The Delicate Art of Upward Communication: Navigating Uncomfortable Conversations with Your Boss

Blog 75 - F
  • May 2, 2019

Just about every employee has felt this at some point in their career: You need something from your boss, and you don’t know how to ask.

Worse yet, many employees are afraid to ask. Although some fears exist because of your own insecurities, other fears are painfully valid because you have experienced a negative, deflating reaction from your supervisor in the past for reasonable requests or communication. Tough conversations with the boss aren’t easy, but your ability to do good work often depends on them.

Effective upward communication doesn’t just get you what you need in the short term, but also delivers long-term benefits that aren’t always as obvious, including:

  • Taking control of your own employee experience.
  • Shaping and strengthening team dynamics.
  • Better relationships with superiors.
  • An improved bottom line within the department and across the entire organization.

Upward communication should be a delicate and intentional practice, and the dilemmas presented in this blog offer ways to navigate tough conversations and get the results you need to be effective and happy.

A Bad Idea That Just Won’t Work

The dilemma: Your boss has a “great” idea for a project, strategy, best practice, or something else that he or she thinks will be a winner. You and your coworkers know better and are rightfully concerned about the consequences.

Your response: Determining your boss’s underlying need that prompted the bad idea often makes coming up with a solution easier. Is your boss feeling pressure from superiors? Does your manager think you need more to do? Is your boss just feeling left out or wanting to assert more authority? Once you figure that out (which, as Dana Brownlee writes in The Unwritten Rules of Managing Up, doesn’t happen instantly), it becomes easier to offer realistic solutions that solve the root problem, such as negotiating a more reasonable goal. Clearly defining what will be required and what resources are available is a strong next step because bosses might not realize how crazy an ambitious deadline really is until they can see the energy their demands might waste. Framing things to respond to heart of your boss’s request can open a conversation about the impact on all contributors and team members.


The dilemma: Your boss is constantly telling you how to do things, asking for updates for the most trivial details, or looking over your shoulder—metaphorically or even literally—at your work.

Your response: Micromanagement isn’t always because bosses don’t trust you; sometimes it means they don’t trust anyone but themselves. Brownlee, who was recently featured in Fast Company on the types of bad bosses we all may need to manage up, writes in The Unwritten Rules of Managing Up, “Not only is it stressful to feel like you’re working under a microscope, it’s equally exhausting and time-consuming to spend so much time preparing and delivering status updates that may not be necessary.” The upward communication skill used here must not be intended to change the micromanager (which is often futile), but rather, to cement expectations that eliminate the need for constant supervision. Offer a reasonable schedule for updates during which you can fill your boss in on the progress you’re making and discuss what you expect to achieve by the next update. Brownlee also suggests another strategy to mitigate the energy drain that micromanagement often inflicts: defining how time-wasting and bottom line-depleting endless, unexpected updates are.

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Job Dissatisfaction

The dilemma: You’re not happy with your job or the way you’re being treated, and your boss is directly or indirectly (even partly) to blame.

Your response: The worry many employees have is that if they bring up their dissatisfaction to superiors, they will be labeled a whiner, or a complainer, or someone who always blames others. Your role at the organization is important, so showing how it impacts the company’s success can paint a broader picture in your manager’s mind. “I’m unhappy” is a “me” statement that might be perceived negatively. However, saying “I’m ready to contribute more to the company; here are some things that can help me realize that potential” incorporates your manager into your success and overall results. For sure, this can be a difficult conversation, but the alternative is continued unhappiness, less engagement, and possibly leaving a job you once loved—and may still hold the hope to love again.

Communication Barriers

The dilemma: You don’t get your boss, and your boss doesn’t get you. The constant walking on eggshells when communicating is draining because you can never predict your manager’s reaction to anything you do.

Your response: This concern occurs even with great managers and happy employees—how do you keep the relationship relaxed, respectful, and productive? Brownlee writes in The Unwritten Rules of Managing Up, “Here the managing up focus isn’t trying to deal with a difficult boss; instead, your task is to make your boss’s job easier so they can be even more effective.” Understanding your manager’s leadership style helps set the tone for your interactions. A boss who’s genuinely interested in your life and career won’t mind you being talkative. A manager who believes in positive leadership and self-initiative will be open to hearing your ideas. A quieter boss might be more impressed by results. Upward communication that’s informed by your manager’s style puts you on the same page and can abate the jitters you might feel because you’ve adapted to their expectations and communication style, making processes more streamlined and efficient.

Upward and Onward

Most bosses still exist in a chain of command and engage in their own upward communication with superiors. These interactions, whether they are positive or negative, can teach them valuable lessons about how they treat their own teams. Just being a manager doesn’t make talking with your boss any less intimidating—a fact that’s important to remember when your employees come to you with a difficult conversation or valid concern.

In Communicate Like a Leader: Connecting Strategically to Coach, Inspire, and Get Things Done, author Dianna Booher writes, “Strategic communication forms the very core of leadership. When you as a leader speak, meet, negotiate, write, or network, you either clarify or confuse, motivate or demoralize, engage or enrage employees. And they, in return, will either give 110 percent of their loyalty, support, and skill to accomplish your mission—or disengage, divert your focus, and drain your energy in dealing with them.” The lessons you learn communicating upward should provide the basis for your interactions with employees and make their own upward communication more effective—and less scary.
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