When you work for a contractor and a different contractor wins the work, hedge your bets. Dear Bob …A bit of background before I get to the meat of the matter:Here in Washington DC, a fair amount of government work is done not by government employees, but by private companies that are contracted to do the work for the government. The contracts between the government and the company have a fixed length, and typically, when the contract expires, the government likes to go with a different contractor, regardless of the current contractor’s performance. (No, I don’t understand it, either.) In May, I started work as a help desk analyst for a company that is contracted to do technical support for a local agency. Its five-year contract expired a few months after I was hired, and there’s been a protracted bidding and legal war between my company, which very much wants to keep the contract, and another company.Finally, just a couple of weeks ago, the contract was awarded to the competing company. Our contract manager says he’s going to fight tooth and nail to get the contract back, and I believe him (he’s an ornery cuss when it comes to this kind of thing, and he’s highly resourceful).When one company wins a new contract in a situation like this, the common practice is for the new contracting company to hire the existing contractors, since that’s advantageous to the new company for obvious reasons, of course, but it’s not a foregone conclusion. So here’s my situation: it’s possible that my company will lose the contract. I want to keep working here. The new contracting company is already recruiting for the contract, even though the contract is still in dispute.Suggestions? A friend of mine, who’s a GS-14 in another branch of the government, says I should get my resume to the new company now. What do you think?And more importantly, if I do contact them, how should I word my cover letter? Standard cover letters don’t seem fitting here. I appreciate any advice you can give.– Beltway BanditoDear Bandito … Here are what I think are your options:1: Toss a coin – heads you stay with your current employer, tails you go with the new one.2: Hedge your bets by having an honest conversation with your manager. 3. Hedge your bets by having an honest conversation with the contract winner.All in all I like Option #2 best and Option #3 nearly as well. Here’s how it goes.From what you say, your manager certainly knows the game. Be straight with him. Let him know you’d prefer to stay with the company if it’s possible. Mention that if he’s willing to offer you a one-year employment contract that isn’t contingent on his winning the renewal, you’ll happily sign it and everything is good. Otherwise, explain that your plan is to apply with the other company to hedge your bets, because you also recognize that if your current employer loses the contract, they’ll have to let you go — nobody I know of among the “beltway bandits” keeps much of a bench.If your current employer wins the dispute, you’re their guy. You hope your manager understands your need to also apply with the other company. If he’s at all reasonable he’ll understand and you’ll be okay either way — even if you resign and join the other company, if he wins the contract dispute you’ll come back.Of course: Base your course of action on your knowledge of your manager’s personality and character. If he’s the kind of person who will take offense (which isn’t rational but that hasn’t stopped managers from taking offense before), do this instead (Option #3): Don’t have the conversation with your manager, do apply with the other company immediately to get the process started, and during your final negotiations before they hire you, suggest that they and you keep everything on hold until the dispute is finished and a formal transition period is established.They aren’t in a position to keep a bench either, so they should be happy as can be — they have a fully qualified employee waiting in the wings, available for work the day their contract begins, with no risks and no expenses until then.Short version: Keep one but not both of the companies in the dark regarding your plans, depending on your assessment of how your manager would respond. As for the cover letter, keep it simple: You’re working for the current contract-holder, like the work environment, the client likes you, and you would like to continue your work after the contract transition.– Bob Technology Industry