8 Steps to Coaching Your Boss to Success

“The medium is the message.” ~ Marshall McLuhan

Stop pulling your hair out over your boss.

The frustrations of managing the boss-employee relationship come up again and again in my executive coaching sessions. The best way to approach this challenge is to “coach up.”

When you think about it, we’re all private coaches at least some of the time. So why not be more intentional about coaching to help co-create the experience you want to have in your relationships; including the one with your boss.

Let’s first debunk one myth. Coaching up your boss is not a sneaky way to get what you want. The coaching model doesn’t work unless you actually care about the person you’re working with. It doesn’t work unless you have created a partnership and designed your alliance together. You don’t have to love the person you are coaching, but you do have to respect them and care about their well being.

Coaching up means learning and using coaching techniques to promote an authentic, positive, and productive relationship with your most significant professional relationship: your boss. When used effectively, coaching up can enrich mutual understanding and often reduce frustration and stress. In fact, use the ‘coach approach’ in all aspects of your life, and it will quickly become second nature and help you succeed through tough conversations and difficult relationships inside and outside of work. Here is how:

1.   Start with the right mindset: Suspend negative judgments about the boss, whether these are conscious and crystal clear or faint and subtle. Suspending does not mean permanent deletion but temporary hold. If you do not do this, you risk your judgments getting in the way of being truly present and open.

2.   Be Curious: Coaching is all about unleashing your curiosity. That means beinggenuinely curious and interested in your boss’ point of view. That may be hard to do if you are at odds with your boss but it is imperative to put things on the right footing.

3.   Deploy your attention:  This means listen with your full attention and ask clarifying questions when needed. If you disagree, instead of getting defensive (default reaction) try getting even more curious. Ask questions like “What factors are influencing this decision?” or “Please help me understand this.”

4.   Ask artful questions: Ask open-ended questions rather than questions that are answered with “yes” or “no.” We begin our questions with “how” and “what” as often as we can.

5.   Work with, not against the grain: This means attending to your boss’ communication and learning style.  Some learners are visual while others are auditory. Some like big picture information, while others prefer lots of detail; some like crisp bullet points, others like longer pieces; some like to be told after actions have been taken, and some like to know our every step before and during our tasks. If you don’t know your boss’ preferences, it’s time for a curious conversation!

6.   Work towards a win/win: Negotiation is a key business skill to learn. For example, if your boss wants a daily written report, and you don’t have the time to compose that each day, ask if she would accept a weekly written report instead. She may say yes, and she may say no. If she says no, offer another solution that will meet her needs as well as your own.

7.   Seek common ground: Begin by understanding your boss’ values. It does not mean you have to agree or have the same values but understanding what they are is a good first step to learning to co-exist. This can also begin to create a sense of common ground and shared values, on which to build your future relationship.

8.   Communicate clearly and assertively: The challenge with assertive communication is that it takes some education and a little practice, particularly for those who weren’t taught assertive communication growing up. Many people mistake assertiveness for aggressiveness, but assertiveness is actually the balanced middle ground between aggressiveness and passivity. Communicate your requests and needs clearly and with confidence. The right balance is between being humble and respectful, and confident and assertive.

A final word:

While effective leaders know their options and their plans, they are also open to shifting gears if they receive persuasive new information. They know that they may not always have the full picture of what’s involved in the complex challenges of the organization. This is particularly true when working with bosses who have a much broader organizational perspective than we do. As you continue to coach up, you may improve your opinion and feelings about your boss. Even if negative judgments do creep back in from time to time, we have tools to work toward mutual understanding, if we choose to use them. Coaching up isn’t a magic bullet, but it is a very good way to enrich our partnership with the boss—that most significant of all organizational relationships. In the end, coaching up is about forging a partnership with your boss so you can produce your best work. And there is nothing wrong with that equation.

Good luck.

Wait! Before you go…

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As a trained co-active coach, I am currently enrolled in a 6-month professional development program to complete my certification. As part of that training, I need practice clients to try out my new skills, and I am offering a huge (>50%) discount for the first five practice clients.

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