Why Hiring Managers Struggle to Recognize Teachers as Leaders

I'll admit, I'm not a hiring manager. I’m sure there’s a lot that goes into it—far more than applicants ever fully see.

Like online dating, it must be exhausting to sift through mountains of profiles, flirt over email, get excited about meeting someone, and then realize halfway through the date that they might be a dud.

There’s also the opposite problem: when it’s going really well. You’re surprised at how well it’s going, and you start wondering if there’s a catch. Is this too good to be true? Should I ask them on another date? They’re definitely seeing other people. Should I make an offer now? And meanwhile, you’ve got a metaphorical boyfriend at home—another candidate already in process—and everyone’s pretending this is fine.

Add to that the very real, likely tedious work of onboarding someone new: benefits, systems access, cultural integration, plus pressure from your own leadership to hire the right person. It’s a lot.

So I do my part. I transform my résumé. I customize cover letters with the right language (because it’s not always the hiring manager swiping—it’s AI we’re trying to impress first). I update my portfolio website. And then—if I’ve wished on a star and the constellations align—I might avoid an auto-rejection and actually meet real human beings!

I'll be honest here. I think I’m a good interviewer. I’m not a crackpot. I dress appropriately. I’m genuinely curious about people and perspectives. I do light research so I can speak intelligently. And—I’ll say it—I’m frickin' funny, and I have a thousand-watt smile.

None of this has landed me a job yet. But I persist.

Because self-reflection is kind of my thing, I adjust my strategies. I evolve. I notice what’s working and what’s not. I persevere. I can feel the soul suck right out of my chest after a rejection and then go to a pilates class, cook dinner, cry about it, and start again the very next day with a revised resumé and renewed hope.

So if it’s not me, it’s you. Right? (It’s a reversal of the dating cliché. You get it.)

After enough conversations and email back-and-forths, I’ve learned that most professionals do respect teachers. As they should—everyone should respect teachers. I was constantly told, “People love to hire teachers!”

There’s a caveat.

Many hiring managers don’t know how to translate teaching into business leadership unless it’s reframed for them.

They hear "teacher" and think:

• Classroom

• Schedule Stability

• Limited Scope

• Children

• "Summers Off"

They don't automatically know:

• Program Director

• Editor-in-Chief

• Crisis Communicator

• Operations Lead

• Cross-functional Collaborator

• Evenings and Weekends

Unless you rename the work, they subconsciously down-rank it.

That’s not a reflection of your value. It’s a failure of translation.

Teaching isn’t a detour from leadership. It’s early, accelerated leadership—misunderstood because it doesn’t come with corporate titles.

Teaching rarely includes labels like “Director,” “Manager,” or “Lead.” The labor is invisible and constant. It’s deeply human-centered, which means it doesn’t always map neatly onto corporate systems or B2B language. But let’s be honest about what the work actually requires.

If you’ve taught for even two years, you’ve already been:

• Managing 25–150 stakeholders daily

• Delivering work on immovable deadlines

• Resolving conflict in real time

• Communicating to wildly different audiences

• Making judgment calls with limited resources

• Holding responsibility without authority

Those aren’t soft skills. They’re leadership skills.

They aren’t unique to education—but educators are required to develop them quickly or burn out. And because teachers care deeply about their craft and the people they serve, they often make this work look easy. Natural. Feminine. Like caregiving.

Which is absurd.

After five years of running a journalism program, I've reflected on even my second-grade teacher and thought, "That woman could have dominated a Fortune 500 company if she wanted to." (Mrs. Sauve, if you're reading this, I love you, and it's so true.)

Again, the issue is translation.

Curriculum development is systems design.

Classroom management is operations leadership.

Lesson planning is project management.

Student assessment is performance evaluation and data analysis.

Parent and administrative communication is stakeholder management.

Reframing teaching experience isn’t about inflating résumés. It’s about telling the truth in a language hiring managers already understand.

The cost of failing this language test is steep.

Teachers internalize the lie that they’re “behind.”

Organizations miss out on emotionally intelligent, resilient, battle-tested leaders.

For a long time, I worried that my five years in the classroom would always be treated as a gap—as if I’d stepped away from the workforce entirely. Now I know better. I know how to translate.

Happy dating.