360° Answers: Caught Between Multiple “Bosses”

Each of our workplace experts has weighed in on the following question from a reader to give you four points of view. Here’s the question, with our experts’ responses below:

My organization seems to make a habit of not following the chain of command. Even in our small division of 10 people, I routinely find myself in situations where the division head gives orders directly to me (bypassing my manager, who is his direct report), or makes decisions that he doesn’t actively support afterwards (e.g., makes a decision and puts me in charge of implementing it, but doesn’t become actively involved when his own direct reports – who outrank me and who are affected by his decision – are dissatisfied with it and start challenging it). As a result, I find myself fighting to support decisions that our big boss made (sometimes without even telling his own direct reports about it), that my boss doesn’t have any knowledge of (except through me, as I usually do my best to keep him in the loop), and that our big boss’s direct reports are completely unhappy with. However, because the big boss didn’t make it clear to anyone that this is his stance on the matter, I lack the credibility to enforce and implement his decisions.

When I go to my boss about it, I get told that a) our big boss is too busy and too overwhelmed with work to be dealing with this and b) that this is all very political anyway. And I don’t want to go over my boss’s head to complain to the big boss about these issues when my boss told me to suck it up.

Question: Am I thinking too rigidly when I expect a clear chain of command to be followed? E.g., Big Boss has a Big Idea, Big Boss talks to My Boss, My Boss talks to me, I execute and deliver within my authority, and where enforcement or selling is needed, delegate upwards to My Boss. Alternatively, Big Boss has a Big Idea, Big Boss talks to me, Big Boss backs me up with his own direct reports (who outrank me completely). I should note that I am under 30 and that this is my first real work experience in a big organization.

Alison Green says…

Chains of command sometimes exist more in theory than in practice, so yes, you’re probably being a little bit too rigid in expecting it to be followed. More specifically, chains of command more often work upward than downward — i.e., you’re expected to follow it and not go over your boss’s head, but the Big Boss? He gets to do what’s most convenient for him, because that’s one of the prerogatives of being the boss.

Now, that said, if someone can demonstrate to the Big Boss that the way he’s doing things is less effective for the company overall – not just for you personally — then he should pay attention to that, if he’s reasonable. (Of course, not all bosses are.)  But the person to make that argument to him should be your boss, not you. Your boss may have done that without success, or she may not have tried because she’s unassertive, or she may not have tried because her position gives her a different perspective than you have and she understands perfectly why the Big Boss is operating this way.

But you do have a legitimate problem in that you’re being directed to implement decisions that don’t have team-wide support, and you don’t have the authority to enforce those decisions yourself. So the next time the Big Boss tells you to implement something, say this:  ”I’d be glad to. I suspect that Jane and Bob are going to push back on this though — do you have any advice on handling that?”   You can also get more information from him about how he wants the chain of command to work by asking him, “If I encounter any pushback from people on this, should I come back directly to you about it, or should I go through my manager?” In other words, anticipate the problem and involve him in solving it up-front when he first gives you the directive.

Eva Rykrsmith says…

First, kudos. You seem to have a very good understanding of the dynamics of a complex situation. I have been in similar circumstances so I understand your frustration in this scenario. I think you have also taken a good first step by discussing concerns with your immediate boss.

However, I question where your expectations for the chain of command come from. If your boss serves as an intermediary for communication between you and Big Boss, there would certainly be some details lost in the translation and besides, doesn’t your boss have other things to do than play telephone? It also seems overly bureaucratic for a group of ten people within a division.

Let me offer a new perspective: Big Boss coming directly to you is an opportunity. The underlying message is that he trusts you in getting a project done and is willing to take a risk to allow you to practice a leadership role. If you succeed, you stand a better chance of getting more projects with greater scope of responsibility and eventually obtaining a promotion and directly reporting to him in the future. Is this something that is in line with your career goals?

If so, the burden of responsibility now shifts to you. What can you do to impress the Big Boss and show you are capable? Identify problems (I think you got this part down) and work to create solutions (your next step is here).  There is a big difference between complaining and expecting others to fix problems for you and identifying a problem, generating possible solutions, and working past difficulties to get things done. Good luck!

Anita Bruzzese says…

One of the results of a down economy has been that organizations have been stripped down to the bare bones and each person has been asked to do sometimes two – or three – times the amount of work as before. It could be that this is what has happened to your workplace – job duties and expectations have changed even though they’ve not been put into writing.

