How to “Coach Your Boss” (and Keep Your Job)

“If you want to be an effective coach, and want others to listen and use what you have to say, first, you must be coachable.” Jeannette Seibly

When your boss gets stuck and could use your insights and coaching, it may be time to coach your boss.

“First off you may not want to use the term coaching. Consider it an open and honest conversation with your boss that focuses on feedback. Framing it this way opens the door for more honest dialogue.” (Forbes)

But beware! If it’s not done diplomatically, you could find yourself sidelined in your job.

A director hated his boss, a VP. When the executive coach asked the director to have an honest conversation with the VP, he resisted. He used the excuse “Everyone else hates the VP since he is difficult to work with.” Under the guidance of his coach, the director had an honest conversation to clear the air with the VP. Afterward, he started treating his boss with more respect and appreciating his boss’s insights when stuck in projects. Soon thereafter, the director became viewed as one of the very few people who could work well with this VP. If the director hadn’t been open to the coaching he received, he could have been sidelined in his job instead of being promoted.

Many team members today have insights, concerns, or problems with their bosses. The challenge is learning how to have an honest conversation to create a positive outcome.

Note for bosses and leaders: Encourage your team members and co-workers to give you honest feedback. It’s the only way you learn and grow, and catch those blind spots before they get in your way.

6 Tips to Coach or Have an Honest Conversation with Higher-Ups

  1. Be Diplomatic. Egos get in the way. So, it’s important to be diplomatic and set aside your own ego. Remember, there are always at least two sides to any issue. Be open to hearing what your boss has to say before offering your insights.
  2. Be Clear About the Issue. Take time to write down the specifics about “why” this conversation is important. Rehearse in front of the mirror until the person looking back at you feels comfortable and confident. Otherwise, your boss will dismiss what you have to say.
  3. Visualize the Conversation. Take the time to visualize or mentally think through the entire conversation. If you hit a snag, rewind, and replay in a positive manner.
  4. Breathe to Calm Your Nerves and Anxiety. Breathe to calm down the urge to go in too strong. Remember, being assertive is important; but, being aggressive will only limit your future job opportunities. Breathe in for a count of 10, pause, then, exhale for a count of 10. Do this at least 3 times before your conversation. This simple exercise will reduce stress and positively impact your results.
  5. Work Through Your Anger or Righteousness First. It’s natural for you to feel that your boss won’t understand or get what you have to say. But if you go into the meeting assuming your boss won’t understand and feel angry or righteous, your boss will only defend his/her actions. Work with your own executive coach first and role-play the conversation. Write out an agenda outlining facts and key points. Stay on-point during the conversation.
  6. Ask Permission. Start with a soft approach to get your boss’s attention. “I have something I need to talk about with you. And, I’m nervous about doing this. I fear you’ll hear it the wrong way.” Do this in a respectful manner. The boss is more likely to hear what you have to say.

©Jeannette Seibly, 2021 All Right Reserved

Jeannette Seibly is The Leadership Results Coach. She has been an award-winning executive coach, management consultant, and keynote speaker for over 28 years. Her focus is getting leaders and their teams unstuck and able to achieve dynamic results. Contact Jeannette for a confidential conversation. 

A note from Jeannette about coaching your boss (and keeping your job): Everyone can benefit from feedback. This includes your boss! Your challenge is the boss may not appreciate how you “coach” them. Instead, take the time to prepare for an honest conversation. If you know you need to have a difficult conversation with your boss but don’t know how contact me for a confidential conversation.

Leave a Comment