You think hiring the right person will solve everything. And sometimes, for a little while, it feels like it does.
When I hired a new team member to take over one of the most critical roles in our ed-tech startup, I thought I was doing everything right. The role was essential to the company’s operations and also personally important to me. It was work I had designed, refined, and cared deeply about.
So I made sure to train her thoroughly. I walked her through every step of the process, explained not just what I did but why, and encouraged her to make improvements. And she did.
She was thoughtful, insightful, and sharp. Within a few months, she’d improved some of our key conversion rates and introduced smart tweaks to the workflow. I was relieved. For the first time in a long time, I could breathe a little. I felt like I had finally found the person: someone who “just got it.” The kind of person every founder hopes to hire.
But then, things started to shift.
When You Don’t Know Why It’s Working
One day, I asked her to take on a new project and she said:
“I can’t. I don’t have time.”
I paused. That didn’t make sense to me. I thought I had a general sense of her workload, but when I tried to assess where her time was going, I realized I didn’t actually know. I had no visibility. I couldn’t evaluate how she was spending her time, what was eating up her day, or whether something could be deprioritized to make room.
So I did what so many well-intentioned founders do; I asked if we could find the time together. I offered to help her reprioritize. But she was vague, and I didn’t have data to back it up. I didn’t feel like I could push back too hard or troubleshoot too aggressively without rocking the boat. So I just… trusted.
Later, when I needed to make projections for future staffing needs, I hit another wall. I couldn’t model how many team members we’d need to support growth, because I didn’t have any benchmarks to base it on. I didn’t know how long tasks took, how efficient the system was, or what was working well and what wasn’t. And when our success rates dipped with a new population, I had no way to isolate where the breakdown was.
At that point, I realized I was in a dangerous spot. My team was growing. My impact was growing. But my ability to manage, plan, and problem-solve was shrinking. I was dependent on one person, and I couldn’t even describe what made her effective.
The Founder Dependency Spiral
I see founders fall into this trap all the time. You finally find someone who seems to “get it,” and you hold on for dear life. You tell yourself they’re a unicorn. You feel lucky. And then, you become dependent.
You can’t plan forward. You can’t delegate sideways. You can’t train anyone else. You can’t even improve the system because it isn’t yours anymore. It belongs to them. And if they ever leave? You’re screwed.
So I tried to regain some control. I asked her to document the process and create SOPs. She resisted. And I had no idea why.
- Was she protecting her job?
- Was she overwhelmed?
- Was she not working that much and didn’t want me to find out?
I couldn’t tell. I had no system. I had no visibility. I had no leverage. And then, a few months later, she quit.
Rock Bottom, Then Clarity
She was gracious. She thanked me for being a great mentor. She told me she’d learned so much and had been offered her dream job. I smiled and congratulated her. Then I hung up the phone and cried.
I felt like the business might fall apart. I couldn’t picture how we’d replace her. I didn’t know how to train a new hire. I didn’t even know what a successful day in that role looked like anymore.
But here’s the thing: her leaving was the best thing that could have happened for the business. Not because she wasn’t good. She was. But because it forced me to face the truth I’d been avoiding: I had never defined what this role was meant to accomplish.
How I Got Out
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