Who Says You Can't Coach Your Boss?

So you’ve been trained, molded, managed, taught, and directed about how to “coach” your direct reports. Your company has led you through seminars, presentations, role-playing, and many other mediums to help you understand the best practices as they pertain to being a good coach and mentor for your team. And as a result, you’re good at it! You’ve mastered it! Your team is successful and motived and more importantly, they’re getting results! Fantastic!


    What about you? Are you working for a boss that is a great coach? Does she motivate and inspire you? How is your relationship? At what level do you truly communicate? Do you work as a team?


    These questions, while simple, are not always easy to answer. It’s complicated right? Yes. But, if you know a few key tricks of the trade, you can actually make huge changes in your relationship with your boss and in your overall career.


    The concept of “coaching your boss” or “managing upward” has been the subject of much debate over the last 10 years at least. Every expert puts his own spin on how this process should look. I believe it comes down to 7 very actionable points with #7 being the absolute most important so if you stop reading right now, skip to #7 and read it!


    Coaching your boss shows initiative when done correctly. It shows thoughtfulness and a professional curiosity that can only be embraced by the people at the receiving end. The key to coaching your boss is asking the right questions that are relevant and insightful.


    Coaching your boss is NOT “getting your boss to do what you want”. In fact, it is quite the opposite. Coaching your boss is a way to find a connection between you and she, establishing trust, and working toward a common goal in a way that suits both of you. The critical first step is to meet your boss “where they are” and walking the path together. This means you have to understand what makes her tick, how she likes to receive information, and how she likes to communicate.


    In short, here are the 7 steps that I believe have brought me the most success:


1.   Understand your boss’ style and DO WHAT WORKS! How does your boss like to be approached? Can you just pop in or is a scheduled meeting more her style? Does she like a weekly meeting or a casual lunch twice a month? What about time of day? Is she more receptive in the morning or in the afternoon? This simple first consideration already sets the stage for good communication.

2.   Don’t try to change them. Don’t try to make your boss like what you like. If you prefer to tackle big issues in the morning and she prefers afternoon, it may be best to schedule afternoon meetings if you want to be more successful in your conversations.

3.   Focus On What Matters. Use your strengths and don’t be afraid to reach out for support on things that may not be where you shine. This speaks to efficient execution. Ask for priorities and focus your discussion on them.

4.   Be a Problem Solver Not a Problem “Stater”. Have you ever been in a meeting with a person who keeps restating the problem over and over? How frustrating is that? State the problem along with well thought out, proposed solutions. This saves time and shows you have put some consideration into a resolution.

5.   Stay Calm and Stay Positive. Listening is much harder than it seems. Truly hearing what the other person is saying is almost a lost art. Most people are trying to compose their rebuttal in their head instead of really listening to the other person. When someone feels like they have been heard, the relationship grows and so does trust. Placing blame detracts from getting the job done and only makes you look like a finger-pointer….no one likes a finger-pointer!

6.   Support Your Boss. Do this even if you are working on a project that doesn’t necessarily make you shine. 

7.   Use the ASK ASK ASK technique. This is the most important item. If you take nothing away from this article, I want you to read this section carefully. Ask questions.....and no, I don’t mean obvious ones. In observing some of the most successful people I know, I noticed one commonality and that is they are not afraid to ask questions! I mean ask insightful questions. Ask questions with the intent to truly understand your boss’ perspective. And, if you feel like there is something you want to state, ask yourself if you should ask a question instead. For example, “That’s interesting, why would you say that?” or “Tell me more about what led you to that conclusion. How do you envision my team and I playing a role in that? Is there a back-story that would help me pull all this together? How do you think I performed in that project?”


WARNING----some of these questions may lead to constructive feedback….that is good! If you accept it positively this can only make you grow as an employee, a leader, and a person.