I usually report to the CEO on my daily work, and as such, I was also given large freedom and self initiatives. I am young and willing to devote all my energy to help this high tech profile company to grow. I worked really hard in the past half year and got lots of things done. I am able to handle a project alone, and from customers feedback I have done a good job.

However, this company recently hired a senior manager who is supposed to be between me and my CEO - an increasing of hierarchy. He is a typical salesman. He does not have much knowledge on our technology (he is learning though). Still, he likes to give opinion, and at the moment, he thinks quite negatively on what I was doing. He has almost turned down one of my plans. He thinks it was wasting time and he was surprised I took my own initiative to call the people on manager level to talk about my idea.

However, I got support from other managers during the meeting which obviously made him feel bad. He was not happy, and finally, on Friday, he told me that I shall not just speak out before I talk to him. I was shocked and sad when I heard about this. I felt like my motivation is going down and I cannot like my job anymore.

Now, everything has to go through him.

I have told my CEO that I would like to talk to him. Our CEO is liberal, he always told me to work in his company we need to be free and responsible.

What should I say to this middle manager in response to everything going through the middle manager, and how can I explain this situation to my CEO without creating more problems?

  • Update 1

For all the people who are trying to help me, I got an update for you. I had a short talk with my CEO today for 10 minutes. I told him I felt a lack of freedom, and demotivated at the moment. Like many people suggested here I did not expect that he will give hand to either of us. He also implied it himself. He suggested me to talk to this new boss myself and find a solution. What I get from this conversation is:

  1. the CEO would like to have both him and me (I hope)
  2. ...to work together
  3. he hired him because he got too much business related stuff going on that he has not time to handle them all himself
  4. he is building a hierarchy in this organisation (when I talk about hierarchy, there is a structural hierarchy and cultural hierarchy, here I am implying a structural hierarchy)
  5. he said the culture of being free and responsible shall not be changed.

So tit looks like to deal with this new boss is my best alternative at the moment. (many people suggest me to run; well I really like my colleagues and CEO and my work, also in the industry we are maybe not the best but one of the most unique company that has a great potential, to run from a company like this with a permanent contact after 6 months might hurt my career, again it reminds me to be prepared in any case, thanks for you all) much appreciation:)

  • Update 2

Delegation is one of the management tasks I think he at least fulfills so far. He got a task from the CEO and forwarded to me: "please have a look at this and think about how to do it."

  • Update 3

From a few colleagues' (from other departments who had a meeting with me) feedback, they all think he is tough and 'not in the context'. However, I don't know how much he put into work so far. The weird thing is that I sit behind him (my CEO placed the seat), 3 out of 5 times I have a glance at his screen he is either logged in to his bank, on a trading website, or on a local financial website checking stock news... - OK, I am really demotivated at work. I probably have to reposition myself.

  • Update 4

Dear all, thanks for those who still look at this post, this guys is going on holiday next week. And I had a feeling that he was about to talk to me (probably about forwarding task to me which i used to do independently). So I just proposed a meeting to him for tomorrow. Besides, we are a company with advanced scientific stuff, I had a feeling that he does not spent enough time in reading publications and articles in order to get more understanding. He just gave away the paper today to an engineer and asked her to give him a summary. We both received the article, i finished reading(even it was hard) and he delegated. I still (really a bad stomach feeling) have not find anything in him that i can look up to. I respect people who might not be that knowledgeable, but hard working is also something I respect, where is it in this guy? well. I am gonna talk to him tomorrow, ... I take this challenge. See you guys later.

  • Update 5

Thanks to all your suggestion. I think I am on my way to 'management upwards'. I posted a meeting for us today. I prepared well a list of topics, divided in two parts: working task and working style. I first stressed that I would like to have things work and want to find the need of both of us in each others job and get the best result of it. I have proposed my working scope and I think we have an agreement now. Besides, I said a lot about what kind of management style I best respond to and I believe he heard it. He also told me what he wanted and his goal in this job is. As a first very formal meeting between us, I am satisfied so far. lets see what happens later - and update you all. Thanks for all your guys help.

OK, a very stupid thing of me happened, I had the page of 'how to manager your boss' open when he passed by my table (after the meeting)... I wonder whether he saw it and so on...

  • Update 6

People are returning from the holidays. So now I have to figure out a way to work with this person. He is once again trying to define what I have to do and what I should not and get things in his control, however I said no so some of the decisions(such as he suggested that we both shall exit my self from the company R&D meetings) later other managers told me I shall participate in it...so.... My principle is

  1. try to be helpful
  2. Communicating
  3. protect my own rights and territory
  4. Avoid free riding

(if any of you audience has a better suggestion, please let me know).

