Ask HN: I'm hiring my first employee – literature recommendations?

I run a small business that is scaling and I'm about to hire my first employee to help me with copywriting and content creation. The plan is to start with a part-time employee in order to both get some experience in being an employer and also to try the employee out. I will therefore hire a student within the field that wants to make some extra cash.

I have two questions for you: (1) Does anyone have any experience in this that they want to share? (2) Are there any recommended literature out there that I really should read being new to this?

  • If you are hiring a student, then consider selling it an internship. A few reasons why:

    1. You can place a clear timeframe (like “internship during the fall semester, potential to renew internship during spring semester and summer”). This way you start them with a clear end date. That way if you are not comfortable firing someone, you have a natural excuse. As a new manager, that may be valuable.

    2. Some local governments may have workforce development grants to cover parts of the expense of an internship but not just a regular employee. I know that is the case in my state (in the US).

    Also if they are a student then by definition they are not an expert. For best results expect to spend time mentoring them. This likely means spending time in advance to outline the general path. In my experience, the more structure you have to start the better your results. After they get going, you can probably reduce the required structure (assuming they are a good hire). If not, get a new intern at the next semester.

    Keep a list of all IT things you configure for them (email accounts, slack, other saas etc). This way you have an easier time to disable them when they leave.

    Lastly treat them like an adult with real company email address, etc. The more professional you look to them, the more professional they will look to the rest of the world. Also, they will certainly talk to their peers about you and your company. So make a great impression.

  • This is what I do for a living and I interview writers somewhat often.

    You need to find someone who sees the difference between writing as an art and as a profession. Look for someone who can research and write fast. They're not going to know what they're doing and since you're not going to get high-quality work you need to get a lot of decent work out of them.

    As part of the interview process, ask them to pitch you a blog topic. Then dig deeper and find out how this post is going to benefit your business, etc. Finally, ask how long it would take them to write this blog post of say, 1000 words. The red flags are anyone who says this would take them more than 6 or so hours and anyone who can't explain the business value of their work.

  • The Prince - Machiavello. Just kidding, if you are in the technology business I strongly reccomend The Manager's Path. It is a very good book to learn how people interacts with the leaders and how to manage your own leadership.

  • 1.) When I hired co-op students in a previous position, I had a lot of luck with an interview style that a cognitive psychologist friend of mine suggested. I would switch between memory questions and creative questions. For example, I would ask:

    "Can you tell me about a specific time when you have had a conflict with a co-worker?"

    then

    "Imagine that I am Steve Jobs and you are pitching me on some new features that would make an iPod more useful. What features would you recommend?"

    I found a couple of things with that style. First, it was an easier way to figure out who they are and what they were like to work with. Second, it showed me a lot about how they could think on their feet and come up with creative solutions on the fly.

    Also, honestly, don't overthink it. You're trying to hire someone who you are going to want to spend a lot of time with. Don't expect perfection off the bat, and if I were you, I wouldn't optimize for skill or experience. Instead, optimize for someone you want to spend 40 hours a week with for the next twenty years. Your relationship with this person and your ability to teach each other things will be key to the relationship.

    Also, when you hire them, I strongly encourage you to build a culture where you encourage them to teach you how to become a better manager. This starts during the interview - be upfront that this is a first for you and you want to learn how to become the best boss they've ever had. Ask them to give you frank feedback whenever it comes up. Ask them to do performance reviews on you. And schedule frequent one on ones where you encourage them to teach you how to become the best boss they have ever had.

    That kind of culture is amazing because the more comfortable and skilled they get giving you feedback, the more comfortable and skilled they will get receiving feedback from you.

    Good luck!!

    2.) I'd avoid books. In fact, if I were you, I'd be very careful about taking any of the advice I gave you in #1. Those are just things that worked for me, and books are generally composed of things that work for the authors. You need to figure out your own style and what works best for you and your organization. Once you figure that out, hiring will get easier because you'll have an idea what you're selecting for.

    I can't believe I just wrote a wall of text, then told you to disregard what I said. :)

  • Literature does not help a lot. It's an add-on to your personal experience, nothing more. If it's your first time then it's a good idea to get someone with strong background is psychology to take part in the interview process. Psychological profile is very helpful in hiring decisions.

  • the best reference i can think of: https://en.wikipedia.org/wiki/Secretary_problem

    i have used it myself, feels somewhat precise.