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When the Algorithm Picks a Human: The Unexpected Power of AI in Relationship Building

  • Writer: bradyux
    bradyux
  • May 1
  • 3 min read

Updated: May 6

How one AI-suggested meeting led to a powerful conversation on trust, growth, and building better habits.

Photograph of Josh Chernikoff seated at an orange table in front of a textured gray wall, wearing a black shirt and red wristband. Text on the image reads: “When the Algorithm Picks a Human – A conversation with Josh Chernikoff.” Brady UX logo appears in the corner.
This image (and blog post) were created with the help of ChatGPT — including the title, copy, and even this caption. The conversation, though? 100% real.

What happens when you let AI choose your next business meeting?

If you're imagining a calendar full of soulless “synergy” calls and LinkedIn pitches from people who treat connection like a numbers game, we get it.

But sometimes… it gets it right. We mean, really right.


A few weeks ago, we did something a little different.

We trained an AI on our entire LinkedIn network — feeding it context about our agency, our goals, our values, and the types of collaborations we’re looking for. Then we asked a simple but powerful question:

“Who should we be talking to?”

Out of thousands of names, one stood out: Josh Chernikoff. No fluffy explanation. Just a confident signal that this person aligns.

So we reached out. What followed was one of the most unexpectedly enriching conversations we’ve had all year.


🎙️ Meet Josh

Josh has a resume that reads like three lives in one:

  • Broadcast journalist turned Redskins insider (with real stories he can’t tell you)

  • Founder of a tutoring company that got “made” on NBC4

  • Serial builder of businesses that actually help people — now focused on coaching founders in the education space


He’s the kind of person who’s not afraid to admit he didn’t love college, but still found a way to thrive by listening, testing, and showing up better every day. You can feel it in the way he talks about his work. You can see it in the people he helps.

And he’s got this rare superpower: he makes sales sound like service.


🤖 From AI to IRL

It would’ve been easy to miss the opportunity. AI said, “talk to Josh.” 

That’s it. But we took the meeting, and something clicked.


As we shared our work at Brady UX — from UX strategy to design sprints for MedTech and EdTech — Josh started building right there on the call.


As we shared the work we’d done on 1st90 — an app designed to build habit and momentum in the first 90 days of onboarding — Josh started connecting dots out loud. You could almost see the idea forming in real-time.


It was one of those wait-a-minute moments — when someone starts to riff on a bigger opportunity they didn’t even plan to talk about. We won’t go into details here (with Josh’s permission, we’re keeping that one close to the chest), but it was the kind of spark that reminds you why real conversations still matter — even when AI initiates them.


And just like that, something sparked.

We didn’t pitch it.

He invented it.

We just held space for it to emerge.


🧠 Human-Centered, AI-Augmented

This wasn’t a sales call. This was what happens when you combine curiosity, clear values, and smart tools.

Josh helps people grow through honesty, repetition, and well-placed nudges. So do we.

And while AI may have opened the door, it was the human part that made it meaningful:

  • Josh talking about his daughter, and the business he hopes she’ll inherit

  • Olya sharing how her Home Depot checkout redesign lifted conversions by 23%

  • Stories of reinvention, failure, and doing things that feel a little scary — like showing up differently


💡 Lessons from the Call

  1. Let the AI help — but don’t let it lead the conversation. It’s a great connector, not a relationship builder.

  2. People remember how you make them think. Josh walked away from the call not with a sales pitch, but a new idea he couldn’t stop thinking about.

  3. The best partnerships don’t start with, “What do you need?” They start with, “What are you excited about?”


✨ The Bigger Why

We say this a lot at Brady UX:

We design tech people love to use.

But that love? It comes from conversations like this. The messy, spontaneous, full-of-laughter kind that remind you that people — not personas — are what make products succeed.

This post isn’t really about AI. It’s about what happens when you stop treating people like leads and start treating them like co-conspirators in something better.

And sometimes… your co-conspirator is just one algorithmic nudge away.


Want to connect?

We’re open to the unexpected.👉 bradyux.com/meet

 
 
 

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