Youβre reading The Messy Middle: weekly deep dives on leadership, startups, identity, politics, and how to make high stakes decisions that are intentional and in-line with your values.
π§ The Best CEO I Ever Worked For
The best CEO I've ever worked for started every Monday morning company meeting with a personal story. Of course, he would share a company update and KPI recap after, but he'd always anchor the time together on a story, sometimes from his personal life, sometimes from his career.
I remember thinking it was strange at first. I'd come from a super corporate finance background, and I'd never been around a leader who shared his own vulnerabilities like that. He'd pull up photos of himself playing baseball as a kid and put them on the company Zoom, in front of the whole org, before he mentioned a single number.
I was a few layers removed from him, but over time, I felt like I knew him. And when he eventually did talk about the business, how decisions were getting made in a tough job market, where things stood with some tricky clients, and where we were headed next, I trusted that he could navigate us through whatever came through. I wasn't just hearing an update through a Zoom screen, but I was hearing it from someone who had earned my trust, even though we'd barely spoken.
β¨ Impressive Isn't The Same As Memorable
Some of you may be absolutely cringing, and still thinking that this is a little much for a company meeting. Not every leader has the personality for it, and not every culture would welcome it. There's a real risk of storytelling reading as performative, or maybe even a little narcissistic, if it's done badly.
And I think that's part of why so many executives default to the opposite.
Most leaders think staying polished and maybe even distant is what maintains their credibility. So when someone gets promoted into leading a team, they lead with this same 'resume' version of themselves: the title, the results, the trajectory. Based on what most of us have seen and been taught, that's not the wrong instinct. But being impressive isn't the same as being memorable, and neither is the same as being trusted.
The leaders who actually earn buy-in and trust are the ones who let something real show, and storytelling is the way they do this. They share decisions that scared them, or a moment where the stakes were high and they didn't handle it perfectly. When you strip away the story and talk only about the outcomes, you're left with credentials. Credentials may establish your authority, but stories are what help people understand who you are, what you value, and why they should follow you.
The Association for Talent Development recently called 2026 βthe year of leadership storytelling,β pointing to research suggesting that stories can increase interest and willingness to act by 261 percent. Yup, you read that right. The same research suggests that people who feel inspired in the workplace show up twice as engaged.
π§ Stories Change How People Hear You
Stories don't just make people more interested in what you're saying, they change how people hear everything else you have to say. Think about how differently we receive information depending on who it's coming from.
β‘οΈ A difficult decision can feel considered or careless.
β‘οΈ A change in strategy can feel intentional or chaotic.
β‘οΈ A big vision can feel inspiring or completely detached from reality.
The information matters, but we're also making judgments about the person delivering it: Do I trust how this person thinks? Do I understand what they value?
That's what good storytelling gives a leader that credentials alone can't: context for how you think, what shaped you, and why you see the world the way you do. Stories allow you to give your listeners not just something interesting and memorable, but also a lens through which to view your decision-making.
And that matters because so much of leadership is asking people to follow you before you can prove that you're right. You're asking them to believe in a strategy that hasn't worked yet, navigate a change they didn't ask for, or make decisions with incomplete information. How people receive the message is inseparable from how they understand the person delivering it.
You already have stories. The question is whether you know which ones help people understand you, and how to tell them when it matters. If you want to become the kind of leader people don't just listen to, but actually hear, let's work on it together.
π Catch Me In Action
Busy week over here! If you want to catch some of this work in action, Iβve got three chances to connect IRL and virtually over the next few days.
π€ [TONIGHT] Wed, Aug 19 | ACE NextGen SoCal β Turning Your Business Story Into Your Best Sales Tool
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I'm leading a hands-on workshop for business owners on turning the stories already inside their businesses into better pitches, content, and sales conversations. [Join me in LA β]β
β [TOMORROW] Thu, Aug 20 | Kismet Coffee Hour β How to Build Trust In An Uncertain Job Marketβ
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A conversation for senior leaders on creating trust and stability for your team when you might not know how things are going to shake out. [Join us virtually β]β
πΈ [NEXT WEEK] Wed, Aug 26 | PurposeBuilt100 β Capital As Activismβ
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I'll be speaking about how where we put our money shapes the future we build, and what that means for which founders, companies, communities, and ideas get the resources to grow. [Tune in virtually β]β
π₯¨ Snacks
π€ A Reframe: The shift from being fearful to becoming a problem-solver just requires this.
π€ AI Pet Peeve: I spend a lot of time reading AI-assisted writing these days, and these 5 giveaways are driving me absolutely nuts. See if you notice them too.
π I'm Thinking About: Why do AI executives keep quitting? And what does that tell us about what's actually happening inside these companies?
See you in next week's mess,
Arshiya
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