boss or friend


You have a small company. Your employees are in close proximity to you with a high level of access. All of you work hard, with long hours. Blowing off steam is important, so you socialize away from the office. That’s where the problems begin.

If you’re the boss, your motives are pure – you want to show your employees a good time, give them time to release some stress, and generally have fun!

However, there are some employees who live for the opportunity to develop a stronger relationship with you as their boss. Some employees will use that relationship with you in a way that causes problems.

Once you become the boss, it can change the entire dynamic. As the boss, you can set the tone for managing both the benefits and the risks of getting closer to your employees. However, If you are a participating employee, you can also have a hand in managing the situation.

Why is this important for you? Once you have gone down the road of mixing business with pleasure, it is more difficult to back up and set the ground rules. Setting the tone and providing guidance for your team will pay long-term benefits.

Here are some situations from my clients’ experiences that may be helpful to you. These clients had already gone down the path of not having the rules of engagement in place, and had a more difficult time turning it around.

1. The owner of a successful growing company frequently accepted and responded to direct texts from some field managers.

Normally, this would not have been a problem, but there was a Director in between the owner and the field managers who were in direct contact with the owner. This resulted in the Director feeling like he was out of the loop with the field managers, and the field managers feeling like they had a direct line with the owner.

2. The owner of a successful mature company was quite active on social media for her business.

She was the face of the company in the community. Many of her employees “friended” her on social media. She often used the social media status of her employees to shape her opinion of their work performance – even if it had nothing to do with their job.

This resulted in negative comments to the employees’ supervisor by the owner based on her social media observations. This caused some unfair bias in the owner and supervisor’s interaction with employees.

3. The owner of a small successful company sometimes participates in “happy hour” sessions with her employees.

She has a great time during happy hour and gains some additional insight into what makes her employees tick. During these fun times, the roles get blurred, so when they return to work and the roles snap back to reality, it often results in an uncomfortable situation.



1. Remember your chain of command. If an employee begins communicating with you instead of their supervisor on a work issue, politely refer their communication to their supervisor and let them know you are doing so. If the communication is more friendly and not work-related, pause before responding to be sure you are not setting yourself or the employee up for a misunderstanding regarding your relationship with them.

2. When you are active on social media for your business, you must mentally separate the “posts” of employees from their time at the office. There are exceptions, of course, but you must be careful to ensure that your judgments regarding them are based on their work performance and not your own bias from reading what they are doing on their personal time. Remember, I said there are exceptions, so this should be approached on a case-by-case basis.

3. When socializing with employees, be very clear in your communication that this time is for relaxing and releasing the stress of the workday. Let them know that when you return to the work environment, all normal rules, policies, and relationships return to “work normal”. You must also be careful when planning a retreat or planning session away from the office that you clearly communicate expectations about behaviors, respecting boundaries, and the purpose of the retreat or session related to a work outcome.

What if you are an employee, what can you do? I haven’t forgotten about you!



1. Honor your supervisor, the relationship, and the lines of communication. By all means, if you have a reportable offense against your supervisor, do not hesitate to follow the reporting protocols set up at your company. However, if in the normal course of business, you have something to communicate up the chain of command, make your supervisor the first recipient of that message. If you have a friendly relationship with the owner of the company or someone else who is above your supervisor in the chain of command, be sensitive to that relationship and do not take steps to use it to your advantage with your supervisor or to gain power with your peers.

2. As an employee, be mindful that your social media posts are out there forever! If you are engaging in activities that might put you in a less than favorable light at your job, take that into consideration before you hit “post”. Consider how your post might be received by someone who may not know your personal life or sense of humor. If you have aspirations of rising in your company to a position of authority, consider the persona you are projecting and how it might be interpreted as a potential future leader in the company.

3. If you participate in socializing with your boss and peers outside of the office, set some parameters for yourself before the event begins. If alcohol is involved, ensure that you keep yourself in a state in which you feel in control and respectful of the working relationship with those in attendance. Also understand that when you return to the work environment, even if you feel you advanced your work relationships to a deeper level, things return “work normal” and the chain of command is back in place.



The situations and tactics I have outlined here are in no way representative of any and all situations that may occur. However, if you take these to heart and think before you take action, you can certainly avoid some sticky situations. The most important thing to think about, whether you are the boss or an employee, is how you set boundaries. 

Think about what is acceptable for any particular situation and use that as your guide. This goes both ways – bosses to employees, and employees to bosses. 



If this is a topic that has hit a nerve for you, please share your thoughts in the comments below. Perhaps you have a situation and can share how you handled it successfully (or where it went wrong…). Each example is an opportunity for us to learn something from each other.



I’ve created a checklist called “WORK VS. SOCIAL – CHECKLIST FOR HOLDING THE LINE”. This will help you with the elements necessary to create successful interactions when you socialize with your work acquaintances. Those who have had issues with this topic have welcomed having this checklist. They find that a little preparation goes a long way. You can click below to download the checklist.

Click Here to Download the Checklist

I’m Tina Meilleur, an Executive Coach, Business Advisor, author and speaker. You can learn more about my story here. I am also the founder of Design Your Success and the Academy for Business Success. My mission is helping high achievers develop the strategies and plans to bring their skills to a level that matches their aspirations for their career or business.  My coaching programs and CRAVE™ process are systematic approaches for making simple “tweaks” or a total up-level of your skill set. I am the author of Your Next Chapter: Five Steps to Creating the Life of Your Dreams to help others with a process to create and execute a future vision. I have a CPA designation in the State of Louisiana and received my MBA from Tulane University in their Executive MBA program. I’m a highly sought-after coach, facilitator of female CEO round-tables, business strategist, and speaker. You can reach out to me at