It is a very good sign, but it is not a guarantee, and understanding the difference matters as you prepare for what comes next.
Meeting with reentry staff is a required step in the parole consideration process, not a rubber stamp that parole is coming. What the reentry team is doing is helping build the foundation of his parole application, specifically the release plan. They want to see that he has somewhere stable to go, a realistic path to employment, and a support system in place that gives him a real chance at staying out. Without that plan in place, a parole board has nothing concrete to approve.
The fact that he has completed this step means he is moving through the process correctly and that the system is taking his case seriously enough to invest time in building that plan with him. That is genuinely meaningful. Inmates who are not being considered for parole do not get routed through reentry planning.
What the parole board will weigh when they actually see him goes beyond the reentry plan. His institutional record, programming completion, the nature of the original offense, his criminal history, and how he presents himself in the hearing all factor into the decision. A strong reentry plan is one piece of a larger picture.
The most useful thing you can do right now is make sure everything on your end is solid. Confirmed housing, verified address, and a stable environment for him to return to are what the parole officer will be looking at when they review the plan. The stronger that foundation looks on paper, the better his chances when he sits in front of the board.