7 Career Questions Retail Leaders Are Asking (and Not Always Out Loud)

What do I say in a reorg? Am I burnt out or just tired? Why does self-promotion still feel awkward?

Sometimes the hardest part of career growth isn’t the challenge itself. It’s admitting you’re facing one. That hesitation is common, especially when the questions feel vulnerable or off-script.

Retail AMAze was created to make space for those conversations. The ones we’re often too shy, too senior, or too unsure to say out loud.

In the latest episode of Retail AMAze, we invited executive coach Kate Sargent to answer anonymous career questions submitted by retail leaders across the industry.

Kate brings two decades of experience as a coach, consultant, and Fractional Chief People Officer. She’s helped leaders at Apple, The North Face, Allbirds, and dozens of fast-growing brands navigate change, build confidence, and design careers that actually fit.

Hosted by YOOBIC’s Kristin Sgroi, this 60-minute live session tackled some of the most quietly complicated moments in a retail career — from navigating reorgs to managing visibility, uncertainty, and feedback. If you missed the event, here are seven themes that struck a chord, and what Kate had to say about each.

1. "I've  hit all my targets but I still feel like I’m invisible to HQ — what can I do to change that?"

In retail, dependability can become a double-edged sword. When you're the person who always delivers, it's easy to be seen as reliable, but not remarkable.

It takes an emotional toll to be the dependable one who never quite gets noticed. Kate's advice? Don’t assume your hard work speaks for itself — you need to be your own best PR.

“We think our work should speak for itself, and it doesn’t. It just doesn’t. You have to be your own storyteller.”

She suggests starting with visibility-building habits: volunteer for cross-functional projects, show your impact through storytelling, and get comfortable saying not just what you did, but why it mattered.

Kate also reminds us that it’s not just about what changed, but how it was experienced. She offers strategies to process your reaction, regain clarity, and set a forward-looking plan.

2. "How can I be a good leader when I still feel like I’m catching up?"

It’s a familiar feeling for anyone who’s been promoted quickly or thrown into change: leading a team while quietly questioning whether you’re ready. That uncertainty can feel like a secret you’re supposed to hide, but what if it’s actually something most leaders are carrying, too?

Nobody expects you to know exactly what you’re doing all the time. Even experienced leaders often feel like they’re learning on the job. The difference is how openly they communicate what they know, what they don’t, and what they’re still figuring out.

Kate reminds us that leadership isn’t about having all the answers. It’s about building trust through small, steady moments.

“We’re leading through fog right now, not blue skies. That means confidence looks different — it’s not about knowing everything, it’s about being steady in uncertainty.”

3. "I keep hearing I’m overqualified and I’m not getting callbacks. What’s happening here?"

It can be tempting to apply for roles you're overqualified for, especially when you just want to land something fast. But those roles often aren’t the right fit, and deep down, you know it. You’re not making it easier for yourself. You’re just making it harder to be seen for what you actually want to do.

Kate breaks down how "overqualified" is often a polite way of saying "you’re not quite what we’re looking for." It’s less about capability and more about alignment. She encourages candidates to be clear and intentional about the story they’re telling — on LinkedIn, in their résumé, and in their networking conversations.

“You’re not telling the story that matches the role you want. If they can’t see how you fit, they’ll assume you don’t.”

Her advice? Go after the roles that actually fit. And tell your story in a way that shows not just what you’ve done, but why it matters for where you’re headed.

4. "I’ve been told I need to be more strategic. What does that mean?"

You might be getting feedback as vague as this, without a clear sense of what to do next. "Be more strategic" sounds important, but what does it actually mean in your role?

Kate helps unpack that. She explains that this kind of feedback is often a catch-all for wanting broader thinking or more proactive planning, but it rarely comes with examples. Her advice? Ask for specifics. What would strategic look like in your day-to-day? Where does your work intersect with bigger decisions?