  • Update 7 ALL IN.

Dear friends, thanks for being patient. Here comes an update. - I was working an excessive amount of time for the past half year. No extra remuneration or over time pay. On one hand I have to deal with this manager's pointless tasks. On the other hand I have made my own agenda and priorities of what is the best for our company and achievement in my to do list. I was lucky too. I sealed a deal for USDM19.5 – that's quite a bit for a danish SME. All cash in + A Joint venture sponsored by the two investors both in capital and Human resources. My CEO told me that I do not have to listen to that manager anymore. I report directly to CEO now. I got a new title 'xxx executive' plus handsome pay raise.

After all I might want to thank that middle manager. I have learned a lot about myself in this process.

Things learned

  • Set out your boundaries and let people know.
  • Work with good ethics and stick on your principle.
  • Be soft to people and hard on principle.
  • 1
    Hi user, welcome to The Workplace SE! Can you edit and clarify your question. Our Q&A format isn't well suited for general advice, so we ask that there be a specific question you'd like answered. I edited the last sentence for you based on what I think you're looking for, but please edit further if my edit is misleading. Good luck! :)
    – jmort253
    Jun 30, 2013 at 18:59
  • 1
    @Celina - I really do hope things work out for you in the long run. Hopefully the new manager got the clue about the free and responsible culture. I'm marking this question as a favorite, and I'd really like to see a follow-up in 3 months as to how it went. Jul 2, 2013 at 23:37
  • 1
    @Joe My CEO hired me and i am working for my CEO, who appreciate a critical thinker and independent self driven worker. This middle just came in and making shoot from the hip decisions without knowing so much about our technology and company culture. I will be screwed if i says yes all what he says. I give argument that supports my feedback to his decision, which i believe can help him as well if he is a good manager. Besides, i am confident about what i am saying. - please give counter feedback and challenge me. :)
    – Celina
    Aug 28, 2013 at 8:38
  • 1
    So what happen now that 6 months went by? I think you quit hoping they will ask you back, but instead the show just went on. Thats life.
    – NickNo
    Feb 28, 2014 at 7:28
  • 4
    Wow. The "good guys" won, for once. Thanks, @Celina, you've given us all hope. Dec 8, 2014 at 16:56

6 Answers 6


Executive Summary

If the CEO thought you were appropriate for this middle management position, you would be the manager. If the CEO thought the position was not necessary, he/she wouldn't have created it. Understanding that this manager is there for a reason is the first step to finding a way to work well with him.

Growing Pains

Let's say you're an intrepid entrepreneur opening an authentic Japanese restaurant. You really want to serve Horumon (beef innards BBQ), but you're having trouble explaining the joy of chewy cow stomach to the local populace for some reason. So you and your staff try all sorts of sauces, different ways of preparing it, and different ways of advertising it. Eventually you find the magical formula and get a few regulars who start evangelizing your offal to their friends and family.

When their friends come in, their friends are not looking for you to reinvent what made their friends recommend it, they want the experience you developed. They don't care about how many times you pivoted your business, or what your menu used to look like, they are there to try what their friends recommended.

Now if you are the chef in this restaurant, you may not be happy that you are now only asked to prepare the food in a single way. You enjoyed fiddling with different recipes, seeing the reactions of the customers, and figuring out how to modify and improve the taste. What do they need you for? Now the act of cooking is just following a recipe, where is the fun in that?

Companies often work the same way. They start with an inkling of an idea, and to make it work they need to be flexible to meet the needs of those first customers. Once they have built a base of revenues, they focus on increasing the market for what they've already created and had success selling. Flexibility loses out to the ability to expand.

The Much-Maligned Middle Manager(s)

If you are a business owner, and you realize that the best way to grow your business is to build up rather than pivot to find a market, you need to start finding people who know how to do that. Generally speaking, people who are great at innovating rapidly are very different from the people who are great at standardizing and simplifying processes.

When you are building the first widget, what matters is that the widget works. When you are building the next 99, you want them to be built just like the first widget but as cheap as possible. That is a very different skill set.

It is also something that can cause friction. If you like fiddling with the widget to make it better, you are going to be butting heads with someone who needs the widget design fixed so that they can produce them at a set level of quality as easily as possible.

From the widget-maker's side it seems like the manager doesn't care about the details of the product. It sounds like they don't care about how cool your widget is, or how much work you put in to making this widget work. Widget-makers don't like someone coming in and making it seem like their work is unappreciated, especially since the widget only exists because of their blood, sweat, and tears.

