Is Your Business Ready For Summer Vacation?

Is Your Business Ready For Summer Vacation?

Have you planned your summer vacation schedule yet?  Does it include luxurious and relaxing time away from your business?

If you answered “no,” let’s you and me talk about some finer delegation skills.

As successful entrepreneurs will tell you, one of the biggest steps that a solopreneur can make in his or her business is to bring someone new on-board.  Aside from the obvious fact that now you have four hands instead of two, it is also the single biggest leap forward you can take to transform yourself from a worker bee into a leader.  And even better – a leader who can actually take vacations!

But the advantages don’t end there. Whether this is your first or 15th hire, the key is to get into a mindset of making sure you have time to do the work of growing your business and not just running it.  One way to do that is to delegate tasks that you are currently doing to contractors or employees who can often do them as well, or better, than you (with a commitment to training on your part)

Whether your business is at the point where you are regularly working with others, or still going at it alone, you need to beware of the “Lone Ranger Syndrome.”  The Lone Ranger Syndrome is the surest killer of vacations plans – it’s the managerial malaise that causes dedicated entrepreneurs (like yourself) to work excessively long, hard hours because only THEY know how to do something right.

Whoa, Silver! There are actually two keys to curing this syndrome.  The first is mastering the skill of delegation; effective delegation is a learnable time management skill that can dramatically increase your effectiveness at work.  The second key, and actually the most difficult part, is that once you finally get a new hire trained and hard at work, don’t fill the newly created time in your calendar with more busy work from your business.

But just like AA, the first step is admitting you have a problem.  

Take my little quiz below to see how far you are down the Lone Ranger path: 


1. In most cases, I can do tasks quicker and better myself than if I delegate.

2. Before I delegate something, I take the time to visualize the end result and to communicate that to the delegatee.

3. I work longer hours (and seem to make less money) than others doing the same kind of work.

4. For larger tasks, I always follow-up with the person I am delegating to after assigning them a new task to make sure there are no issues or unclear instructions.

5. If I get back work that is not what I had in mind, I discuss it with the person to sort out where the misunderstanding occurred and how it could be different in the future.

6. I often find it’s quicker to do it myself than to explain it to someone else.

7. I include a due date for all assigned tasks. I encourage those who cannot commit to the timeline to renegotiate. I reassign the task, if necessary.

8. Even though I work constantly, efficiently and effectively, I miss important deadlines.  There’s too much for me to do.

9. I use project management software to track ongoing projects (or I’ve created my own system).

10. I check-in almost daily with my staff – the key to smooth projects is early communication to avoid problems.

11. I’m not a micro-manager. I care more about the results rather than managing the whole process. I love when my staff uses their own strategies and creativity to accomplish a task.

12. I never have time for my most important projects.  I find myself spending too much time on smaller stuff rather than revenue-generating business strategizing.

13. When delegating, I always indicate what resources are available and what support I can give.

14. I am grateful for a job well done and even thank people for their efforts, even if it needs revision.

15. I am familiar with the strengths of all my staff and contractors and use this knowledge to consider who would be the best for each task.

16. I carefully evaluate job candidates–employees, subcontractors, volunteers or interns–before hiring. I check references and conduct “trial tasks” before committing.

17. I am never completely satisfied with my employees and subcontractors.  They never do as well as I had hoped.

18. My subordinates are often asking me for work because they have nothing to work on.

19. I delegate only the jobs I don’t like. It’s not worth hiring someone to do something I like doing.

20. I’ve come to peace with the fact that not all my delegated tasks will be done perfectly.


Give one point for each “True” for numbers 1, 3, 8, 12, 17, 18 and 19, and for each “False” to the remaining statements.

If you scored 7 or below: WAY TO GO! You are on your way to honing your delegation skills and maximizing the effectiveness and the morale of your delegatees.

If you scored 8-15: You need to spend some time and energy on your delegation processes if you want to lead your business successfully to more growth without burning-out. Consider engaging a coach to help with the process or at the very least, sit your delegatees down and find out what’s really working for them and what isn’t.

If you scored 16-20: Let’s be honest – you need help! Consider this your wake-up call to the fact that vacations and sustained business growth will keep being wishful thinking if you don’t start boosting your delegation skills and processes.

Please leave a comment below with your score and what your biggest delegation challenge is.

Quiz Adapted from © 2008 Claire Communications

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.


  1. travel on May 28, 2013 at 3:43 pm

    Hi there, just wanted to tell you, I enjoyed this blog post.

    It was practical. Keep on posting!

    • Jo Ilfeld on May 28, 2013 at 4:12 pm

      Thanks so much for letting me know Muriel! I really do appreciate the feedback and am glad you found it useful!

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