Have you experienced reporting to, or at least, working for, multiple bosses? That one says one thing while the other says another and you do not know which one to follow? Or even both of them asking for something important, let alone urgent, and you don’t know which one to do first?
Well, with the current trend in organizational structure of any business, this may be something that most of us have gone through. (Or, you may be going through right now and are lost at what to do).

Evolution of organizational structure
Before we dwell on the problem of reporting to too many bosses, let’s take a quick look at organizational structure and how it come to be.
This is not a history lesson but rather to give you a quick understanding of why organizational structures are designed as such and differently between companies. The reason why we need to understand this is because whatever the structure is, it affects the chain of command one has to follow. In effect, it could become challenging and results to reporting to at least two bosses.
Big organizations or companies deals with a lot of tasks. Departments are created to work on these such as financials, logistics, employees’ well-being, and operations. No one person can do everything and simultaneously run a smooth business. Therefore, departments are created that focus on these specific tasks to ensure nothing is missed.
As the business grows, more departments or more hierarchies are created. More employees around are needed and more supervisors and managers are hired or promoted to oversee the work. Departments split into sub-departments to create a more dedicated focus on more subtasks.
The organizational structure expands either vertically, horizontally, both, or even interconnected-type. You may be aware of the first two where one reports to one boss. The third one, interconnected or a network map, is a type wherein each person can be assigned to multiple departments, multiple bosses, and work on multiple projects at the same time. It shows how one person’s work is connected to someone else’s and who is ultimately responsible and accountable for the work.
And this type of structure is what is subtly happening in the workplace right now.
Multiple bosses
In one of the companies I worked for, I was reporting directly to a boss that oversees my work and performance. We talk and coordinate on a daily basis, almost every hour, to tackle daily issues and ensure our work is done both mine and the rest of my team. Our daily interactions involves chats and calls, not to mention emails, which made tasks and projects move and progress as we want them to.
While I am directly reporting to this person, I am also “dottedly” aligned to another person. With this other person, we work together to ensure other tasks are moving and hitting deadlines. Our interaction is not as much compared to the person I am directly reporting to. However, there would be times when the work they both endorsed to me was important and urgent, and sometimes conflicting. This is when things become confusing.
It is easy to say that to solve this issue, one must prioritize and consider which work, or which boss, should be dealt with first before the other. That is easier said than done. In reality, even if you have this figured out, the nagging feeling will still be there that there is another work that you need to accomplish. In effect, you rush the work to get it out of your plate so you can deal with the other one. Or you start your day very early and put in more time than usual to get everything done thinking this will help you. But, tomorrow will still be the same.
You would also think that prioritization is the key. That is true. Identifying which work or boss is more important could help you navigate a pile of tasks. It can be done. But, as a fair warning, the reality of the workplace is that prioritization is subjective. What you may think is a priority may not be the same for your bosses. Of course, they would always think that what they ask for takes precedence over anything else. They may agree with you but at the back of their mind, they will expect you to complete what they ask from you in the shortest possible time.
Communicate clearly the work
First and foremost, we all need to understand and accept this fact. There will always be cases when we need to report to multiple bosses. This is done because creating a new department for just one task is not financially viable, let alone efficient for the company. Thus, for this, dotted lines at created.
Second, the work from each boss will only coincide because of timing and deadlines. This, if you would notice, happens every end or start of the month, quarterly or annually. There would be some urgent tasks that will also occur but, that does not happen every day. If that is the case, then it is a result of poor managerial skills and work management.
Third, one of the ways to ensure that we can manage reporting to multiple bosses without getting stressed out is to communicate the work. Communicating means discussing with both of them the work you have for each other so they can help you prioritize when you are at a loss. Each of those bosses will have a different perspective than you. They could see the bigger picture considering they know something that you don’t. By discussing with them which one to prioritize and setting a clear deadline, you can better manage your work.
Fourth, and I think we all fall prey to not doing, is sticking to your daily deliverables. This means working on each item regularly on a daily basis so it progresses one bit at a time. This follows the saying “You’ll never know when will life get you.” A regular day would always be simple so make sure that regular deliverables and long-term projects are touched on and worked on each and every day. So, when the time comes that urgent and priorities are at your door, you can manage it with fitness.
Contradicting directions
Well, it happens. One boss wants to do one thing while the other one wants to go in a different direction. This is not something new. I bet we all experience this. Fear sets in. We get confused about which one to follow. In the end, we just do what the higher-ranking boss told us and just explain later. Sometimes, we just do both to be sure we are covered. However, doing this creates unnecessary stress and duplicate work.
As mentioned above, to resolve this, we must communicate. Speak about the situation to both bosses and get clear guidance. Tell them that the direction is contradicting and you only have time to do one, not both. It will be confusing in the beginning but it will help you in the long run. By doing so, you set boundaries that both bosses understand and eventually will manage the workload being given to you.
Summary
Having multiple bosses is not something new. With the modern structure of how companies are set up, there will always be that “dotted” line in where we report to someone else aside from the person we directly report to.
Establishing good communication between the two fosters a good relationship and creates a balance between multiple works. By making them understand, we are able to prioritize and put our focus on what matters the most.


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