Confronting a Boss/Friend

Question

I'm working for a friend in a start up and the dual role as employee/friend isn't working out. And while I really like the work and the flexibility and autonomy, she's just not a good boss for me -- hasn't articulated expectations despite being asked numerous time and now won't call me back, after being asked. I'm blessed that I don't need the income, but I do love having something to do beyond parenting, home-making and volunteering. I guess I just need to call her, but UGH! I hate confrontation. Advice?

Kay Fittes · Answer

Regardless of the circumstances there are always going to be conflicts in the workplace due to different personalities, styles and needs.  It's exacerbated when working with a friend, as it's easy to assume we will be on the same page.  So many people struggle with uncomfortable situations in person and on the phone, so email and text can be your friend.  You may want to preface you comments with your strong goal of making this situation work and then moving to more specific questions.  Consider these questions: 'Describe the ideal behavior for this role.'  'What is your definition of success with contributions from this position to your business?' 'What would be the first step in us making this work?'   Remember, there are other opportunities if this one does not work out.

Shinesa Cambric · Answer

Since she is not returning your calls it seems she may be struggling with how to have difficult conversations as well and she may be afraid of damaging your relationship. What I’ve found to be successful is making it clear when you are discussing items from the perspective of an employee versus the perspective of a friend.  Because you are friends and you’ve stated that you enjoy the autonomy and flexibility, she may take that to mean you don’t need feedback. She may not realize that as an employee you would like more structure around your role/responsibilities and she may not be clear on what “hat” to wear when having a conversation with you. I would suggest that you schedule a time with her and make it clear it is a 1:1 check in as an employee to get her feedback as a manager on your role.  Based on that conversation, you should consider building a 30-60-90 day plan of what needs to be accomplished within your role that both you and she can use as a framework for expectations and for later check ins on progress.

Stacey M. Woods · Answer

My advice would be to have an open, honest conversation with your friend.  State your intentions upfront and share from the heart.  Your friend could be feeling the same way and could be struggling to find the appropriate time to address and words to say.   Considering its a start up, she is likely juggling a lot.  It's all about approach and ensuring positive intent is understood on both sides.  You both will walk away relieved.  All the best to you!

Jana Berg · Answer

Working for a friend can be a sticky situation. I, for one, wouldn’t consider it but that’s just me. If this friendship means a lot to both of you, then you need to tell her everything you just stated in your post. It’s a hard conversation to have, but necessary. And if this startup is to work and your friendship is at stake, then you both need to come to some kind of understanding and expectations need to be clearly defined so that you’re both on the same page. Best wishes!

Jennifer Haje · Answer

You have to have a frank conversation that you would like to set boundaries that work for you.   Hopefully that would improve your situation. I hope this helps you out.

Uzma Islam · Answer

Honestly, your situation reminds me of Fallon and Kirby from the series 'Dynasty' haha. Working with a friend can be quite conflicting, because the roles of being a friend and being in a professional relationship are very different. Moreover, an people may end up making hurtful comments and ego might get in the way too.

So maybe you guys can have a heartfelt, matured conversation about how to keep your professional and personal lives separate. If you just keep your feelings to yourself and don't speak up, they will most probably just accumulate and become detrimental to the bond you both share.  On the other hand, if she is too immature, maybe you can just tell her that this is not working out and apply for other similar jobs where you do not know the person you will be reporting to too personally.

Hope this helps xx

Christina · Answer

The best friendships survive difficult conversations and conflicts. If you can't speak openly and honestly and set clear work/friend boundaries then you'll quickly learn whether it's a friendship worth keeping. If it's just a casual kind of friendship then what do you have to lose by talking it out?  You can also try practicing the conversation with someone you're more comfortable with first and get feedback. That can help ease your fear and make you more relaxed when you do end up doing the tough talk.

Hannah Oates · Answer

This is a great question to a struggle that is more common than we realize. I was in a similar boat a couple of years ago, when I became the boss over a few co-workers that had been friends of mine. It was definitely awkward at first but, I tried a few tactics to help, and the situation ended up working out well!  Similarly, you can try these in your situation with your  boss/friend. 1)Try to have an open and honest conversation about expectations, goals, etc...without this first conversation being a confrontation... like Barb mentioned in one of the earlier comments. 2) Also, write down what you want to say ahead of time... that way, it's more matter-of-fact, and less room for extra emotions to rise up, and get in the way of what you need to say. 3) Schedule a time to have this conversation so you can mentally, emotionally, and professional prepare for your end of the conversation. I hope this helps and I wish you all the best!

Confronting a Boss/Friend

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