In the first year. Every alternative to departure takes longer than the time usually left when companies start thinking about it. Count prior time at the outset, put the ceiling date on the calendar, and hold a genuine review at the midpoint rather than at the final extension.
The limit is fixed; only the preparation is flexible
There is no mechanism for extending beyond the maximum, so the only variable is how much notice everyone has. Counting prior time at the outset establishes the real ceiling, which may be earlier than five years from now. From there, work backwards through the options.
A move to a managerial classification requires that the receiving company actually has a structure for him to manage, which sometimes has to be built deliberately over two or three years. An immigrant petition involves several stages and, depending on category and chargeability, a wait for visa availability that can be substantial. A return to Canada requires succession at the receiving company and a role to come back to.
None of those is arranged in six months. Meanwhile keep a contemporaneous record of time spent outside the country, since recapture depends entirely on documentation created at the time. Hypothetical example: a vaccine cold-chain company wants its sensor-network specialist in the United States before a new warehouse opens.
The first review confirms the continuous qualifying year abroad, captures the specialised-knowledge evidence, and compares the proposed start date with petition processing options. Pay records and travel history settle the employment-year calculation; signed project plans settle when the specialist is actually needed. The company should avoid assigning the employee to ordinary local support while awaiting the transfer, because that can blur the proposed role.
A rushed filing often fails by describing urgency without first documenting the precise knowledge the opening requires.