Do you typically do your annual kick off at the beginning of January or the end of January? Do you think there's an advantage to one over the other?

We usually kick off the planning in Q4 and execution in Jan mid

It's depends on many factors the Fiscal year, New year, Lunar new year. Usually Beginning of Q1, sometimes after Lunar new year, or end of Q3 (ex: Japan)

If your companies fiscal year begins in January, my opinion is your kick off should be early in January to ensure you are taking advantage of as much of the fiscal year as possible with your initiatives. Many organizations I’ve been with tended to have strategic planning late in the year, even into mid / late Q4. This tended to push budget approvals into Q1 of the next fiscal year, which would lead to lag in kicking off initiatives. My strategy was always to begin cybersecurity planning early in the year, Q2 drafts of updates to a three year plan, revise in Q3. This provided time to socialize the plan and ensure buy in, then kick off early January to gain momentum into the new fiscal year.

Mid Jan, after everyone takes vacation, and before Lunar New Year if you have teams in Asia.

We usually hold our annual kick-off in mid to late January, allowing the team time to settle back into routines after the holidays. By then, we’ve typically finalized year-end results, budgets, and resource and project prioritization from the previous year, providing a clear foundation for our discussions. This timing feels like a natural point to set the tone for the year ahead and dive into execution.