As a political junkie, I've been watching the Presidential primaries, and now the general election campaign, with interest. I've said before that elections are like really long (REALLY long!) job interviews and I always enjoy seeing how the different candidates approach the process. (And no, I'm not going to tell you which one I'd choose if I were hiring - that's not the point of this post).
This year I've been interested in Barack Obama's proactive approach to negative issues, because it mirrors the advice I give my clients about addressing potential negatives upfront. With various rumors swirling about his background and religion, Obama has started the general election campaign with a TV ad in which he talks about his all-American background. His team have also established a website that is used to counteract email rumors about him.
The website has caused a lot of discussion among political pundits, since in order to fight a rumor, you have to first restate it. People have wondered whether the website does more harm than good by repeating the rumors.
Personally, I don't think so. And this is where we get back to your job search. I think that if there are potential "negatives" in your background, it is better to face them head on, address them, show why they're actually NOT negative and then move on.
For example, if you have diverse experience across a wide range of positions, you might worry that employers will see you as "a jack of all trades, master of none." Well, they might! So you have to take that and address it head on. You might start your resume introduction with something like this:
"'Jack of all trades' who has consistently excelled in every position, no matter how diverse and how little training is provided."
Or start your resume with a direct quote from yourself:
"No matter what the assignment, you can trust me to succeed. I've done it time and time again in a variety of industries and functions."
Or find the common thread that runs through your experience and highlight that:
"Whether working in IT, Marketing or Sales, I have always been able to quickly assess the situation, develop a workable action plan and motivate others to succeed. I've never missed a deadline and every one of my employers have grown in revenue during my tenure."
You can also address perceived weaknesses in your cover letter and by raising them during an interview. Say something like "many people have wondered about the fact that ..." or 'Maybe you're wondering..." and then take the opportunity to address that issue.
There are many other ways to address potential negatives and how you address them is less important than making sure you do address them. Just don't let them sit there like the elephant in the room because if there is a concern, you may never be told about it and you may well lose out on the opportunity without ever understanding why.

I'm Louise Fletcher. As President of 
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