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Hiring plans look clean on a roadmap until real candidates, real timelines, and real markets show up. We unpack a practical, humane approach to building a support team that can handle peak seasons without sacrificing quality: plan backwards from your busiest dates, define the role around outcomes, and keep a flexible grip on how you staff it.

Charlotte welcomes Matt Dale to dig into the details leaders wrestle with every year. We talk through working from your go-live date to set posting windows, ramp time, and notice periods, then pressure-test those assumptions against service level goals and budget. Matt shares hard-won lessons on when to hire cohorts for frontline coverage and when a so-called “unicorn” role should be split into two focused positions. We get candid about the risks of fear-based hiring, how to establish contingency plans before you need them, and why automation and AI rarely deliver instant headcount relief.

Interviews, we argue, are more first date than crystal ball. Consistent loops and clear rubrics matter, but so does accepting uncertainty and raising the bar for mutual fit. We highlight the power of candidate questions—what they ask reveals how they think—and offer specifics to encourage better two-way conversations. Along the way, you’ll hear strategies for aligning with finance on headcount versus service levels, using contractors to build foundations, and resetting a search when the market tells you your role is mis-scoped.

If you’re hiring for customer support or customer experience this year, this conversation gives you a framework to time your postings, avoid settling, and build a resilient team prepared for the real workload, not the wishful slide. Subscribe, share this with a fellow support leader, and leave a review with your top hiring tip—what’s the question you always ask to gauge fit?