I expected the personnel portion of this class to mostly be about deciding which employees a startup needs. What I found more difficult was deciding when the company actually needs them. Hiring too early is expensive. Hiring too late creates an entirely different set of problems. That became obvious when I was building the employee plan for Mindful Money. I initially had to put dates beside positions because the assignment required an actual staffing plan. I ended up treating those dates more like planning points than guarantees.
For example, I might expect to need a Financial Coach around Month 4. But what if Month 4 arrives and customer demand is half of what I expected? Hiring someone simply because my original spreadsheet says Month 4 would be ridiculous. At the same time, waiting until everyone is completely overwhelmed is not a great plan either. Hiring takes time. You have to find candidates, interview them, make an offer, wait for them to start, and then train them. If you wait until the business desperately needs another person, you are probably already several weeks or months behind.
I think startup hiring is different from hiring into an established company. Someone joining a large company can usually expect a fairly clear job description, established systems, training, coworkers who already understand the business, and some idea of what success looks like. An early employee may be helping create all of those things. That changes what I would look for. For Mindful Money, I would still care about relevant experience, but I would also want people who are comfortable when things are not completely defined. Early employees might have to do work that technically belongs to another department because there simply is not another department yet.
This is also why I like the idea of work samples in the hiring process. I would rather see how someone handles a realistic situation than conduct five rounds of interviews where everyone asks slightly different versions of the same questions. I do not think there is a formula that tells a founder exactly when to hire. The better question may be whether a real bottleneck has started forming and whether another person can remove it.
Reference
Wasserman, N. (2013). The Founder’s Dilemmas. Princeton University Press.