When sending out resumes and cover letters to employers, you have to acknowledge the fact that this is, whether you like it or not, the first impression you will make, and your application documents contain the only information employers will have about you unless they decide to call you in for an interview.
With this in mind, it is even more important that information be accurate and forthcoming—even if it is not particularly flattering. Anything employers read as misleading will automatically land you in the cylindrical file of no return.
For this reason, consistency of content is more crucial than ever. Some of the biggest concerns for candidates with sketchy work histories are time spent unemployed and positions that were short-lived. There is, however, a completely legitimate way to present this material without lying and without putting on a Vanna White-esque display for the world to ridicule. The easiest strategy is to simply list all employment dates using years but not months.
Employers will eventually discover that your tenure at Company ABC from 1999 to 2000 really lasted from November 1999 to February 2000, but if they are checking references and asking for additional information about your work history, your foot is already in the door, and you have less to worry about.
As it is extremely important to remain truthful to prevent your foot from going back out that door in a heartbeat, be willing to discuss your work history when asked. Short-term positions are not the end of the world if you do not appear to be hiding something to begin with. Honesty is key.
Terminations are another sore spot for many candidates. It doesn't matter how long it has been since the layoff or firing occurred. Any termination is a sensitive subject, and—let's face it—it's never going to be an ego booster, so we have to find ways to cope. If an employer checks your work history or references, it is bound to find out about a termination in your past, but this does not mean you cannot eliminate suspicion from the beginning.
Your cover letter is the perfect place to explain away unseemly dismissals. Before your references are even called, you have the opportunity to prevent any unnecessary questioning of your abilities by describing your dismissal in a favorable manner. (This includes describing your former employer favorably.)
Instead of going on a rant about your horrible boss, explaining that funding for your position was no longer available will suffice. Remember that any negative commentary on a previous employer may reflect on your potential to backstab a future employer if things don't work out. Human resources departments typically are not fond of disloyal employees and trash talkers.