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Charlotte Ward •

290: From Timelines To Fit: Making Smart Support Hires; with Matt Dale

About this episode

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?

Matt Dale

Transcript

Charlotte Ward: 0:13

Hello and welcome to episode two hundred and ninety of the Customer Support Leaders Podcast. I'm Charlotte Ward. Today, welcome Matt Dale to talk about hiring the right people. Hey Matt, welcome back. Lovely to see you again on the podcast so soon in 2022.

Matt Dale: 0:38

Likewise, Charles. It's like when it rains, it pours. We get we get to hang out with each other, we get to talk about cool stuff. I love it. So thank you.

Charlotte Ward: 0:45

There is uh there there is nothing I like better than you know, uh a repeat visit from Matt in quick succession to see off the new year. Like we're we're in mid-February now already. I we're definitely past the new year vibes. Um, but it still feels early enough. Like, you know, it's it's good to hang out, like, you know, and just yeah, accelerate towards spring, right?

Matt Dale: 1:09

The entire month of January, the Dale family was like sick, one one or while the other of us. So it still to me feels kind of like New Year because I'm still getting back to the swing of things. So yeah, it's it's it's great to to be back and to have a conversation. And and I think talking about a topic that is maybe on some people's minds, certainly on my mind, and I think it's on your mind, and that's really getting the right people on the team, working through the process to you know make sure that you you're being fair, that you're you're looking for the right folks, you've got good, clear definitions of what you're looking for, um, and going there. So I'm excited to talk about that today.

Charlotte Ward: 1:39

It is it and I think it is actually the time of year as well, a little bit where hiring conversations often come up because we we wrap up all of those like end-of-year reviews, we've done our planning, we've got our budget lined up, and we're beginning to think about getting the job ads out there that we need for you know that next critical role, just to just to fill, you know, get get us off to the right

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