IWC Portuguese Chronograph
IWC Portugieser Automatic Chronograph
Model number: IW390302
Size: Men's
Case Material: Stainless Steel
Dial Color: Silver
Bracelet/Strap: Alligator/Crocodile Leather Black
Clasp Type: Deployant Clasp
Movement: Automatic Chronograph
Screw Down Crown: No
Bezel: Fixed
Crystal: Scratch Resistant Sapphire
Case Back: Transparent
Case Diameter: 42mm
https://www.chrono24.sg/iwc/portuguese-chronograph–id9478128.htm
Paying attention to not just the watch, which is important, but we have other clues here:
The watch is placed on a closed binder which is usually indicative of a law or EO signed imho. In addition to that we have an earlier Q drop which states "Note the desk". I believe the message here is who was at the signing of that EO or Law the Who, is the owner of that watch. After an extensive search I believe I have a candidate. Note the watch description.
Searching through images I came up with Robert Herjavec as being an owner of this particular watch. (I don't have the software necessary to super impose the image, I am hoping an anon would be able to do so.)
Robert Herjavec: quick bio
Herjavec was born in 1962 in Varaždin, Croatia (formerly Yugoslavia), and grew up in Zbjeg. In 1970,at the age of eight, the family left the country, which had previously incarcerated Herjavec's father for speaking out against the regime. According to Herjavec, "He’d drink a little too much, say bad things about Communism, and got thrown into jail 22 times for being an anti-Communist." Herjavec's family arrived in Halifax with a single suitcase and only $20. The family eventually settled in Toronto, where they lived in the basement of a family friend's home for 18 months. or Herjavec, who spoke no English the transition proved difficult. Having grown up on a farm and raised by his grandmother among neighbours with similar lifestyles, he now found himself in a much poorer economic class than his neighbours. Herjavec's father got a job in a Mississauga factory, making $76 a week—or $464.26 adjusted for inflation, in 2015. erjavec cites his father, whom he describes as "a really, really tough guy", as a major influence in his life. Herjavec has described a seminal memory of his, when he came home one day to complain to his mother that his classmates were making fun of him. His father who used to walk to work to save money on bus fare, came home, and when he heard what his son described, instructed his son never to complain, which became a guiding principle in Herjavec's life, one which he says sparked his sense of perseverance. Another influential episode in his youth came when Herjavec's mother was persuaded by a travelling salesman to buy a vacuum cleaner for $500, which was seven weeks' salary. As a result, Herjavec swore his family would never be taken advantage of again. In 1984, Herjavec graduated from New College at the University of Toronto, with a degree in English literature and political science. After a three-year retirement as a stay-at-home father to his three children, Herjavec founded Herjavec Group in 2003, a security solutions integrator, reseller and managed service provider, of which he is currently the CEO. Herjavec Group is one of Canada's fastest-growing technology companies and the country's largest IT security provider, according to the Branham Group.
https://en.wikipedia.org/wiki/Robert_Herjavec