Maybe not ‘Preferred Pain’, but now is the heart of ‘Mid Year Review’ season for my erstwhile Microsoft brethren. Facebook has been filling with comments of long nights and dizzying spreadsheets. It’s an annual ritual of masochistic purification that the organisation goes through to exhaustively (literally) review its business from top to bottom. Some might say that many businesses do this as a part of their annual planning cycles. Microsoft also has a planning process towards the end of its fiscal, but it is mild compared to the dreaded ‘MYR’. The strength of the timing is that the business has the chance to do ‘course correction’. Rather than miss numbers at the end of the year and try again with a new FY, Microsoft takes a half-time break to figure out how to make the numbers. The excruciating scrutiny is part of the mythic Microsoft ‘sack cloth’ that I alluded to in my very first piece (“Microsoft is actually preoccupied with failure. It’s the sort of place that if a project scores 9 out of 10, the follow up review meeting will not be celebrating the 9, but dissecting why we didn’t get the 10th.”)
One of the most profound lessons I learned in my 15 years at Microsoft, one which contributed to my obsession with embracing failure right here, is the notion that “It is better to fail and know why than to succeed and not know why.” The adage came from Mid Year Review when executives got praise who even though missing their targets had a solid understanding of what was going on and how they were going to address it. Conversely, no matter how sterling your scorecard was, if you didn’t have a sound understanding of what led to that success, it was a serious CLM.