Colin McConnell, chief executive of the Scottish Prison Service, claims law-breakers are being unfairly negatively portrayed.
The prison boss blamed society for being too quick to label prisoners as "bad" and suggested the public should not dwell on the crimes committed by inmates.
Mr McConnell outlined his ideas in a speech published last week on the SPS website, before delivering it in a seminar to the International Futures Forum, a philosophical body that invites speakers to "make us think".
The speech stated: "Those who commit offences generally, particularly those sent to prison, are commonly labelled as 'bad' or somehow different and 'not like us'. The Scottish public shuns them and passes on the other side of the street.
"For the most part, this common descriptor is not true and I will argue that the public labelling of individuals in this way reinforces stereotypes which can restrict or deny those seeking to recover or rehabilitate."
Mr McConnell blamed the difficulties of rehabilitating offenders on "the unwillingness of Scottish society to embrace the possibility of positive change".
He spoke of the "labelling theory", according to which people are labelled on the basis of how others view their behaviour, which in turn forces people to act according to those labels.
The chief executive added: "While there is undoubted merit in these criticisms, it is my firmly held belief that 21st-century Scottish society still avails itself of every opportunity to label and stigmatise the 'offender', the 'criminal', the 'prisoner'.
"I believe, if we are to break the cycle of reoffending, we need to challenge this perception. We need to convey that these people are individuals with their own hopes and aspirations. We need to argue for the transformational capacity of forgiveness and redemption."
Scottish Conservative chief whip John Lamont said: "The rehabilitation of offenders is incredibly important and in everyone's best interest, but the way to do this is not to stroke their feathers and tell them they've done nothing wrong."