Why Hiring Sucks: 5 Things I Learned the Hard Way

I still remember the sweat on my palms before my first-ever interview... as the interviewer. I was a young founder, my company was just three people in a cramped office, and we desperately needed a fourth. I thought, "How hard can this be? I'll just find someone smart who can do the work." Oh, the sweet, naive optimism of my younger self.

That first hire was a disaster. Not because they were a bad person, but because I was a bad hirer. I didn't know what I was doing. Hiring isn't just about filling a seat; it's about building a team, shaping your culture, and betting a significant chunk of your limited cash on a person. Get it right, and you accelerate. Get it wrong, and you can set your company back months, or even kill it. After a decade of building teams, I've learned that while hiring never gets easy, it can get smarter. Here are the five hard-won lessons I wish I knew from day one.

1. The Job Description is a Blueprint, Not a Wish List

My first job description was a masterpiece of delusion. It asked for 10 years of experience for an entry-level salary, mastery of five different coding languages (including one I'd just heard of), and the communication skills of a UN diplomat. I was looking for a unicorn. The result? Crickets. The few candidates I got were wildly unqualified or justifiably terrified.

The Lesson: A job description is a blueprint for a role, not a fantasy wish list. Its job is to attract the right people and filter out the clearly wrong ones. Ditch the jargon and focus on three key areas:

• Must-Haves: The 3-4 non-negotiable skills or experiences needed to do the job on day one.
• Nice-to-Haves: Skills that would be a bonus but can be learned on the job.
• Outcomes: What will this person be expected to achieve in their first 3, 6, and 12 months? Focus on impact, not just tasks.

Here’s how that looks in practice for, say, a Junior Marketing Manager role:

2. Cultural Fit Isn't About 'Hiring People Like Me'

I used to think "cultural fit" meant finding someone I'd want to grab a beer with. This led me to hire people who looked like me, thought like me, and agreed with me. We had a great time at lunch, but we also had massive blind spots. We created an echo chamber, not a dynamic team.

The Lesson: True cultural fit is about shared values, not shared backgrounds or personalities. Instead of "culture fit," start thinking about "culture add."

Culture Fit asks: "Will this person assimilate into our current team?"
Culture Add asks: "What new perspective, skills, or energy will this person bring to our team?"

Focus on your core company values (e.g., radical transparency, customer obsession, bias for action) and ask behavioral questions to see if a candidate’s past actions align with those values. A diverse team with shared values will always outperform a homogenous one.

3. The Interview is a Two-Way Street (And They're Interviewing You, Too)

Early on, I treated interviews like an interrogation. I'd grill candidates with brain teasers and "gotcha" questions, trying to prove how smart I was. I was so focused on whether I wanted them that I never stopped to think if they would want to work for us. Unsurprisingly, the best candidates often politely declined my offers.

The Lesson: The interview is a conversation, not a test. Yes, you need to evaluate their skills and experience. But you also need to sell them on your vision, your company, and the opportunity. Top talent has options. They are assessing you just as much as you are assessing them. Be prepared to answer tough questions about your business model, your leadership style, and the company's future. Be honest about the challenges. The best candidates aren't looking for a perfect company; they're looking for an exciting problem to solve with people they can trust.

4. Onboarding is More Important Than the Offer Letter

You did it! You found the perfect candidate, they accepted the offer, and you breathed a sigh of relief. The hard part is over, right? Wrong. The hiring process doesn't end when the contract is signed. It ends after the first 90 days. My first few hires were met with a laptop, a password, and a vague "let me know if you have questions." It was a recipe for confusion, anxiety, and low productivity.

The Lesson: A structured onboarding plan is one of the highest-leverage activities you can do. It turns an anxious new hire into a confident, contributing team member. It doesn't have to be complicated. A simple 30-60-90 day plan works wonders:

• First 30 Days: Learning & Listening. Focus on systems, people, and processes. Schedule meet-and-greets. Assign a buddy. Set up small, achievable wins to build confidence.
• First 60 Days: Contributing & Collaborating. The new hire should start taking ownership of smaller projects and contributing more actively in meetings. Start integrating them into key workflows.
• First 90 Days: Owning & Driving. They should now be fully integrated, taking initiative, and driving their core responsibilities with minimal supervision. Check in on progress against their initial goals.

5. Gut Feeling is a Guide, Not a Decision-Maker

"I just have a really good feeling about this person." I've said it. You've probably said it. And sometimes, that gut feeling is right. But relying on it alone is a dangerous, bias-ridden trap. Our "gut" is often just a subconscious reaction based on familiarity, which is why it often leads us to hire people who are just like us (see point #2).

The Lesson: Use your gut feeling as a signal to dig deeper, not as the final verdict. You need a structured, consistent process to validate (or invalidate) that feeling.

1. Use a Scorecard: Define the key attributes for the role before you start interviewing and score every candidate against the same criteria. This forces objectivity.
2. Ask Behavioral Questions: Instead of "Are you a team player?" ask "Tell me about a time you had a conflict with a teammate. How did you handle it?" Past behavior is the best predictor of future behavior.
3. Conduct Thorough Reference Checks: Don't just ask if they'd rehire them. Ask specific questions related to the scorecard attributes you're testing for. "Can you give me an example of how they handled a tight deadline with changing requirements?"

Conclusion: Make Hiring Suck Less

Hiring will probably always "suck" in some way. It’s high-stakes, time-consuming, and emotionally draining. But it’s also the most critical lever you have for building a great company. By shifting your mindset from filling a seat to building a team, from seeking unicorns to creating blueprints, and from testing candidates to having conversations, you can turn a painful process into a powerful strategic advantage. The goal isn't to never make a hiring mistake again—that's impossible. The goal is to learn from every single one.