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So often when we start our creative business venture we start out alone. We are the creative force behind the business, the chief cook and bottle washer, the lone ranger. And for a time, that is good. But as the business grows and becomes more successful, there is a shift. Time becomes more precious and you begin to worry about getting it all done. You start toying with the idea of hiring someone to help with the business. And then you take the big leap! You hire your first employee or contractor. Suddenly you are not just a business owner and entrepreneur, you are also a manager.

Being the Boss

Almost no one likes the term “boss,” but once you hire people to work for you, that is what are. The choice is whether you are going to be a good boss or a bad boss. As Richard Miller, my manager when I worked at Ernst and Young, said to me on the eve of leading my first team, “You are now the boss they will be talking about to their friends and family; the trick is to make sure they talk about you in the way you want.”

Being the boss doesn’t mean you have to be bossy. But it does mean you may, from time to time, have to make decisions that the people who work with you don’t necessarily agree with and/or understand.

Understanding this dynamic is particularly important when you work with people you also think of as friends. Whereas a friendship is based on a give and take relationship where both parties generally have an equal “say” in the relationship, that is not the case in good manager/employee relationships. Although smart managers will always listen to their employees’ input and insights, some key decisions are ultimately the manager’s domain. And unless both parties clearly understand this dynamic, there is a high probability for hurt feelings at some point in the future.

Laying the Ground Work

The more professionally you go into a manger/employee relationship, the more likely it will remain on solid footing. As an experienced employer, Dona Zimmermann of Websters says, “Make a point to be organized starting at the time of hiring with a detailed, written job description, and all the forms and paperwork in-hand and ready to go.” By doing so you can address questions quickly and make sure you are both on the same page.

Although a written, detailed job description may seem like over-kill for your first hire, it will actually provide clarity for both you and your employee on setting expectations. It also provides a basis for performance reviews, change in job duties, and ongoing communications.

In addition, it is also highly recommended to create an employee manual. Even if it is a very simple document in the beginning, it can be updated going forward. Employee manuals are designed to remove the need to make assumptions about the workings of the business. Even a simple concept, like arriving to work on time, doesn’t necessarily mean the same thing to different people. The more these things are spelled out, in detail, the less likely there will be issues around them. 

Communicate Consistently

Communication is key to developing and maintaining strong manager/employee relationships. And although it seems obvious, it rarely is done well within a small-business environment. Because the business is small (2 or 3 people), communication is often handled in a casual manner, grabbing time when available. The problem is this leads to bad habits.

For businesses to run effectively, communication must be consistent and consistency usually implies the need for a regular schedule. Even if the business is two people, having a regularly scheduled company meeting, no less than once per month, ensures that all the topics that need to be discussed have a forum, and it provides a time to share information in both directions.

In addition, it is important to establish regular review periods. During the first year once a quarter allows for open dialog, acknowledging achievements and making course corrections as necessary. After the first year, continue to schedule reviews at least annually to keep communication regarding individual performance and working relationships open.

Assigning Tasks and Delegating

One of the biggest mistakes people make when making their first hire is not really knowing what aspects and/or functions within the business will be turned over to this new employee. Not only do you need a list of the tasks, you also need the processes and procedures for those functions clarified, simplified (if possible), and documented in a manner that allows for knowledge transfer.

You also have to be willing to let go.

This is not nearly as easy as it sounds! As Lauren Caselli of Lauren Caselli Events recently said on the What Works podcast episode 184, “Hiring someone is just a process, it’s just a practice. And you’re not going to be great at it in the beginning and you have to forgive yourself for that.” But just like learning anything new, with practice and repeated effort, you will get better over time.

Delegating work to a new person is a multi-step process that takes time.

  1. Transfer the task to the employee – you still own the decisions when needed
  2. Allow the employee to make decisions – you still own the result of the task giving corrections as necessary
  3. Give the employee the responsibility of the result – you define the benefit to the business but they are responsible for achieving the outcome with minimal input from you.

Over time, if you are able to move an employee from step 1 to step 3, not only will you have more time for other aspects of the business, the employee will usually feel much more fulfilled in their work. It truly is a win-win.

Hiring your first employee or contractor is a big step in the life of a business. Learning to be a good manager is just another new skill to master as part of being a creative entrepreneur. By investing the time with your employees to create a strong foundation, keep communication lines open, and fully delegate tasks over time, you will reap the benefits of having time for aspects of the business for which you are mission critical and bring you greater satisfaction as you rediscover the passion for the business you love.

Being the Boss without Being Bossy: Managing Your First Hire
Gwen Bortner

Gwen Bortner


Leveraging her breadth of operational expertise, Gwen Bortner works with female entrepreneurs to design a business that aligns with their deepest desires. Gwen describes herself as an operational strategist. She works with owners to improve business operations and leverage goals effectively to create a business that meets each individual’s unique definition of success. Find out more at https://everydayeffectiveness.com/

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