GoKawiilThis story appears in the July 2026 issue of Entrepreneur. Subscribe »
Sure, it’s important to have a winning product, and solid financials, and a reliable supply chain. But ultimately, any seasoned entrepreneur will tell you that people are what make or break a business. For that reason, and the fact that livelihoods are in the balance, decisions around your employees are often the most difficult and emotional. Here, six business leaders share the hardest personnel decision they ever had to make, and what they learned from it.
1. When you know, don’t wait.
Early on, we only had budget for one engineer, but my cofounder Marcelo found two he really wanted to hire. I told him to hire both, and we’d figure it out. One is our CTO today. When you see the right person, you have to move. The same is true when something isn’t working. The instinct is to wait and hope it resolves itself. It rarely does. In both cases, don’t let the discomfort slow you down. — Job van der Voort, cofounder and CEO, Remote
2. Toxic leaders aren’t worth the short-term gains.
I once had to let go of someone who, on paper, was hitting every KPI. They were delivering on short-term results, but consistently falling short as a people leader, which I knew would ultimately erode trust with our team. When the issues didn’t resolve, we went our separate ways. It was necessary to protect the other people invested in building Ritual to a higher standard. — Kat Schneider, founder and CEO, Ritual
3. Don’t confuse loyalty with what’s best for everyone.
I had a head of marketing who’d been with me since the early days. I felt loyal to her, but could feel the gap widening. I knew for almost a year before I acted. When an audit of the business uncovered significant “ghost spending” — tools and initiatives that weren’t driving any return — I realized I was avoiding a hard decision. Keeping someone in a role they’ve outgrown doesn’t serve them either. — Kerry Benjamin, founder and CEO, StackedSkincare
4. For young companies, flexibility trumps expertise.
I once hired someone with the perfect résumé. I knew they weren’t a cultural fit, but convinced myself the expertise would make up for it. The mismatch showed up almost immediately. This person wasn’t willing to do things differently than they had at a more established business. The friction was constant. I waited too long to act, because I’d pushed for the hire. At an early-stage company, attitude and flexibility beat expertise every time. — Lindsey Newton, CFO, A-Frame Brands
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