How to "Coach Up" to Your Boss

Throughout my career, I have had the pleasure of working as an executive coach and teaching those desiring to be coaches. In almost every class I lead, I frequently hear the same thing: "This is such great information, I wish I could get my manager to act more as a coach!" Of the classes I teach, there are often upper management and vice presidents, but rarely does the CEO make an appearance. So short of signing your boss up for the course, how else can you impart coaching competencies up the chain?

My answer is: through you. Your change in behavior will begin to change the environment in which you operate. Changing the way you have conversations with your boss can lead to increased trust and collaboration.

Many of my coaching clients at the executive level seek out my services because they want a trusted advisor and confidant to work through decisions and challenges facing their organization. While the need for executive coaches is key for professional development, having internal coaching conversations across the organization creates more openness and transparency and can often allow for quicker decision-making or course corrections.

So what is the best way to coach up? I mentioned changing the conversation earlier. By changing your intent and tone to incorporate global listening as well using dialogue techniques you can strengthen your conversations.

Let's say that your boss has just learned that he will take over a product group that has been struggling to make revenue numbers. He has called you into his office to discuss the situation and you can see that he is visibly stressed.

Boss: Our team has been doing great, but the addition of this new group is going to bring extra work and risk to our numbers. I am thinking the best solution is to fire the director of their group and have Tim from our team take over.

You: I can see where this situation puts more pressure on you, can you help me better understand how this would play out by painting me a picture of the new operating environment?

This approach allows you to demonstrate empathy for your boss without agreeing with what they said. You have acknowledged their stress and as a way of helping them calm down and walked them through their thinking. This is the process of asking "laddering questions", or questions that build on the premise presented, without agreeing or disagreeing with it. Laddering questions are helpful in demonstrating you understand a concept, but without committing yourself to a position regarding it.

The two most valuable laddering questions you can ask are "can you help me better understand ___?" and "tell me more about ___". These force the speaker to clarify their meaning but aren't so vague as to be unhelpful.

Often as coaches, laddering questions are the key to helping our clients develop a well-rounded opinion on an issue. Leaders don't need an echo chamber when making strategic decisions or goals, but they do need intentional conversation about the merits of their solutions.

The next time you have the opportunity to help your boss by coaching up, be sure to thank them for bringing you into the conversation and let them know that the next time they have decisions to work through and would like to bounce ideas around, you will make yourself available. This is a great way to elevate your value as well as to be a partner to your boss. 

About the Author

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Jennifer Stanford is a sought-after Trust Coach and the CEO of Emergent Performance Solutions, as well as an author and speaker. Her entrepreneurial spirit, combined with years of practical experience gives her specialized insight into business and psychology.

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