Deadlines. They are never just another day at the office. Just when you think you’ve planned far enough ahead, bluffed and cajoled to get things in on time, something gets added to the pile. It is then that one of my mantras seems extremely useful. “Sell all thou hast, and buy Photoshop.”
The story goes like this. My friend is a warm, decent, friendly guy who has suffered the ravages of age like we all do. He was the newly minted president of a large organization. As the figurehead an announcement and some photography was in order.
Now, I am usually happy to see him, but when he “dropped by” the office and the boss scheduled an impromptu, (zero planning) photo shoot, I was a bit panicked. Clearly he wasn’t any happier than I … “I only have 5 minutes” he growled.
Portrait photography should be handled by a pro. A photographer’s fees are well worth it as he/she can really do wonders with pose, light, etc. However, when your boss says “get a photo” you do it. I got him to relax and laugh, got the exposure right, outdoor morning light from behind him with a flash fill to take care of the shadows, blur the shrubbery background…yada yada.
The pressure continued to ratchet. “Let’s announce this position in the next issue” (the magazine was within hours of the deadline). IT WAS A GOOD PHOTO of an upper-middle-aged white guy. What I needed though, was a visual image of the warm, affable guy he is. Seriously, he’s funny, intelligent, has great instincts and insights … but age creates a lot of distractions. So I pulled out the magic art director’s shoe horn and went to work.
Success in these situations depends a bit on skill and a bit on judgement. You want the person to look better than they do, but you don’t want anybody to easily see what you did. It’s rather like makeup…when it’s done right, the face is what you see, not the makeup.
I blew up the high-resolution photo and I moved the lapels of his coat (cut and clone) to hide his middle aged spread. Then, I cropped enough of the photo so that the really incriminating evidence went away.  His smile has the normal number of teeth that are a bit crooked, one eye doesn’t open like the other, etc etc, so I just generally did the sort of touchups that make a photograph a bit more pleasing without removing the character of the person in the photograph.
I knew that I had a success a couple of weeks later when a staffer from his new organization’s in-house magazine called me with a question. “Hey Bob, can we use your photograph? We just can’t seem to get a good photo of this guy and yours looks great.”
I laughed and for the sake of full disclosure I then walked them through what I had done in the photograph. Before my explanation, they didn’t see it and neither did their new president.
Rules

1. In most cases, it is better to make the ask before you make changes even if it is just the off-hand remark during the shoot, “I’ll touch this up and make you look great.”
2. ALWAYS be honest about what you’ve done and care for the feelings/permissions of the person involved…(hence the photo isn’t here for your enjoyment).

And if you are a beginning art director, sell all thou hast, and buy Photoshop.