Go Ahead, Give Your Boss A Piece Of Your Mind–Just Do It Effectively

No boss wants another Yes Man. But if you want to put in your two cents, it won’t hurt to develop a strategy.

Go Ahead, Give Your Boss A Piece Of Your Mind–Just Do It Effectively

In the course of his three terms as New York City’s mayor, the late Ed Koch was famous for asking “How’m I doing?” Whether the brash and combative Koch was genuinely interested in an answer is anyone’s guess, but the question is fairly rare for a leader–in politics or business.


When’s the last time your boss asked you that kind of question? If he or she did, how would you answer it?

My guess is that most people would muster a banal “You’re doing a great job!”–a nice, but not particularly useful answer. And in many work settings, that kind of response might be seen as sucking up.

But whether you have positive or negative feedback for your boss, how you introduce and explore specifics around it makes a huge difference–for both the leader who would benefit from knowing and an employee capable of stepping up to the role of reliable and trusted straight shooter.

Employee feedback to the boss is one of the most common workplace challenges, but few people know how to do it. Feedback to employees is a far more common practice and there’s plenty of wisdom around about it, even in the most readily accessible forms. Yet as common as employee feedback is, leaders often struggle with telling employees what behaviors they need to change.

If feedback to employees is tough for leaders, telling the boss how you think he’s doing is the equivalent of touching the third rail for many people. But feedback to the boss is crucial for driving results and achieving success.


Bill Gates was once quoted as saying his most important job as a CEO was to take action when presented with unpleasant news, or face the consequences. If a CEO doesn’t act, said Gates, “people will eventually stop bringing bad news to your attention, and that is the beginning of the end.”

Gates is said to be a tough boss–going to him with bad news must have posed a challenge. But for Gates, or anyone else’s boss, giving a leader specific and timely feedback helps him or her be more effective, with obvious implications across the organization.

Here’s a structured approach to telling your boss what you think when things aren’t going so well:

Ask for permission
Acknowledging that the leader has the option to say “no” shows respect and reinforces trust. Choose a good time–when your leader is not under extraordinary stress, and as closely tied to the event about which you are giving feedback as possible. Also pick a neutral, private place. To boost your chances of receiving permission, emphasize that you’re aligned with the leader’s goals and that you believe this feedback will help you both accomplish them better and faster.

Describe your boss’s behavior
Describing behavior provides a common and specific point of reference for the conversation. This step is critical, yet it’s the one that’s most commonly skipped. It’s important to keep the conversation focused on behavior and not personalities or your interpretation of the behavior. Center feedback on what you have seen or specifically heard, not what you believe or think. For example, “In Monday’s meeting we were brainstorming ideas to build traffic on our site. You told James he ‘didn’t understand the implications of his idea.’”


Describe how your boss’s behavior impacted you or others
Saying how you or others were affected helps the leader see the consequences (often unintended) of his or her behavior. For example, “I noticed after you said that James didn’t understand the implications of his idea, James didn’t speak up again and participation in the brainstorm slowed.” Use feedback to inform, not advise. Keep it simple and specific, too. It’s not necessary to mention every aspect of his or her behavior at once.

Ask your boss about his or her perception of the situation
Asking the leader for his/her perception surfaces the link between the behavior and the unintended consequences. You might try, “How did you see the situation?” Be careful here and make sure to ask the question out of curiosity and without blame or judgment. This puts you in a consultative position, serving as an ally to help surface the disconnect.

Ask for or make a suggestion or request
A specific suggestion increases the likelihood that the leader will stop a behavior that impedes performance or continue a behavior you find helpful.

For example, “Given your leadership role and the associated risk of hindering meeting participation, I wonder if you might consider refraining from judging or criticizing ideas when the group is brainstorming.”

Build an agreement on next steps (if any).
Creating an action step supports your boss in following through on commitments and sends a strong message that you’re looking to support his leadership. For example, “You might want to check in with James to reinforce the value you place on his ideas.” This points the leader to accountability and will provide you with the opportunity to give positive reinforcement after the next meeting.


No less a leader than Jim Kim, president of the World Bank Group and former president of Dartmouth College, says the biggest commitment leaders can make is to listen to their teams with humility–and to constantly seek advice from colleagues in order to improve. Kim also admits that listening to his employees was foreign for him at first.

Obviously giving leaders feedback is a delicate business. And there is no guarantee that doing so will change your boss’s behavior. Yet providing timely, behavioral feedback can put you in the role of trusted advisor. Because so many important initiatives are hung up or derailed when feedback to the boss is missing, you can also help to ensure that yours won’t be one of them.

Beth O’Neill is a senior consultant at Interaction Associates, a global leadership development firm based in Boston and San Francisco.

[Pennies: Joellen L Armstrong via Shutterstock]