August might be Patrick McClymont’s preferred month when it comes to entering the CFO office.  “September is great, but you may want to show up a little before in order to get your feet wet,” comments McClymont, who last September became CFO of Hagerty, a once–stand-alone insurance agency for classic automobiles that has now morphed into an automotive enthusiast brand that in addition to insurance products also serves up to its car-minded customers a menu of “membership” programs and experiences. It should perhaps serve as no surprise that McClymont’s timing preference has everything to do with the industry’s annual planning process and the opportunity that it affords newly appointed CFOs to convert the fall rite into a learning process Observes McClymont: “You must ask not only ‘How do I learn from this?’ but also ‘What are my intuitions?’ and ‘What do we need to change?’” To better highlight the rewards of CFO timing, McClymont tells us about an earlier CFO chapter with entertainment technology company IMAX. Having joined this firm in August of 2016, McClymont found that the fall planning process enabled him with the insight necessary to more confidently signal a possible lane change during in his CFO stint with the company. In early 2017, only 5 months after stepping into the CFO role, McClymont began to see some negative trends within the company’s operational data, prompting him to raise his concerns with IMAX CEO Rich Gelfond. “Richard had this tremendous intuition about the business, so he kind of saw where I was coming from and said, ‘Okay, let’s closely monitor our performance on the next three movie titles that are coming out, and if we find that we’re not on track, then let’s have a real conversation,’” recalls McClymont, who adds that this approach provided him with an opportunity to set up an “early warning system.”   Besides the benefits that a CFO can garner from “learning while planning,” McClymont’s experience highlights the critical CFO–CEO relationship-building that transpired during the early days of his IMAX career. While he does not tell us whether a “real conversation” ever actually took place, McClymont does let us know that the conversation that CEO Gelfond had in mind would have involved IMAX’s stakeholders at large. Comments McClymont: “He said, ‘Go get ready for that real conversation now—we need to start working on what to do if we end up in a spot where we need to pivot.'” –Jack Sweeney