Archive FM

Entrepreneurship Simplified

Are You Hiring Too Fast and Firing Too Late?

Broadcast on:
09 Apr 2025

Ever felt like you hired someone just to fill a gap and then paid for it later? Yeah, me too. I’ve been there more times than I care to admit. In this episode, I wanted to speak directly to business owners and entrepreneurs who feel the pressure to hire fast but aren’t always confident they’re making the right call. I recorded this one pretty spontaneously, but it’s something that’s been on my mind a lot lately, especially with the work I’ve been doing at Boxed Business Solutions.

Hiring used to be something I dreaded because, truthfully, I wasn’t very good at it. I’d hire based on instinct or likeability, and that only works for so long. Over time, I’ve figured out a more systematized approach: mixing in things like behavioral assessments and even a little AI to help clients (and myself) make better decisions. It’s not about being perfect, but it is about being intentional. And once you start tracking what works and what doesn’t, you begin to see patterns that really help.

But the part we don’t talk about enough is firing. It’s uncomfortable. It feels personal. Even when someone’s clearly not a good fit, letting them go can be gut-wrenching. I walk through the process I use now, one that’s respectful, clear, and keeps things from dragging on way too long. It’s about setting expectations early, giving people a chance to improve, and being firm when it’s time to move on.

If you’ve ever hired someone because you were desperate or kept someone way past the point you should’ve, this episode will speak to you. I’m sharing what I’ve learned the hard way, in hopes it saves you some stress (and maybe even your company culture). And hey, if you’ve got questions or want to talk more about how to get better at this stuff, I’m always up for that conversation.

EPISODE HIGHLIGHTS:

00:00 - Introduction

01:17 - The trap of hiring too fast

02:36 - The benefits of systematizing your hiring process

04:50 - The power of behavioral assessments

06:19 - Why firing still sucks

07:32 - The 3-strike system I use

11:42 - Keeping it fair but firm

RESOURCES:

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