Why I started NAVRYN: from a blank AI text box to a personality-aware coach
I was sitting in front of ChatGPT with a blank custom instructions box and no idea what to put in it.
AI had just introduced memory and custom instructions. The promise was clear: give it context about you and it'll give you better answers. But staring at that empty text field, I realised I didn't know where to start. Not because I'm not self-aware - I've spent 15 years leading product teams and thinking about how people work. But distilling "who I am" into a text box that an AI can use? That's a different problem entirely.
What do you put in there? Your job title? Your communication style? The fact that you avoid conflict but also hate when things aren't said directly? How do you describe the patterns that shape your decisions without writing a novel?
That question - what makes me me, and how do I give that to an AI - is what started everything.
The assessment came first
I went down a rabbit hole. Myers-Briggs, StrengthsFinder, HEXACO, Big Five, DISC, Enneagram - frameworks that each capture something real about personality but none of which give you the full picture on their own.
So I combined them. I took what's validated and useful across these popular frameworks and shaped them into a smaller set of questions. 78 questions that give you 11 different perspectives on who you are. That was the first version of what became NAVRYN - just a personality assessment and your scores.
I called it psych-portrayal then. It was rough. But it worked.
Thirty people and a problem
I got about 30 friends and colleagues to try it. The interest was real - people were genuinely fascinated by their results. Deep, multi-dimensional reads on how they think, work, and relate to others.
But then it just sat there. Scores on a screen. Not much you can do with that.
This is the part of product building I actually know: watching how people interact with what you've built and noticing where the energy drops. The assessment was interesting. The results were interesting. But there was no next step. No way to take what you'd learned and do something with it.
That's when I saw the intersection.
Where it clicked
What you know about yourself, combined with what you can give to AI, creates something neither can do alone.
Your personality data - structured, multi-framework, specific to you - fed into an AI coach that remembers every conversation? That's not a chatbot. That's a coach with context. It knows your tendencies, your blind spots, your patterns. It doesn't start from scratch every time you open it.
I built the first version of the AI coach directly into the assessment. When you finish your 78 questions, the coach already has everything it needs. And as you talk to it - about work frustrations, relationship dynamics, career decisions - it adds memory. It learns more. The conversations compound.
That was the moment NAVRYN stopped being a personality quiz and started being something I couldn't stop thinking about.
My sister found something I didn't expect
My sister was one of the early testers. She took the assessment, got her results, and then did something I hadn't planned for: she compared her results to her partner's.
The insights were immediate. Differences in how they process conflict. Complementary strengths neither of them had named. Patterns that explained arguments they'd been having for years - not because either of them was wrong, but because they were wired differently in ways they'd never articulated.
Were these things obvious in hindsight? Maybe. But they were below the surface. The kind of thing you sense but can't name. Having it laid out clearly - here's what's different about the two of you, here's what that causes, here's what's complementary - that was something neither of them had access to before.
I turned that into a feature called Dynamic Duo. You can compare your personality profile with anyone - a partner, a colleague, your boss. It's free, and I think it's one of the most powerful things in the product.
The coaching gap is personal
Here's something I don't usually lead with: I've never had an executive coach.
For most of my career, coaching was something that happened to other people. Senior executives with budgets. High-performers flagged for succession planning. It was expensive, exclusive, and far out of reach.
I've developed a lot of self-awareness over the years - through experience, through mistakes, through leading teams. But I know plenty of smart people who haven't had that exposure. People who would benefit enormously from a good coach but will never get one because it costs $300–500 an hour and requires scheduling weeks in advance.
What if coaching didn't require any of that? What if you had someone available at 11pm on a Tuesday when you're spiralling about a decision? Someone who knows your patterns, remembers what you said last month, and can point out what you're not seeing?
That's not a replacement for human coaching. It's access to something most people have never had at all.
Teams made it harder - and better
Something kept bothering me: those 30 early users all took the assessment individually. But so much of how we work is relational. Team dynamics. How you and your manager clash. Why meetings with certain colleagues drain you and others energise you.
The cost of traditional team exercises - spending a day or two learning whether you're "red" or "green" - puts real team understanding out of reach for most organisations. I wanted to change that.
Adding team functionality was the hardest thing I've built. Workspaces, members, seats, invitations, permissions - the product complexity jumped significantly when it wasn't just about one person anymore. I wasn't prepared for how much that changed the architecture.
But when it came together, the value was obvious. When an AI coach has context on an entire team - not just your personality but how you relate to each person around you - the guidance gets remarkably specific. Not generic team-building advice. Actual insight into why you and Sarah keep misaligning on priorities, and what to do about it.
Where it stands today
NAVRYN has four core pieces:
- The assessment - 78 questions, 11 personality perspectives, your Personal Map
- The AI coach - persistent memory, personality-aware, available anytime
- Dynamic Duo - compare yourself with anyone and see what's driving your interactions
- Teams Map - team-level dynamics, complementary strengths, friction points
I'm not going to pretend it's finished. It's a product I'm actively building, mostly in the evenings and on weekends, and I need people to try it and tell me what works and what doesn't.
But I believe the core idea is right: the quality of AI coaching is directly proportional to the quality of context you give it. And structured self-knowledge is the best context there is.
If you've ever stared at that blank custom instructions box and wondered what to put in it - that's exactly why this exists.
I'm Cameron Bailey - product builder, founder of NAVRYN. I write about AI coaching, building products, and the things I'm learning along the way. If any of this resonated, try the assessment at navryn.com - it takes about 15 minutes.