Man who is an Msp startup with pictures of people deciding when to hire employees

When to Hire Employees

A very often asked question of new or growing business owners is when to hire employees. The answer is not very cut and dry, as there are a ton of factors about it. One thing I do know, most business owners wait too long.

After I started my business the first task, I needed to do was find clients. I’d done a marketing plan, so I knew the niche I’d best succeed in, and I targeted my demographics closely. In most cases, the ones who were willing to talk showed frustration with the current provider in some way.

Avoid Burn Out

While it wasn’t common, there were a number – more than 3 out of 20, who said something like “Well we had this IT guy but he [is dead | had a medical crisis and had to close his business].” Say what you will about probability and statistics, and I’ll listen, but that seems awfully suspect.

So, I started to do a little research on the subject. You might be surprised to learn that of business owners who start technology support businesses, there is an unusually high rate of burnout. Not just “oh I’m sick of this”, but like cardiac arrest burnout. Of course, these numbers are still quite low, and the vast majority of owners lead long healthy lives but compared to many other businesses the rate is still scary.

Then we have to ask why – why do these folks burn out? The answers are indeed myriad, but the vast majority simply take all the work on themselves and never delegate. Worse, if they do delegate, they might not train the employee well enough. The employee can’t be successful and then the owner is back to being on their own.

Growth in your business can be dramatic (like mine was) and feel uncontrolled. I was ready to fail gracefully, but I didn’t prepare for huge growth as fast as it came. But the key there is I was ready to grow, which means I was ready to hire.

In the Plan

That’s the first question we need to answer about when to hire, and that is, do you have a plan for your employees?

Your business plan should include some estimates and predictions on sales and market conditions to support how you intend to grow the business. Typically, you might set up a 5- or 10-year plan for your business and include things like number of employees, roles of employees, what it is you’ll be doing, and so on.

If your plan includes employees, that is an expense for your business which needs to be planned as well. You already forecast sales so you should be able to formulate how much you’ll have to pay these folks. Then you’ll need to consider benefits and sufficient wages to retain these people. As your business grows you will come to depend on not only the people but the knowledge they gain about your clients. These growing experts will need the compensation to want to stay.


Here’s one that is often overlooked, and that is the timing of when to hire employees. This requires a little bit of planning, a dash of divination, and perhaps a bit of luck. Why? Training. You only get one chance to train an employee the first time. Spending time with them, showing them how your tools work, your standards of service, and details about clients to ensure a smooth transition.

Hiring probably shouldn’t occur during or immediately before a big project. If you have some seasonal business volatility, you may wish to plan around that. Bonus points in adjusting your schedule with placeholders for not just training, but all the resumes to review, interviews and time posting the job. It seems to always take longer than it should.

Next Steps

So, you think you’re ready to hire employees, the plans are there, timing is all lined up – what’s next? Get with your business insurance agent, accountant and/or bookkeeper right away. You need to have all the things in place to make sure taxes, benefits, and payroll are ready and there’s no surprises. You’ll probably get advice to have some extra money in the bank, as some direct deposit functions will require it. Be prepared for forms, fees and more forms.

I’d say that at the first moment you consider hiring, you begin that journey with these professionals to make things as smooth as possible.

This article broadly covers many variables to every state and even some cities about hiring and what steps you might have to take. If you have some specific questions about hiring, please consider booking some time with me. I set aside a certain amount of time regularly for quick questions. Feel free to email me and I can send a quick reply, or we can schedule a phone call.

Leave a Comment

This site uses Akismet to reduce spam. Learn how your comment data is processed.