Across Likeable Media (sold to 10Pearls in 2021), Likeable Local, Apprentice (sold in December 2025), and Remembering Live, I’ve personally hired or signed off on the hire of more than 1,000 people. Many worked out great. A handful changed my life. A few were catastrophic.
Over those 18 years, I’ve come to recognize three red flags that almost always predict a bad hire — no matter how impressive the résumé, no matter how good the referral. I have written before that my time selling at Radio Disney taught me four business lessons that still hold up 20 years later, and that there were seven things I’d tell myself when I was building my first startup. Spotting bad hires is on both lists, and these three red flags are how I do it.
Red flag No. 1: They speak negatively about a previous employer.
Listen to how they talk about their last job. And the one before that. And the one before that. If every single boss was “toxic,” every team was “dysfunctional,” and every founder was “out of their depth,” you have a pattern. The pattern is not the bosses. The pattern is the candidate.
I’m not saying everyone needs to glow about every previous role. People leave jobs for real reasons, and some companies are genuinely terrible. But a great hire can name what was hard, take ownership for their part, and speak with grace about the people they left behind. A bad hire blames the world. Two years from now, you will be the next bad boss they tell their next interviewer about.
Red flag No. 2: They can’t tell you about a time they failed.
I always ask: “Tell me about a real failure — and what you learned.” The candidates who say “I once worked too hard on a project” or “I’m a perfectionist sometimes” are telling me they don’t yet have the self-awareness or humility to be a great teammate.
The best hires I’ve ever made told me about a launch that flopped, a hire that didn’t work out, a quarter where they missed quota by 40 percent. They named what they did wrong. They named what they’d do differently. They didn’t pretty it up. The willingness to be honest about a real failure is the single best predictor of someone’s ceiling. Failure is data, and great teammates are good at reading the data.
Red flag No. 3: They’re not curious about you, the company, or the role.
At the end of every interview, I leave 10 minutes for “What questions do you have for me?” The answer matters more than anything else in the conversation.
If they have no questions — pass. If they have one or two boilerplate questions about benefits or vacation policy — pass. If their questions are all transactional (“What’s the comp range? When does it vest?”) — pass.
The hires I’ve been thrilled with came in with a list of 8-10 sharp, curious, specific questions. About the customer. About the product roadmap. About my own management style. About what failure would look like in this role. Curiosity, more than any other trait, is the leading indicator of how high a person will rise.
The bonus tell: how they treat the receptionist
This isn’t a red flag in the interview itself, but it’s the most reliable tiebreaker I have. After every finalist, I ask whoever greeted them at reception how they were treated. If the answer is “polite, warm, made small talk” — great hire. If it’s “didn’t make eye contact, was rude when they had to wait” — pass, every time, regardless of how brilliant the rest of the interview was.
Résumé gets you to the interview. Pedigree gets you considered. But how you talk about your past, how you talk about your failures, and what you’re curious about will determine whether I make the offer. Watch for those three signals on every hire and you will dramatically improve your batting average.
This post originally appeared at inc.com.
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