Handling the Difficulties of Wearing Many Hats


Founder at HappilyEver



In small companies and growing startups there is a need for a lot of roles. Yet, due to financial restraints it is difficult to staff a person to each of one of those roles. For example, say that there are only five people in the organization but there are nine job titles, instead of hiring on four more people those original five will inevitably pick up the work and begin to wear multiple hats. Whether its official or unofficial, managers especially will be taking on the roles of multiple positions and tasked with the duty of doing a hundred different things. While the company saves money because fewer people are needed, there are some negative aspects to it as well.

Actions taken

Wearing yourself out People tend to get burnt out because they're doing too many things at once. Although it is sustainable for a while, sometimes years, it's best to find ways to avoid getting to that point. I think that those with a lot of responsibility tend to become very good at time management and stress management. It's similar to how parents cope with having children. Your mindset shifts to become super methodological. So when you are working your mind is constantly thinking: Do I need to do this now; Should I even do this; At this moment how do I feel; Should I spend this time focusing on this or something else? It's a shift in perspective where you need plan much deeper, and question whether you should do something, if someone else can do it, or if it can wait. You need to become very thorough and rigorous in your approach to work, this is how you survive. And if you survive, that means that you are a better version of yourself than yesterday. Otherwise the alternative is to burn out and die. Confusion about your role: Which hat are you wearing? The people who you are working with don't often know what to expect from you because they're not sure which hat you are wearing at any given time. This can be especially true for remote workers. For example, at one time I was wearing the hats of project manager, architect, and head of quality. Speaking to a developer I commented about deadlines, how the architect should look, and I also mentioned a use case he may have missed. This was overwhelming for that person and he became frustrated. While I haven't found the perfect resolution to this problem, I have implemented a technique that assists with guiding people's expectations. When I begin talking to someone I will tell the person beforehand which hat I am wearing. For example: "I am wearing a project manager hat now. Let's talk." "I am wearing a QA hat now. Please understand where I am coming from." "I am wearing an architect hat. Let's not talk about anything that has to do with scheduling or testing." I clarify before the conversation starts so that everyone's expectations are clear on whom they are speaking to. This has worked well for both local and remote workers. Accumulation of power Wearing multiple hats is the equivalent of being much higher in the company than each individual role is separately. Though each hat might be lower in the cabin, together they accumulate power. With this comes a power struggle. People who are new to the company or who are at a much lower level will think that you are dictating things. More so, people tend not to express their concerns and are less open to giving feedback if they don't know you and the role that you are playing. I think being more aware of this and other power dynamics that happen within the company can be helpful. Especially realizing the power of your words. The higher up you go in your career, the more impactful your words are, even the smallest of them. So while you may ask a question for clarification purposes, if you never mention that you are trying to clarify something people may think that you are actually asking them do it it. Thus, you need to be very clear why you are saying something when you are saying it. Be very cognizant on when you speak and what you speak at work, especially when communicating with others whom you have an impact on.

Lessons learned

  • I did get burnt out sometimes, though I had a manager who gave me some freedom and time to relax. In fact, he told me that if my mind wasn't relaxed by the time I got to work, then I shouldn't come to work at all. This was because I was in a role of constantly making decisions and if I made a wrong decision it would have a big impact on the company. So he'd rather I not go to work than have a negative impact on the company.
  • I learned that many people were frustrated with me wearing multiple hats. I found this out through my manager who pulled me in his office and gave me a talk. That's when I knew that I had to be explicit about which hat I was wearing so that I could preserve the integrity of the work environment.

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Founder at HappilyEver

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