Communication is Key

These issues can be eased with good communication. Understanding where your CEO is taking your business, and understanding the role of the middle manager are essential to minimizing the friction and frustration on the part of the employees.

Many start-ups have a staff without experience pivoting from a flexible product-development based organization to a sales-based organization. They may not know how to communicate the shift to their employees. They may not realize how this shift affects many of the people who work there, or how it affects the work style. They may expect the middle manager to know and handle it themselves.

This is where you should step up and take an active role in communicating with your manager (first) and if needed with your CEO. I would sit down with my manager and have an honest chat. Something along the lines of:

Hey new manager. Sorry that there's been a bit of friction between us recently. I've been working at this place since it had X employees and everyone reported directly to the CEO. I'm not so used to having a manager act as a filter for development of the projects, which has caused a few problems. I was hoping you could explain what you want to accomplish, and how you think we fit in. Such a big change in the way the organization flows is going to take some time to develop, so I hope we can regularly discuss how things are going to make the transition smoother.

Listen to what he wants to accomplish. Figure out where he wants to go. Give him positive feedback (at the very least explain that you understand where he's going with it). Ask him if he would mind sitting down from time to time to discuss how things are going, and what potential hurdles there may be in accomplishing his goals. Trust that he means well and that he's willing to work with you rather than against you.

Don't Subvert the Manager's Authority

If you need outside confirmation, you can schedule a chat with your CEO too, and just say something like this:

Hey CEO, we've been working together for X years since there were only Y employees. I really enjoy working here because of the freedom you give to your employees, and the responsibility you expect from them. Recently there have been some big changes, especially the hiring of middle management as the business has grown. I will do my best to work with him and keep growing the business, but I was hoping that with such a big change that you could spend some time with the employees to let them know the direction the business is headed and what the goal of the new management structure is. That would make us feel a lot more comfortable.

Whatever you do, I strongly recommend against complaining about the new manager, trying to subvert his authority, or otherwise do anything that resembles going over the manager's head. The CEO hired him to get a job done, and if you complain about the manager your CEO is placed in an impossible position: imply that it's okay to go around the manager if you don't like his decision, or side with the manager and upset an otherwise productive employee.

At the End of the Day...

Some people thrive in the start-up environment. They enjoy result-based work and are willing to work long and hard to get something done when they feel ownership of it. Other people are more process-based and enjoy seeing something great come from a system rather than just individual effort/heroics. If a company moves from result-based to process-based, and you are a result-based person, there is no way to reverse the tide as a regular employee most of the time. You can push long-term to keep an entrepreneurial niche in the company (and locate yourself there), you can adjust to a process-based work environment, or you can always leave.

But there is no way to know the direction of the company, or what your actual work environment will be like without talking to the people involved. Before making any rash decisions, have honest discussions with your manager. Most people have good intentions and are willing to compromise to find something that works. Chances are he's feeling out of place at the moment too -- being the first manager for a group is definitely a tough job. After an honest discussion you will have a better idea and will be able to make a better decision about what you want to do.

Don't act rashly -- it won't end well.

  • 9
    This is a good write, however I see an important flaw in the logic. The CEO indeed hired the MM to do some things, but we have no proof that said MM is actually up to the task. And completely different resolutions are needed for the competent and incompetent case.
    – Balog Pal
    Jul 1, 2013 at 10:15
  • Thank you for the comment, you have all been very helpful.
    – Celina
    Jul 1, 2013 at 12:09
  • First comment,maybe I forgot to introduce a bit about my background. I started to work for our ceo who hired me from the beginning of this year. And I graduated from master last year, I am simply a young ambitious 'little' girl. If I am the ceo I will not hire my self as señor manager. :)
    – Celina
    Jul 1, 2013 at 21:11
  • 1
    @BalogPal No, we have no proof the MM is up to the task, we only know that the CEO assumes that they are up to the task (or otherwise wouldn't hire them). If you can explain how you think questioning the MM's competence (and the CEO's judgment in the process) wouldn't cause issues, I'd love to hear it.
    – jmac
    Jul 1, 2013 at 23:19
  • 1
    @jmac: anything you do normally "cause issues". Avoiding them is not a primary objective. Unless you suggest to just suck it up. And everything else that comes. The CEO hired the new manager in hope things will go better. If they instead go worse (workers unhappy, possibly some leave), he can reconsider. Having that MM around is not a goal. A good resolution is everybody's interest.
    – Balog Pal
    Jul 1, 2013 at 23:36

I've been through this more times than I can count. I have made it a personal policy not to work for anyone other than the person who's money is on the line, in short the person whose business will succeed or fail based on the results of my work. This rules out just about every public agency and major corporation.