Like Eva, I see this as an opportunity. Embrace it. Run with it. If you’re worried about covering your assets, so to speak, put your actions in writing and shoot off emails to concerned parties so that it’s clear who gave you the directions and how you’re following them. Keep a journal for yourself of any personal comments that are being made by unhappy coworkers because you always want documentation in case there is a dispute later. Writing it down will also help you analyze the information without the emotion involved.

At the same time, think about someone in your life – possibly a former professor or an older family friend – who might be able to serve as a mentor. You’re young and it will be difficult to navigate all of these political shenanigans in your office. A mentor’s advice could be very useful.

Alexandra Levit says…

Hierarchies are on the way out, especially in smaller organizations that are being run, more and more, like start-ups.  Nobody has the time because we’re all just scrambling to get things done.  I understand that you are uncomfortable with the situation, but look at it this way: it will be good practice for more ambiguous arrangements that are certain to come up if you continue working in today’s business world.

You’ve obviously made a terrific impression on the Big Boss – otherwise he wouldn’t be coming to you directly.  Live up to his positive perception of you by being responsive and conscientious and doing a better job than he expects on the assignments he delegates.  Focus on doing your job to the best of your ability and try not to worry about the Big Boss’ grumbling direct reports.  Factually report what you’ve been told to do, and don’t apologize for it.  If they are unhappy, it’s their responsibility to approach their boss.

It’s a good idea to continue to keep your immediate boss in the loop, though be careful about complaining too much about a situation that’s out of his hands.  This will only serve to annoy him.  If you make an effort to be independent and solve problems on your own with a great attitude, he will view you as positively as the Big Boss evidently does.

Do you have questions you’d like our exerts to answer? Ask them below and we’ll consider them for our next 360˚ Answers!

Alex Hastings

Alex manages social media for Intuit QuickBase. Her goal is to help users connect with the QuickBase community and build a constructive discussion around the product.

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  • Scott M

    I think that only Allison’s answer is really helpful.  Everyone else seems to be saying “that’s the way it is, just deal with it’, and I don’t think that’s the best advice.

    Hierarchies may be on the decline, but that doesn’t mean they should disappear entirely.  Managers exist for a reason, and it’s more than just being a ‘telephone’ to pass on instructions from the Powers-That-Be.  Managers are supposed to take “Big Ideas” and break them into smaller tasks, assigning them to their subordinates, according to each employee’s abilities and job responsibilities.  Bob handles I.T., Jennifer handles the HR part, Connie handles purchasing, etc.  The manager handles the big picture, and the employees handle their own specific area because that is probably what they were HIRED for (not to mention that is what they know and where their strength lies).

    And, I’m sorry, but I call shenanigans on turning this into an “opportunity”.  Its not an opportunity.  It’s bad management.  Big Manager may not have given this job to you because he thought you were the best person for the job.  Chances are he did it because you were a warm body that didn’t move out of the way fast enough. 

    As far as using this as a stepping stone to a promotion – not everyone wants to take on management responsibilities.  Good managers know what their employee’s career goals are, and do their best to make sure each employee is in the right place.  Bad managers assume that everyone hates their current position and want to be promoted to management.

    In short, this is a bad manager.  My suggestion is to push back as gently but firmly as possible.  Make clear the problems this is causing (not to you, but to the company and to the Big Idea). 

    If all else fails (and I will get a lot of flak for this suggestion) you can even feign ignorance.  Constantly ask questions – “How do you do this?”, “Who do I call?”, “What do I do next?”.  When the Big Boss realizes you aren’t going to completely absolve him of his management duties, he’ll learn to follow the hierarchy.  Or more likely, he’ll dump his Big Idea on the next poor shmuck who couldn’t hide fast enough.

    [Reply]

    Alison Green - Ask a Manager Reply:

    It’s also possible that the middle manager (the person who directly manages the letter-writer) is the bad manager, for not pointing out to the Big Boss that this is causing problems. The Big Boss might reasonably think he can count on the Middle Manager to point it out if he needs to do something differently!

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    Scott M Reply:

    That’s a good point.

