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Why I Hire People with Multiple Jobs (and My One Red Line)
Companies obsessed with time-tracking are completely overlooking top talent. In today’s market, the real hiring challenge isn’t monitoring hours—it's identifying conflicts of interest.
Let’s talk about an employer's ultimate nightmare: accidentally hiring someone who works for a direct competitor.
It recently happened to me. I run a company where part-timers make up about a third of our workforce. One of our star employees has been with us part-time for five years and consistently outperforms expectations. Frankly, I couldn't care less how many hours someone clocks in a day.
However, during a recent interview for a new role, we discovered the candidate was actively working for a competitor. He wasn't trying to hide it; he simply didn’t think it mattered. He was wrong. It mattered immensely.
While some companies might view this as a sign to stop hiring people with multiple roles, we took the opposite approach. It simply meant we needed to inject absolute clarity into our hiring practices.
The Power of the Poly-Employment Philosophy
We don't just tolerate employees having multiple jobs; we embrace it. In our experience, juggling multiple roles heavily correlates with top-tier talent.
Most employers assume people take on extra work purely for the extra income or as a safety net against layoffs. While the cash is great, that’s rarely the whole story. The best professionals choose this path because they want to stay sharp. They view a diverse range of experiences as their true security blanket and the fastest vehicle for personal growth.
To make this work, every role in our company is measured strictly by expected results.
It’s a dead-simple rule that most companies completely miss. Think of it this way: if you hire someone to sweep a courtyard, what are you actually paying for? The physical act of sweeping, or a clean courtyard?
We don't pay for responsibilities, time commitments, or the optics of "being the first one in the office." We pay for results. That clarity makes it immediately obvious whether a part-time candidate can deliver.
Hacking the Interview Process
Traditional interviews are broken. Candidates have become masters at playing the game—reciting tailored background stories, acting out simulated stress scenarios, and using coaching, courses, and AI plugins to hack the process.
To cut through the noise, we rely on two core principles:
Problem-Specific Querying: Instead of asking generic questions about past experience, we ask if they have solved our specific problems before. In short: “Have you actually cleaned a yard like this before?”
Upfront Reference Verification: We tell candidates right out of the gate that we will be verifying their stories with previous employers. We let them know we will literally call and ask: “Can you confirm John kept the yard clean 20 days out of every month?”
The moment you introduce this, the sales fluff vanishes, and the conversation gets real. Furthermore, we never rely on a single reference; two is our absolute minimum.
When you hire this way, you stop worrying about how many jobs a person holds, what perks they need, or what their abstract strengths and weaknesses are. While cultural fit and team chemistry still matter as an initial filter, the ultimate question remains: Have they actually achieved the goals you are aiming for?
The best part about working with high performers is their self-awareness. We’ve had top talent voluntarily step back because they realized they could no longer maintain their own high standards. At this level, their professional reputation is their biggest asset, and they guard it fiercely. That level of radical ownership beats a rigid 9-to-5 schedule every single time.
The One Red Flag: Legal Exposure & Transparency
We only have one non-negotiable red flag: working for a direct competitor.
While conflicts of interest are part of the issue, the most severe risk is legal exposure. Employees often carry non-compete obligations or proprietary, confidential knowledge from concurrent roles. If you are a small, stagnant company, you might never notice. But as you scale, these early oversight decisions will come back to haunt you as massive liabilities.
The antidote is defining boundaries early and clearly. If you operate in a flexible environment, transparency is not optional. You must ask direct questions and establish clear expectations from day one regarding what constitutes a conflict.
During the interview with the candidate mentioned earlier, we began connecting the dots as we discussed the industry. His knowledge of the space was simply too specific and too current. When we asked him directly, he confirmed that his other employer was indeed a competitor. After that, parting ways was a straightforward business decision.
Accountability is the Real Benchmark
It is easy to blame these situations on the rise of part-time work or "overemployment," but that misses the core issue.
Team performance doesn't break because people work fewer hours or hold multiple jobs. It breaks when accountability is unevenly applied. That has nothing to do with employment type and everything to do with character and integrity.
Remember: The performance of any team will eventually drop to the level of its least productive member. Left unchecked, mediocrity becomes a cultural contagion.
On the flip side, exceptional people take full ownership of outcomes, flag issues early, and bow out when they can no longer deliver. If you build your company with that standard in mind—and demand radical transparency where it matters most—the only thing you'll ever need to worry about is whether everyone is delivering on the one thing they committed to do.