I didn’t expect to be writing an article with the word “boobs” in the title, writes Katie Moss, chief executive of Otium Concierge.
But then again, I didn’t expect “Are your boobs real?” to be the FIRST thing said to me on my first day in private banking.
No handshake. No tour of the building. Just:
“Are your boobs real?”
It’s a moment I’ll never forget.
Partly because it was mortifying, partly because everyone else just carried on.
No one blinked. No one pulled him aside. The room kept moving, and I was left standing there, wondering what universe I’d just stepped into.
Run your own IT-led biz as a woman? No power play necessary
Today, I run Otium Concierge, a premium lifestyle and business concierge service that helps busy people get their time back. We sort the chaos, so you don’t have to — without inappropriate questions or power plays!
But before I could build my own tech-enabled business based on clarity, trust and decency, I had to learn a few things the hard way.
And I know I’m not alone.
So, here’s what I’ve seen, what I’ve learned, and what I wish someone had told me before I ever put on my first work lanyard.
Inappropriate questions: Top 5 considerations, and realities
1. Not all 'banter' is harmless
Reality check: If someone makes a comment that leaves you smiling on the outside and spiralling on the inside, that’s not banter. That’s boundary-crossing dressed up in a joke.
What women in tech can do:
- Call it what it is. “That’s not appropriate” is enough. You don’t have to give a TED Talk on the patriarchy.
- If it’s a pattern, log it. Keep a record. Your notes might not feel useful today, but they could be vital tomorrow.
- Don’t feel obliged to ‘play along’ to keep the peace. The peace that costs your dignity is too expensive.
2. The Line Moves… but only for you
Here’s the trickiest part:
You’ll be told to lighten up. Then, in the same breath, told to be more professional.
You’ll be encouraged to “speak up”… but penalised if you do.
You’ll be praised for being confident, right before being labelled as “Too Much.”
What to do as a woman in tech:
- Decide what YOUR standards are. Stick to them.
- Learn how to say “No” without explaining. Boundaries don’t need justification.
- If someone doesn’t like the line you’ve drawn, that’s not a signal to move it. That’s your sign they’re not safe.
3. Compliments can be a weapon too
“You look nice today” sounds sweet until it’s followed by “…for a techie.”
Or “…makes a change.”
Or “…but are those heels allowed?”
What a woman in tech on the receiving end can do:
- Don’t feel rude for shutting it down. A simple “Let’s keep this professional” does more than you might think.
- If humour’s your armour, try: “Next time, I’ll bring a glittery evaluation form for my outfit. Until then, shall we focus on the project?”
You don’t owe anyone comfort at your own expense. Full stop.
4. If you stay silent, you don’t stay safe
A hard truth I’ve learned — not speaking up doesn’t always protect you.
Sometimes it just PROLONGS the nonsense.
Top tips for women in tech:
- Speak up early, before it becomes the ‘norm.’
- Find allies. Ideally ones who don’t just nod, but step in.
- And if you’ve already let something slide for too long? It’s not too late. The conversation you’re scared to have is probably the one you need the most.
5. The power of building your own table
There’s something wildly liberating about leaving a space that didn’t value you, and building your own.
That’s what I did by launching my own technology-facilitated business.
I took the lessons (and the sheer frustration) from years of awkward encounters, bruised confidence and invisible ceilings — and channelled them into a company that respects time, boundaries and people.
Underrepresented in a meeting, remember -- it’s not you; it’s definitely them
If you’ve ever sat in a meeting and thought, “Is this really happening?”
If you’ve laughed at something just to get through it.
If you’ve spent hours replaying a moment wondering if you were “too sensitive”… here’s your permission to stop.
You’re not imagining it.
You’re not overreacting.
And you’re not alone.
Finally, my three ‘Ks’
Keep showing up. Keep doing the work. Keep doing what’s truthful or right by you.
And with the latter tip in mind, if I hear “Are your boobs real?” again, I’ll be ready. “Yep… and so is my ambition. Shall we move on?”
Katie Moss
Katie Moss is CEO of Otium Concierge, delivering premium lifestyle support to busy professionals and families. With a background in banking and over 10 years in business, she blends strategic leadership with operational excellence. Her expertise spans concierge services, client experience, and high-performing team development. Katie also champions work-life balance and values-led leadership.