Kate also explains what it might mean to actually be strategic. Are you being reactive instead of proactive? Are you diving into tactics before stepping back to see the broader goals? Are you communicating your strategic thinking clearly to the people who need to hear it?

“Strategic doesn’t mean complicated. It means connecting the dots — showing you understand how your work moves the bigger picture.”

5. "How do I ask for constructive feedback without looking needy?"

Positive feedback is reassuring. It lets you know you’re appreciated, that you’re doing well. But when it comes to growth, it’s often not enough.

Kate explains that constructive feedback is vital for development, and that asking for it isn’t a weakness, it’s a leadership skill. Her take? You need to create ongoing permission for feedback. Make it part of your vocabulary. Normalize asking for input and offering it in return.

“The best leaders I know are constantly asking, ‘What am I missing?’ They build feedback into their rhythm — not just when something goes wrong.”

Why do we think asking for feedback makes us look needy? Kate argues it’s one of the most mature and underused tools a leader can have.

6. "How do I balance transparency without causing too much panic with my team?"

With new tariffs and sweeping operational changes, staff across the U.S. are asking for clarity. The challenge? So are their leaders. Everyone’s trying to make sense of things in real time, and that creates an ongoing transparency gap.

Kate suggests doing what she calls a bit of calming. You may not have all the answers, but you can still offer structure. Share what you do know. Communicate consistently. 

“You don’t need to have the full picture to communicate clearly. Say what you know, share what’s stable, and let people know when more is coming.”

If you're still working on a solution, say that. And don’t fill the silence with speculation, especially if you're in a leadership role.

Transparency doesn't mean a full download of everything you're thinking. It means giving enough to reassure and orient your team, even when things are still in motion.

7. "How do I deal with these constant reorgs?"

Reorgs can be disorienting. They disrupt your pace, leave you second-guessing your role, and create a constant cycle of resetting expectations. If you’ve found yourself reintroducing who you are and what you do every few months, you’re not alone.

Kate offers a powerful reframe: your boss isn’t the only person who can advocate for you, and they may not even be the most important one. There are leaders above them, peers around you, and a broader network that shapes your trajectory.

Her advice? Let your work speak for itself. Build a personal brand that isn’t reliant on a single manager’s attention.

“Let your brand be louder than your boss. That way, even if they change — your reputation doesn’t.”

 New bosses are stepping into your world — it’s their job to understand you, not the other way around.

Reorgs will keep happening. But with the right mindset, they don’t have to throw you off course.

🎥 Watch the full episode

These were just snippets of the  seven questions answered — the full conversation covered even more. If you’ve ever questioned your path, your pace, or your position, there’s something in this session for you.

Kate goes deeper on each theme, including her own career pivots, thoughts on imposter syndrome, and why so many of us are operating from outdated definitions of success.

👉 Watch now on YouTube — If any of these questions hit a little too close to home; you're not alone. Watch the full episode for the full insights.

Special offers for the Retail AMAze community

What you read here is just a fraction of what Kate brings to the table. If you want more tailored support, you can work with her directly, whether you’re navigating a tricky career moment or building something brand new.

Career Coaching Packages
Special referral pricing for Retail AMAze attendees (3, 5, or 10+ sessions). Just mention YOOBIC when you book your intro call.
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Use code LAUNCHPAD250OFF to save $250.
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Don’t forget to follow Kate on LinkedIn for daily insights.

Presented by YOOBIC

Retail doesn’t slow down — neither do we.

YOOBIC is the frontline engagement platform built for retailers who want more from their operations. More alignment. More agility. More impact.

We replace clunky processes with one intuitive mobile-first app that keeps store teams, field leaders, and HQ connected and performing at their best — every shift, every store.

350+ brands like Michaels, Mattress Firm, Ralph Lauren, Lidl, and Krispy Kreme use YOOBIC to turn retail execution into a competitive edge.

We’re not just another vendor. We’re retail’s ride or die.

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🎧 Check out the FRONTLINE FRIDAYS podcast for more great career content.