The 2 Hiring Mistakes That Cost Me Everything

I've interviewed over +700 people in my career as a founder.

And I've made every hiring mistake you can imagine.

But two mistakes stand out as the most expensive, frustrating, and completely avoidable errors that nearly broke my companies.

Here's what happened, and how you can avoid making the same mistakes.

Mistake #1: Showing Up Exhausted and Asking Surface-Level Questions

Here's the brutal truth: I would show up to interviews already exhausted.

Running a company is draining. By the time I got to hiring, I had zero energy left for the deep work of actually evaluating people.

So I'd ask surface-level questions. If the answers sounded "good enough," I'd convince myself they were right for the role.

I was dead wrong.

They'd start the job and completely suck at it. Why? Because I never actually tested their skills or challenged them during the interview.

I was hiring based on how well people could talk about work, not how well they could actually do work.

The cost? Months of managing underperformers, redoing their work, and eventually firing them anyway.

Mistake #2: Letting Desperation Drive My Decisions

The second mistake was even worse: hiring out of desperation.

When I urgently needed to fill a role, I'd see red flags and ignore them. I'd tell myself "I need someone ASAP" and justify away obvious problems.

Those same red flags would then blow up in the company.

Other employees would see the problems first. They'd come to me and ask why the hell I hired that person.

And I wouldn't even be surprised! Because I saw the problems and chose to ignore them.

Now I had to find someone to fill that role AGAIN. Double the work, double the money, double the energy.

The Hidden Cost of Bad Hiring Decisions

Here's what no one tells you about hiring mistakes:

The financial cost is just the beginning.

Yes, each bad hire costs between $20,000 and $50,000 in lost wages, productivity, and team morale.

But the real cost is momentum. While you're managing problems, competitors are moving faster. While you're having difficult conversations, opportunities disappear.

Your A-players watch you tolerate mediocrity and start questioning your standards.

What I Learned: Test Real Tasks, Trust Your Gut

After years of expensive mistakes, I developed two non-negotiable rules:

Rule #1: Test Real Tasks in Your Interviews

Stop asking "Tell me about yourself" and start giving them actual problems to solve.

If they'll be writing code, have them write code. If they'll be managing people, give them a management scenario. If they'll be solving customer problems, present them with real customer issues.

Watch how they think, not how they talk.

Rule #2: Trust Your Gut When Something Feels Off

I don't know who needs to hear this, but TRUST YOUR GUT.

When you can't pinpoint exactly why someone doesn't feel right for your company, trust that feeling.

It doesn't matter if their resume is brilliant. It doesn't matter if you can't identify clear red flags.

That something that feels off to you now? It will show up again once they're inside your company.

Mark my words. And when it does, you'll be kicking yourself for ignoring what you already knew.

The System That Fixed Everything

After making these expensive mistakes over and over, I built a system:

Energy Management: I only interview when I'm sharp. If I'm exhausted, I reschedule. The cost of a bad hire is always higher than the cost of waiting one more day.

Skills Testing: Every interview includes real work. No exceptions. I want to see them solve actual problems they'd face in the role.

Red Flag Documentation: I write down concerns as they happen. I don't rationalize them away or hope they'll disappear.

Gut Check Protocol: If something feels wrong but I can't explain why, that's a no. My pattern recognition has processed thousands of signals my conscious mind missed.

Desperation Discipline: When I'm desperate to fill a role, that's exactly when I need to be most careful about my standards, not least careful.

The Two Questions That Change Everything

Want to separate good candidates from great ones? Ask these:

"Walk me through solving this real problem we're facing." (Give them an actual challenge from your business)

Ask for two previous boss references during the interview, then use this technique:

"Give me the names of your two most recent bosses. I'm going to call them for reference checks, so let's save time and see if we can design a plan to make this hire work."

"When I call [Boss #1], what are the three strengths they're going to tell me about you? And what are the three growth opportunities or areas for improvement they'll mention?"

"And when I call [Boss #2], what strengths will they highlight? What weaknesses or challenges will they bring up?"

Then ask: "Given that I'll be calling them later, let's just save time now - how do we address those growth areas to make you successful in this role?"

Why this works: Honest candidates give you real insights and show self-awareness. Dishonest ones panic or give vague answers because they know their references won't match their story.

Plus, you get a preview of exactly what the references will tell you before you even call.)

These reveal more about capability and character than hours of traditional interview questions.

Why Most Founders Keep Making These Mistakes

Because hiring well is hard work, and when you're already running a company, it's easier to take shortcuts.

But those shortcuts are killing your business.

Every hiring mistake cascades through your organization. Bad hires don't just underperform - they lower the bar for everyone else.

Meanwhile, great hires do the opposite. They raise standards, attract other A-players, and accelerate your growth.

The choice is yours: Keep gambling with hope, or start hiring with systems.

Final Reality Check

I turned my hiring disasters into a repeatable system that works.

The energy I wasted managing bad hires could have been spent growing the business. The money I lost on hiring mistakes could have funded real growth initiatives.

Don't make my mistakes. Learn from them instead.

Stop hiring based on exhaustion and desperation. Start testing real skills and trusting your instincts.

Your future self will thank you for the extra effort you put in today.

Ready to stop losing $20K+ on every bad hire?

I've taken everything I learned from 700+ interviews and turned it into the system my private coaching clients pay $3K-$5K to learn.

The Mastering Recruiting & Hiring course gives you the complete framework - from job postings to final decisions - that stops you from gambling and starts you hiring A-Players with confidence.

What you get:

• Complete hiring framework beyond CVs and interviews
• Real skills and culture testing (not HR theater)
• Founder's playbook from my experience scaling and exiting companies
• Step-by-step guide you can apply immediately
• Lifetime access to repeat and refine as you grow

Why this works: In 90 minutes, you'll learn a system that saves $20K-$50K on every bad hire you avoid. The ROI is immediate.

→ Get Instant Access - Start With Lesson 1 FREE

Learn the system that turns hiring mistakes into hiring wins.

- Ignacio

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