The Authenticity Framework: How I Went From Disingenuous to Real
This is the tactical companion to A for Authentic. On Friday I wrote about how I embraced authenticity as a solo founder. Today I’m sharing the system I built to practice it.
After I botched my first pitch competition, I did what any desperate founder would do. I put 'How to be authentic as a founder' in ChatGPT. You know what I found? Nothing useful. The basic recommendations to 'be vulnerable' and 'show up as your true self.' But not one explaining how.
Then I stumbled on an article about founder communication that actually had tactical advice. I took that, mixed it with months of bad calls and awkward pitches, and built my own system. TLDR at the bottom!
Three steps. Nothing complicated. But doing them changed how I show up on every call, in every email, and at every event.
Step 1: The Self-Audit
Before you can be authentic with other people, you have to get clear with yourself. That sounds obvious but I skipped this step for months. The cost was that I kept defaulting to whatever sounded "professional" instead of whatever was true, because I hadn't done the work of figuring out what true actually sounded like in my own voice.
So I sat down and worked through three layers of questions. If you do nothing else from this post, just do this.
Layer 1: Your foundation
These are the questions about your relationship to the work. You need clear, honest answers to these before you get on any call or send any email.
How did I get here? Why does this problem feel personal to me? What part of this work energizes me, not what should energize me, but what actually does?
Write your answers in full sentences, not bullet points. You’ll hear the difference between what sounds true and what sounds rehearsed.
When I did this, I realized that the part of Shezaar that actually energized me wasn’t “solving fashion waste.” It was removing the inefficiencies in the current system of routing inventory to the right place at the right time. That’s a very different answer than the one I’d been giving people. And it was a much better one because I could talk about it for twenty minutes without running out of things to say.
Does this mean I stopped telling my origin story? Absolutely not. But getting clear on what actually drove me meant I had real substance to back the emotional story. The origin story opens the door. The specifics keep people in the room.
Layer 2: Your communication style
These questions are about how you like to show up.
How do I naturally communicate best: written, verbal, one-on-ones, groups? What conditions do I need to feel prepared? When have I communicated well and what was different about that moment?
This was the most revealing layer for me. I am a shy and reserved person. That’s not a flaw, but it is a fact. And once I named it, I could work with it instead of fighting it. I stopped trying to be the high-energy founder who can talk on the fly and started leaning into being the calm, specific, prepared one. That was more me. And people could tell.
The calls where I showed up as the quiet, well-researched person went ten times better than the calls where I tried to match someone else’s energy. It also allowed me to listen more and react better because I wasn’t consumed by performing. I was actually present.
I also learned that I communicate best one-on-one and in writing. So I stopped dreading networking events and started following up with people by email after, where I was sharper. That’s not avoiding authenticity. That’s knowing where yours lives.
Layer 3: Your edges
These are the harder questions. They’re about the fears and defense mechanisms that get in the way.
What am I afraid people will find out? What do I overcompensate for and why? When I hold back, what am I protecting?
You don’t have to share your answers to these with anyone. They’re for you. But I’ll share one of mine: I was afraid people would find out that I am a solo founder with zero background in fashion and retail. So I overcompensated by not asking the supposedly “dumb” questions, and that wasted an absurd amount of time during discovery. Weeks of confusion that a few honest questions would have solved.
Once I saw that pattern, I stopped. I started owning being the outsider. And what surprised me was just how many people were happy to answer my dumb questions. Eager, even. The shift was small but the difference in how people responded was enormous.
Step 2: The Pre-Call Prep
This was the single biggest unlock. I learned that confidence and authenticity come from the same place: preparation. When I know who I’m talking to, what I want, and what I can offer, I can just talk.
So, before every call, I answer three questions. Every single time. I keep them in a note on my phone and I fill them in fifteen minutes before the conversation starts.
→ What do I want to get out of this?
Be brutally specific. “I want it to go well” is not an answer. “I want to learn how they handle unsold inventory”, “I want an intro to their ops head”, or “I want to know if this person can connect me to the decision-maker” are.
Here’s why this matters for authenticity: when you don’t know what you want, you overshare. You fill the silence with information hoping something sticks. When you know exactly what you want, you can be selective and intentional about what you share because everything you say is in service of a clear outcome.
