The Secret to Your Success May Equal Coaching Your Boss

When you are hired for a job, no one tells you that one of your responsibilities is to manage up. Perhaps it’s simply assumed that you are in business of managing your boss and yet wouldn’t something so critical be mentioned? It’s mostly absent from job descriptions. The area’s most often included are leading a team and the expectation of grooming and growing them. And yet one of the most crucial aspects of your role is to indeed manage your boss.

Especially today in a COVID landscape when emotions are running high, really checking in with your boss to find out how they are doing – authentically – and holding the space for them to be people too is critical. Brené Brown said recently that people are farther north of fine now more than ever. Your boss is no different.

Keeping in mind how they are doing is imperative and so is having their development areas in mind. That’s where coaching “up” comes in. Coaching your team is clear, especially if you are evaluating someone’s performance and the decision for promotions, bonuses or raises rest in your hands. With your boss, none of those factors are true – you don’t evaluate your boss or promote them or give them raises. It’s further tricky since there is a power dynamic at play. However, if your intention is to create a development environment and one with open feedback, that means not just for your direct reports, it would ideally include your boss too.

Coaching in any form requires consent and agreement. If someone reports to me, we still need to agree between us how we are going to communicate, how they want feedback and where are areas for development and growth. This is no different with your boss, it’s simply nuanced.

As an example, let’s say your organization broadly is going through layoffs. Your team so far has been unaffected. Your boss to date is a hands off leader, who gives you freedom to create and make decisions as well as manage your team. He is introverted and reserved in meetings and speaks up sporadically, choosing his timing wisely. He is a mentor to you. Now in this new environment your boss is micromanaging, diving deeply into your work, skipping over your level of authority, attending every and all meetings and speaking up and over executives in key leadership meetings. You want to speak with your boss about his behavior however you are not sure if this is your role and it’s most likely going to be an uncomfortable conversation. What do you do?

  1. Consider what the big picture intention is for your conversation. An intention is separate and distinct from an outcome. An intention holds the vision of your conversation. It’s why you are having the conversation. Examples could be awareness or alignment. This big picture framework focuses the conversation for you clearly and distinctively.
  2. Know your role. If your role is to be a coach, as I suggested earlier, then your job is to ask great questions, listen intently and show a great deal of empathy.
  3. Ask for permission. If you are going to begin diving into a coach role, you’ll need to get permission for beginning a discovery process. One way to do this is you could say, “You and I have known each other for a long time, I’ve seen you in many situations, right now I’m seeing you display behaviors that are uncharacteristic for who I know you to be. Would you be open to talking about it with me?” Asking permission creates an opening for you both. It’s respectful and demonstrates back trust and creates an environment of safety where he can express what he needs to – only if he gives you permission to start diving into the conversation.
  4. Lean in with curiosity. If your intention is awareness, then the real question is why is your boss acting this way? One could assume he’s afraid of losing his job or of the team losing their jobs, however you don’t fully know the source of his angst. Even if he said he’s “stressed,” that’s a broad statement that doesn’t give you or him the answer to what he’s feeling. He could be feeling overwhelmed or disappointed or frustrated. He could have unmet expectations or is simply feeling uncertain and that’s the real cause for his actions.
  5. Don’t move into action too fast. As a coach, if you are asking probing questions – ones to which you don’t know the answer or have an agenda for him knowing the answer – then do what I call “following the breadcrumbs.” In this case he will share with you his perspective and ask questions based on what you are hearing and what is “underneath” his answers. For example, if he says he’s uncertain, find out what conditions are contributing to it. You may assume you know – the company is laying off people, most people would feel shaky about this. However, what if his boss that he’s had terrific alignment with has started shutting him out of conversations? That would certainly contribute to real angst.
  6. Create a new narrative. Could be that every time your boss engages in a team meeting, conversations with his boss or other leaders the story he’s telling himself is “I’m going to be let go if I don’t perform” or “don’t fail this” or “screw this one up and you are a goner.” Those stories can either manifest themselves into reality and/or they can also derail our decision making, take away from our capacity to pay attention, impact our relationships and impede our performance and creativity. What new narrative can you assist him stepping into if he’s willing?

I have found that in times of stress, coaching can get put on the sidelines for advising or telling people what to do. The opportunity to explore, to inquire, gets put aside for the perception that if we tell someone what to do or move quickly into action that’s the fastest road to performance. Not really.

If the boss in this case keeps being down on himself or thinking the worst then he can’t perform to his highest. If you’ve ever seen the Olympic swimmer Michael Phelps prepare to compete, he has his headphones on, is focused and listening to music to get him into the game of winning. That’s the same intention and focus we need not just for ourselves, for our bosses too.


Esther Weinberg is the Chief Leadership Development Officer and Founder of The Ready Zone. To dive deeper into the ideas and strategies offered in this article, complete our Needs Assessment and we’ll schedule time to connect.

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