Getting help when you need it: a business owner’s guide to delegating

Entrepreneurs are a brave, tough, and independent lot. It takes more than a little tenacity to run a successful business. But this magical combination can be troublesome when it comes to asking for help, especially when you’re used to having control of all parts of your business. 

It starts with delegation. This word can be scary and intimidating but compelling and energizing—all at the same time. In order to focus on the parts of the business that truly need you (and back away from the parts that don’t), you have to take a step back and follow a few simple steps: know when it’s time to delegate, figure out what you can hand off, and identify the people that can get the job done right. 

Determine why, and be honest

No matter your business industry or size, a key business lesson is understanding the problem before taking action. Delegation is no different.

As a general rule, there is no “wrong” answer as to why you wish to delegate. However, if you aren’t honest with yourself, you can easily go down the wrong path, winding up with more of a headache than you originally had.

So, before you start casting off tasks, take a deep breath, and ask yourself some leading questions: 

1. Am I burnt out, overwhelmed, or both?

The drive to delegate is often a symptom of both burnout and overwhelm, which makes perfect sense. We could all use some help when we feel our backs are against the wall. But those two feelings can also put you in a state of mind where you may make rash decisions.

If you find yourself in this situation, breathe and take a second to assess the situation. Pay special attention to how you’re approaching the delegation process. Check-in with yourself to be sure you’re making moves based on good judgment and not just the quickest fix to the problem.

2. Is this something I’m simply not good at? 

When starting a business, you’re often the one who is doing it all: balancing the books, maintaining your website, running the counter, cleaning the floors. You’re the go-to person making everything happen.  

That might work at first, but eventually it will likely become clear that you’re not best suited for every job that keeps the business running. When you find yourself ready to delegate, it’s good to start by identifying the things you know others could do better.

3. Is this something I’m good at but don’t enjoy?

Another place to find tasks that can be delegated is within the part(s) of your business that you simply don’t enjoy.  

Tired of spending half your day on social media? Find a part time or hourly person whose sole purpose is to handle a business’ online presence. How about taxes? Have an expert take that off of your calendar. This will not only help you focus on tasks that you are passionate about, but it may even be that they are able to do the job better than you could.

4. Do I need time to focus on other responsibilities?

As your business grows, it requires you to focus your attention on certain aspects best handled by the owner. You need to work on—rather than in—your company. When that time comes, it’s time to delegate.

Clearly identify what to delegate

Now that you know why you want to delegate, it’s time to figure out what.  

What are you looking to take off your plate? Is it a few, disparate tasks or an entire arm of your business? The answer may be crystal clear, or it may just be a quiet (or shrieking) voice telling you that it’s time to let some things go.

Either way, your answer is the cornerstone of your delegation foundation. Next comes three easy steps:

  1. Make a list of all the tasks that you want to delegate.
  2. Organize it by priority, highest to lowest.
  3. Pick your top one(s), and write down the details of that task or project.

Tip: The more detailed your list is, the easier it will be to pass on and remove those tasks from your to-dos.  

Brainstorm how to best delegate

Now that you’ve identified the why and the what, it’s time for the how. There’s a best way to manage the transfer of each thing you delegate. Below are a series of questions designed to help you find it.

1. Can you use technology to automate a process?

Delegation comes in many forms, and it isn’t always another person. Many operations involve programs, apps, or other digital resources that have the ability to automate nominal tasks. You may think these one-off tasks are quick and easy to handle yourself, but they add up and rob you of the greatest prize held by any business owner: time.

Take a look at your list of your daily, weekly, and monthly activities. Which ones can you automate? There’s nothing quite like the feeling of relief you get when you “set it and forget it,” freeing up the part of your brain that’s silently trying to remember to do it each and every time.

