Does he let them work through stretches of poor play, or step in with a more forceful approach with words and deeds?
On Thursday at Haas Pavilion, down by 11 points to Oregon State with 15:49 left to play in the second half, Montgomery chose to express himself.
"You don't want to know what I said specifically. You can't handle the truth," Montgomery joked. "We were just getting our butts kicked and I explained it to them in no uncertain terms."
The talk took hold, as Cal rallied for a 71-68 win that seemed improbable based on the 24:21 before Montgomery delivered his message.
Cal allowed Oregon State to shoot 60 percent from the floor in the first half. Cal held Oregon State 33.3 percent (10-of-30) in the second.
Cal attempted 14 three-point shots in the first half, despite making 9-of-16 shots inside the arc when it chose to attack the Oregon State zone defense, too often settling for long jumpers instead of "probing" inside, as Montgomery termed it. Cal was far more aggressive in the second, including on the game-winning basket when Allen Crabbe attacked the baseline for a one-handed runner, then again when a driving Justin Cobbs dropped the ball off to Richard Solomon for a dunk to set the final margin.
"They came back and got a little more aggressive, and when we are more aggressive we tend to make some plays," Montgomery said.
The template is clear and has been all season long. When Cal attacks on offense and defense, they can compete. When they don't, they go to the locker room trailing by eight to a team with one win in the Pac-12.
Montgomery has to make that clear to this group, one he openly admits "doesn't necessarily self-motivate themselves all the time," during every game the rest of the way. He doesn't have a Jorge Gutierrez or Harper Kamp to do it for him, as he did last season. He doesn't have Ricky Kreklow right now and might not have Jeff Powers, who sustained a nasty-looking knee injury in the first half, to deliver the message through the energy they bring coming off the bench.
They also lack a natural basketball IQ, which showed itself in the early defensive rotation. By the end of the game, Montgomery had learned his lesson and took back-to-back timeout with 17.6 second left to play to reinforce how he wanted to defend the final Oregon State possession.
"It was more to clarify what it was we wanted to do so there was no confusion," Montgomery said. "In that situation, we were talking about how we wanted to defend the possession. Did we want to switch, did we want to foul, what it was we wanted to do. I didn't feel after the first one there was clarity of information in terms of what we wanted to do, so we took a second one to emphasize."
Montgomery did not want to foul.
"I just don't have confidence in when we would foul and how we would foul, understanding how to legitimately take a foul," he said. "I just told the guys, ‘No threes.'"
For a group that tends "to take things pretty literally," they did exactly what that, forcing the ball into the hands of forward Joe Burton and Oregon State never getting a final shot in the ensuing chaos to come away with a potentially season-saving result.
The challenge now for Montgomery is replicating the effort and intensity of the second half for 40 minutes a game the rest of the season with an inherently flawed team. It probably won't happen, as even the stated revised goal of a top-four finish and first-round bye in the conference tournament seems like a fantasy, but the veteran coach will do he can to make it happen.
He has tried the carrot, but the stick has proven time and again it is the only way to reach this team.
You can't handle the truth?
Cal should ready itself because there is going to be a whole lot of it coming from Montgomery.
Dan Greenspan writes about the Pac-12 for Fox Sports Next. Follow him on Twitter @DanGreenspan.