Work Life

Talking to Your Boss’s Boss Isn’t Automatically Going Around Your Manager

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As part of our ongoing “HR Won’t Tell You” series, we’re taking a closer look at the workplace realities that can have a major impact on your career—but aren’t always explained clearly by HR, your manager, or your employer. Our goal isn’t to make you cynical about work. It’s to help you become a more informed, confident professional who understands how organizations operate and knows how to protect and advance your own career. In this installment, we’re talking about skip-level relationships and building visibility with senior leadership—without undermining your manager or playing office politics.

Some employees treat the organizational chart like a fence.

Your boss is here.

Their boss is there.

And crossing that line feels dangerous.

It doesn’t have to be.

Healthy organizations often encourage skip-level relationships—professional relationships between employees and leaders one or more levels above them.

That doesn’t mean complaining about your manager behind their back.

It means creating appropriate visibility beyond your immediate supervisor.

If a VP asks about your project, explain what you’re working on.

If senior leadership hosts an open meeting, participate thoughtfully.

If you have an opportunity to present your work, take it.

If a senior leader asks for your perspective, have one.

This matters because advancement requires more than doing excellent work.

People need to know you do excellent work.

Fashion professionals can be especially vulnerable to the “head down” trap. Designers design. Planners plan. Production teams solve emergencies. Merchants prepare assortments. Salespeople chase accounts.

Everyone is busy.

Then promotion time arrives and leadership asks:

“Who is ready for more?”

Visibility matters.

Of course, there’s a right and wrong way to build it.

Don’t constantly bypass your manager.

Don’t undermine them.

Don’t take credit for other people’s work.

And don’t use senior leaders as an audience for complaints you haven’t attempted to address appropriately.

Instead, think of skip-level relationships as part of your broader professional network.

Your manager should ideally be one of your strongest advocates.

But your entire career shouldn’t depend on one person knowing how good you are.

Build relationships across departments and levels.

Be useful. Be professional. Be visible.

Because the person two levels above you today may be the person deciding who gets promoted tomorrow.

Chris Kidd is the owner of StyleCareers.com, StylePortfolios.com, StyleDispatch.com, FashionCareerFairs.com and FashionRetailCareers.com.

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