1) I thought I could hire "head of sales" that would run the /department/ not need extensive hand holding, and worse, I did it more than once - went through several vp of sales. Of course they interview well, they are sales people. There has to be "verify" and really understand what is going on
2) The skills to get a product off the ground are very different than scaling a business; people have written about the "3 ceo's" but I think there is a similarity with technical founders; I had multiple co-founders but few stuck it out until the end, in retrospect they were needed at a given phase, not the whole time
Your point (1) applies more broadly, I think. As you grow any company, you are at some point going to have to bring people in with more expertise in an area than you have. You need a strategy for this and to develop effective ways to evaluate performance outside of what you know closely. BS detector calibration can get you part way, but it takes more than that to efficiently differentiate "really good" and "really busy". Of course over time this tends to become clear, but you don't have that time.
One thing about legal and financial is that there is more accreditation and industry guardrails around them - HR too to a lessor degree. I think this makes it easier to get to "this person can definitely do the work" than some other functions.
1) I thought I could hire "head of sales" that would run the /department/ not need extensive hand holding, and worse, I did it more than once - went through several vp of sales. Of course they interview well, they are sales people. There has to be "verify" and really understand what is going on
2) The skills to get a product off the ground are very different than scaling a business; people have written about the "3 ceo's" but I think there is a similarity with technical founders; I had multiple co-founders but few stuck it out until the end, in retrospect they were needed at a given phase, not the whole time
3) know if you are trying be rich or king ( https://www.highalphainno.com/articles/rich-vs-king-the-corp... )