Getting a headshot doesn't have to be a pain anymore. If you have in mind ahead of time your ideas and plan.
To get inspired pay attention to television shows, commercials, and ads you like.
Take a look at magazine covers to get inspired too. Usually the eyes are strong and the face is intriguing, the smile is refreshing and welcoming. Even bringing the magazine or commercial idea to the shoot is a good idea.
Consider when looking at the characters on TV or Music Videos or Soaps or Commercials: What are they wearing in the shot, commercial, or television show? What color? How is their hair? What do their eyes say?
Think of the roles you want to portray, and bring this mind set to your shoot.
Don't just say "cheese!" and there is the shot, put some personality into your shot can be as simple as paying attention to the business you want to be in. And the jobs you want to get.
You should have diversity too.
A nice fun going smile
But also a serious and edgy shot too. Show your persona and range.
You want to give your agent, and yourself opportunities to be sellable.
Having one bland look will not get you far.