Thinking of Bossing Your Boss?

Those instructions seem as clear as mud. You find yourself regularly rechecking the numbers for monthly reporting. The boss says nothing when you bring up concerns. 

Like a child in a dysfunctional family who parents their parents, sometimes employees find themselves bossing their own bosses.  

What do you do when you think your boss calls for some bossing? 

This tends to be a delicate situation that requires a lot of awareness. Here are a few strategies: 

  1. Get Curious… While your boss’ words or actions may be frustrating, the behavior meets a need. Not addressing an issue meets a need for comfort and ease (albeit typically for the short-term). When you think about every action as an attempt to meet a need, it opens space for empathy and understanding. Ask yourself, and your boss, what do you need?  
  1. Show Empathy. Through active and reflective listening, you help your boss feel seen and heard. Acknowledging a thought, feeling, or action does not mean you agree. It shows that you understand, or what you understand about, the situation. This usually helps build connection and trust.  
  1. Know what you need. When instructions are not clear, you likely need clarity to best perform the task. When your boss says nothing, you may need acknowledgement or support. When rechecking numbers proves frustrating, you may be looking for respect and more efficiency. While you may have strong ideas about how to resolve the issue, be sure you know the underlying need and not just how you would meet the need. See Naming Needs list for guidance.  
  1. Clarify the impact and wishes. Let your boss know what you see or hear from a neutral standpoint. This means stating the facts of what you observe. For example, “I hear you give ___________as instructions, I want to make sure I understand. Will you please confirm that what I just said is what you meant?” or “When I tell you that these numbers do not match up correctly, and I hear you say nothing about it, I feel frustrated. When numbers do not match, how, and when would you like me to bring it to your attention?” Or you may set a clear parameter. “If I do not have the correct numbers by ____ date, I will not be able to have the report to you by the date you requested. “ 
  1. Offer up options. You may have ideas about what works best. Your boss may have quite different ideas. Before delving in, think about the costs and benefits of both approaches, as well as the overall mission. Then you may say, “It sounds like we both agree that it is important for the organization to____________(ultimate goal). My understanding is that you really would like it done ________(boss’ way), and I wonder if it might help to________(your idea). What if there was a way to get to _____(ultimate goal) by ________(combining ideas)?” When you consider everyone is heading to the same destination, you might see multiple ways to get there. And you might just co-create a third way that is even better still.  

Your boss may or may not welcome your input. The energy you bring to the situation makes a huge difference. Notice whether you approach conversations with deep care and commitment to the organization’s mission and sincere desire to understand your boss. Engaging from a place of compassion and understanding creates different results than showing up from a place of anger and frustration.  

If you need help preparing for any conversation, reach out for coaching or attend a creating connective communications class.  

Remember, if you think your boss could use some bossing, treat your boss with the level of dignity and respect you wish to receive.

Sherry Ann Bruckner

Sherry Ann Bruckner

Most widely known as Lonzo's human, mediator, speaker, and author Sherry Ann Bruckner works with leaders and organizations to create peace, resolve conflict, and transform visions into results.

From her twenty-plus years' experience practicing civil and family law, and her own personal experiences with silence and violence, Sherry Ann understands how much inner peace impacts outer peace. A graduate of Hamline University's College of Liberal Arts and William Mitchell College of Law, she also studied conflict resolution at Rothberg International School in Jerusalem. Sherry serves as a neutral on matters ranging from bias and employment discrimination to marriage dissolution and caring for aging parents. A speaker and trainer on the global stage, Sherry gives you and your audience practical skills and the confidence to use embrace your personal power to create peace. Through helping thousands of people navigate their way through conflict, and finding her own way to inner peace, she shares the transformational power of clarity, compassion, curiosity, and cribbage.

Visit to learn more or give her a call at (320) 808-3212.
Sherry Ann Bruckner

Be gentle with you. Be gentle with all. Be the peace.