It's a good problem to have, right? The business you started and have managed solo to date has grown. You're at the point that you're so busy you can't see straight. You're swamped and stressed and living day-to-day in fear that you're going to drop one of hundreds of balls you're juggling. You're considering hiring help.

It would be great if there were obvious milestones or metrics that made hiring feel more certain and less risky. However, like many of the strategic decisions we face as entrepreneurs, choosing whether or not to hire somebody new is never cut-and-dry, and you don't know if you made the right choice until later.

Asking yourself a few important questions, though, can help you make that decision. Answer the questions below to see if the time is right to hire somebody.

  • How many hours are you working on average each week? How many would you like to be working?
  • Do you sense that there are aspects of your business that could be done much more efficiently by someone who knew better what they were doing?
  • Do you have a clear idea of what skills would be needed to do that work more efficiently?
  • How many hours would this work would take on average?
  • Do you have the money to pay someone now, or would their salary be dependent on additional revenue?

The key to making this important decision is data. Before you pull the trigger, take a month to document everything you can about your solo operation today. Keep track of how many hours you're working and what you're working on. Make a list of the things you'd like to pursue but don't have the time or skills for.

If, after taking all of this into consideration, you've made the decision to hire, consider this wise advice from two entrepreneurs and thought leaders who have hired hundreds of people and lived to tell about it.

Derek Sivers, the creator of CD Baby turned writer and speaker says, "Delegate, don't abdicate." Recalling a period in his business, Derek said, "Delegation doesn't come naturally to any of us. But I was trying really hard to be good at it. I knew how important it was to get into the delegation mindset. I was trying to empower my employees -- to let them know they could make decisions on their own, without me." With this goal in mind, he began to distance himself from the day-to-day decisions. Later, he learned that without his involvement or oversight his employees had set up a program to give all of the profits back to themselves.

This was a tough lesson learned. He now warns of the risks of abdicating responsibility for parts of your business to someone else; in other words, giving control to someone who knows better how to complete the specific role or task. Without some basic understanding of each role in your business, you're simply not able to provide the needed oversight. Make sure you know the basics first -- or have the employee teach you -- so that you can have confidence that they're performing the work to your standards and in a way that aligns with your company values.

"No one works for me until they've worked for me," says Seth Godin in his Startup School podcast. He hires freelancers to fill open positions--and not just for traditional services. He hired his COO this way. Seth argues that working with somebody is the best long-term job interview you can possibly have. The trade-off is that you limit your pool of potential people, because not everyone is willing to work this way.

Hiring help can be an exciting rite of passage for many entrepreneurs. It's the day you go from being on your own to leading a team. Bringing on staff comes with a tremendous amount of obligation and responsibilities--one that you shouldn't take lightly. Make sure you're ready for the extra work and responsibility that comes with bringing on additional help.

I share some additional thoughts on hiring in this short video.