When he took over the coaching role at Glasgow Hawks this spring, they had just been relegated for the first time in their history, sparking a mass exodus of players and leaving a cloud hanging over Anniesland.
For some, that might have been the catalyst for a prolonged period of introspection and navel-gazing, but, instead, Dempsey and such willing confreres as Jim Sinclair and Kenny Hamilton have effectively torn up the old script and orchestrated a revolution.
Although Hawks only lie second, behind Watsonians, in the Scottish National League, they have made positive strides, particularly given the disruption which greeted Dempsey. "It was pretty interesting at the outset," he said. "We had 36 new players with the bulk of the former team either retiring or moving elsewhere.
"We sat down and worked out what was the best way to build a sustainable future, which could help everybody at Anniesland.
"Nobody is under any illusions: given the population and number of rugby players in Glasgow. We need to have representatives in the RBS Premiership and that isn't the case at the moment.
"We are working to spread the gospel, appeal to as many folk as possible, and get into more and more schools in the city.
"It's not an overnight process, but, in the present economic climate, we have to unearth and develop our own talent and we are confident we are making progress."
Hawks' prospects would be even brighter had they not suffered defeat at Myreside after leading by more than 20 points.
But, true to type, Dempsey didn't dwell on the defensive deficiencies which precipitated that collapse, preferring to stick to his belief that such experiences can stiffen the sinews and force players to step up a gear or two.
"It was disappointing, but it wasn't fatal, and I like to think the manner in which we imploded in the last 20 minutes will simply act as a spur to the guys to never want to go through anything like that again," Dempsey said. "We have played four matches since then, won them all, and are still very much in the mix for promotion."
If things remain as they are, Hawks will tackle the club which finishes second bottom of the Premiership. Dempsey added: "It's a tough division, not least because there are five Borders teams in the league and we have to go down to Kelso this weekend, which won't be easy. The crowds are passionate in the Borders, you always have lots of verbals flying around, on and off the pitch, and you have to close out the noise and concentrate on playing the better rugby. But the boys are ambitious; they are learning all the time, and that helps me as a coach."
The Glaswegians are in transition, but cannot afford to loiter in the second tier. Dempsey understands the importance of steering the club back to the highest echelon at the first attempt, but, ultimately, he appreciates that the ongoing Anniesland project requires care behind the scenes as well as momentum in the heat of battle.
"We didn't want to come out with any long-term goals during the summer; the emphasis was on being stronger and fitter with a healthier infrastructure," Dempsey said.
"But, of course, we knew we could go straight back up and we have planned for that happening and also if it doesn't. The main thing is that the standard improves across the grassroots circuit in Glasgow, because that is the best way to sell the game in the city."
Dempsey doesn't brook any obstacles or countenance the blight of failure. On the contrary, his restless demeanour shows how he aims to have the Hawks soaring again as fast as he possibly can.
PERFORMANCE OF THE WEEK
Few Scottish sides arrive at the Greenyards as favourites, but Gala maintained their Premiership charge with a hard-fought win over Melrose. The outcome not only demonstrated the tough-as-teak mentality which George Graham has instilled in his Netherdale troops, but also killed stone dead the faint title hopes of their Border rivals.
Will the SRU look seriously at the achievements of domestic coaches such as Graham, Kenny Murray and Craig Chalmers in their search for a replacement for Andy Robinson? If not, why not?