What I finally learned about putting my portfolio together was that my cereal ad wasn't there to sell cereal, my airline ad wasn't there to sell seats, and my whiskey ad wasn't there to help people socialize at the end of the day.
They were all in my book to sell the same thing: me.
Creative directors aren't going to read your portfolio the way your friends read a magazine. They look at it mainly because they have to. At the end of a long day making and critiquing ads for their clients, their job description says they have to look at more. They have a position to fill, have to help a young person start her career, or simply take the temperature of the available talent out there.
Keep all that in mind. The creative director or recruiter is daring you to make them smile and even laugh. Your job has to impress. Break the ice. Demonstrate that you can land running. Your job is to convince them they need you. Not because you knew how to sell cereal, but because you can come up with ideas for them, to make the creative director rich and famous.
Your work has to be the kind the creative director doesn't want to slip away.
It doesn't always work the way you want it to, though. When I was in my 20s and in New York on a photo shoot, a headhunter made an appointment for me to show my reel at one of the top ad agencies. The creative director went nuts over one of my commercials for Hush Puppies shoes. He called all his art directors and writers into the conference room to "show you the kind of commercials we should be doing".
After his department saw it and filed out, I asked to hear more about the job. "No", he said,"I don't think you're right for our agency".
Two weeks later, that same commercial got me a job at another agency. It also sold a lot of shoes.
Today your samples have to be online, and it's even easier for the creative director to push the delete button. You may not be there to explain the problem and what a nifty solution you came up with and how the client gushed over it.
Your work will be there, all alone, with a creative director who has seen everything.
And is about to look you over.