Before you hire
You are working too many hours, things are slipping, and the obvious move is another pair of hands. Sometimes that is exactly right. Sometimes it is the most expensive way to make the same problem permanent.
The short answer: hire when the constraint is capacity, meaning the work is already defined and there is simply more of it than the team can absorb. Do not hire when the constraint is structure, meaning the work only exists in your head, every decision still needs your approval, or nothing is written down. In the second case the new person inherits the bottleneck instead of relieving it, and you have added payroll to a problem that was never about headcount.
Both feel like being overwhelmed. Both produce the same late nights and the same sense that there is more work than person. That is the trap: the feeling is identical, so owners reach for the same solution, and only one of the two problems responds to it.
The work is understood. Someone could be shown it and do it. There is a way of telling whether they did it well. You are not the only person who knows how it goes. What you are short of is hours, and hours are the one thing a hire genuinely buys.
The tell: you could write down what the person would do next Monday, and it would not read like "follow me around."
The work is not really defined; it is improvised each time by you. Quotes need your judgment. Exceptions need your call. The knowledge of how anything actually gets done lives in your head and nowhere else. What you are short of is not hours, it is a business that can be handed over.
The tell: every attempt to describe the role turns into a description of yourself.
There is a way to tell which one you have, and it takes about a minute.
Picture the new person's first Monday. Now take yourself out of the building for the whole day. What do they do? Not what would they eventually learn to do; what do they do that Monday, without asking you anything.
If you can answer that concretely, you have a capacity problem and a hire will help. If the honest answer is that they would need you beside them for the first several weeks, the constraint is not capacity. It is that the work has never been made transferable, and no amount of hiring changes that on its own.
Most owners find the second answer uncomfortable, because it means the thing in the way is not the market, the staff, or the hours. It is that the business was built to run through one person, which is a design outcome rather than a personal failing.
The first month usually feels better. Someone is absorbing tasks, the inbox is shorter, and the decision looks vindicated.
Then the pattern returns, because nothing about the routing changed. Work still comes to you to be scoped. Decisions still come to you to be approved. Now there is an extra person who cannot move until you answer, so your queue gets longer rather than shorter, and you are managing on top of doing.
This is the part that surprises people: many owners are busier after hiring, not freer. More people around an unclear structure produces more coordination, not more output. The business did not gain capacity; it gained dependency, and a payroll line.
When the role can be described without describing yourself. Concretely, that means you can write down three things:
The outcomes they own. Not the tasks they perform; what is different in the business because they were there this week.
The decisions they are allowed to make alone. If the answer is none, you have not hired an employee, you have hired a queue.
How anyone would know they did it well. If the only measure is your instinct, the role only works while you are watching.
If all three are answerable, hire, and hire with confidence. The business is ready to absorb someone.
If they are not answerable yet, the cheaper move is to make one of them answerable first. That is usually a week of work, not a quarter, and it costs nothing per month afterwards.
Because you have compensated for it for so long that the compensation is invisible. When you are the person who fills every gap, you stop noticing the gaps; you only notice being tired. From the inside it reads as a workload problem, and workload problems have an obvious answer.
You only know what you know, and you only see what you see. That is not a criticism, it is the condition of running the thing from within it.
The free pre-screen takes about five minutes and shows you where your structure is under pressure, so you know whether the next hire will relieve the problem or inherit it.
Start the free pre-screenRelated: how do I get more leads · how do I get funding · why your business depends on you · what these terms mean · what kind of owner are you