Montolivo has been described as a versatile player capable of playing anywhere in the midfield, especially on center positions. Originally a sweeper, he was moved higher up the pitch in his early teenage years. His main and favoured role is in the centre as a deep-lying playmaker, which best utilises his technical ability, creativity, vision, and range of passing, although he is also capable of playing as an attacking midfielder, even though this is not his preferred position. He also possesses an accurate and powerful shot from outside the penalty area. With the Italy national team, under Cesare Prandelli, Montolivo also played in a new role as false attacking midfielder in a 4–3–1–2 formation, in particular at Euro 2012; he has also been fielded in the “mezzala” role. In recent years, he has also been praised for his work-rate, physical qualities and for his defensive attributes, including his ability to read the game, intercept loose balls, break down possession and subsequently start attacking plays, which led manager Siniša Mihajlović to deploy him in a holding role as a ball-winner. However, Montolivo has also drawn criticism at times for his lack of pace, and has been accused of being inconsistent, and of lacking leadership qualities, despite having served as Milan’s captain. He has also struggled with injuries throughout his career. Montolivo was born to a German mother and an Italian father in Milan, soon before his family moved to Caravaggio, where he spent most of his childhood. He has an older brother Luca who is a lawyer. In addition to holding an Italian passport, Montolivo also holds a German passport – his mother, Antje, was born in Kiel and later moved to Ascheberg and his maternal grandparents are from Heidkate at the Kieler Förde on the Baltic Sea coast, where he spent all of his summers as a child. In addition to Italian, Montolivo also speaks fluent German. In his youth, he looked upon Francesco Totti, Zinedine Zidane and Frank Lampard as his idols. On 22 May 2014, Montolivo married the Florentine model and presenter Cristina De Pin, with whom he had been engaged since 2007. The couple has two children, Mariam, born on 12 May 2016, and Mathias, born 20 October 2018.