Walking a Mile in Your Boss’s Shoes: Why Empathy Should Go Upward Too

One of my clients was nervous about having lunch with their CEO. The CEO had a reputation for being aloof and moody. But during coaching, we explored the possibility that this behavior might be masking something else.

It’s easy to assume that because someone is “the boss,” they have it all figured out – how to advance, how to behave appropriately, how to engage warmly.

But bosses are human too. Just like anyone else, they have bad days, insecurities, personal pressures, and the occasional self-doubt. The corner office might come with a better view, but it doesn’t come with immunity from stress.

The Hidden Pressures of Leadership

While it may seem like leaders are in control, they’re often juggling a complex mix of responsibilities. Your boss (or you) may be dealing with:

• Pressure to perform — The expectations only increase at the top. Results are scrutinized by boards, investors, or stakeholders.
• Difficult decisions — Letting people go, managing budgets, or navigating change can weigh heavily.
• Loneliness — Leadership can be isolating. It’s hard to confide in others when you’re supposed to have the answers.
• Desire to be respected (and liked) — Just like everyone else, leaders need validation, connection, and trust.

Don’t Assume. Get Curious.

At lunch, my more outgoing client took the lead  — cracked a joke, shared a personal story—and disarmed the CEO. Turns out? The CEO was shy. No one knew, because he overcompensated with distance and intensity. That lunch changed everything between them.

Don’t forget: leadership can be lonely. Sometimes, you should be the one to lead upward — with empathy.

Tips for Getting to Know Your Boss

• See the human, not just the title
• Use your emotional intelligence upward
• Take the initiative to connect
• Offer grace—they need it too

Empathy Isn’t Just a Downward Skill

We often talk about leaders needing emotional intelligence to manage their teams. But as someone in the organization   — at any level —  you can (and should) use emotional intelligence upward as well.

Being a great leader or team member isn’t just about managing those who report to you. It’s also about managing relationships with those to whom you report. Sometimes, the best way to grow your career is to understand the human side of leadership — and show your boss a little grace.

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