Conquer Your Fear of Speaking Up to Your Boss

Have you ever observed someone who struggled with speaking up to the boss?

I could share hundreds of stories about professional men and women who didn't share their opinions, point out mistakes (even costly ones), or address conflict with the boss. 

Of all the fears I've helped people overcome as an executive coach, this one is the most common, even though the person I'm coaching didn't initially describe the issue this way.  

The fear of speaking truth to power is also detrimental to teams and organizations.

Recently, Stephanie, an executive director, reached out to me after a crisis resulted from the board president significantly overstepping her bounds. The overstepping had been going on for some time, in small increments, but Stephanie didn't know how to handle the situation. You could say she had blinders on.

When the board president interfered with staffing decisions--which she had no authority to do--Stephanie found it difficult to confront her. Stephanie feared conflict. Instead of acknowledging her fear and actively searching for a way to conquer it, she remained stuck until key staff members started resigning because they felt unsupported. 

Stephanie's story isn't unique, which is why I coach people to raise their emotional intelligence so they can increase their awareness of how emotions like fear impact their behavior and decision-making. 

When you realize there is something you're afraid to discuss with your boss, follow these steps for processing your fear and voicing your concerns:

  1. Name the fear. Acknowledge that your emotional state is influencing your decisions and actions. Identify which type of fear you're feeling: is it something that needs to stop because it's dangerous OR something that causes anxiety because you don't know how to do it?  
    Next, ask yourself, "What would I do if I weren't afraid?"  
  2. Clarify your thinking. Find a coach, friend, or trusted colleagues outside the organization to work with you as you identify possible solutions. Before you attempt the conversation with your boss, practice with your sounding board (I also call this an EQ Circle) until you've found the right words to say what you want to say. 
  3. Reconnect with your values. What we value motivates us toward action. Stephanie is passionate about helping people, so when the mission and the staff were threatened by the board president's actions, she was finally compelled to act. If you're afraid to speak up about an issue, consider your values and challenge yourself to live by them.
  4. Engage with empathy. Take a few deep breaths and stand in your boss's shoes. Would you want someone to tell you if she thought you were overstepping your bounds? If you had made a mistake? If the results were causing unintended consequences? Also reflect on past interactions. When you (or others) were able to get the boss's attention, what worked?
  5. Practice people reading. Apply your knowledge of both DISC and motivators to communicate effectively with your boss. Stephanie knew she faced a board president with a clear preference for a dominant communication style; having that awareness guided Stephanie to adapt her own style. I also encouraged Stephanie to practice her conversation out loud. I gave her feedback about how she would come across to the president and what the likely questions would be.
  6. Speak as an ally, not an enemy. You and your boss are on the same team and you ultimately share the same goals. That's a great place to begin your conversation. Literally sit on the same side of the table and verbalize that you are doing so as a symbol that you want to be on the same side of this issue.
  7. Ask for what you want. Be very clear about what you want. Before she even sat down with the president, Stephanie knew she wanted to maintain a collaborative relationship where each party listened deeply to each other. She wanted clarity on norms and an agreement to abide by them. She also wanted permission to address issues again in the future.

Stephanie's story has a happy ending. She spoke up to the president and was successful with her influence strategy.  Two of her staff members returned when they heard that Stephanie was willing to lead rather than be reactive. Having learned from this experience, Stephanie encouraged the formation of EQ circles in her organization to support raising the emotional intelligence of everyone on her staff--herself included. She's decided it's the best way to create a culture where people feel connected, cared for, and empowered to express their concerns.