One of the most critical decisions you can make that will, more than just about anything else, determine the success (or lack thereof) of your company or department is who you surround yourself with. For entrepreneurs, the next hire might represent and inordinately large percentage of his staff (perhaps up to 50%). The small business owner cannot afford to make too many hiring mistakes. To use a baseball analogy - you really need to be hitting doubles, triples, and home runs with your hires as opposed to mere singles, or worse: strikeouts.

The first place to start, if you aim to do better, is with your next hire. If you are on the other side of this, and are looking to land a great job, this time you invest in reading this article will be worth your while. What follows are the top 5 questions I ask, as a technical entrepreneur, when I am considering whether or not to hire someone.

[1] How much will I have to manage him?

Time is money, and the more time I believe I will have to invest in making sure he is productive, the less likely I am to hire him. Earlier in my career, I doubt I would have hired myself. I truly am thankful a few kind souls did take a chance and were patient with me. Looking back, I had to be managed prescriptively. If you told me what to do next, then next, then next, I would happily set about doing that and usually had enough ability to either accomplish it on my own or with a little help get it done. Write me a prescription, and I would fill the order. If you have too many employees like the early career me, though, all you will do is spend your time saying “Are you finished, let’s see what you’ve done…Go back and fix this and then come back to me when you are finished. Or, good work, now the next thing you need to do is this.” So, what’s wrong with that? I would much rather manage someone who can take a task and not only complete it, but also

• Work efficiently, taking care to be rigorous and thorough.
• Double-check his own work and doesn’t leave it to others (e.g. his manager, the QA department, or the customer).
• Avidly look for productive things to do to try to help the business in the meantime while waiting for a chance to review his work with his manager.

When I was a still living at home as a young teenager, my dad would ask me to help him with yard work. He knew he couldn’t load me up with several tasks in my queue, because I would merely forget what he said after task #1 left his mouth. But if he didn’t watch carefully and check often on me to see if I was done, or working diligently, then I might just operate at 10% efficiency. Or, I might finish the task and then start shooting hoops rather than coming to get the next task in the queue. As a father of four, I now understand the frustration he went through! Some people never graduate beyond this early teenager mode. Oh, they get a little more polished in their approach, but if they get their work done they are busy surfing the net or doing something unproductive until you make the time to check on them. Here are the questions I ask the prospect that helps me determine the answer to my underlying question: “Can you show me some of your previous work (or describe it) and describe how it evolved over time and through iterations?” If he doesn’t have a good answer here filled with interest and passion then he might still be a good employee - for someone else. This can work even for new graduates. I look for people constantly working on their own projects or excited about projects they did at school. The answers and the body language tell quite a tale to me.

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