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Speaking Truth to Authority – Criticizing and Contradicting Your Boss

At a team meeting, your boss comes up with an idea for a new way of performing your team’s work.

While the idea has some merit, it does not really work given real-world conditions. What do you do?

What if your boss frequently sends double messages – one day she praises a work product and a week later uses it as an example of how you and your team need to improve your performance? Or, if he is constantly making your job harder by putting up roadblocks or not protecting you and your team from the roadblocks that others put up.

Contradicting the Boss

One of the most anxiety producing situations at work is criticizing on contradicting your ‘boss”. When you are a project manager or business analyst, your boss may be a manger, sponsor or client, or all of them, to one degree or another.

While it is generally viewed by management experts that it is your boss’ responsibility to create a safe place for such confrontations, how often is that found in the real world? It is up to you as an individual to balance the values of being candidly truthful and maintaining a good relationship with your boss. Of course, the same thing is true for anyone with whom you have a relationship, though for this article we will focus on the relationships in which you are subject to your boss – a person who has the power to fire you or give you a performance review.

The Benefits of Truthfulness

In general, being candidly truthful is beneficial. Individuals, teams and organizations optimize their performance when constructive criticism or opposition is offered and received in the spirit of continuous improvement. The Abilene Paradox is a wonderful reminder that withholding negative input makes it less likely that problems will be avoided, and optimal solutions found. It reminds us that it is everyone’s responsibility to speak up and provide their views.

Yet, there are limits. Personalities and psychological tendencies can get in the way. Some people take any kind of criticism or opposition as an attack and a sign of disloyalty, becoming defensive and angry. That is bad enough if the person is a peer or subordinate, but when it is your boss, you can be fired, given a bad review, labeled as a trouble maker or just told you to shut up and follow orders. That being so, fear gets in the way of being candid.

Navigating the tricky issues of managing the relationships in hierarchies is more of an art than a science. There are no easy formulaic approaches, though there are some guidelines and skillful practices that will make the task easier.

Four Questions

Before giving feedback – critical or otherwise – address these questions:

  • What are you criticizing?
  • What is your motivation?
  • Will it do any good?
  • How will it be perceived?

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Criticize Things, NOT People

Criticizing a person generally results in defensiveness. Separate the source, the person who created the thing in question, from the target. Criticize an idea, a statement, behavior or work product as opposed to a person. The person is the source but not the thing itself. Changing behavior or the content of a document, as hard as it may be, is far easier than changing character.

While the source may identify with his or her creation, you must separate the two. When you do, you are able to assess the situation and communicate so as to minimize personal attachments.

Ideally, the issue of not identifying the issue with its source has been addressed in a training or team building exercise. That way it is possible to remind one another to promote objectivity to achieve improvement. But, remember that even then the author is likely to be somewhat attached to and identified with his or her result.


The question of motivation is an important one. Are you criticizing an idea or action because it makes you feel smart and important or because you are trying to help the other person, the team or organization? Is anger or frustration driving your need to criticize? Is fear the reason you are holding back?

The ideal motivation for giving critical feedback is to promote improved performance. Though, often, there is a combination of motivating factors. You may feel frustrated or motivated by showing how smart you are and, at the same time, think that what you have to say is beneficial. That is where the next question comes in.

Will it Do Any Good?

Will your criticism have a beneficial impact, will it change behavior so that the result is a better deliverable or a more effective process?

Even when there is a likelihood that what you have to say is beneficial, you still must consider the risk you are taking vs. the reward. Here is where social awareness comes into play. Social awareness consists of the ability to sense what others think and feel and an awareness of organizational norms and relationships.

It is in anyone’s best interest to be open to useful criticism, simply because it gives them the ability to reflect on their idea or behavior and opt to change it. Though, there are those who don’t believe that and feel that criticism is an attack to be defended against.

How will it be perceived?

How your criticism is perceived strongly influences whether what you have to say will have a positive effect.

For example, if your social intelligence tells you that your boss is averse to any kind of criticism or that you are in an organization in which any criticism from a subordinate is culturally forbidden, no matter how accurate and perceptive your criticism is, it will not be perceived well and therefor will not have the beneficial effect you intended it to have.

How to do it?

Having assessed the situation and made the decision to go ahead and give your input to the boss, do it skillfully.

Timing is critical. Depending on your organizational culture, it may be perfectly acceptable to have your say in public, as the idea is being aired. In other situations, you will get better results if you take your boss aside and have your say one-on-one and doing it in a way that will allow your boss to come back to the public forum exhibiting his intelligence and ability to critically reflect on his or her own ideas and change his opinion.

Whether in private or public, send ‘I’ messages. “I think there may be a more effective way to handle this, because …” as opposed to “your idea has some flaws.”

Stick to facts and objective criteria as opposed to unsubstantiated opinions.

Ask questions like “Have you considered X as an alternative?” or, “What would happen if ‘Z’ occurred?” or, “What were your decision criteria?”

You might also begin your criticism with some praise – “What a creative idea?” – before getting into the meat of your input. Close with something positive, like “Do you think we (or you) can resolve the problem more effectively by looking at some of these options?”

In the end, well-meaning criticism, presented skillfully, sensitive to personal feelings and cultural inhibitions, is a means for continuous improvement.

George Pitagorsky

George Pitagorsky, integrates core disciplines and applies people centric systems and process thinking to achieve sustainable optimal performance. He is a coach, teacher and consultant. George authored The Zen Approach to Project Management, Managing Conflict and Managing Expectations and IIL’s PM Fundamentals™. He taught meditation at NY Insight Meditation Center for twenty-plus years and created the Conscious Living/Conscious Working and Wisdom in Relationships courses. Until recently, he worked as a CIO at the NYC Department of Education.

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