When Your Boss is Your Friend


I have had a lot of bosses.  Unlike our parents and grandparents that would stay in the same job at the same company for decades, my generation and those after change jobs like we change hairstyles.  Other than the military, I have also worked for small business owners  with only a couple of exceptions.

I LOVE small businesses!  I LOVE the fact that a 4-employee coffee shop or a small non-profit organization or a one person consulting firm can drive so much good in a community and collectively in our nation.  When you work in a small business, and the owner has put the right team together, you then become like a family.  It is fun to go to work!  It is fun to experience new things!  It is fun to celebrate the successes, no matter how small!

I tend to take jobs that make me the second in command.  That means I get to work with the boss a lot closer than the other employees.  One of the advantages and disadvantages of that is we tend to become friends, not just colleagues, and this can change the employer/employee relationship drastically.

Case in point, one of my dearest friends and mentors was my boss for about three years.  We had an awesome working relationship.  We had an awesome friendship as well that allowed us to be totally candid with each other without losing respect for each other.  She is no longer my boss and we parted ways amicably.  But then things got complicated.  Current employees were calling me for help in learning how to navigate her decisions.  Her requests were erratic and all over the map.  The staff I trained before my departure was now getting contradictory direction from her, she let a key employee go within a month of my departure (as was her right as the chief executive to do although I didn’t agree with the decision), and she took all the operational processes and procedures we had worked so hard to put in place and put them through a meat grinder.  So what did I do?  I tried to coach the remaining employees through it and then I screwed up.  AS A FRIEND, I SHOULD HAVE GONE TO HER IMMEDIATELY AND SAID “WTF?”.

I left the most important piece of the equation out of it all.  I didn’t go to my friend and talk it through with her.  I was hurt and angry and disappointed that she had taken this “family” and the organization we had thrown our lives, blood, sweat and tears into so it would grow and thrive and completely turned it upside down with no apparent rhyme or reason.  I was hurt that she didn’t consult with me – why would she, I didn’t work there anymore – and that she had so little confidence in what we had built together that she could just tear it all down.  I let my emotions cloud my judgement and not only did I lose a boss, I may very well have lost a friend because of it all.

I won’t tell you that you should never have a close relationship with the boss.  I will tell you that if you have a relationship of accountability with someone, you should hold on to that and foster it and nurture it regardless of emotion and circumstances.  I found this great article from the Wall Street Journal a few years ago that reminds us that friendship matters.  I may have forgotten that.

Will you share your boss/friend story with me?  I would love to hear it and learn how you navigated through it.

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One thought on “When Your Boss is Your Friend

  1. Pingback: Give your boss a raise | The Career Advisor

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