The CEO is interested in the integrated whole. The 'middle manager' has a far more parochial view. The first thing (s)he is looking for is your compliance with procedure. Depending on what those are, it can effectively prevent you from doing your job.

'Knowledge of technology' is not the problem. The mistake (which is becomes patently obvious in many other posts in this discussion area) is that managing engineers/developers/programmers is a fundamentally different problem from managing clerks, warehouse workers, or service technicians.

Most organizational procedures are structured around 'immediate response'. Therefore, if someone drives in with a car that needs a tuneup, the service writer writes it up, the technician racks it up and makes the changes, and the clerk runs the credit card through the reader and the customer is on their way. In restaurants this means 'turning tables'.

Engineering and software are the production of 'capital goods'. The nearest analogy is building oil refineries or power plants - one is engaged in a project that takes months or years to complete. During that time, no customer is involved. Internal users that are going to have to use whatever you're producing should be intimately involved in how the interface and functionality are designed, and this should be 'everyone' that's going to use the system, not just the people in 'your group', whatever that means.

Of the people with short-term mindsets, salespeople would be the worst. Most sales activity is focused around the alteration of perception: making the poor sucker buying your product think the junk you're selling is gold. The last thing they're interested in is something that will take a long time, and 'hard numbers' are as foreign as Pluto. The only hard numbers (s)he deals with are commissions.

It's unlikely that you will be able to explain this to your present 'manager'. Therefore, one can see several paths through the situation, the most likely of which is that someone will conclude you are no longer effective and will let you go. Another path is that your CEO will recognize that the personal chemistry between you and your manager is bad and will restructure your reporting relationship - this might take a few months. The best thing for you to do is be ready to jump ship. Find work elsewhere, and be ready to go should the situation prove to be hopeless.

  • 2
    The customer is very involved over the years during which a power plant/oil refinery is being built in most situations. They are making sure that the milestones are met and arranging payment (adjusted for liquidated damages if not on schedule), as well as coordinating between contractors if not a full turnkey project.
    – jmac
    Jun 30, 2013 at 23:39
  • 1
    @jmac: reading the post more carefully, the OP is doing work for external clients. In that case the analogy is correct, he is a 'consulting engineer', however were he working 'internally' the client's customers would not be involved until the product deployed. The broader rule still applies, this is a long process with numerous feedback loops, and a 'manager' is second guessing the developer's initiatives. Senior executives often 'give the manager a chance' to settle in, usually giving them at least six months slack. If the manager is a real doofus, the team is gone at that point. Jun 30, 2013 at 23:51
  • 1
    Ordinarily, I am the one saying "stay low and deal with it." However, when you have a manager who is trying to isolate the boss from the work, run. Don't walk, don't look back, just run. I've been through this three times. I stuck it out once and it was a disaster. The two times I left quickly, they were also disasters (I learned later), but they weren't disasters that I was in. Seriously, find another job and FAST! The only thing I disagree with Meredith on is timing. Jul 1, 2013 at 5:00
  • 1
    @WesleyLong: IMO it's worth to try and eject the new boss while fresh, at a startup company it can actually happen. (For a large, hierarchy-based company or when the attempt fails I agree).
    – Balog Pal
    Jul 1, 2013 at 10:05
  • 2
    @Celina - I think I see what's going on, now. From what you've posted, you're probably in your mid or late 20's? This guy is in his "last shot" to make it. If he's retraining at 52, he hasn't found a niche, yet. This is his last chance, and he knows it. You're a threat to him. He needs your talent to shine, but he can't let people see that he's not the bright light, he's only the window. This man is trapped in his mediocrity, and it's terrifying to him. You have youth and promise, and it scares the hell out of him. Give it 30 days. If there is no improvement, bail. Jul 1, 2013 at 21:39

First of all: Don't take it personal (until you know it was meant to be).

From what you write it's not clear (to you) why that manager was put in place or why that management position was introduced at all. So your CEO clearly has a communication issue here that you should address - with him.

Inquire about his motivations for creating that management position, which objectives he pursues with it and what made the selected manager the ideal candidate for reaching these goals. You can also extend your questions to the company's strategy and organizational development scenarios in general.

