Growth / Team Development

The Small Business Owner’s Guide for Delegating to Your First Employee

Jake Johnson

Updated: Jun 11, 2021 · 7 min read

Toolkit for download in this article

employee and boss walking through office

You’re putting in 12- to-14 hour days. You feel burned out. You’re not sleeping well and actually dreaming of work. Everything is on your shoulders. And worst of all, your business growth is stalling. Up to this point, you’ve done everything, and it’s paid off as the business scaled quickly. But now you’ve reached the end of your ability to carry this thing all by yourself.

Congratulations! It’s time to hire your first employee.

So you do an extensive search. You vet the candidates. You fall in love (platonically, of course). You make the offer. They accept. And then the first day comes…and it’s time to delegate. And it’s kind of like this.

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Most small business owners fear delegation. It's hard to let go and trust someone else with your business and customers. You’re full of excuses on why you can’t delegate one thing or another.

Delegation doesn’t have to be hard. In fact, it can be a relief. And it can help your business grow by freeing you up to, as Michael Gerber put it, work on your business, not in it.

But it takes a plan to be successful. You wouldn’t start a business without a plan, and you shouldn’t delegate parts of it without one either. Here are seven steps to making sure delegating to your first employee results in success.

Make a list of your key daily responsibilities

Begin by listing out on a spreadsheet every regular, repetitive task you do. These are things like responding to customer queries and support requests, data entry, marketing emails, etc. If you do it regularly, put it on the list. You’ll be amazed at the variety of things you put down—and the amount of work you’ve been doing. Believe it or not, this is cathartic. It’s like finally admitting you have a problem.

Bonus: Group your list by functions like marketing and sales, finance and accounting, human resources, etc.

Determine what only you can do

Now take a good look at your list. On a scale from one to five, with one being a monkey could do it and five being only you can do it, rank each task.

The key here is to be honest with yourself. Your tendency will be to think that they are all fives. They’re not. That’s a lie. Just say “no” to that way of thinking.


Once you’ve scored the items on your list, do a quick sort by the scores and hide the ones that are fours and fives. Everything that is scored one through three are tasks that you can delegate to your first employee.

Guess what…the delegation begins! I’ve made a spreadsheet template (complete with cool color-coding) so you don’t have to. Download and use it right now!


Now, pick a reasonable number of those tasks and make them the first ones you delegate to your new employee. 

Determine the key strengths of your employee

Once you have the tasks you’re ready to delegate, utilize that list to make up your job description, listing out specifically the skills and experience necessary to complete the job.

Use this job description to determine if a candidate is worth consideration for hire. As Nick Braun, owner of, says, “The best advice is to be very judicious in who you hire first and make sure they understand the challenges and tasks needed to succeed.”

But remember that a candidate can look good on paper but not necessarily always pan out once on the team. It’s key to both call references, as well as do a test run.

Braun suggests considering a contract to hire offer for the right candidate to be sure they are a good fit. “If you make a hiring mistake,” he says, “it will set you back months and create a ton of stress.”

Joel Gross, owner of Coalition Technologies, says, “The single most important thing to do is to skills test your job applicants…identify what key skills the person will be using each day. Then create a basic test that shows how well they can perform those tasks.”

Taking the time to hire right will go a long way toward peace of mind when it comes time to hand off key parts of your business to your employee.

Already have an employee on board? No sweat. You should have a good idea of what they’re capable of. Assign tasks appropriately. If they’re not good at much of anything…well, that’s an entirely different problem.

Train and document

Once you have the right hire, it’s important to prepare for on-ramping them in a way that ensures they will succeed. That means having excellent training and documentation ready for the new hire.

For example, Jason Hilliard, owner of York Street CrossFit, has a very extensive and effective process for new coaches. “First, the hire had to complete 50 hours of shadow coaching. This provided the hire a good understanding of how to coach and how our demographic reacted to certain coaching experiences. Additionally, he was provided an employment contract, a handbook, and a personal note from myself congratulating him on the opportunity.”

It’s important to realize that no job is static. To the best of your ability document how to do the job for day one. But keep that as a living document, adding and adjusting as needed during the course of work.

Also, as Ninh Tran, the owner of, says, “Be mindful that people can’t learn everything overnight and only give them what they can digest.” Don’t overload your new employee. Give them only what they need to be successful today. You can always add more later, once they’ve mastered the job at hand. 

Set clear expectations for success

As part of your training and documentation, set clear expectations for what success looks like. Your employee should be able to know when she’s done a job well.

If you don’t provide the necessary training and articulate what success looks like, you can’t blame people for failing. “If my new employee fails within the first six months,” says Tran, “it’s ultimately my failure because of lack of training, planning—whatever the reason.” 

Let go, but do check in

Yes, document and train. Yes, set clear expectations for success. But don’t micromanage. To some extent, leave room for job ownership. Regarding this, Bryan Claton, CEO of GreenPal, shares one of his favorite quotes General George S. Patton, “Never tell people how to do things. Tell them what to do, and they will surprise you with their ingenuity.”

This letting go is the hardest part. In some cases, your employee will do things differently than you. You have to be OK with that and trust that different methods can still achieve the same goals.

Craig Bloom of has a system that helps minimize some of the stress related with letting go. “I eased into delegating by passing along tasks I’ve done before, as opposed to something the company was doing for the first time, which mitigated the risk to the business,” he says.

Still, it is appropriate to check in. In fact, your employee will want regular feedback. Make sure to schedule regular meeting times to discuss how things are going, field any questions, and help think through any challenges. Personally, I like doing weekly one-on-ones. 

Leave room for failure, as long as they learn

Finally, leave room for mistakes to happen. In fact, celebrate them as opportunities to grow and learn. And when something wrong does happen, don’t point fingers. Rather, collaboratively work together to develop an action plan for moving forward.

“We never pointed out his mistakes,” says Jason Hilliard. “We always asked what ‘we’ could do better. This was a team effort and we wanted him to know he was never alone. When he failed, we failed. So we worked together to make things better.” 

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