Your Boss Is a Flake—and You Want to Help?  Ask Madeleine

Dear Madeleine,

I like my boss and I think she is smart—but she is a total flake.

She loses documents, she is always late, and she can’t seem to understand how our calendaring system works so she misses meetings because they aren’t on her calendar. 

This isn’t obvious just to us, her team; her peers and her boss have noticed it, too. On a recent video conference call, we were all waiting for her. I was texting her to see where she was, and I saw one of her peers roll his eyes.  It kills me. 

She is super creative and visionary, she gets a lot done, and people respect her.  But I keep seeing her shoot herself in the foot, and I can’t stand it. 

I want to say something to her.  Should I?

Want to Manage Up

Dear Want to Manage Up,

No.  You can’t go at this directly.  The only way you might have an opportunity to give feedback is if you were invited to be a participant in some kind of 360-degree feedback process.

I can tell you care about your boss and you want to help. I really can.  But this situation is just too fraught and if you get involved, you will almost certainly lose.  You have heard the old adage no good deed goes unpunished—and I can assure you this would be the case for you.

Here is what you can do:

  • You can offer help with the scheduling system. Say something like “Hey, I figured out some really cool features about (name of system). Would you like me to walk you through some of them?”  Then show her things that may be obvious to you, but not to her.  I think this is a common problem. I constantly get meeting requests from people who should be able to see that I am already booked. It is maddening.
  • You can send her reminders for meetings you know you are both expected to attend. You can also check in on projects she is supposed to deliver on, to see if they are on her radar.  I share some of your boss’s traits and I have a direct report who does this for me.  I really appreciate it.
  • You can report behaviors you see. Say “Hey, I just wanted you to know that Joe rolled his eyes in front of everyone when you were late for the review meeting yesterday. I thought you might want to know.”

It is possible that one fine day your boss will ask you directly for feedback and you can say something. So be ready to point out ways she may be able to increase her credibility in the organization.

Until then, stay subtle, keep watching her back, offer help when you can, and report others’ reactions when possible.  She will notice—and it will add up to her knowing you have good intentions and she can depend on you.

Love, Madeleine

About the author

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

Got a question for Madeleine? Email Madeleine and look for your response here next week!


2 thoughts on “Your Boss Is a Flake—and You Want to Help?  Ask Madeleine

  1. Hi Madeleine,

    This is indeed a delicate issue to address. I agree with your recommendations as a way to subtly provide feedback to the boss.

    Let me play Devil’s Advocate – taken to an extreme, this approach seems to enable the boss to continue the frustrating, and frankly, less than professional behavior. If the boss is expecting excellent performance from his/her team members, then she needs to be a role model of the same.

    Assuming there is a trustworthy relationship with the boss (and if there isn’t, that’s a whole other can of worms), I would suggest the team member look for an opportunity to provide feedback in a more direct manner. Here’s a link to an article that discusses Blanchard’s approach to having challenging conversations:

    My best,


  2. This is great, thanks Randy. I agree, gong at this directly is preferable but can be oh so dangerous. I literally have a letter in the Ask Madeleine line up in which an employee did exactly that, and is now dealing with a damaged relationship, and is probably on the way out. So…I try to give advice that isn’t going to potentially end up with someone losing their job. A dangerous business, this giving advice!

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