Tell me your “I wish I'd known then what I know now” stories from hiring your first employee

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November 21, 2020
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November 21, 2020

Tell me your “I wish I'd known then what I know now” stories from hiring your first employee


Bootstrapping startup and I've never hired before, so it's going to be a huge step for me!

In my mind I have three really simple selection criteria:

  1. Can they do what I need them to do, or pick it up in a reasonable amount of time?
  2. Will I enjoy working with them and vice versa?
  3. Can I afford them?

Number 3 is easy to deal with and from what I've researched it's achievable on my budget. I have a fixed limit of what I'm willing to safely spend so if I can't find anyone within this range I'll have no choice but to persevere for a while. It'll slow things down a lot but I'll get by.

I think I have a fairly good plan of how to verify number 1. It's a software engineering role and this is my background. I've been through enough recruitment processes on the other side to know what works and what is respectful of a candidate's time and effort. This criteria is also easier to manage since I'm willing to invest a bit of extra effort on support in case someone doesn't initially meet expectations. In the unfortunate scenario that they're incapable of making progress or they're actually dragging things down with no sign of ROI it's also easier to justify letting them go.

I'm expecting number 2 to be the hardest. In fact I'm not really sure how to tackle this problem. I suppose it's whether I get along with them in the interview? I'm aware that gut feel is a terrible approach but I can't think of a way to quantify “team dynamic”. It's my biggest concern for things go awry since this kind of drama can be disastrous. I suspect it would also be more challenging to let someone go on these grounds.

So now that you have some context and insight into the kinds of things I'm thinking about, I want you to fill me with anxiety by revealing your hiring horror stories, or revel in your times of triumph, or any other tidbits/advice you think might come in handy to me. Let me bask in your wisdom!

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