Okay, so not everyone who criticizes their boss suffers the fate of Cicero, who was executed after being declared a public enemy by Antony. Perhaps he should have made his comments privately. 
Don’t think it’s impossible to communicate upward just because of the unusual number of Korean Air plane crashes, attributed to co-pilots not feeling empowered to correct their bosses. (In their hierarchical culture one is obliged to be deferential toward one’s elders and superiors in a way we can’t imagine here in the U.S.) They have had this problem of the co-pilot searching for the acceptable way to tell the boss he made a mistake and oops… meanwhile the plane crashes.
One of the most delicate communication situations is giving your boss constructive feedback. The safest rule of thumb is “Don’t do it.”
If you feel strongly enough to override this suggestion, read the following. What helps your boss usually helps you. Take some tips from the communication skills involved in successful international negotiations.
- It starts through the relationship.
All communication travels through the fine filter of relationship status. The relationship is strong, then you’re looking good and sounding sharp. The relationship is tottering; you’re looking a bit fraudulent and sounding unreliable.
Bosses, contrary to appearances, are often delicate and fragile. In any case, they are subject to the usual human frailties and some are quite paranoid. (The Care and Feeding of Bosses)
Before offering helpful suggestions, make sure the relationship is solid.
2. Operate from the motive of helping the boss first, then you.
If you’re even considering giving your boss some constructive feedback, then you’re thinking like a leader. However, she is still the boss and you need to manage her as someone “leading from below.”
What are the benefits of giving this feedback to your boss? Why would you put yourself through this precarious experience? You’re definitely in the position of “selling it” so make it clear this message is in the boss’ best interest.
3. Correction through omission.
If you have a consistent habit of praising very specific actions, for example, great images on a presentation, then your boss is being trained to expect that from you. AND…when you fail to praise something, the boss, depending on the level of EQ, may notice your lack of positive reinforcement.
4. Mirror the style of your boss.
Sync up, as they say. Fast talkers like fast talkers. Quiet folks appreciate brevity. Just like you wouldn’t wear a tuxedo to play tennis, don’t use an inappropriate style in talking to your boss. If you’re not sure what is the appropriate communication style, put on your Sherlock hat and observe the following: how your boss dresses, favorite words, tone, speech speed and body language.
On the topic of leadership communication, McKinsey just put out a fascinating article about how the talkers, the ones who usually dominate the meetings, are most often seen as “leadership material” to the detriment of the organization. It’s called Finding Hidden Leaders.
5. Don’t make a big deal about it.
This is my personal go-to. Rather than wait for big moments, I sprinkle in suggestions when the occasion arises, as is the style of a professional educator. As is our accepted communication norm, sandwiching in the suggestion between two sincere remarks of appreciation, works well.
A simple way to “sprinkle suggestions” is asking leading questions like
Why don’t you….?
Have you tried….?
What about….?
Excellent communication doesn’t happen by accident and upward communication is always the most delicate. Start with building a strong relationship and manage your boss along the way by having a clear goal in mind and a strategy to get there.
Make the boss look good and that light will reflect back on you.
For additional insight on the valuable skill of feedback, 3 Tips on Giving Feedback that Actually Works.
