Calling All Entrepreneurs: Help Wanted? The Ultimate Guide for Solopreneurs to Knowing When, How and Who to Hire


This month I interviewed my awesome friend Natasha Vorompiova of SystemsRock  about what entrepreneurs really need to know about when to get good help and where to find it.

Jo: First tell us a little about yourself.  How did you become so passionate about designing entrepreneurial systems?

Natasha: I had just moved from Cyprus to Belgium, where my husband is from.  I found myself in a situation where I was working from home for a Cyprus law firm, taking a 12-hour a week Dutch course, doing translation projects on the side, keeping the household under control, looking after my baby boy, and—after 40+ hours of work a week—laying a foundation for my own business.

It was insane.  I often wound up being so fatigued that I couldn’t focus on tasks that would help me grow my new business.  All I could do were mechanical tasks like chores around the house.  Plus, I was irritable and not pleasant to be around.  I had reached a point where I knew something had to change.

Systemizing has always been my strength—I’d often taken on projects at my previous corporate jobs involving organizing and restructuring.  But it wasn’t until I started applying the same techniques to structuring my daily workload that my sanity returned, my family got me back and my productivity skyrocketed.  As the systems I created for my own business started to work, I knew the approach I used would work for many other mompreneurs like me, who dreamed of the freedom of having a thriving business while working from home and actively participating in raising their kids.  That’s when SystemsRock opened for business.

Jo: What are the signs that you use to diagnose an entrepreneur that should be outsourcing more and/or hiring help?

I’ve heard all kinds of reasons why people avoid delegating.  For a lot of my clients it’s not an easy step to make.  It’s even more challenging to give delegation a second chance if they’ve tried it before, but it didn’t work out the way they hoped it would.   Generally, these are the signs that an entrepreneur should be thinking about getting more help:

  • They feel overwhelmed by their daily business activities.   It seems as though they’re spending all their time answering emails, maintaining their Facebook page, managing their Twitter feed, reading other people’s blogs, and doing marketing research. They’re freaking out because they’re barely able to stay on top of things.
  • Things are falling through the cracks despite their best efforts.  They can’t keep track of what’s happening in certain areas of their business.  They end up putting out fires left and right because they missed a deadline, or forgot to pay an important supplier, or missed out on a partnership opportunity with an industry influencer.
  • Time-consuming projects that they don’t even like to do (and might not even be good at) are eating up their energy.  They insist on resizing a picture for their website even though it takes them half a day.  They sit for 2 hours in front of a blank page trying to start a blog post.  They start researching blogs to guest post on, but end up buying a book on 
  • It’s difficult to give enough attention to responsibilities outside of their business, and their frustration about the state of their company spills over into their personal life, negatively affecting their loved ones.  They have to interrupt a romantic dinner to handle a client’s request.  They feel guilty for not working when playing with their kids.  They snap at their partner when reminded of a social engagement made a long time ago.
  • They have little or no time for themselves.  Their phone constantly beeps, notifying them of another email or business appointment.  When the phone doesn’t beep, they check it non-stop to make sure the technology works.  They have to base vacation decisions on where they have good phone reception and fast internet connections.  Even worse, they don’t remember when they last went on a vacation.

Jo: What are the top questions every entrepreneur should ask themselves before hiring help?

Natasha: Delegating is a partnership.  Therefore, before you hire someone, you’ve got to ask yourself:

1. What tasks could I delegate?  A great exercise is to keep a log of your daily tasks for a few days and then categorize them into:

(a) Tasks of managerial or creative nature that only you can do,

(b) Administrative/organizational tasks that need to be done regularly, even if each one of them doesn’t take long (you’d be surprised how much time it ends up taking by the end of the week or a month!).

(c) Tasks outside your area of expertise that drain your energy and take you unnecessarily long (multiply the time spent on these types of tasks by your hourly rate.  I bet the amount will be significantly higher than if you’d outsource it).    

It will certainly depend on your budget, but categories (b) and (c) are the ones you ultimately need to delegate.

