How to Talk to Your Boss Like a Boss (And How to Listen to Your Team)

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One of the things I love the most about my team is our cultural diversity, which currently spans 15 countries. As a Sri-Lanka-born, Australia-raised, current resident of NYC, I understand a thing or two about the value that different perspectives can bring to the table. My experiences shaped my determination to create a global workforce representative of everyone living on this pale blue dot.

Recently, I sent out our annual, anonymous, end-of-year team survey. This format invites honesty without the potential awkwardness accompanying truth-telling in the work environment. Every year, I am impressed with the thoughtful feedback.

My admiration for these noteworthy observations made me think about how feedback works in an organization and how I could foster more. I wondered about the roles that company and individual cultures play in the grand scheme of collaboration and progress. In the context of a remote international team, what factors are at play regarding feedback?

I started to think about my own past experiences. One of my last “day” jobs had an interesting work culture. Human Resources often felt weaponized rather than being a resource for the human workforce. Almost every day, I overheard the casual, “Oh, I’m going to HR.” I didn’t feel safe to be myself in this type of work culture for fear of saying anything that could result in a visit to HR.

The only time it felt safe to speak up was in the employee engagement survey administered yearly. Sadly, I and other team members often felt that the suggestions we made and the feedback we left weren’t heard. Nothing ever changed or got acknowledged. From that experience, I realized that there are two things team members need: emotional safety to be able to share honest feedback and suggestions and a response or acknowledgment from management.

Related: Open vs. Anonymous Employee Feedback — Which is Better?

Identify the cultural influences

Two types of cultural influences affect our comfort level when it comes to speaking up. The first is the culture we come from as individuals. This refers not only to where you grew up but also to how you were raised. In some cultures, different concepts of hierarchy can discourage open communication with superiors. Whether or not a person feels comfortable having a direct conversation- and providing feedback to the boss- depends in part on these individual cultural norms.

The second culture at play is workplace culture. Fear of Speaking Up, or FOSU for short, can be a real problem if it goes unnoticed at the top. If you’re not getting feedback or hearing suggestions offered by your team regularly, then you might consider whether or not people feel comfortable coming forward in your work environment.

Advice for leaders: Stop talking and start listening.

Here’s the thing: the boss doesn’t always have to have the answers. You’re the decision-maker, and the buck stops at your desk, but that doesn’t mean you always have to be the one to come up with the solutions. In fact, you probably shouldn’t be.

If a team member comes to you with a problem, try asking their opinion first rather than shooting off your answer right away. This simple invitation opens up the door to a feedback loop. This becomes a triple-win for you because it does a few things in one fell swoop:

  • It empowers your team, which builds confidence and creates a sense of ownership
  • It gives you additional insight and ideas that you might not have considered previously
  • It alleviates FOSU by letting people know that you really do value their opinions

Related: The 4 Levels of Listening: Why Every Good Entrepreneur Should Talk Less

Advice for employees: How to start the conversation.

If speaking up feels hard, you’re not alone. Maybe you grew up in an environment where kids were “seen and not heard,” or you had a bully for a teacher who instilled fear. This trajectory of powerlessness is one thing when you’re young, but problems can arise if they follow you into adulthood, particularly when you enter the workforce.

It’s important to work toward overcoming this hurdle, however uncomfortable it might be initially. Otherwise, you risk falling victim to what Andy Molinksy, Professor of Organizational Behavior and International Management at Brandeis University, calls the liability of deference. This refers to the gap between deferential cultures and those that operate a bit more loosely when it comes to hierarchy.

If you struggle to speak up and feel uncomfortable around authority figures, it can significantly hinder your ability to progress. This is because relationship-building is critical to getting noticed, being considered for promotions, and moving up. So the big question is, how do you shift your mindset and make this career necessity less uncomfortable?

Author and podcast host Karin Hurt believes that a space where ideas are shared helps a company thrive. She offers a few tips for confidently speaking to your boss.

  • Remind yourself why what you want to say is important. Recognizing your why will give you a surge of confidence.
  • Don’t ruminate on past experiences that didn’t go well with other authority figures. Instead, think about positive experiences you’ve had when you spoke up.
  • Start the conversation by letting your boss know how much you care about the organization. This creates a connection through shared values.
  • Think about what you want from your boss’s perspective. If it’s a raise or more administrative support, be able to back it up with numbers.
  • Value their time. Be polite, ask how their day is going, and then get to the point.

Related: How to Communicate Like a Boss

If your workplace is one where you feel your opinion is valued, then that speaks well for your leadership team. For leaders, it’s important to know how to leverage the unique values and perspectives of those under your wing. Focusing on creating and contributing to a positive workplace culture becomes a force multiplier that positively affects retention and your company’s long-term success.

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