As I travel around the country speaking and training people to hold potentially difficult conversations, I am frequently asked if the skills and processes which I teach can be used with one’s boss. I forcefully affirm that one can be more effective as a communicator no matter to whom they may be speaking. Many times people respond with something like, “Well, sure it works if they have had the training.”

Often I am disappointed when I hear such a response because the underlying assumption is that they can’t manage the communication dynamic based on their current skills; that success hinges entirely on whether or not someone has had the class. Such a statement essentially becomes the excuse for not practicing the skills that they have learned. The statement also signals that people may be uncomfortable in a situation where they don’t know what the outcome may be. This is certainly understandable.

But let me be clear. “Managing up,” as some call it, is not about manipulation. It is really about being more influential or even selling an idea or solution in a way that helps your manager understand the situation from a different perspective. If the additional insight will have an impact on results, then any right-minded manager will be interested in what you have to share.

The challenge in holding a conversation with someone who is in authority over you has to do with the quality of the relationship. The quality of respect and relationship will have an impact on results every time. Given that the quality of the relationship is what may provide consideration for your idea, let’s consider some questions that may help you determine the status of your relationship and allow you to gauge what improvements need to be made.
<h3><strong>What is your current standing with your manager?</strong></h3>
If you have been argumentative or combative each time your manager has made a decision or set a direction, then you probably don’t stand much of a chance of being heard or influencing the current situation. This can be a difficult situation which will take time and effort to correct. By following some of the suggestions below and consistently managing your behavior when you don’t agree, you will be well on your way to building a more positive relationship.
<h3><strong>Can you create a different atmosphere with your manager going forward?</strong></h3>
This may take a degree of humility on your part. If I wanted to create a different space with an individual with whom I had not frequently agreed and if I had acted badly in the past, I might begin the attempt with the following statement: “I have some pretty strong differing opinions on this course of action. Would you be willing to talk about them with me?” If your manager indicated that he or she was willing to talk about the current issue, you at least succeeded in getting your foot in the door.

If they are not willing to engage with you, then I hope that you will take the opportunity to consider what you might do differently going forward. Taking the time to ask questions to enhance your understanding, keeping your emotions in check, and complaining in front of everyone that the manager’s decision is wrong are behaviors that should be eliminated if you hope to improve the relationship.
<h3><strong>Can you set your own perspectives and opinions aside to hold the conversation?</strong></h3>
If you are the type of person who always has to be right, then this may be difficult for you to do. You need to recognize that you might not know everything and accept the fact that there is something that you need to learn rather than being firmly entrenched in your own views. Sometimes these types of conversations can turn into a debate. That is the last thing you want to have happen.

We have all had experience with people who continue to push their own views. When you don’t agree with them, they seem to want to push harder. Because I communicate differently, I have often wondered why they do this and have wondered, “Why can’t they recognize that no one is going to endure a barrage of ideas and suddenly come to the realization that they were wrong!” When one party insists that they are right, then the other party tends to become more defensive and reinforces their own position. This whole scenario does not lead to an exchange of ideas and a mutual collaboration of any kind.
<h3><strong>Are you willing to prepare to hold the conversation?  </strong></h3>
If your manager is willing to talk about an issue, the next question I would ask is, “Would you be willing to allow me to prepare to hold the conversation?” If they answered yes, then I would ask them a few questions that would help you to think through the issues around the current situation. For example, you might ask any of the following questions, “What about the current situation should I understand? What is the ultimate goal in the current situation? Of all the issues that we are currently dealing with what takes priority? What criteria do I need to consider that would help me understand the current situation?”

Be sure to establish a firm timeline for holding this conversation. Some leaders would rather talk about the issues right then in the moment. You need to control their potential impatience by identifying a specific time to talk that day.
<h3><strong>Do you have sufficient evidence or data that would support your view?</strong></h3>
Sound data should be the basis of all good decisions. If you have information that you believe would help the manager make a different decision, be prepared to share that information in a spirit of collaboration and support. Don’t be surprised if the manager is already aware of the information you are offering. If they don’t, allow them time to consider what data you are offering and allow them some time to make their decision given the new information.

If they still don’t make the decision that you would like them to make, then ask questions to try to understand their perspective. This has to be done very carefully. If in the past you have been obstinate or contrary your tone must be calm and you must approach them in the spirit of learning. They may have a different set of priorities or a different set of criteria for making a decision than you do. If they do, then ask them to help you understand and teach you the basis for making such a decision. You may not agree with them, but you will learn a lot about how to interact with this leader going forward.
<h3><strong>Are you prepared with a number of different solutions?</strong></h3>
Because many managers are Type A personalities, they are often frustrated by individuals who want to expose a problem and then have no suggestions for solving that problem. If your manager has taken the time to answer your questions, you should have been able to recognize a number of their concerns. You need to be prepared with more than one solution that addresses their concerns. If you have information that they may not have, then you have the opportunity to prepare solutions that include the information that you have. Taking time to think through and offer solutions will help you be seen more positively.
<h3><strong>Are you willing to support them if the decision doesn’t go your way?</strong></h3>
This is hard for many people to do. You may be right in what you are proposing, but if you can find it in your heart to support this person, it will vastly improve the quality of this relationship. When you express support, you increase the chances of being supported later.
<h3><strong>Can you honestly thank them for engaging you?</strong></h3>
If they have taken the time to explain themselves to you, answered your questions, given you the time to prepare and think through the issues, and given you more time to actually discuss the issues, I would hope you could sincerely thank them for their time and consideration. This will set the foundation for speaking with them in the future. It will tell them that you honestly want to understand and that you want to share from the perspective of improving the work or the outcome.

It is possible to manage up, but you have to do it from the perspective of being part of the solution, not part of the problem. You can disagree without being disagreeable. And you can make a difference if you take the time to understand how to approach an individual that allows them space to think and reason, rather than feel like they have to defend themselves or their ideas. When irrationality rules the day, irrationality will make the decision. We could all do a better job of understanding how to respectfully approach one another when we disagree.