Managing a Challenging Manager

This post was originally published on March 25, 2013.


A wonderful recent college grad was seeking advice … about how to give advice.  Her organization is one that’s trying to do the right thing by giving the front line (where she is) lots of feedback AND asking for lots of feedback from them to their managers.  This can be very challenging, because though the system is set up for feedback, not every manager is. “Why?” she wondered out loud to me,”does this guy not seem to ‘get’ anything I’m saying?”  She asked me how I thought she could give feedback that got through.

Almost everywhere I have ever worked or consulted, the front lines did not feel like the line “above” them truly listened to feedback — even when they claimed they wanted it. How is this possible? And what do you do about it. Two things.

First, it’s that old walk-in-the-moccasins thing. Kids complain about parents, parents complain about teachers, teachers about administration…and everybody complains about congress! But try serving in these jobs and you quickly find out that they are bombarded by many perspectives and competing voices; as an Israeli once said to me on the streets of Jerusalem, “Two Jews, three opinions.” That’s the truth about all of us; to a boss or a coach, one person wants order, while another demands flexibility, and you change the context and those same people will flip sides. I am not saying, “whatever a boss, teacher or congresswoman does is right.”  I’m saying that if you want to be effective with them, you first have to TRY to understand the variety of forces that tend to impinge upon them.

The second thing to do is act like YOU are “the” leader in the situation.  That’s hard! You don’t have the title, the pay, the sticks, carrots, reputation, perhaps the age or experience. So,what do you have?  The capacity to do what leaders do:  encourage the other — in this case the boss; describe why something is in their best interest (in leadership-speak we call this “sharing a vision” of success); ask how you can support them, share tools and knowledge you have.  Of course, these actions have to be filtered into an appropriate context.  Thus, for example, I don’t walk up to the Dean of the Law School and pretend he should listen to me as though I’m the Chancellor of Berkeley to whom he reports. But I do for example encourage him. I listen for how I can help. I talk about “my issues” in the context of the values that I know he cherishes for his institution. I share knowledge from my unique vantage point that might be useful.  I try to “walk” the talk of the institution.  And I do my best to open myself completely to his feedback and input; so that I grow, but also to model the way of listening eagerly to feedback, which is what I hope he and others to whom I report will reciprocate.

So, on the one hand (or since I’m talking about the proverbial moccasins, on the one foot): Respect the position, the title, the suit of authority and the pressures that your manager  must feel.  And then do your best to offer everything you can to help the person in the suit to thrive.

I hope this might help as you:

Lead with your best self!


  • Good Morning.

    I agree Dan, with your second point especially. – act like the leader.That point is also made by Robert Kaplan in his HBR piece “Reaching Your Potential”(July/Aug 2008; Reprint #R0807C) To it I would add “Lead in those areas where you have the most control.”

    There are two more points that might assist as well. One is “the medium is the message” perspective. . In which medium is your boss most receptive – memo, informal discussion,
    etc. ? And second, limit your suggestions. Too many make you into a threat, especially if they are good!.

  • Dan,

    Providing “performance feedback” is an important responsibility of leaders. So, what’s performance feedback all about?

    The word “performance” makes it seem as if we are on stage. Success at work is our applause, the managers and leaders of our organization are the directors and producers, and our successful performance run is obviously the bottom line. Very few actors walk away with a Tony or an Oscar for mediocre performances. That is also true in the work world. Survival as an organization rests on the quality of our work. Without stopping to playback our performance, we might find that our run will be much shorter than we anticipated.

    As leaders, we need to get people on a positive course by helping them face and then manage weaknesses. How this is done is through the feedback process: honestly, respectfully, openly, thoughtfully and with a sense of purpose.

    More at:

    • John,
      I appreciate that you are always adding valuable stuff. But I’d ask you to take a closer look at what I’m writing.
      Today’s column, for instance, was not about giving performance reviews, which you link to — managing down. It was about managing up.
      You write, “as leaders, we need to get people on a positive course…” My premise is that the manager is NOT the leader. The point of the column is that you can lead from “below.” Indeed the young person I wrote about in reality was probably way more capable than her boss. So, the shorthand that he is “the leader” is fundamentally flawed. And the point of the column was NOT to help managers give performance reviews — however helpful, and progressively designed as you write about in the column you link to. The point was how to do the difficult work of managing up.
      Sometimes I feel like you post in order to direct people to your site. That is fine. They can go or not. But my request is that you offer input that is truly relevant and not just a quick link to something no doubt valuable on your site.

  • There’s a difference between a challenging manager and a tyrant. We have a manager that came from the military (not that all military are this way) but acts literally as an “in your face” drill sergeant if we say anything. She has centralized control over everything and is uncompromising. We couldn’t help or offer anything to her – she knows everything.

    I’ve never encountered anyone like her in my career. In this case, it’s best to recognize that as an employee, you won’t have any impact on the situation and just move on.

    • cag –
      Now, that’s a very challenging situation.
      The military folks I know invite a private discussion with the person’s commanding officer. If that doesn’t work, and there is an issue of mission/values, then soliders/sailors/etc., have a right if not an obligation to talk to the CO’s officer.
      Of course, you may not want to stay in a place that is so oppressive…

  • Right. Recognize that front-line workers have the “tree” view, which is important information that managers need to know AND ALSO that manages have the “forest” view. In other words, managers have to be responsible for work flow, worker training, budgets, productivity, equipment maintenance, compliance with government regulations and / or grant requirements, and a host of other things, not just customer service and employee satisfaction. All are important to keep things running smoothly. Just because a front-line worker has needs does not necessarily mean that a manager has the capacity to implement changes immediately, or ever, even if it seems simple to the front-line workers. Business is complicated!

    Front-line workers need to understand that the boss may listen to their concerns but be powerless to do anything about it. If the business plan calls for all part-time workers and no overtime, then the business could fail if the boss starts assigning some people to 48-hour weeks just because they have certain skills or need a living wage.

    …so it’s well for front-line workers to share their input but not “own” outcomes. They need to leave it up to the boss about whether anything changes, and if so, when. Middle managers especially often have their hands tied by upper-level management. It’s rotten, but true!

    Also right that it’s well to model the active listening skill if that’s how you want your boss to respond when you have some input.

  • Years ago I read an airline magazine article titled “Act as if you were the boss” and I have never forgotten the good advice. It caused me to take a good look at the company I worked with and LEARN the “ins and outs” of many things which were not under my department’s care. It turned out the entire company was under our care, and it changed my life.

    Thanks for the reminder to live “as if” I am the boss, even when I do not want to be.

  • Managing a manager is a fascinating idea. What I have noticed in that kind of situation is that often it is not the manager immediately above you who needs to be managed. You may be in an organization or under a government where the ultimate authority/ decision makers cannot be reached since they harden themselves from communication with almost everyone. They use your manager to enforce their policies and decisions, and so the manager, no matter how well approached or managed, is stuck doing what they are doing, and how they do it. I have no solutions for the situation I just described other than political methods using pressure from outside the organization or government. Things like putting a light on what is going on, or organizing a boycott.

  • Good afternoon, Dan. I do love your articles, always great advice. They get me to think positive, to still keep trying. Thank You, sir.

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