After my last article on how to coach the boss, one of my readers sent me a few points that can make coaching the boss pretty difficult.

KTL said, “I think the most
difficult parts are to make the boss openly listen to you and admit there should be
something to change (they feel they are superior), build formal coach/coachee
relationship (some bosses may not  believe in coaching)  and spare time for the
coaching (bosses are always busy).”

Thanks KTL. Those are 3 valid reasons. And they all depend on the boss being committed to coaching. So the question is, how to build a strong incentive for your bosses to be coached by you so that they are willing to listen to you, develop the relationship and spend the time necessary.

It might be easier to solve that puzzle by turning the question around. What would it take for YOU to have a strong enough incentive to be coached by one of YOUR employees?

Here's my list of answers, with the most important qualities first. How well do you measure up in your boss's eyes?

To be coached by an employee, a boss would need…

…certainty that the employee is completely trust-worthy in terms of keeping confidentiality. This is a basic requirement of any good employee. But many people greatly devalue themselves by sharing confidential information and gossiping. I have personally coached several bosses who wished they could trust their staff with inside information, but they were consistently proven wrong.

…to know that the employee greatly respects the boss, enough to care about his/her feelings and respect his/her authority. This is extremely important, often more important than people are willing to admit. This is also something you can prove to your boss in your day-to-day interactions. Prove it by listening well, being responsible and relating to the boss in whatever way gives them the most support.

If you don't respect the boss, you can't coach. And if it's not possible (or constructive) to change your attitude, then you might consider changing your boss. But I don't recommend giving up easily, because as you stretch yourself to respect people of all kinds, you'll grow your personal power tremendously.

…confidence that whatever the boss reveals will not negatively influence the employee's morale or performance. One of the first coaching skills to learn is to be comfortable with discomfort. Let your boss see clearly that you are not upset by uncertainty, not phased by challenge and not demoralized by difficulties, and he/she may dare to share with you some of the challenges he/she faces.

…belief that the employee will understand the complexities of the boss's position and thinking. Just think how frustrating it would be to explain a complex problem and be met by a blank face. Upgrade your understanding of the higher level of complexity that your boss faces.

…respect for the coach's perspective, mental agility or certain useful skills or knowledge. You don't need to be more experienced than your boss, but it will help to know exactly what aspect of your knowledge, experience, skill and perspective could be useful to your boss. For example, you may be more in touch with the attitudes of the lower ranks in the company, and that perspective could be very useful in setting strategies for performance improvement. Or you may be very good at seeing the positive side of events. Share your skills and knowledge in subtle ways that are convincing, not bragging.

...to know that by discussing current issues or challenges with someone who listens will, asks useful questions and gives constructive feedback, the boss can significantly enhance the quality of his/her thoughts and actions. In  short, the boss would need to have experienced effective coaching before (by any name) or be willing to try it. Many people know intuitively that they can benefit from good conversations. But many view coaching as some kind of directive activity and they will resist it from someone who is junior to them. The easiest solution may be to avoid naming the coaching you do and simply call it meetings or conversations. If the conversations are beneficial, they will be worth repeating.

If you work on proving yourself to your boss in these ways, you may find coaching conversations emerge naturally. But you may also fail to ever reach your boss. Everyone is different.

Through practicing yoga I've learned that it is not important that you can complete the position successfully. What's important is the experience and what it teaches you.

The practice of coaching (which begins when you begin the relationship) can teach you about service, respect, trust, confidence and personal power. Start today!

If you've got specific cases to share, I'd love to tackle them, anonymously if you like. Are you still looking for solutions?