Oct 17, 2026 · 27 min · 10 segments
Casey Jacox joins Tailwind for a conversation on humility, vulnerability, and curiosity and why those three qualities make sellers and sales leaders more effective. We talk about how curiosity…
Casey JacoxGuestAustin BuellHostI mean, like, hearing this, I'm, I'm hearing, like, the, uh, all those, like, top level, like, recommendations for a salesperson as they're going through training.
It's very much like here are the, the tactical things that you need to do, and I don't often hear, like, the underlying more emotional aspect or more, like, foundational bedrock aspect of it.
But it's like okay, but, you know, being humble, being curious, that's a more deep version of saying, like, "Listen twice as much as you talk." Um, have you noticed that, like, as you focus on those things or you've trained from that d- direction or that l- underlying thing that you're seeing a more impactful, like, set of actions? Like, somebody's actually saying, "Tell me more," from a actually more interesting per- uh, perspective because they're thinking of it from being those three, those three things at all times?

And I think one thing that when you're curious, your tone has to be be thoughtful.

So if I just say, if I just say, "Hey, tell me more about that," well, that was kinda firm and direct.
I mean, like, hearing this, I'm, I'm hearing, like, the, uh, all those, like, top level, like, recommendations for a salesperson as they're going through training.
It's very much like here are the, the tactical things that you need to do, and I don't often hear, like, the underlying more emotional aspect or more, like, foundational bedrock aspect of it.
But it's like okay, but, you know, being humble, being curious, that's a more deep version of saying, like, "Listen twice as much as you talk." Um, have you noticed that, like, as you focus on those things or you've trained from that d- direction or that l- underlying thing that you're seeing a more impactful, like, set of actions? Like, somebody's actually saying, "Tell me more," from a actually more interesting per- uh, perspective because they're thinking of it from being those three, those three things at all times?

And I think one thing that when you're curious, your tone has to be be thoughtful.

So if I just say, if I just say, "Hey, tell me more about that," well, that was kinda firm and direct.
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