Bad Hires

Hiring is a skill, but over the years, I have made a few bad hires. Here are a few of the bad hires that I have learned from.

Carter Cathey

11/27/20251 min read

Over the twenty years, I have hired so many amazing and talented people. But, I have also had a few hires that didn't work out so well. Here are four colorful bad hires:

1) The Bad Referral: We conducted a Zoom interview with a candidate relocating to my city. Upon arrival, it was evident he was struggling with serious substance withdrawal symptoms. During a one-on-one training session on day two in my office, he fell asleep and didn’t notice when I left for lunch. By day four, he was unaware of who his boss was, despite having been trained by her for several days. On his last day, he made an inappropriate comment to a co-worker, and we later discovered he had consumed a significant amount of leftover beer from a party.

2) The Sloth: I hired an intelligent woman who appeared self-aware. However, she struggled to adapt to our fast-paced environment. She spent excessive time planning and was uncomfortable with the speed at which we operated. Despite her thorough preparation, her outreach was minimal, and I suspected she was juggling another job, leading to deteriorating relationships within the team.

3) The Magician: I was excited to hire a candidate who excelled in training. However, after a few weeks, he unexpectedly didn’t show up for work, leaving his laptop and badge behind. HR reached out to his emergency contact, only to learn he had decided to move on to another job without any notice.

4) The Entertainer: I had a team member who frequently fell asleep at her desk. After several nudges, I learned she was working a night job as a dancer and couldn’t sustain her schedule. Despite her interest in the role, she ultimately decided to resign as she couldn’t balance both jobs.

Have you experienced any challenging hiring decisions?Related Articles by Carter Cathey

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  3. Growth & Scaling: Why Early Success Creates Bad Habits

  4. For Whom the Bell Tolls

  5. Is Lifetime Employment Still Possible?

About Carter Cathey

Carter Cathey is a sales and revenue leader with more than 20 years of experience helping market research, technology, and private-equity-backed businesses scale revenue, improve operations, and build predictable growth systems.

Throughout his career, he has led sales transformation initiatives, pricing strategy projects, subscription business model transitions, operational redesign efforts, and commercial growth programs.

He writes about leadership, organizational design, business systems, data-driven decision making, and the challenges companies face as they scale.

Learn more about Carter Cathey