The Hiring Rollercoaster: Ups, Downs, and Lessons of Hiring an Assistant Teacher
By: Jennifer Kempin | January 12, 2025
This winter, I took on the next big challenge in growing my microschool: hiring an assistant. It wasn’t an easy decision, but it became clear that if I wanted to expand and truly give my students my best, I needed another adult on board.
So far, I’ve managed my school with four students at a time. And while I’ve taught classes of 30 in the past, the responsibility of running a microschool solo meant that even four kids felt overwhelming at times—not because I couldn’t handle it, but because I lacked a backup adult in case of emergencies. I realized that if I wanted my school to grow and continue thriving, hiring wasn’t optional—it was essential.
The Rollercoaster of Hiring
I’ll be honest: the process of hiring has been anything but smooth. It’s been a journey filled with twists, turns, and a lot of learning on my part. Here’s how it unfolded.
Stage 1: Avoidance (a.k.a. “Not All In”)
At first, I wasn’t fully committed. I casually mentioned to others that I was looking for an assistant and posted a carefully worded (read: overanalyzed) paragraph on social media. Predictably, this approach led nowhere. I got a few half-hearted inquiries, but I wasn’t interested in hiring someone who was “kind of” interested in working at my school.
Stage 2: A Nervous Search
Realizing that my half-efforts weren’t cutting it, I stepped things up. I wrote a proper job description and scheduled posts on social media. I expanded my search to platforms like Care.com, Indeed, and local Facebook groups.
This strategy flooded my inbox with resumes—mostly from Indeed—but very few applicants seemed genuinely interested. I spent countless hours reviewing resumes, responding to messages, and setting up interviews that often ended in ghosting. Frustration and burnout started creeping in.
Stage 3: Desperation (but with Purpose)
Things shifted when I began hearing from families desperately seeking a better school environment for their children. Suddenly, my motivation for hiring became bigger than my fears.
Speaking of fears, I had many:
- What if I hire the wrong person?
- What if they don’t align with my philosophy?
- What if they harm the culture I’ve built?
- What if I can’t support them?
- What if I don’t get more students and end up not needing them?
But none of these fears mattered when I thought about the children who needed a safe, supportive place to learn. Their stories reminded me why I started this school in the first place.
Stage 4: Getting Serious
This time, I got strategic. I dropped Care.com and Indeed, which weren’t yielding quality leads, and focused my efforts on Facebook groups and my personal network. I also boosted one of my Instagram posts to reach a wider audience.
I paid close attention to where qualified leads came from and poured my energy into those areas. I also ramped up my overall social media presence, ensuring my accounts were visible to more people.
Interviews: Finding the Right Fit
When it came time to interview candidates, I prioritized qualities like experience with children and alignment with my school’s philosophy over specific degrees or certifications. Here are a few things I looked for:
- How do they feel about not forcing children to complete work?
- How do they approach discipline?
- What would they do if two children were arguing?
Sharing my son’s experience with school and bullying was often a litmus test for their empathy and perspective on children.
After interviews, I invited candidates to visit the school. These visits were the most revealing. I observed how they interacted with the kids, responded to challenges, and approached our unique environment.
Lessons Learned
I wish I could say I nailed it on my first hire, but I didn’t. Twice, I’ve hired people who weren’t the right fit. Looking back, I realize I ignored red flags because I was desperate to fill the role.
Now, I approach hiring from a place of abundance. I trust that the right person will come along—even if it takes interviewing 20 more candidates.
Here are a few concrete takeaways that I hope you can apply to your next search:
- Craft a Clear Job Description
Take the time to write a detailed job description. Look at examples from others to get a sense of what resonates with you and what doesn’t. Be specific about the skills, values, and experiences you’re seeking. - Be Selective About Platforms
Avoid platforms like Indeed if they haven’t yielded quality candidates for you. Focus on sources that align with your community, like local Facebook groups, homeschool networks, or word-of-mouth referrals. (I don’t recommend Indeed for smaller jobs) - Reflect After Each Interview
After every interview or visit, take a moment to evaluate. What did you learn about the candidate? What new questions could you ask next time? Use each interaction to refine your process and identify what matters most. - Refine Your Requirements
Don’t hesitate to narrow your criteria. Being clear and selective will help you find someone who aligns with your vision, rather than settling for someone who is “good enough.” (I learned that my candidate really needed to have a college degree or serious work experience) - Stay Patient, Not Desperate
Desperation can lead to settling for the wrong fit. Trust that the right person is out there and focus on building a process that attracts candidates who share your values. (It’s ok to wait!) - Leverage Your Network
Share the opportunity with your personal and professional circles. Parents, colleagues, and community members can be invaluable in connecting you with the right candidates. - Observe Interactions in Action
A visit to your school can be a revealing step in the process. Watch how candidates engage with children and handle new environments. Look for alignment with your values and approach. - Keep Learning and Improving
The hiring process is a journey. Every step—whether a success or a misstep—provides valuable insights for the next time. Embrace the growth and stay committed to finding the best fit for your school.
Why It’s All Worth It
This microschool journey isn’t for the faint of heart, but it’s worth every minute. Watching my students grow into their happiest, truest selves reminds me why I do this. And, as challenging as it is, the process has helped me grow into a more authentic, powerful version of myself.
So, to my fellow microschool founders: keep going. The right person will show up, and the work you’re doing is worth it—not just for your students but for your own growth, too.
What have your hiring experiences been like? I’d love to hear your stories!