A letter of recommendation is sometimes difficult to write because it is challenging to articulate all the positive features about a person in one place. A letter of recommendation for someone on parole is particularly difficult because his future is at stake, and while the letter is not likely to be a deciding factor in his future, it is important to successfully share his best characteristics. Write the letter with sincerity and in your own voice in order to show the recipient that you are sharing your honest opinion.
Format the letter like a professional business letter, with your address at the top right and the recipient's address below that on the left, followed by the date and salutation. Try to find the proper name and title of the person you are sending the letter to. If this is not possible, use a general salutation such as "To whom it may concern." When writing the paragraphs, use clear, concise language and break up each point into separate paragraphs so it is easier to read.
Start the letter by stating how long you have known the parolee, your relationship and how you know the person. Include any positive information that will look good for the parolee; e.g., if you volunteered together in the past or were colleagues for a long period of time. This shows that the individual contributes to society and is able to hold a job.
Focus on the positive characteristics of the parolee, especially your experiences with him. For example, if he was punctual and professional when you worked with him, include this information. If he is polite, courteous, honest or reliable, then share this in the letter.
Express how you feel the individual will do in society, but only include positive information. Explain how you will be able to help, if appropriate. For example, if the parolee has a job or family support, talk about this. If you will be renting a room to him or can provide transportation, this will look good for the parolee.
Conclude the letter with a final thought, such as, "In conclusion, I trust this person and believe he deserves a second chance." Use a valediction like "sincerely" to close the letter. Sign your name by hand at the bottom.