3 Delegation Nightmares You’ll Avoid Thanks To These Strategies For Systematic Success

One of the most impressive things about Laura Roeder is how quickly she transformed LKR Social Media into a highly lucrative empire.

During my recent interview with her, she shared part of what made this remarkable growth possible:

“If you want to grow your business past a certain level, you’ve got to add more people. You’ve got 24 hours in the day, and you’re never going to get more. So if you need to take care of more stuff. . .because that’s what you need to do to grow a business—do more stuff—you’ve got to add other people’s 24 hours. You’ve GOT to delegate!”

Yup. You can’t refute that. What Laura says is so true.

But why do so many entrepreneurs resist delegation? Why do we refuse to do something that’s absolutely essential for expanding our offerings and raking in great profits?

We fear the nightmares.

We’ve either experienced disastrous delegation experiences or heard about them from our friends:

Delegation Nightmare #1: The Referral We Think Is Totally Amazing But Who Quickly Falls From Grace & Messes Everything Up

A colleague referred you to this awesome project manager, and during your Skype interview, she wows you with her knowledge, examples of how she’s made her other clients’ lives easier, and assurance you’ll be in great hands if you hire her.

The first week is blissful, but then things start falling through the cracks. She starts disappearing and then reappearing a week later with a good explanation. She promises things will be different from now on. You know “things” happen, so you give her the benefit of the doubt. But nothing changes for the better. Things get worse.

She drops the ball completely and it’s messed up your launch. Now you have to deal with damage control, which means you’re actually doing more work now than you had to do before.

“Not worth it,” you say to yourself.

Delegation Nightmare #2: The Contractor Who Promises To Get The Job Done But Then Tells You That You Have To Invest In Other Software & Slams You With An Outrageous Invoice

Before you hired the contractor, you had a great session where you laid out all the details of the project and the software he needed to use to complete it. He totally got it—said he’d done it a hundred times and that this was going to be easy.

Everything runs smoothly at first, but then he sends you an email telling you that there are some limitations to the software, so you shell out the extra $500 because you want things done perfectly. Your contractor’s back on track and finishes the project, but. . . .

 He didn’t deliver the exact results you agreed upon, though he seems to have done his best under the circumstances. You’re disappointed, but are ready to move on until. . . .

He sends you an outrageous invoice. . . billing you for the extra hours he had to put into the project he swore he’d done so many times before and which far exceed your original agreement.

“Never again,” you swear to yourself.

Delegation Nightmare #3: The Virtual Assistant You Hire Out Of Desperation & Who Turns Out To Be A Burden

You’re at your limit. You can no longer handle everything by yourself, so you hire a virtual assistant.

Groovy!  Things are going to get better.

But you quickly realize that you can’t really use her because everything that needs to be done is in your head, and you need to spend more time explaining things to her than it would take for you to do it yourself. You try to spend a little time here and there to train her, but managing her becomes more of a burden than a help.

You fall back into your old routines. Keeping your assistant becomes pointless and now—more overworked and disappointed than ever before—you let her go.

“What’s wrong with me?” you mutter to yourself.

But YOU don’t have to be the one telling these cautionary tales to anyone who’ll listen. Swipe these strategies for systematic success when delegating, and pretty soon, the only nightmarish stories you’ll tell will be the ones from “back in the day” when you did everything yourself.


You’ve got to start small. Trial periods and test projects are great for seeing your new hire in action.

Use those trial periods to assess the quality of your contractor’s skills in relation to the project, get a sense of how respectful they are of deadlines, and see how they can manage their workload if they have other clients.

Slowly increase their responsibilities to monitor how well they take care of the delegated tasks. This approach will also give your contractor time to streamline the delivery of your tasks.

Lastly, don’t forget to regularly follow up. Follow up is crucial if you want to ensure that things are done the way they need to be done and keep everything on track. To avoid micromanaging when following up, establish a reporting system.


All too often when we hire someone, we rely on verbal agreements. They’re not enough. You’ve got to protect yourself and your investment.

Use agreements to specify the scope of the project, outline the payment schedule, list the performance metrics of your contractor, and, if applicable, state penalties for projects delivered late or that are of poor quality.

Granted, technology might be tricky. But you can always outline possible implications in your agreement so that you are not slammed with an unexpected invoice at the end.

Unless it’s a special limited time project or assignment, always try to negotiate fees per project and get away from paying per hour.

new hire quote


In my recent interview with Danny Iny, he mentioned that best time to hire an assistant is when you’re at about 75% capacity, so that there’s enough bandwidth to train them. However, he admitted, it’s not always possible, because we tend to wait to ask for help until the very last minute when our situation becomes unbearable.

If that’s how you tend to approach delegation, I recommend starting to organize your back end processes long before hiring someone. Outlines of how you do repetitive processes will become the foundation of a training manual you will easily be able to easily share with your new hire down the line.

Documenting processes doesn’t have to be a time and energy suck. You can use (free) software like Jing to record your screen as you show and narrate how you do something (e.g., uploading your blog posts). Later on, your assistant can turn it into a step-by-step procedure.

For repetitive tasks that don’t require visual directions (e.g., the steps for signing up a new client, putting together a gift basket for a client, or ordering instructions), you can record audio instructions. Once you have an assistant, they can turn those audios into a checklist.

Save those documents in Google Drive or Dropbox for easy sharing. This way, getting stuff off your plate and having your new hire be of true assistance becomes incredibly easy.

Back to You

What are you going to do today to start overcoming your fear of delegating so that you can grow your business?

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Natasha Vorompiova is the founder of SystemsRock, creator of Systematic Success Guide and a Certified Book Yourself Solid Coach. Her clients are small business owners who start their businesses with passion and a desire for freedom, but find themselves stuck and buried in day-to-day operations. Natasha creates systems that ensure clients get more done in less time and pave the way for greater profits and long-term success. Check out the FREE Systems Chick’s Guide to Transforming Busyness Into Business for simple ways to grow your business.


  1. Katya Barry says:

    Great post, Natasha. I particularly like third point you make, definitely works for me.

  2. I’ve found that when I try to tell someone how to do a task, I improve the process for myself.
    It can be difficult to know what systems you are using and will eventually want to pass off onto someone else before you are at 99% of your capacity, but I like the idea of just talking it out and recording it as you go. This seems like an efficient way to overcome the barrier of starting to document your processes.

  3. Excellent post.
    I have been in the business since 2002 and have learned to help guide and “educate” through the learning curves and apprehension associated with delegating. It can present challenges as well as represent a leap of faith and high level of trust to be able to outsource your business processes, tasks and various projects.

    Choosing an executive virtual assistant does require due diligence and some research. I would think most business owners are more interested in an established entrepreneurial assistant versus a call center as we are more like minded and understand what it requires to operate a business. Personally, I treat every client’s business like it is my own. I am a vested business partner, with a real interest in the success of my clients.

    Thank you,

    Ace Concierge, LLC