Early on I got on a call with a sustainability manager at a mid-size brand. I went in with a vague goal of “building a relationship.” I ended up spending 25 minutes explaining my entire business model, my vision for the circular economy, and my personal backstory. She was polite. But she was not the right person to talk to. If I’d gone in with a specific goal like “find out who handles inventory disposition and get an intro,” the call would have been ten minutes tops, more focused, and I would have actually gotten somewhere.
→ Who am I speaking to and what might they want?
Look them up. A quick LinkedIn search is table stakes! Check if they’ve posted or spoken about anything relevant. If they’ve written about a problem your product solves, mention it. If they’ve recently changed roles, acknowledge it. The more you know about them, the more you’ll have an actual conversation.
This also helps you calibrate your story. If you’re talking to an ops director who cares about logistics and unit economics, lead with that. If you’re talking to a founder who’s been through the same grind, you can be more personal.
I once cold-emailed a brand founder whose LinkedIn showed she’d spent ten years in supply chain before starting her label. Instead of leading with “we help brands reduce fashion waste” (the generic version), I wrote about the specific operational challenge of managing dead inventory across multiple sales channels. She replied in two hours. Just because I matched my message to what she cared about, and that made it authentic to the conversation, not just authentic to myself.
→ What is my ask?
One of my professors at Kellogg always said: you need to have an ask ready in case someone offers to help. I took that to heart. Every conversation should have an ask in your back pocket.
It doesn’t have to be big. “Could you intro me to your ops lead?” or “Would you be open to a 15-minute follow-up next week?” or “Can I send you a one-pager to share with your team?” are all fine. But if someone says “how can I help?” and you don’t have an answer, you’ve wasted the moment. I’ve watched it happen to other founders and I’ve done it myself. Someone offers to open a door and you freeze because you didn’t think about what door you needed opened.
Write your ask down before the conversation starts. Even if you don’t use it, having it ready changes how you carry yourself.
Step 3: Practice. There Is No Shortcut.
I want to be honest about this part because it’s the least satisfying advice and also the most important. There is no hack. Authenticity is a skill and skills require reps.
I got better with every rep. The first ten times were rough. I rambled. I over-explained. I used filler phrases like “basically” and “kind of” as shields. By the time I’d done it fifty times, my origin story came out the same way whether I was talking to an investor, a brand partner, or someone at a coffee shop who asked what I did.
That’s when I knew it was actually authentic. Not because I’d memorized it, but because I’d told it enough times that only the true parts survived. The filler fell away and what was left was the version that was real.
A few things that helped me get my reps in:
Talk to yourself. I’m serious. I practiced my pitch in the car, in the shower, on walks. Not reading from a script. Just talking, the way I would to a friend. The goal wasn’t perfection. The goal was finding the version that felt easy to say.
Record your calls (with permission). I started listening back to my Zoom recordings and it was painful but useful. I noticed patterns I couldn’t see in the moment. I said “kind of” eleven times in one 30-minute call. I noticed when I got nervous I would speed up and stack three ideas into one sentence. You can’t fix what you can’t see.
Debrief after every conversation. Not formally. Just one question in my head: Did I say anything that wasn’t true? If yes, I’d figure out why. Usually it was because I didn’t feel prepared enough, which meant the issue was Step 2. If no, I was on the right track, even if the call didn’t go the way I wanted.
You cannot think your way to authenticity. You have to practice your way there.
The quick reference TLDR
The Self-Audit (do this once, revisit quarterly)
Your foundation: How did I get here? Why is this personal? What actually energizes me?
Your style: How do I communicate best? What do I need to feel prepared? When have I been at my best and why?
Your edges: What am I afraid people will find out? What do I overcompensate for? When I hold back, what am I protecting?
Before any conversation (5 minutes, every time)
What do I want to get out of this? (Be specific.)
Who am I speaking to and what might they want?
What is my ask?
After the conversation
One question: Did I say anything that wasn’t true?
This is a tactical guide to the A to Z of Building Solo series. On Fridays I share the lesson. On Tuesdays (sometimes) I share how to use it.