“The Many Hats Entrepreneur” Syndrome: When You Should Start to Outsource and How to Mitigate the Risk

With a plethora of available online tools to automate workflows and administration today, there has never been a better time to run your own business. There’s a great range of affordable, or even free, software solutions that have been life savers for many fledgling entrepreneurs with low levels of investment capital. You can get FreshBooks for finances, Hootsuite for content management, Canva for design, or MailChimp for emails, to name just a few popular tools.

However, all those digital possibilities can be deceitful. Even with automation, entrepreneurs get buried in numerous different tasks that are not a part of their expertise but still necessary to run the business and “keep the lights on”. On top of their work, they are running finances, writing offers, sending dozens of emails, creating content, engaging in self-promotion activities, scheduling meetings - the list goes on.

Before they know it, they end up becoming hustlers who are working 16 hours a day and wearing many different hats. It may be the widely accepted norm across various entrepreneur communities but, in the long run, it’s not a sustainable business model.

The Growth Factor

So, what happens when business starts to take off, the number of clients grows, or fresh business ideas come in, which need your full commitment and attention? At some point, the super-capable, hustling entrepreneur will realize that he needs assistance. There are only 24 hours in a day, and if an entrepreneur spends too much time on administration and other business necessities, he may risk losing new opportunities, and in the long run – his entire business.

“As an entrepreneur, you are a problem-solver. Don’t let that strength become a weakness by taking on too many processes that could be better addressed by outside experts who are more capable than you.” – Andre Bourque, a Fortune 500 Product Manager in his CIO article.

Be honest with yourself, do a personal SWOT analysis, and identify areas you are not so good at. Your list of weaknesses could act as a starting point in which you can decide what parts of the business could you hand over to another professional.

Typically, entrepreneurs outsource:

  • Web development/maintenance
  • Graphic design
  • Social media
  • Accounting
  • PR
  • Writing/content

Hiring several different professionals full-time is probably not an option for most entrepreneurs with uncertain businesses or for bootstrapped companies, which is why outsourcing provides a fantastic alternative. There are many benefits to it, but also some drawbacks, so let’s look at outsourcing from both angles.

4 Reason Why You Should Consider Outsourcing

1. It saves you money

Outsourcing skills among freelancers and agencies will cost much less than payrolls and benefits, plus it can free you from some legal and tax-related obligations required in the full-time employment scenario.

2. It saves you time

You could do some of the tasks on your own, but most of them have a learning curve that you need to overcome, and the odds are you don’t have the time to do it (or a genuine interest in the area, whatsoever).

Marketing is one typical example. Facebook advertising and social media look easy when you read about them but when you get inside you will quickly find it to be very time-consuming and complicated, with many trends that constantly change, and techniques that you would have to master to set up a successful campaign. There are people all over the world that do this for a living, are practicing this every single day, and unless social media ads are your secret passion, you should consider hiring an expert in this area.

3. It improves your quality and efficiency

As mentioned above, every job on this planet requires practice and many years of effort put into mastering a specific skill. When you outsource to other professionals to take care of one particular part of your business – usually one that is not your area of expertise - you can expect much better results than you could achieve on your own.

4. It can add new value to your business

Let’s say some skills could be learned in a short time-frame and you could overcome them as a side-hustle if you chose to do so. However, some specialties would take you much longer and are not that easy to master from scratch. If you’re not into coding, for instance, and you would like to complement your services with a great mobile application, (Link to Clover mobile apps) the odds are you will have to outsource some professionals to do it for you.

2 Reason Why You Should NOT Consider Outsourcing

1. Giving up control

This might be difficult for some entrepreneurs used to do things their way, but it is an essential quality of great leaders. If you want to grow, you have to accept the fact that you cannot supervise every detail. Tonya Thomas, president of The Small Business Assistant, learned firsthand that letting go was the hardest part of delegating:

“At first, I felt like I was the only person who could do the work efficiently; I wanted control over everything […] but I wanted my business to grow and to do that I had to let go and start delegating,” she says.

2. Trusting a task to the wrong person

Yes, it happens too: it can be a big waste of time and money if you bring in a person that cannot ensure the level of quality required to maintain your brand standards or even fulfill the basic agreements in your contract. The cheapest freelancer quote might be one sign that you cannot expect top quality services. That’s why outsourcing has to be thoughtfully and carefully planned.

How to Find the Right People for the Job

When trying to build a project-based team, rather than relying on one method, it is best to take few different strategies and ensure yourself the option to choose the best fit. Here are some tips:

Use your network – Before you publish a job ad online, talk to the people you already know and trust to see if they know anyone who would be interested in taking on your project task. Join Facebook and LinkedIn groups and ask for recommendations and advice. Do the same when you attend conferences and different networking events.

Post a job ad in the right place – Don’t hop straight away on Fiverr or Upwork hoping to find a skilled professional who will be invested in your business. Instead, post on a skills-specific job board and network on social media.

Research the rates and the candidates – Investigate the going rate for the services you’re seeking before you post. Quality freelancers know their worth and won’t accept a project for less than a fair price. Also, do some online digging of the people who replied to your job posting.

Ask for work samples – Always check their portfolio but don’t expect it to be too fancy. If they have solid examples of their work, you’ll get a good idea of how they may perform for your business.

Require a (paid) test project – This is an excellent way to set your parameters and see if your candidate can meet your expectations and follow direction before entrusting them with a larger project that might be critical to your business… and your reputation.

Pay attention to the questions candidates ask - Someone who cares about adding value to your business will have just as many questions for you as you have for them. After all, these conversations may help you tweak the message for the freelancers in a more focused and clear manner, which will help you eliminate the not-so-fit candidates and attract the ones you want.

Interview the shortlisted candidates – if the task you are trying to outsource is of high importance and is crucial for the success of your project, it would be good to talk to your top three candidates before you make up your mind. Get to know them better in a live conversation, where you will be able to ask more questions about their work.

Work Smarter

In a way, outsourcing skills is very similar to hiring someone full-time, which means it should be the result of a well-constructed procedure. Sure, it presents some risks, but that’s what you signed up for when you chose the entrepreneur lifestyle, didn’t you?

Think of all the benefits that outsourcing professionals can bring to the table and, most importantly, more free time for you to do what you love. One of the most famous sayings in the entrepreneur world is: “Work smarter, not harder.” Outsourcing is the first step to doing that.

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