๐ฐ The Dreaded Question
A client was recently promoted to Director of Client Relationships. One of her first business lunches in her new role brought her to a 1:1 conversation with a 60-year-old man from a legacy family in the South...the kind of person whose network can open doors for her and her organization, beyond what we can probably imagine.
She had done her research, and had a slew of amazing questions to guide the conversation. She felt great...until her client asked her the ONE question that unravels her poise every single time: Tell me about yourself.
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Her armor of keeping the focus on other people crumbled immediately.
โ๏ธ This Week In The Mess
If you're new here, welcome!
This is The Messy Middle, a newsletter about the leadership journey no one tells you about. I'm Arshiya Kherani, an executive and founder coach & speaker, and I write about the things most people skip in professional spaces: identity shifts and what it actually takes to lead with intention when the path isn't always clear.
This week, we'll explore telling your story through the lens of where you're going, instead of where you've been.
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When Everything Is Going...Right?
My client, let's call her A, is a daughter of the diaspora, and she wondered how to talk about the realities of her life with colleagues who had significantly different lifestyles.
For example, she'd casually mention parts of life to colleagues that felt normal to her as a first-gen immigrant, like living in a multi-generational household as a financially independent woman in her 30s, not drinking, and having family responsibilities that took up her weekends...only to be met with looks of surprise that made her feel isolated instead of more connected.
Here's what's interesting about A: she's already good at her job, and her promotion proves it. She didn't want to work with me because something was going wrong, but actually because it was all going right. She's already in the right rooms and is well-respected at her firm, but she hadn't imagined what it would actually feel like once she got to this point in her career.
As A grows into bigger and bigger relationship-building roles, she's wrestling with something internal that she didn't anticipate: how do you create authentic professional connections that are true to your experience, without feeling like you're Othering yourself every time you open up?
This is where I come in.
๐ก A Different Kind Of Tired
The classic "Tell me about yourself" question is unnerving because it's so damn broad. Where do you even start? Your most recent role? Your family? Where you grew up? Are they asking for a resume walkthrough, or something more personal?
Most people default to starting with something in their past, or maybe a current role, a title they hold, or a snapshot of their resume in talking form.
None of this is wrong, per se, but for someone like A, who carries intersectional identities into every room, it can feel like wearing a costume. She's spent nearly two decades in corporate spaces code-switching, deflecting personal questions, and carefully managing which parts of her story she lets people see.
And it's exhausting. She's now experiencing the kind of tired you don't notice until you're sitting across from someone at lunch, being asked a question that feels like it should be easy, and realizing you don't actually know how to answer it as yourself anymore.
โจ The Reframe
I've always wondered: what do people actually want to know when they ask "tell me about yourself"? And more importantly, how do you make it work in your favor instead of against you?
What if you answered this question not with where you've been, but with where you're going?
I've developed a 4-part framework that I use with clients to completely change how they introduce themselves. When you can anchor your introduction with your vision for the future and what lights you up, the conversation stops feeling like an interview and starts feeling like an invitation. You're not just reciting a background, but instead, you're inviting someone into your world and your worldview. If something you're sharing resonates with them, the personal details that come up later land completely differently.
For someone like A, that makes all the difference.
Instead of mentioning her family responsibilities or her lifestyle and watching someone's face do the math, she can choose to introduce those details after someone already knows what she cares about, and why. Shared values, established early, create a neutral foundation to build from. And context makes you relatable instead of the other.
You still get to reference where you've been, but with more control on the narrative. And the person across the table doesn't just remember you, their first impression of you is anchored in the world you're creating.
That's the power of storytelling at work: a question that's scarily broad becomes a blank canvas. You get to break both the pattern of your own thoughts, and sometimes what people even expect of you entirely.
โ๏ธ Your Introduction Is Waiting
Do you see yourself in A's story? I'd love to walk you through the 4-part framework I use with clients to introduce themselves with confidence in a 90-minute Power Session designed exactly for this.
๐ฅจ Snacks
โ Save The Date: Building a portfolio career? Join me for this FREE roundtable on how to talk about it on May 28th.โ
๐ฎโ๐จ This Week In The News: Billionaires are apparently feeling like a marginalized group...Jacobin has thoughts.
๐ The Only Debate That Matters: Rice cooker or stovetop?
๐ Worth Knowing: Black employees experience less workplace stress when they have more autonomy. File this under: things that make sense.
See you next week,
Arshiya
๐ PS: thanks for your patience on the late send this week! I was traveling yesterday and didn't get to proof it in time! I'll be back on Wednesday next week, as usual.
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