Some automation examples would be:

  • Set electronic payments to autopay
    • Credit card, loans, utilities, etc. 
  • Schedule recurring calendar or phone reminders for recurring work
    • Weekly financial updates
    • Monthly newsletters
    • Annual employee reviews
  • Create automatic and/or templated communications to both shorten your response time and handle routine interactions
    • Email standardized replies to vendors or business partners
    • Book appointments, take orders, or receive quote requests through your Yelp Business Page 
  • Employ content creation and scheduling tools to distribute communications
    • Share industry-specific content via a newsletter, and schedule it to be emailed out to your subscribers
    • Use a social media management platform to upload your content and post at specific times

2. Is there a service or contractor better equipped to handle the job?

Think about who is best suited to handle the task you need to offload. In many cases, the answer isn’t an employee. There are countless contract specialists whose primary job is to make your life easier.

A great example is an accountant. You may decide to handle your bookkeeping in-house, but it’s unlikely you need a certified accountant as a member of your staff. Specialized professionals like this are best hired out, either on a project or contract basis.  

Another more specific example is laundry. You can pay a local company to provide you with fresh towels weekly. Sound frivolous? Not if you’re familiar with the hospitality or fitness industries. Clean, sanitary linens are a must, and trying to wash them at home is a surprisingly soul-sucking task that is worth every penny it costs to delegate.

3. Can you hire someone virtually?

When you do need help from another human, it doesn’t always have to be in person. Virtual assistants, freelance contractors, and other such digitally based professionals are available through the power of the internet.  

With the onset of sheltering-in-place that the pandemic brought about, working virtually is no longer a foreign concept. Millions of people are now comfortable working remotely, and that opens up a world of possibilities as you look to delegate various tasks and responsibilities. 

Even positions that once were only thought to be in-person are now (and have been) moving to the virtual world: project managers, personal assistants, customer service representatives, accountants, therapists, personal trainers, voice coaches, and more are available to you no matter where you, or they, are.

4. Does this require one or more full- or part-time employees?

Once you’ve gone through all other delegation options and decided that an employee is the best way to go, do some work beforehand to ensure a smooth transition.  

  • Decide if you need to hire someone new or are going to add responsibilities to an existing employee. 
  • Determine the details of what you will expect from the employee—new or current—and what they should expect from you.
  • For an existing employee, consider how the additional tasks will affect their ability to get both their current and new workloads done (and done well). Also determine if these new duties will come with an increase in pay. No one wins if an employee is expected to shoulder significantly new responsibilities without appropriate compensation.
  • Be ready to manage. Don’t make the mistake of bringing someone on board only to dump all those unwanted tasks into their lap. Successful delegation still requires oversight, be it by you or a member of your team.

Prepare before you delegate

Armed with the why, what, and how, you’re nearly ready. But before you delegate with abandon, you have to be prepared.

Whether your goal is to outsource certain tasks or entire areas of operation, you have to set the stage. Do the prep work upfront, and outline all needs and expectations.

Here are a few things to consider before you delegate:

  • Schedule time to learn new programs or apps before implementation
  • Estimate the cost to delegate, and determine how you’ll pay for it
  • List the skills and experience you require from a virtual or local new hire
  • Ask for recommendations for trusted contractors or service providers
  • Be sure your HR and employee policies are set up and working well

This is by no means an exhaustive list but rather some examples to get you started. Your specific tasks will dictate the required prep work, so develop and implement your own prep list before you move forward.  

Initially, it will take effort on your part to successfully delegate, but by taking your preparations seriously, you’ll come out with much better results.

The power of delegation

Understanding that your business is best served when you don’t do it all is a true game changer. There are areas of your operation that will simply run better without you, and the time and energy you gain by delegating will allow you to work on the job of growing and improving your business. That’s where your gifts, passion, and drive are best directed.  

Apply the above tips in your own delegation adventures, and the power of successful delegation will be yours to wield.

About Tia Agnew

Tia Agnew, founder of The Joy Pilot, is a business success coach and serial entrepreneur based out of Gulfport, Florida.

Before taking off as The Joy Pilot, Tia was the founder and CEO of New Day Craft, a manufacturer, wholesaler, and retailer of craft mead and hard cider.  

She brings nearly 20 years of hard-won small business experience, sharing lessons for success in business and life. 


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