2. What are my pet peeves that I need to communicate?  You have your style, preferences and requirements about how things need to be done. The more information you can give your potential hire about what to expect from working with you, the better you’ll set up the expectations and the easier it will be for them to adjust.

3. Can I devote time to clearly explain the tasks I’m delegating?   Many solopreneurs keep all their processes in their heads.  So, even when there’s someone to help, they can’t use them because they don’t have time to explain what needs to be done (it’d be faster if they did it themselves!).  You’ve got to be willing to take the time to show your new hire how to do things AND ask them to start documenting your business processes for you. 

4. Can I add regular follow-up with my new hire into my schedule?  Delegation is not a “give-it-away-and-forget-it” arrangement. You’ve got to find balance between giving them space to perform the tasks yet regularly checking in to ensure they are making a progress. 

Jo: When an entrepreneur is ready to hire help, where should they start looking?

When you feel you are ready to delegate, the very first thing you need to create is a job application.  The tasks you want to delegate will give you a clear picture of the types of skills your new hire would have to have.  Here’s a template you can use to create a job description.

Where to look for the best applicants will greatly depend on the type of help you are looking for—an intern, techy, professional VA, personal assistant?  Click here for an extensive list of resources.

Just make sure you prepare the application before posting anything.  Also, never underestimate the power of recommendations.  Describe the person you are looking for to your friends or social media following.  You never know who can be referred to you.

Jo: What are the top ?s every entrepreneur should ask a potential hire before saying “yes?”

Hiring is not an event, it’s a process.  You’ve got to take your applicants through a series of steps to confirm that they really qualify for the position: from giving them a clear list of instructions to follow to apply for the position and rigorous selection process to a face-to-face interview and a test project.

Once you get to the point of having a face-to-face meeting with them (whether in person or via Skype), it’s important to ask your applicant:

  • Why they are interested in this position,
  • How they see their work adding value to your company,
  • How do they see their skills helping them to meet your expectations
  • How would they handle a hypothetical situation that might happen in their line of work if they get hired, etc.

You’ve got to make sure you ask a combination of questions related to the applicant’s hard skills as well as behavioural questions.  If possible, have someone else present at the interview, so that they can give you their opinion.

Jo: Let’s say you’ve made that hire but something’s not right.  What are the signs it’s not working and what can an entrepreneur do about it once they occur?

If your relationship with the new hire is not working out—e.g. you see that his/her qualifications are not at the level you wanted them to be, they are not progressing as fast as you’d want them or you simply have this nagging feeling that this is not the right person, don’t disregard the signs.  You’ve got to let them go, because this relationship will not benefit either of you.

This is where the trial period comes in very handy.  If you agree with your new hire from the very beginning that they will be on trial for a certain amount of time, it will be that much easier to have a conversation if you have to let them go.

This being said, my ultimate piece of advice is not to rush things.  You’ve got to put a lot of thought into everything from selecting tasks to delegate to nurturing the relationship with your new hire.

Jo: So now you see why Natasha is such an amazing resource.  To grab her valuable short 5-part free course on mastering delegations skills – head to her website and sign up there to learn how to:

  • Overcome your fear of delegation
  • Find your dream team of affordable experts
  • Communicate so nothing falls through the cracks
  • Get the results you want every single time
  • Delegate even if you don’t have a team

You’ll also continue to get her amazing content aimed at simplifying the lives of solopreneurs.

So now here’s my question to you, my fabulous blog readers – comment below and let me know if you’ve made your first hire yet and if so, how you knew it was time to hire someone.  If you haven’t yet – how do you think you will know you’re ready?

Jo Ilfeld, PhD

An executive leadership coach, Jo helps C-suite leaders, executives, and high-potential managers develop the flexibility, skill, and frame of mind to meet the challenges of the next five, ten, twenty years…. and beyond. She works with individuals, teams and organizations on four core areas of leadership development. Check out Jo's bio page for more information.

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