A retro comic-book-style blog cover shows a sharp-suited professional using a laptop with a cartoon AI robot on the screen. The full blog title, “How I Built a Culture-First Hiring System Using AI,” is clearly visible on the left in bold, cream-colored letters over a starburst yellow background, with teal and navy halftone patterns adding texture and flair.

How I Built a Culture-First Hiring System Using AI

Business Growth & Real Estate
October 28, 2025•3 min read

Here’s the system I’ve created to protect and scale our culture while hiring. It’s not about removing the human element—far from it. It’s about amplifying discernment, reducing blind spots, and designing a repeatable process that aligns with how we work best.

🧠 Step 1: Train a Custom GPT on Our Cultural DNA

First, I built a custom GPT (a personalized version of ChatGPT) and loaded it with:

  • Our Cultural Blueprint: mission, vision, core values

  • Our Operations Manual: SOPs, internal workflows

  • The Personality Profiles of existing team members

This isn’t fluff. This is real documentation that reflects how we think, communicate, and execute as a team. The model learns what “fit” looks like—not just in theory, but in practice.

📄 Step 2: Draft Job Descriptions With Precision

Before I even post a role, I start by consulting the AI to craft the job description. It helps me clarify:

  • The actual outcomes we want this role to drive

  • The personality traits that align with our culture

  • The soft skills that matter in our team dynamic

Instead of just listing tasks, I write from a place of alignment and expectation—and the AI helps me see what I might be missing.

📥 Step 3: Use AI to Evaluate Resumes Against Our Culture

Once the resumes start coming in, I feed them into the GPT and ask:

  • Does this candidate’s experience suggest alignment with our values?

  • Are there gaps that might cause friction?

  • What’s worth digging into further?

It doesn’t replace my judgment. It sharpens it. The AI flags subtle cues I might overlook in the rush of day-to-day operations.

📞 Step 4: AI-Generated Interview Questions That Dig Deep

Once we select candidates for phone interviews, the GPT helps us generate customized interview questions based on the candidate’s resume and our culture map.

These aren’t generic “what’s your greatest weakness” questions. They’re probing, behavioral prompts designed to reveal:

  • How the candidate approaches conflict

  • How they handle ambiguity

  • How they align with our pace and communication style

We record these interviews (with permission), transcribe them, and feed the transcripts back into the model for analysis. The insights we get? Gold.

🧬 Step 5: Analyze Personality Fit and Craft Second-Round Interviews

For in-person interviews, we ask each candidate to complete a personality assessment—DISC, Kolbe, or something similar.

We feed those results into the GPT and ask:

  • Where are the potential points of friction with the team?

  • What coaching might this person need?

  • What follow-up questions should we ask to validate alignment?

We don’t use this to eliminate candidates. We use it to understand how they’re wired—and how we can set them (and the team) up for success.

🎯 Step 6: Personalized Onboarding Plans

Once we make a hire, the GPT helps us build a custom onboarding plan based on how that person learns best.

Fast processor who loves freedom? Give them the big picture and get out of the way.

Detail-oriented builder? Give them SOPs and structure early.

Verbal processor? Pair them with a team mentor for real-time dialogue.

This approach has radically improved our time-to-productivity and cultural cohesion.

The ROI of a Culture-First Hiring Process

Since implementing this system, here’s what we’ve seen:

  • Fewer mis-hires and costly resets

  • Faster ramp-up times for new team members

  • Higher morale across existing staff

  • Clearer alignment between role, person, and culture

It’s not magic. It’s intention, powered by the right tools.

I don’t use AI to replace human connection.

I use it to protect it—to ensure that the people we bring into the business strengthen the culture we’ve worked so hard to build.

Final Thought

Culture isn’t just a “vibe.” It’s a system.

And just like any other system in your business, it can be designed, protected, and scaled.

If you’ve been burned by bad hires or feel like your team dynamics are drifting, don’t just double down on intuition. Add some AI horsepower.

It’s not just smart. It’s leadership.

👉 Want to see how this AI hiring process could work in your business?

Comment “CULTURE” below or shoot me a DM. I’ll send over a free checklist of the exact prompts and tools I use in our process.

Let’s build teams that scale sustainably—without sacrificing soul.

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