Shop confidently - 14-day no-hassle return policy

How to Delegate as a Small Business Owner

Beautiful blue peacock posing for the camera

Have you ever heard the story about the guy who traded his way up from a red paper clip to an actual house on Hawaii in the span of one year?

Back in 2005 (I’m sooo dating myself here because I just cannot fathom that this went viral over a decade ago), a Canadian blogger named Kyle MacDonald negotiated his way from a single paper clip to a house in only 14 online trades, including a snowmobile and a box truck.

You can read all about it over on One Red Paperclip if you’re curious, but the reason this story came to mind today is because I was thinking about how starting a business is a lot like that paper clip.

It takes a lot of small wins over time to get to the next level. Instead of dealing with paper clips, you trade up by finding your first client, securing your second client, increasing your pricing, collaborating on joint venture webinars, and—this one’s a big one—outsourcing pieces of your business.

When Kyle made that jump from a box truck to a recording contract, it was much like the burst in momentum you’ll make when you hire your first employee and slowly grow it into a team. But a team by itself doesn’t propel your business forward, it requires a leader who knows how and when to delegate.

Out of all the skills you could have as a business owner, delegation is arguably the most important.

Imagine your business as a balloon. You can only blow it up so big before there is no more capacity for growth. Then, you’re going to need another balloon. You can’t do everything alone in your business, so the more successful you are at delegating, the more you can grow your business into something extraordinary.

Delegating doesn’t always come naturally though... it’s hard to let go of control of your baby… especially when you have a very clear vision of what needs to be done.

Personally, I suck at asking for help until I’m literally drowning. (Just ask me about the time I was on a ski lift trying to take a few hours off and literally crying over Slack begging a teammate to take the crushing weight of all these emails off my plate.)


Delegating takes practice, just like any other skill, and the good news is that even if you’re painfully possessive of your work or incredibly uncomfortable asking for help, you can master delegation in a way that works for you. (And believe me, you will be so glad when you do.)

5 tips for successfully delegating as a business owner:

1. Plan ahead.

Finding and hiring the right fit may take some time, so start looking before you’re ready to hire. You’ll have a much better idea of who’s out there, what their skills are, and what you can expect to pay when you’re doing it from a place of stability and not when you’re on the verge of a breakdown (see above—luckily I had Katie waiting in the wings!).

When you do find someone who resonates with you, set up an interview and be sure to ask the right questions to make sure it’s a good fit (for both of you!).


2. Get yourself organized.

If you don’t, you’ll be answering a LOT of questions in the beginning. You want this person’s time to be spent doing the actual work rather than trying to sort through your disorganized task list.

You should expect that there will be questions at the beginning, but if you get your act together ahead of time, you can avoid a lot of stress and rework. After all, if you’re hiring someone to help free up your time, and they are requiring a lot of your time, it kind of defeats the purpose of hiring someone!

You should know exactly what (and how much) you’re delegating and be able clearly communicate the tasks and your expectations before hiring someone.

3. Remember that you will need to devote time in the beginning to train.

Some people think, “Hooray, I’ve hired help!” and throw everything at the person.

Um, newsflash, that’s not going to be a success for your biz and likely won’t make anyone eager to help or work with you.

Instead, take the time to explain your expectations and the job at hand. Give feedback consistently in the beginning to help them improve; it’s so much easier for the person to course-correct now rather than months down the line when they’ve fallen into a rhythm of doing things in a certain way.

4. Get out of your own way.

If you find that your new person isn’t doing things the way you like, the last thing you want to do is take the work back and do it yourself.

First, ask yourself if you’re actually unhappy with the work or if you would rather it done your way. Sometimes, it’s really a matter of letting go of control. If you are really dissatisfied, you need to give the person a chance to right the ship.

This means providing honest feedback as well as being patient to see if the person can put it into action. If it seems like he or she is totally lost, working through it together could be a good option, as long as you’re taking the backseat and encouraging the person to come up with solutions.

5. Give autonomy.

Think back to what attracted you to owning your own business and why you didn’t want to be stuck at a corporate job reporting to someone else. I’m going to guess there’s some element of wanting to be self-directed and the captain of your own ship.

If you’re hiring a contractor or consultant, remember that he or she is also a business owner and likely felt the same way. Even if you’re hiring an actual employee, it’s still a good idea to promote self-management and autonomy with your team.

This not only means avoiding the dreaded micromanagement, but also giving them a sense of having a stake in your business:

  • Share your successes, and thank them for their part.
  • Reward them as much as possible, if you can.
  • Ask for their opinions to show you value their expertise and give them a part in the decision-making process.
  • Welcome and encourage their suggestions and feedback.

Bottom line: be the boss (or client) you’d want to have.

If you had unlimited $$$$ what would you outsource RIGHT NOW? Let me know in the comments.

Download the Non-Disclosure Agreement if you're planning to hire an employee or engage in a joint venture.

Outsourcing and delegating is SO HARD

Leave a comment

Comments will be approved before showing up.

Also in The Blog

11 Clauses You Should Include in Wedding Contracts
11 Clauses You Should Include in Wedding Contracts

How to Name a Business in 6 Steps
How to Name a Business in 6 Steps

Avoid this fake check scam
Avoid this Fake Check Scam (2024)