My AI Assumed I Was a Man

If you had told me that one of my clearest moments about women in leadership would come from an AI making an assumption about my gender, I would have laughed.

Spoiler: I did laugh.
And then I opened I opened this document.

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I have what I would generously call a relationship with my AI tool.

And I mean that in the most professionally appropriate, deeply dependent way possible.

This tool knows things about me that many of my friends and colleagues don’t.

It has reviewed contracts with me late at night. It has helped me build job descriptions, stress-tested business plans, and pressure-checked financial projections. It has helped me navigate cross-border tax questions, plan international travel, calisthenics workout programming, and, I’m embarrassed to admit, served as a sounding board before I called an actual doctor.

It also knows what’s in my refrigerator.

We have history.

So when I started working with it to rebuild my website - refining my About Me, updating my coaching and consulting offerings, refreshing generally how I show up - I assumed it had a pretty clear picture of me.

We worked through my background: President & COO, Senior Vice President, boardroom experience, advising high-growth companies, coaching CEOs and executives.

The usual résumé highlights.

Then we moved into a section on speaking.

When it asked what topics I would want to cover, I listed a few: leadership, culture, alignment… and of course, women in leadership.

The response came back enthusiastic. Thoughtful. Well-structured.

It described how powerful this perspective would be.
How relevant. How differentiated.

From a man.

I paused.

Then I clarified - gently, because once again, we have a relationship - that I am, in fact, a woman.

And then I asked it a very direct question:

Why did you assume I was male? Give me an honest response.

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To its credit, it didn’t hedge.

The first thing it pointed to was my background - COO, President, boardrooms, advising companies, coaching Executives - it mapped, by default, to male.

It also acknowledged that bias directly.

Second, and in fairness, it pointed to my name “Max”, as reinforcing that assumption.

And then it said the part that mattered most:

It never asked.

Nothing in our conversation required it to know my gender. But it also never stayed neutral.

It simply filled in the blank.

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I want to be clear, this is not a story about AI being the villain.

The system wasn’t being malicious. It was doing what it’s designed to do, recognize patterns and fill gaps based on what it has seen before.

And those patterns reflect the world we’ve built.

A world where, historically, many of those roles - those titles, those rooms - have been predominantly occupied by men.

That reality shows up in data. And the data shows up in the outputs.

But what makes this moment worth paying attention to isn’t the technology.

It’s the mirror.

Because the same kind of pattern recognition doesn’t just live in algorithms. It shows up in how résumés are read, how speakers are selected, how leadership is perceived. Most of the time, it isn’t intentional. It’s automatic.

Which is exactly why it’s easy to miss.

And exactly why it matters.

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All that said, and if you know me - I laughed. And then I started writing.

Not because the moment was shocking, because it was clarifying.

It forced me to look more closely at how I describe my own work, and how much of it has historically been tied to titles rather than impact.

Over the past few weeks, I’ve been rebuilding my site with that in mind.

Simplifying. Refocusing. Creating space for the work I care most about - coaching, advising, and working directly with leaders navigating the real, often messy parts of growth.

Less about the roles I’ve held. More about the work I do now.

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This will likely become the story I open with now when I speak about women in leadership.

Not as a critique. But as a reflection.

AI is powerful - remarkably so. We certainly didn’t break-up.

But it is not neutral. Not yet.

And moments like this are a useful reminder of that, and of the assumptions we carry with us, often without realizing it.