Do’s and Don’ts for Small Business Owners Outsourcing Work

Hiring help is a big step for a small business. These six dos and don'ts will make the process more successful for you, your business, and your new employee.

I recently reached an exciting point as a small business owner: I hired my first employee.

Hiring someone to help you out is both an incredible and stressful milestone for business owners, whether you’re bringing on a full-time employee, a part-time assistant, or a regular contractor.

Wonderful because your business is growing, and you’ve reached a point of financial stability that allows you to bring on someone new.

Stressful because, let’s face it, your business is your baby. You’ve invested your energy, your love, your weekends and evenings. You want to make sure your business thrives, which means hiring the right person, creating a productive, successful relationship, and making sure you can afford the help you need. That’s not an easy task.

Luckily, you can take a few steps to make sure you feel more of the wonder and less of the stress.

Six Dos And Don’ts To Follow When Hiring Help For Your Small Business


In my case, I’ve worked on multiple sides of this equation: as the only employee in a small business, as one of several employees, as an independent contractor, and now as the owner doing the hiring. So I’ve got a few thoughts about the dos and don’ts or hiring and employee or outsourcing work.

After all, hiring help is a big step in the life of a small business. You want to make sure you do it the right way for you, your business, and your new employee.

Do Think About What Tasks Are Worth Your Time

Since the beginning of my writing career, I have divided my time between working in my business and ON my business.

My business includes researching, writing, editing, consulting, emailing, invoicing, accounting… all of those everyday things that keep a business running. In addition, working on my business means pitching new clients, communicating with leads, writing my website, putting together newsletters, creating my resource library, developing new product offerings… everything that helps a business grow and change.

Both of these are necessary, and they were all done by one person: me.

But I’ve reached the point in the last year when some of those tasks stopped being worth my time.

I discovered I was making enough client work to make hiring help feasible. But, at the same time, I realized that everyday tasks were taking up so much time I couldn’t focus on growth.

As a business owner, it can be challenging to let go of any part of the process. So, to maintain my work’s integrity, I decided that writing and consulting were NOT tasks I was willing to outsource. But other tasks, the ones that support that writing and consulting, were suddenly not worth the time I was spending on them. And so, I hired help.

Don’t Pass The Buck

Choosing to outsource part of your work is challenging because you have to trust someone else to maintain your image and standard of work.

You have to trust a new employee to interact with customers if you own a store.

If you hire a website manager, you must trust them to post content you approve of.

If you hire a researcher, you have to trust them to find accurate and helpful information.

This might affect what tasks you choose to outsource. To maintain the integrity of my work, I decided that writing and consulting with clients were tasks that I was not comfortable with anyone else doing. You may choose to be the only one interfacing directly with customers, maintain strict control of product production, or be the only one updating your website. You may decide that you’re ready to bring on help at every stage of the process.

Whichever route you choose, remember that you are ultimately responsible for how your business appears and what it produces as the owner of your business.

If a customer is unhappy, it’s your responsibility to provide more training for your employee.

If something shocking ends up on your website, it’s your responsibility to apologize.

If information is incorrect, it’s your job to double-check the source.

You are the owner. That means the buck stops with you, no matter what.

Do Set Clear Expectations

Depending on your business model and the type of help you are hiring, there are infinite variations in the relationship and expectations with the people you hire.

Are you expecting a certain number of work hours, or do you only care about the final product?

Do you need your new employee to be available at certain times?

Is there additional training or study that will be necessary?

Will you be paying on a specific schedule?

Are you expecting a certain number of revisions?

The list goes on. And if you fail to set clear expectations, you’re going to run into a lot of issues, possibly to the point where you feel like outsourcing was the wrong move.

The best way to set these clear expectations is to write them down in a contract.

A contract protects both parties by ensuring everyone knows what is agreed upon. So whether you’re hiring a friend, a colleague, a family member, or a stranger, putting things in writing is the smart, safe, professional thing to do.

Don’t Expect A Mind-Reader

Your new hire can’t read your mind, just like you can’t read theirs.

That may seem obvious in the abstract, but when something happens that you did not plan for or expect at all, it can throw you for a loop.

I once had a writing client ask me (in complete seriousness) if I was trying to sabotage their business because the draft of an article I turned in was shorter than they were expecting. But guess what? This client had never specified a word count or desired length. I wrote the article that I thought made the most sense. They expected something different. Who justified both of us in our expectations. But I don’t think I’m out of line to say how they reacted was entirely unnecessary.

Because here’s a truth we all sometimes forget: things that seem obvious to you may never occur to someone else.

Expecting your new hire to know what you want without being told will damage your professional relationship and cause you a lot of unnecessary stress.

When you first start working with someone new, there will be a learning curve for both of you.

If you expect that, rather than panicking about it, both of you will be happier and more productive.

Do Communicate Clearly

On that note, if the person you hired does things differently than you are expecting, there’s a good chance that’s because you didn’t communicate those expectations in the first place.

You might only take work calls that have been scheduled in advance, but your new employee thinks calls are more efficient than email chains. You might want every email you send to be acknowledged, but your new VA only replies to emails that require follow-up.

Also Read: The Do’s And Don’ts Of Hiring A Management Consulting Service!

Or maybe you have a particular idea of how things should get done: a certain way of packaging merchandise for shipment, a specific type of source used for research, a particular phrase used when replying to customer emails.

Your new employee’s job is to meet your expectations. But for that to happen, you need to communicate those expectations firmly and politely.

“I’d like you to answer the phone, “Boston Bridals, David speaking, ho can I help you?”

“Please send a quick acknowledgment to my emails. “Got it” is fine, I just need to know you saw them.”

“That web page looks too cluttered to me, I’d like the slider removed and these three images used instead.”

And if something goes wrong? Communicate that, firmly and politely too. Explain what the problem is, and, if appropriate, invite your employee for thoughts on how to fix it.

As in any relationship, the days go more smoothly, and the problems are fixed more quickly when everyone communicates.

The more clearly and precisely you communicate, the happier everyone will be, and the faster and more professionally the work will get done.

Don’t Be Afraid To Set Boundaries

I don’t answer work emails after 5 pm or on weekends. I use email and my cell phone for work, but not texts. I charge extra for rush jobs because rush delivery means extending my work hours, so I don’t deliver something else late.

I never work without a contract.

When I started working for myself, spelling out these boundaries with clients made me very nervous.

But boundaries have made my work life infinitely better.

Setting boundaries has protected me professionally. It has helped me balance my work and my time. It’s made my clients happier because they feel empowered to set their boundaries. And now it makes me new hire feel more secure because we both feel secure in our professional relationship.

The idea of setting boundaries may feel unnecessary or high-maintenance. But once you begin working with other people, good boundaries keep everyone involved happier, calmer, and more on-task.

That’s good for your professional and personal well-being.

Do Pay On Time

Does this need to be said?

Yes. Yes, it does.

Pay the amount you agreed on. Pay it when it is due. Full stop.

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