That will be easier if he can convince his players to play without fear. Especially when competing against big hitters like Celtic and Rangers.
Never one to be constrained by the age of his team or how they stack up compared to others in terms of cost or experience, at Central Coast Mariners, he not only helped develop and blood young talent, but by winning last season’s A-League, despite having the lowest budget, he proved that money doesn’t always guarantee success.
“It’s well documented it was the youngest team to ever win the A-League,” said the bright, young manager. “It was the lowest budget. So, to win the competition last season, I think everyone doubted it, but I never had any doubt.
“It was my job to make the players believe that despite the clubs with the big budgets, money has never won a game of football. On the pitch players win you games of football.
“Of course at the top level there’s a lot of money but the reality is I had to put the squad together. And after missing out the previous season it was important I got the right players and right staff.
“It was a massive achievement. To win the final as emphatically as we did I don’t think anyone would have predicted that. But I’m definitely proud of what we achieved.
“Now my full focus is on Hibs and being head coach of a club of this stature and giving everything I can every single day to bring success back to the club.”
The Leith side may not have the most financial clout in the Scottish top tier but, as one of the biggest clubs in Scotland, neither are they paupers.
Money has been paid out in recent transfer windows and Montgomery has been assured he will get further backing in the future but regardless where they rank in the spending charts, the new Hibs boss believes in delivering the biggest bang for every buck.
“My remit was to make [the Mariners] play without fear against the big teams that had the big budgets and that’s what worked for me over there. It’s about educating the players, especially the young players and having a game plan.
“That’s what we’ll work on during the week and executing it is ultimately down to the players but you have to adapt. I’m not saying it’s exactly the same here.
“I enjoy a challenge, anybody who knows me knows that. Right now the challenge is to pick up a team that hasn’t started the season well and to get the results and give the team belief that we can finish as high as possible. That is not easy. It is a very competitive league, the challenge for me is to come in now and get the team playing, have them believing we can have a really strong season because it’s really early. It was a fantastic result that Dave [Gray] got at Aberdeen and hopefully we can kick on and get some momentum going.”