Hot Take: Challenging Conversations with My Boss
My boss preaches an open door, but it sure feels shut to me.
BIG thanks to one of our first submissions.
Please keep them coming. Conflicts big or small always hold a nugget of insight we can learn from together. We also have a little curve ball coming next week, so stay tuned. You can count on one thing: things are always changing. We will be sharing a few updates on who we are, what our plan is here, and a bit more structure to this stack.
Angie wrote to us frustrated with her boss. The boss regularly says she wants an open, healthy culture and keeps an “open door” policy in theory. When Angie tries to take her up on it, the conversations hit a dead end.
Here is how Angie put it:
“Each attempt to talk to her seems to be met with immediate rationale and defensiveness which makes me just want to keep my mouth shut. Is there anything I can do to try to get through to her? I have some important issues to surface but I feel gaslit each time I try to bring anything up. I also need better help prioritizing my work but she continues to toss things over the fence without much context. Are there any tips you can share to try to open ‘the’ door?”
Katie’s take:
Thank you for sharing this. I know this dynamic well and it is a tough one. Work relationships carry a different kind of weight. In marriage, partnership, or friendship the stakes feel emotional. At work the stakes are tied to your livelihood and security. There is no shared love story that brought you together. It is a different kind of conflict, so we need to look at it through the right lens. Your job.
We have to name the hard truth that we cannot change other people. We can only communicate our needs with clarity and hope they can meet us there.
This turns the conversation into an “I” conversation. Something like:
“I wanted to grab some one-on-one time to talk through a couple of my professional goals. One goal is to feel more empowered to have open and challenging conversations with both my team and leadership. I know this is important for my growth, and I want to be able to surface tough stuff without overthinking it. I appreciated hearing in our last all-hands that your door is open, and I want to take you up on that. Here is what is on my mind, and I would love to collaborate on some solutions.”
You are restating her own words and creating a gentle accountability. You are not saying, “You are not doing what you said.” You are reminding her of the commitment without accusation. You are also making it about you, because that is the part you control. These conversations matter for your growth.
You can also try:
“I need some help prioritizing my work. I heard you ask for XYZ and they all sound important. As someone who takes pride in my work, I want to make sure each deliverable gets the time it needs. I would love to understand what ‘done’ looks like to you and what your expectations are for timing and output. Once I have that direction, I can plan my time accordingly.”
Marta’s take:
Exactly right, Katie.
I would also add that many of us are out here paddling our own boat to safety. Most people are doing the best they can with the skills and resources they have. Leaders included.
This is where reasonable expectations matter. The best gift you can give yourself is engaging in these hard conversations at all. Progress does not always look like a perfect ending. It often looks like showing up and speaking clearly even when the outcome is uncertain.
You also never know what battles someone else is fighting. We all hope leaders have the soft skills required to lead well, but that is not always the case. You cannot change her skill set. You can recognize that she might be limited in her ability to meet you halfway. That awareness can do a lot for your own mental health.
Our hope is that this helps spark ideas for communicating through the lens of what you need. Focusing on self, with positive intent, is one of the strongest ways to lower walls and make room for real dialogue.