Why and How You Should Compliment Your Boss (Part II): The How To

Complimenting Your Boss Pt. 2 of 3
photo by boneskinny

How Do I Compliment?

1) Considerations
“Praising up” can be a challenge and will require some thought and effort. It’s best to focus your praise on your direct supervisor: Complimenting those at levels above can tend to cross a familiarity line, not be appreciated, or come off suspicious.

Also, of course, you’ll need to take into account the culture of your office, your relationship with your supervisor, your personality, and hers. I’ve had bosses who preferred as little interaction with employees as possible to personable ones who’ve helped shape me as a professional and gave me advice when asked, long after we worked together.

Complimenting and encouraging can be done face to face, via email or phone—and some companies have certificates of appreciation or company thank you notes that employees can use to convey praise or recognition to anyone in the company. This can facilitate the process and make the effort less awkward.

The group spin (“We think ____ and just wanted to say ____”) can be used if needed or when starting off. When delivering compliments, I prefer to let what feels right guide me as far as the what, when, and where of it all.

2) Sincerity
Whether you’re talking to your supervisor, wife, husband, etc., your compliment must be sincere. Hollow compliments can cause a manager to feel justified in not promoting a brown-noser and that that employee is immature.

On the other hand, building a reputation as an encourager can go a long way with being received as genuine when giving compliments, so look for opportunities to praise your coworkers as well.

Finally, don’t come off like you’re judging your manager’s performance or giving compliments you might have just as easily withheld. And don’t rehearse what you want to say or overthink it. Just be natural, authentic, and honest in your comments.

3) Specifics
Mentioning something specific will also facilitate acceptance of the compliment and promote behavior change better than a generic compliment. Look for ways your boss has helped you or things he’s worked hard on and successfully accomplished. You can also observe behaviors he’s modeled that you’d like to develop. If there’s not something exceptional often enough, think about praising solid consistent performance, “You manage ___ aspect of your job really well…”

How Often?

Encouragement shouldn’t be robotic. You don’t want to create a situation where your boss rolls her eyes and thinks, “It’s 9am on a Monday. Here comes Megan to drop another one on me.”

Saying something every once in a while, when you observe something worth complimenting, or when she exceeds expectations is appropriate frequency, since not everyone does something noteworthy every week. Be alert, and look for appropriate opportunities to praise. Think about how often your boss compliments you.

Another prime opportunity to encourage is when you sense your manager is having a rough day or is down—and it doesn’t have to be a compliment. Even something like, “Hey Caryn, I know you’re having a rough day. I’m sorry about ____, but it will all work out alright.”

Thanks to Clay Faircloth, Pam Meek, Paul Havlik, and Terry Warren for their insight. Other sources:

  • “Office Hours: Bowing to the boss: Everyone Likes To Be Praised, But It Can Go Too Far.” Guardian [London, England] 9 Dec. 2002. Business News: page 4 by Sally O’Reilly
  • “To brown-nose or not to brown-nose?” USA Today. (Nov. 18, 2009): Business News: p01B. © 2009 by Del Jones
  • “Ways To Compliment Your Boss.” Asianetindia.com, 3 Nov. 2015
  • “Your Difficult Boss May Be Insecure.” Khaleej Times [Dubai, United Arab Emirates] 24 Aug. 2013 © 2013 SyndiGate Media Inc. by oksana@academiaofhumanpotential.com


Looking for a new job? Want to get what you want fast? Check out my book, Here Today, Hired Tomorrow, and subscribe to my blog (kurtkirton.com) for free monthly advice on your job search.