The Cost of Hiring the Wrong People at the Wrong Time (And What I’ve Learned)

Hey there,

I wanted to take a moment to share something I’ve been thinking a lot about recently, especially as our company continues to grow. It’s one of those lessons that I wish I had learned a bit sooner: hiring the wrong people at the wrong time can set your business back more than you realize.

As the CEO of a SaaS company, I've had the chance to experience a variety of hiring challenges, and I’ve learned a ton along the way. While hiring is often seen as a necessary part of scaling, I've come to understand that timing is just as important as talent. Getting it wrong can lead to frustration, missed opportunities, and—let’s be honest—disappointment on all sides.

I remember the early days of my business when we were trying to do everything—wearing multiple hats and juggling a million things at once. We needed everyone to wear multiple hats, but in hindsight, I realized some hires were premature. When you're in startup mode, you're moving fast, everything is chaotic, and sometimes it feels like you need all the expertise right now. But in reality, what you often need is someone who thrives in that chaos—a person who can roll up their sleeves, take on different tasks, and adapt quickly.

I’ve made the mistake of hiring someone who seemed perfect on paper—someone with years of experience, a strong resume, and leadership skills. But, here's the thing: our company was still figuring things out. We didn’t yet have the processes in place to allow for the kind of leadership this person needed to succeed. It wasn’t their fault at all, but they needed a stable, structured environment to thrive—something we just didn’t have at the time.

That mismatch created tension, led to frustration on both sides, and ultimately, we parted ways much sooner than I would have liked. It was an incredibly valuable lesson, but one I could have learned without the pain of that experience.

On the other hand, I've also seen the consequences of hiring too many junior people at the wrong time. When your business is ready to scale and you’ve outgrown that startup chaos, the reality is that you need more than just energy and enthusiasm—you need experience. More junior-level hires are great when you're still in the trenches, but when you reach that next stage, you need people who understand how to build scalable systems, who can mentor others, and who can lead initiatives without needing constant guidance.

So, how do we avoid these pitfalls? The answer is simple, but not always easy to implement:

1. Know Your Stage. Every business is different, and the timing of your hires should reflect where you are. Are you still in the rapid-testing phase, where flexibility and adaptability are key? Or are you starting to scale, where processes, leadership, and strategic thinking are essential? Understanding where you are in your journey will help you make the right hiring decisions.

2. Don’t Hire for the Job You Wish You Had. Early on, I found myself hiring for what I hoped we’d need six months down the road rather than what we needed in that exact moment. Hiring too far ahead of the curve can create an uncomfortable mismatch in expectations. Hire for the role and the challenges you are facing now, not just what you think you might face in the future.

3. Hire for Where You’re Going. That being said, you also want to make sure you’re thinking ahead. I’ve learned that the best hires are those who can see the future and help guide the company there. They need to have the right mindset and skills for what’s coming—not just what’s happening today. But again, timing is key. You don’t need an all-star team when you're still figuring things out, but as you scale, you need people who can step in and make those bigger moves.

4. Culture Fit Matters More Than You Think. I’ve learned that a strong cultural fit can be the difference between a new hire flourishing or floundering. Having the right skillset is important, but so is aligning with the company’s values, vision, and the current phase of the business. A culture mismatch can create tension, confusion, and even resentment—and that’s something no team needs.

5. Don’t Rush It. This is perhaps the most important lesson I’ve learned. It can feel like you need to hire someone immediately to fill that gap, but rushing can lead to costly mistakes. Take the time to hire thoughtfully and strategically. It’s far better to have a gap for a little longer than to hire someone who isn’t the right fit for your company’s needs at that moment.

At the end of the day, hiring is one of the most important decisions you’ll make for your business. The right person at the right time can accelerate your growth and help you tackle challenges you didn’t think were possible. The wrong hire, on the other hand, can slow you down and drain your resources.

If you’ve made a hire that didn’t work out or had a moment where the timing just didn’t line up, trust me, you’re not alone. The key is to learn from those experiences and continue refining your approach. It’s all part of the journey.

I’d love to hear about your experiences with hiring. Have you made any hiring mistakes you’ve learned from? What tips would you share with others in the same position? Drop me a note—I’m always up for a conversation.

To your continued success,
Angelo