In all the communication coaching that we do, one question seems to come up all the time. "How do I get my boss to realize he/she needs some coaching as well?" Most bosses are really good at identifying your areas of possible improvement, but typically they are really bad at identifying their areas of possible improvement. So how do we help our boss take a good look in the mirror? This is a big topic, too big to be discussed to completion in a single blog post. But the overarching themes throughout should be Trust and Respect.

Instead of your focus being, "How do I find a way to jam feedback down my boss's throat?" I think the focus should be, "How can I build a relationship built on trust so that we can have open communication between us?"

Here are a few things to keep in mind:

Every Boss Has People They Trust

Figure out who those people are, because they will be your best pipeline into the boss's ear. Senior leaders won't take feedback from just anyone and everyone. But they will take it from a trusted advisor.

Any Feedback Message Needs to be Crafted with Respect

This is true no matter who it is going to, but especially if it is being given to someone above you on the organizational chart.

Some Bosses will be Open to the Idea of Doing Something Better

If they are legitimately interested in self-improvement, then the message can be, "This will make you a better/more effective leader." But other senior leaders will not entertain the possibility that they can be better, and in those situations, you might be able to get the executive to take on some skill building or professional development, as a way to "set the tone for the rest of the team." Even if they don't see it as professional development for themselves, if we can simply get them to participate, for the good of the team, you may see some positive results.

Consider Finding a Way to Go Above Your Boss When Necessary

Sometimes it's necessary for the feedback to come down from above, from your boss's boss. This is hard to navigate, because getting caught going around or above someone you report to will cause big trust issues. I know I would hate having someone on my team go around me. But if I'm just not hearing the message, the people who work with me might have no choice. Choose this step carefully, and discreetly and respectfully.

Do you employ a little humor to start? Perhaps some modest (but not overly annoying) flattery? Maybe some form of gratitude. This is no different from effective interactions with any person ... you always want to know how to get someone into a comfortable place for listening.

Your relationship with your boss is similar to all other relationships you will have in the workplace. The greater the level of trust and respect that is shown, the more likely that the relationship will be built upon honesty and open communication. If your relationship is not built on those things, you have little chance of delivering an unflattering message.