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10 Biggest Hiring Mistakes First Time CEOs Make

7 min readJul 30, 2025

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Successful startups are all about hiring the right team. Yet so many first time CEOs screw up their hiring, and destroy their startups.

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I don’t want that to happen to you. I’m going to share with you the 10 biggest hiring mistakes first time CEOs make, and how you can avoid these mistakes. And I’ll share what to do if you’ve made these mistakes.

I hope you like it.

Let’s start with number one on our list:

1. Hiring the executive a board member or investor recommends.

The biggest recruiting mistake I ever made was hiring “Tommy” to be our VP of Sales. Sales were growing, but we needed someone who’d been there before to help scale our sales organization.

Magically, two of my board members, Gill and Barry, recommended Tommy. He previously had scaled sales in a similar company that Gill and Barry were involved in to a very nice exit.

I met with Tommy several times. He had the right experience, that was clear. However, something seemed off. I ignored it because Gill and Barry kept singing his praises.

I had the other board members meet with Tommy. “Raul” said after meeting with Tommy, “I’d hire him based on Gill and Barry’s recommendation.”

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brett fox
brett fox

Written by brett fox

I work with startup CEOs to help them grow their businesses . I built several businesses from $0 to >$100M. Learn more at https://www.brettjfox.com