Legal and medical questions pose a real hazard for librarians, because we have to avoid "Unauthorized practice of law" in most states. But we can suggest places for folks to look, such as the state law and other Massachusetts sites noted in the earlier answers to this CORI question. Though they are no doubt heavily burdened by the present economic situation, it still might be worth looking into the Office of Labor and Workforce Development to find websites or local offices that could help advise you how to deal with these records.
At public or academic libraries you can also search in full text magazine, newspaper or journal databases, to see if anybody has written about how to handle the problem of a conviction record when applying for jobs. For example, the Masterfile Premier database, common at most public libraries, gets 59 articles for the TX-ALL Text search: "criminal record" and getting w3 job. The "w3" is a "Proximity" search - requiring that the words be no more than 3 words apart. This is important in full text searches, because words often are so far apart in an article that they are completely unrelated to each other. Most public libraries will have full text newspaper databases, to find articles by using searches similar to the above ones. If you are near an academic library, LexisNexis Academic may well be available, or even Factiva (known for business research, but very good for newspapers in general). Lexis and Factiva use a slash after the "W" for proximity search. Factiva gets 72 hits in the past 2 years, for the search: "criminal record" and apply* w/4 job. Please note that we can't link to these searches, because the commercial publishers charge money for them. You have to go in person to the libraries that subscribe to them, or login using a public library card number (sometimes along with a PIN, maybe the last 4 digits of your phone number, for example).
Google appears to include proximity search for its "Relevance" ranking, so that words closer together will tend to get hits listed on the first pages of a big list. But unfortunately, Google won't let you "force" output to be limited to a precise proximity search - you have to choose either the phrase: "Criminal record" or criminal AND record. But even with Google, there are some tricks that will help you, such as limiting to site:gov, site:edu, etc. The search: "criminal record" "applying for a job" site:gov gets 134 hits (about 88 unique ones). Compare USAsearch.gov which searches state government as well as federal websites and online publications. It gets 75 hits for the search: "criminal record" "applying for a job"