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    Anonymous Reply:

    Thanks for such a thoughtful response, Scott!  I hope that a lot of our managers are reading it because you cite a lot of best practices.  Unfortunately for all of us, though, bad management will always exist, and if your success is dependent on your boss’ ability to manage you effectively, you may find yourself stuck.  The use of the word should (i.e. my boss “should” be a better manager, some form of hierarchy “should” exist) doesn’t take into account reality and tends to lead to frustration and disillusionment. 

    [Reply]

    Eva Rykr Reply:

    Excellent, excellent point. While there are many things we can do to “manage up,” the focus should really be on what we can do … not what they should be doing. 

    [Reply]

    Scott M Reply:

    I understand that this is not a perfect world, and that reality often does not conform to our expectations.  However I rarely see an acknowledgement of the fact that this IS bad management..

    Managers read these blogs too.  When they do, they only see the advice like ‘it’s an opportunity’, ‘run with it’, ‘it’s good practice’.  This lets them justify their bad management actions by saying “hey everyone does this, and its good for the employees too!”

    I wish I would see something like “This person is an incredibly bad manager.  They are causing irreparable harm to their business and their employees.  Having said that, here’s how you can minimize the damage…”.  Of course, I exaggerate, but you get the idea.

    And this subject is a pet peeve of mine so it always gets me riled up anyway! :)

    [Reply]

    Eva Rykr Reply:

    Also a good perspective, thanks for the addition. I don’t think there is one right answer (the beauty of this multiple perspectives format!) and, as you suggest, the appropriate course of action will depend on the OP’s goals, the organizational environment, etc. 

    [Reply]

  • Sociacademic

     Alison’s advice is always spot-on and practicable and devoid of vague generalities – I love it! In this case I think she’s exactly right to advise that the OP ask the Big Boss how he wants him to handle pushback from his direct reports.

    I also like Anita’s and Alexandra’s suggestion to let the direct reports know the facts of what you’re doing and who told you to do it so they know to take it to the Big Boss (or perhaps the OP’s boss) if they’re disgruntled, since the OP is just doing his job.

    Honestly I think Eva’s advice fails to address the OP’s issue and comes across as condescending. :/

    [Reply]

    Alison Green - Ask a Manager Reply:

    Thanks, Sociacademic!  I think Eva makes a good point about not having to deal with details getting lost in translation if the Big Boss was going to Middle Boss and the Middle Boss was going to the letter-writer. On such a small team, it can be more efficient to just talk directly, and I could see the Big Boss thinking he didn’t need a middle man in these cases…

    [Reply]

    Anonymous Reply:

    I also think the OP needs to be prepared that she may not get the answer she wants from the Big Boss (i.e. a good response to the direct report pushback).  However, it certainly can’t hurt to ask.  I always like putting the ball back in the boss’ court in situations like this.

    [Reply]

    Eva Rykrsmith Reply:

    Apologies to the OP if my response came across that way. I was just genuinely impressed by their analysis and first steps; most would not be so astute in this situation and having a good handle on what is going on is always the first step in resolving conflict.  

    When I was in a similar spot, I certainly did not see it as an opportunity at the time. I only realized it years later when roles were reversed. Seeing the situation from a different perspective while in the midst of it is a huge advantage and can help with decision-making about how to best move forward. 

    [Reply]

  • A4amanda

    As an emplyee in a non-manager roll, this is something I actually encounter a lot, and Allison’s suggestions were right on! But the best advice I got from a mentor was don’t get intimidated by employees who are higher-up in the food chain, and to remember that Big Boss (or the Owner, in my case) has the most authority and in the end, the guy who signs my paycheck. When I have encountered push-back from others, I normally say something like, “yes, Jane, I see your point, but Big Boss has specifically asked me to implement this, and I got the impression he anticipates everyone being on board with the decision.” This approach reinforces that Big Boss wants this, and Big Boss is their boss too. This works almost all of the time, and when it doesn’t I have a follow-up conversation with Big Boss to discuss any negative reactions, and try to frame that conversation in a positive way (ie: “Well, Jane was concerned that this would cause a delay in xyz project”, or something along those lines).
    Good luck!

    [Reply]

    Eva Rykrsmith Reply:

    Really great advice Amanda–can’t go wrong with straightforward communication, directly handling pushback yourself, and keeping the original authority in the loop about any open issues.  

    [Reply]

    Anonymous Reply:

    Great approach, Amanda.  I think the message is great, and I’d just be mindful of tone too.  In pushing back (because the Big Boss said so), you want to come across calm and confident rather than defensive or wishy washy.

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