“Even dream jobs are meant to be outgrown”
-Nabeela
You’ve made it to the top of your field. You work for one of those iconic companies—the kind that people clamor to get into. The company is well-loved, the leadership is respected, and on paper, everything looks perfect. Yet here you are, contemplating your next move.
Maybe you’ve outgrown the place.
That’s exactly where a senior executive I know found herself recently. She had spent her entire career climbing to an executive role at a company people dream of working for. But after years of the same leadership, slow processes, and diminishing opportunities, she knew it was time for something new.
So, she began her search, casually at first. Interviews came, but so did the rejections. The roadblock? A deceptively simple question:
Why are you leaving your current employer?
Recruiters and interviewers couldn’t wrap their heads around her desire to leave. It didn’t make sense to them—why leave a company that’s so prestigious, so beloved? And the executive, despite her deep expertise, wasn’t sure how to answer. She felt stuck. That’s when she reached out to me.
The Perception Problem: Why Prestige Can Be a Trap
From the outside looking in, success at a top-tier company should be enough. The cachet of a high-profile employer gives you credibility, network access, and opportunities most people can only imagine. However, external success doesn’t always align with your internal experience.
I’ve seen it happen to countless high-performing leaders. They stay in roles long after their curiosity and ambition have been dulled by slow-moving bureaucracy or stale leadership structures. The result? They outgrow the role—but have trouble articulating that growth in a way that others understand.
That’s where this executive was. People assumed that leaving a "dream" company meant she was unhappy or that something was deeply wrong. But her reasons were subtler and more nuanced. She wanted a faster pace, new challenges, and fresh perspectives. The problem was explaining this without sounding like she was complaining or burning bridges.
Step One: Focus on Where You’re Going, Not Where You’ve Been
The first piece of advice I gave her was to shift her mindset entirely. In interviews, it’s tempting to explain what’s not working at your current company. But that can backfire. Employers don’t want to hear a laundry list of grievances. Instead, you need to lead with where you’re going and why the new role excites you.
In her case, she wasn’t running from her current role—she was running toward something better. She wanted a culture that valued agility, where decisions weren’t bogged down by layers of approval. That’s what she needed to emphasize: the opportunities she saw at the new company, not the frustrations of her current one.
This kind of positive framing can make all the difference. It shifts the conversation from “why are you leaving” to “what’s driving you forward?” And that’s a much more compelling narrative.
Step Two: Create a Common Thread
Next, we focused on crafting a career story that connected her past experiences with her future aspirations. It’s not enough to say you want a new challenge. You have to show potential employers how your skills, values, and leadership style align with their goals.
For this executive, the common thread in her career was connection. She had worked in both the food and beverage and retail industries, always striving to create meaningful experiences that brought people together. Whether she was building talent pipelines or driving organizational culture, her work centered on fostering connection.
We used that theme to bridge the gap between her current role and the one she was pursuing. She spoke about how she could help the new company strengthen its internal and external relationships in ways that aligned with its mission and values.
By creating this narrative thread, she could turn the interview into a conversation about shared goals and future potential rather than a defense of why she wanted to leave.
Step Three: Frame Challenges Constructively
Of course, not every recruiter will drop the question of why you’re leaving. Some want a direct answer. But even then, you have to be strategic. No one wants to hear a tirade about poor leadership or bureaucracy. Yet honesty is important too. The key is to balance candor with professionalism.
I advised the executive to reframe her frustrations in terms of growth. Instead of saying, "The company is too bureaucratic," she could explain:
"I’ve gained valuable experience working within a highly structured organization, but now I’m eager to bring those skills to an environment where I can have a more immediate impact."
This approach acknowledges the challenge without sounding critical or bitter. It also reinforces the narrative of seeking growth rather than fleeing a bad situation.
Step Four: Prepare Like You’re Pitching an Investor
Finally, we tackled her interview preparation. For someone so senior, her preparation was... underwhelming. When I asked how she prepared for interviews, she admitted it was mostly surface-level research—visiting the company website, scanning a few news articles.
That wasn’t going to cut it.
I told her to consider the interview a high-stakes pitch to an investor. Imagine you’re asking someone to invest $300,000+ in you—that’s the equivalent of a senior leader’s base salary. How much preparation would you do for that meeting?
This reframing clicked for her. I asked whether she’d read the company’s ESG reports from the past three years. She hadn’t. Had she dug into their 10K filings to understand their business model and financials? No. Did she have Google alerts set to track the company’s press releases and news? Also no.
I explained that these steps are non-negotiable for a senior leader. You need to know the company’s strategy, challenges, and leadership inside and out. The more prepared you are, the more confidently you can articulate your value in the context of their business.
The Power of Intentional Career Growth
Leaving a prestigious company isn’t a failure; it’s a sign of growth.
Careers are dynamic, and the roles that once fueled your ambition won’t always fit forever. What matters is how you navigate that transition.
By focusing on your future, crafting a cohesive narrative, framing challenges with grace, and doing deep research, you can position yourself for success. And in the process, you’ll remind recruiters and hiring managers of an important truth: even dream jobs are meant to be outgrown.
Until next time, take care of yourselves and those around you.
In Partnership,
Nabeela
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