Once you fully understand the situation, go over to your personal situation. Ask how confident he is with your work, how he sees your future career path (in and out of the company), where your strengths and weaknesses lie and in general what he expects from you. State that you will of course talk through these same questions with your manager (which you should).

It would be advisable if you prepared your personal career objectives. From my management experience it's always hard to cope with employees that are just unhappy with their current situation but don't have any measures on what they'd want instead.

As a side note: Yes it's normal that as businesses grow they need different organizations (and people). As a manager, you can only schedule that number of meetings per week/month. Consolidating direct reports through a middle manager is a fair solution. Don't expect to be the single non-manager reporting directly reporting to the CEO.


and finally, on Friday, he told me that I shall not just speak out before I talk to him.

I'm sure he has no right for such request. If I was in the situation I would have pointed that out quite directly. And unless he takes it back as misunderstanding, I'd ask this order in written form. From there whatever route would be interesting.

Is it normal for problems to occur when startups grow to the point where more layers of management are needed? I

Yes, it is pretty common that growth makes the existing management forms not working well enough, making leaders overwhelmed. And a common response is to get some outsider. And as usually there's little experience on telling good from bad, it's easy to pick up a genuine bad apple with good fast-talking skills. Or one that would be good elsewhere, but not a good fit for that company. I heard stories in all directions, including where the new mid-manager was dropped after a few months and the team restored to good work. Also where he was kept and half the team left or got reorganized.

If you really have good standing with the CEO, you may ask yourself out of that pyramid forming a separate branch -- maybe even with some team members.

And until the dust settles you can use the 5 WHY method, make the manager explain everything not evident, recursively. That way you might dig out incompetency, or learn that he is right after all. It's quite fail-safe. (And if he just refuses or can't answer, that is sure indication of a douche.)

  • Thank you for the comment, you have all been very helpful.
    – Celina
    Jul 1, 2013 at 11:55

First you can not go to the CEO for a talk in a way that will not be perceived poorly by your manager since the action you are taking is intended to subvert their authority.

Instead I would suggest explaining to your manager that it seems the expectations of you and your role have changed and that you are uncertain about the role you are expected to play in current organization of the company. Explain to him what your role was in the past and talk about some of the projects you have had that have been successful for the company. Then ask your manager what his expectations of your role is. Listen to them and express any concerns you have to him first giving him an opportunity to address them.

If you are still unable to resolve the issues then explain that you have always felt you had a good working relationship with the CEO and would like to meet with him and your manager to discuss the expectations of your role going forward. Realize at this point chances are that the CEO is going to back his new manager and you could be forced to find a new job. Your relationship with your manager is unlikely to be easily repaired if you do this and it could make your work life difficult. It is also possible the CEO will not look kindly on your questioning his leadership decision. I would not take this step unless I was willing to walk away from the position unless my concerns were addressed. There is quite a bit of risk here with out much chance of a reward that makes it worthwhile.

  • You are Right i am indeed in a very difficult situation. :(
    – Celina
    Jul 1, 2013 at 19:20

So your issue can be detailed into the area of "Managing upwards". It's one of those things that people rarely get training on.

First and main point is. This person is now your boss. Not the CEO. As such there are rules when dealing with a manager (to get what you want). Breaking these will almost guarantee damaging your relationship.

  • Not being loyal.
  • Going behind a bosses back.
  • Not delivering on goals set, or being unreliable.
  • Not making the manager aware of any surprises.
  • Being unprofessional.

Based on what you have written so far it looks to me that you broken a few of them. So you need to make amends for that.

I would recommend to have a 1:1 and apologise for the actions (even if you don't believe you were wrong). However don't come out and say sorry. You need to do something like this:

"At first I did not see your point on ... , but now I realise you are right or have more information then I do".

Also explain in depth the relationship you had with the CEO, and why you did the things you did.

You need to get a clear picture of why the manager is doing something a certain way. They would be privy to more information then you. It could be a matter of budget for example. You also need to learn the managers style so you can better understand how to get them to action what you need.

At the end of the day, you still might not like them. But you need them to get the job done, so it important that you learn to work with them.

If you want any reading material in this area I recommend "The leadership skills handbook (2nd edition)" by Jo Owen. There is also some good material on the Harvard website.

  • 1
    Hi Simon, thanks for the very insightful comments, yes my solution is a managing upwards aka a negotiation process and i am going to take the initiative of this kinda conversation. Since i have been bothered by the bad feelings i have indeed broke some rules like you listed.Many thanks for reminding me!
    – Celina
    Jul 17, 2013 at 9:23

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