How to Master the Delicate Art of Coaching Your Boss

The control freak. The interrupter. The too-nice boss. The drama king (or queen). The dump-and-disappear boss. The vague explainer.

There are as many problematic behaviors in bosses as there are in those who report to them.

Can, and should, you coach your boss into more productive behavior? The answer is yes, but proceed carefully. No one gets better at their job without productive feedback, but coaching up requires a delicate touch.

Here are three key steps to follow when coaching your boss.

1. Identify the problem

Analysis is a key first step in helping your boss. Ask yourself: What specifically is the problem? You must go to your boss with a clear, concise explanation of the issue and a potential solution – just like you would with any coaching situation.

Next, consider your boss’s temperament and circumstances. Questions to consider: How long have you worked with her? How well do you know him? Is she open to feedback or more closed? Is he tentative because he’s a new leader? Is the problem behavior the result of company culture or individual preference?

The answers to these questions will shape how you approach your boss.

Rather than thinking of this coming conversation as criticism, frame your thoughts as ways your boss can help you (or the whole team) do your job better. Avoid using the term “coaching.” This is an open conversation that focuses on feedback and honest dialogue.

2. Frame the conversation

You should follow the same rules of coaching whether you are coaching up or down the hierarchy. Focus on the good, and be specific about the not-so-good without belaboring the point.

One of the best things you can do is help your boss understand how his behavior is keeping him from accomplishing his goals. For instance, if your boss tends to interrupt you during meetings, ask for a quick debrief immediately after the meeting.

You might start with: “I’d like to ask you about something that happened in the meeting.” Once you are in a private place and have his attention, move forward: “I know that collaboration is important to you. But when you cut me off mid-sentence, it makes me want to withdraw and not participate.” Or, “You have always encouraged me to set high goals and believe in myself, but when you snap at me like that, I don’t want to contribute.”

Listen for your boss’s answer and shape your response carefully. Don’t spew or rant. Calmly explain how the interruptions make you feel, such as, “I think that the interruptions undermine the staff’s confidence in my ability to manage and it makes it hard to concentrate on what needs to be discussed next.”

Always begin with the assumption your boss wants to perform well, just as you do.

3. Be mindful of how you say it

An option to opening your conversation might begin with, “I want to give you some feedback. Do I have your permission to speak openly?” Then, proceed with diplomacy and specifics.

As with any other coaching, it’s best to deliver the feedback as soon after an incident as possible. However, recognize that it may take some time to find the right way and the optimum time and place to speak with your leader.

You may need to build a more positive relationship with your boss first. You may need to take some time to get to know him or her better.  It may also take some time before you feel comfortable voicing an opinion and speaking frankly. It may simply take a few days or weeks to find a private moment together.

In most cases, your boss may be clueless about the behavior that’s making it hard to work well together. Assume good intentions and trust that they want to work well with others, just as anyone else does.

It is important to be aware that you can have no expectation of change when coaching up. However, good leaders respect feedback and want to grow and develop into even better leaders. Great leaders recognize that someone else may know something they don’t, or something they could benefit from, and are open to suggestions from people who are willing to take a risk to coach their boss.

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