I'm not sure about the specifics of Massachusetts law, but I can provide some common-sense advice that I give my California clients.
Probation is an alternative to jail or prison. The judge wants to see how well you follow orders. Sometimes the conditions of probation will keep you from doing things other people are free to do, like drinking alcohol or staying out late at night.
Probation officers generally want to see acceptance of responsibility, remorse for the crime committed, and desire for rehabilitation. I don't know how this PO is failing to "support this individual," but the person should ask for the services he or she wants. If that's job training, substance abuse treatment, counseling or whatever, ask for it.
When the client is going to talk to the probation officer before sentencing, I tell them to explain how sorry they are for their actions. They've embarrassed their family, caused problems for everyone around them, and they want nothing more than a chance to show the judge, their family and society that they can turn their lives around. They accept full responsibility... and for the sinking of the Titanic, which happened decades before their were born, but is their fault, not the iceberg... and the extinction of the dinosaurs was their fault, not a meteor or climate change, as scientists say...
The last two examples are jokes, of course, but I use them to stress how important it is to adopt an attitude of humility with a probation officer.
Now, if you go complaining to the probation officer's supervisor, do you think it's going to help the probationer's relationship with him or her? If it doesn't result in assignment of a new probation officer, that relationship is going to be more difficult for the remainder of the term of probation.
Remember the saying, "This too shall pass." Probation isn't forever, and saying "Yes, sir" for a visit to the probation officer once a month may be worth the long-term outcome.
Dealing with a probation officer is always a tough issue.
But in this case, you have said no reason to request the change?
Without specifics, there is no guidance.
I agree completely with my colleague's advice but I would like to add a word. The goal of the criminal justice system is not to punish, deter and rehabilitate as we are taught in law school. In CA, the Penal Code says that the goal of the system is to punish. Period. So if you get probation the system considers that it has done you a favor and you should be grateful by obeying your PO's every wish and command no matter how absurd. From my point of view the goal of criminal law is to break the human spirit and there are probation officers who act with this in mind.
If you are as old as me you may remember Paul Newman's movie "Cool Hand Luke." Luke was jailed for public intoxication and petty vandalism in a hell hole that resembles Parchman Farm in Mississippi. Every time the warden said a word it was a command and every command had to be responded by "Yes Boss." What's clear in the film is that Newman's offense was minor but what kept him at Parchman was his refusal to give in. Eventual he is killed for his insubordination.
The problem you face on probation is that you have to have a "yes boss" attitude while you preserve your dignity inside you. This is not easy to say the least. But as Mr. Marshall says complaining will only make it worse.