Here are 3 questions to guide you: 1. Do you really NEED another employee? When you’re first starting out, you’re hiring someone for one of two reasons: (1) because you have pushed your own limits of how much you can work in a day (aka you’re going insane by working so much), or (2), the person you’re hiring has a skill that you simply don’t have and the time spent learning that skill would not be worth it for your business. Think of yourself — how many hours you put in, how much work you do to spur your business or the business you’re working for. Now duplicate yourself. Is there actually enough work to be done that there could be a clone of you working simultaneously and not be bored or off-task throughout the day? And if you simply don’t have a skill needed, rethink that aspect of your business. Is there anyone else already on the team that has that particular skill? Is that task that you think needs to get done absolutely core to your business? If yes, then hire. If not, then hold off until it’s absolutely necessary. 2. How do you hire? Immediately, or a trial period? Companies bring new hires onto the team in different ways. Some startups tend to hire people like developers on a Friday as salaried employees, and ask them to be at work on Monday — mostly because their skill set is definite and because their job takes place in a space that needs to be confined. (We can’t have our engineers working from Starbucks while writing all of our code to improve security on our site.)