time of day that you're shooting. A lot of people will caution you against shooting early in the afternoon or around noontime, just because the sun is directly up in the sky and you're going to get very harsh shadows under people's faces.
Another thing to take into account is also the weather. All photographers love cloudy days. And it's not because photographers are depressed people. It's because when it's a cloudy day, the clouds act as a giant diffuser -- an umbrella, if you will -- over the sun -- your light source -- and as a result, you just get really, really beautiful soft light with no shadows.
A really great time to shoot is what is called magic hour or golden hour, and that's when the sun is at one of its lowest points in the sky and just kind of illuminates the surroundings with a really beautiful golden light. And it only lasts for about 15 to 20 minutes. Here's an example of it. This is shot during what's called Manhattan-henge, when the sun lines up directly with the grid of Manhattan. Happens twice a year. And it's just a really great time to shoot, and you can get some really interesting results. So keep that in mind.
I'd also like to mention that in addition to the hour or, you know, little bit of time window before the sun goes down, it's also the same as when the sun comes up. That time right when it's at its lowest point in the sky, before it reaches too high. That's also golden hour.
Avoid noontime. Avoid direct sunlight. Go for those clouds. And if you're going to shoot in the sun, shoot for golden hour.