Gray Areas

I lead a small software company in a niche industry. Our head of product and I both shared a boss earlier in our careers. I considered him a mentor and friend, but she decidedly did not. Years after we all worked together, she shared that the two of them had an intimate relationship that did not end amicably. They were both single and consenting adults, but she was younger and junior to him. She considers the relationship exploitative and unethical. She never told any superiors back then but is frustrated that he skirted accountability.

Now, our company has reason to explore a partnership with our former boss’s new company. I have every reason to side with my employee — our old boss’s behavior was inappropriate. But if I’m being honest, I still consider him to be a good person and a worthwhile partner. What is my obligation to my head of product? What is my obligation to my company? Should I refrain from exploring this new business relationship out of loyalty to her? Should I encourage her to seek closure? If I think proceeding is in the interest of the business, how should I approach my relationship with our head of product?

— Anonymous

What is more important — developing a new business relationship with your former boss or maintaining a good relationship with your head of product? You are obligated to not put her in an uncomfortable situation and, frankly, to not put junior staff members in a situation where they might be exploited by a known exploiter. You should refrain from exploring this new business relationship, not merely out of loyalty but as an act of care for every woman in your organization. To be clear: Your former boss did not commit a crime. People have relationships in the workplace all the time. But when there is an imbalance of power in that relationship, it is a problem. Many would argue that what happened between your former boss and your head of product was a personal situation that should not affect your present-day professional decisions. But engaging in a romantic relationship with a subordinate is predatory and unethical. You do not want to do business with someone you know is and/or was predatory and unethical. It’s as simple as that, which I think you already know.

Managing My Manager

Over the last few years, my manager has normalized a peer/friend dynamic. Co-workers have confided that he falls short on projects, which forces others to pick up his slack. I’ve unfortunately started to experience this while collaborating with him closely on an intense project. He is not the most organized or focused individual and tends to lean on me and others (mostly women). He is a supportive, well-intentioned and empathetic person, but he has also made a habit of dumping his own emotional work/personal baggage onto me, some of which crosses boundaries. All of this puts me in a tough spot as both his direct report and as his “friend.” I’ve lost some trust in him, and I’m being taken advantage of.

I am reaching a point where his struggle to perform effectively is directly impacting and possibly hindering my own potential growth and opportunity for promotion. If I am candid with my manager’s boss, it will likely have a negative impact on his future here, because of their contentious relationship. Am I enabling my manager’s mediocrity at work by being overly concerned with our interpersonal dynamic, rather than taking steps to hold him accountable?

— Anonymous

When the boundaries between professional and personal blur like this, it can be incredibly uncomfortable. And as the subordinate in this circumstance, you are at a grave disadvantage. Your manager has all the power and you are providing emotional labor and having to compensate for his professional shortcomings while his issues compromise your standing. Yes, you and many others are enabling your manager’s mediocrity. There isn’t an easy way forward, but have you addressed some of these concerns with him? I would start there and articulate that it’s too difficult to balance your professional and personal relationships and as such, you would prefer to remain friendly but professional. If talking to him doesn’t help, then it may well be time to communicate the professional issues with your direct manager to your manager’s boss.