Here’s how to impress your boss

Are you miserable at work? Do you feel misunderstood, like your boss is incompetent


Samantha Da Silveira

3 years ago | 8 min read

There may be many reasons for not getting along with your boss that are completely beyond your control. But before you let it affect your productivity, or even worse, quit your job and remain with a bad boss impression for the rest of your days, hear me out first.

I used to think there was only one ‘correct’ way of working.

I had usually worked a certain way in my previous jobs. In the very beginning as a junior designer, I was managed by the project manager of an IT team where there were clear roadmaps to follow and sprints with clearly defined tasks. In other companies, I was managed by the lead UX designers which involved the UX team brainstorming to figure out what needed to be worked on next based on the roadmap and the required deliverables.

I had never worked as a true freelance designer nor have I ever worked for any design or consulting agencies before, so I was used to working in-house and in team scenarios where everything was decided as a team. I had clear tasks and deliverables to work on and track, in my tasks management application of choice.

I shouldn’t have let my past roles influence my current one.

I definitely got a wake-up call when changing over to my current company. In my previous role, I had once made an attempt to intervene in the head UX’s roadmap with an idea of my own which was shot down swiftly with a comment that I wasn’t there to contribute in plannings, but rather to help out in making things usable.

I didn’t perceive this as a negative thing, I just realized that in that particular role my job was to help the head UX designer accomplish his roadmap projects, and that was fine. I guess when I changed over to my new role at my current company, I arrived with this mentality. Big mistake!

The company lacked a UX culture mentality.

The company in question deals with the B2B (business to business) sector and has remained stationary throughout time with regards to all their internal software which is used by the employees to manage customer content and other media type services.

I think part of the problem is that because they use the software internally and it is not sold directly to customers, yet, they have been able to kind of “get by” without having to improve the software to high-quality standards.

It was only until I was hired that they, for the very first time, had a designer to work on and improve the internal applications. Long story short, there was no design team, no design culture, no UX principles, NADA. That’s why this role was so appealing, I had a real chance of making a big difference.

Initially, I projected the role of head UX onto my boss but he was not a UX professional.

My boss, who had been hired 6 months prior to me, is somewhat of a visionary, no joke. Coming from a broadcasting background himself, he had already developed innovative solutions from his previous role and wanted to bring that spirit to this company. He is a great product manager, but he was my only point of contact for creating and working on the products.

Because of this, I had considered him as my “head of UX”, like I had in my previous roles and worked with him within this mentality.

That’s where I made a mistake. I should have managed expectations with him better. I thought that he would be the one telling me exactly what to do, what to produce, what deliverable to develop, as if the two of us were a UX team together, but we weren’t. He had product goals but needed my guidance to achieve them. I was expecting to get specifications thrown at me so I could organize them neatly in the bi-weekly sprint, but this was not the way he worked (thankfully!).

The inevitable disappointments from miscommunication.

In the first year of working at my company, this resulted in a couple of disappointments from his perspective. He had an idea of what was expected of me and in my head, I had the idea that it was his responsibility to tell me exactly what he required of me as I had this bias from my previous roles. In retrospect, this doesn’t make any sense.

Upon reflection, how could he tell me exactly what I needed to do and what deliverables I needed to produce? He’s not a UX designer, he doesn’t know my process or all the work that goes into creating the final polished interfaces.

That was my job. It was my job to, first of all, understand exactly what he wanted of me and then work out what was required from my side to produce these final results. It took me a couple of projects working with him to finally understand this, after which I was able to quickly adapt.

I was able to turn things around by applying my UX process to this problem.

Once I adapted, he could sense it right away and mentioned it to me too. He praised me and even rewarded me for it. He told me that it was this current performance that he had expected from me from the very beginning. This was very satisfying to hear because, in the end, the way I approached working with my boss was built on the same principles as my UX process (oh the irony!), so it validated the usefulness of my process outside product development.

UX process applied to “working more efficiently with my boss”:

  • Realize that there was a problem (my boss was complaining and unhappy);
  • Identify the problem (my boss was dissatisfied with my work and performance);
  • Explore the problem (going back through all our interactions and identifying key points that could have contributed to him being disappointed);
  • Empathize with the user ( talking with my boss about my work, how we work together, what he expects of me and what his definition of success is for each project);
  • Analyze the data ( considering what my boss said and understanding it, finding patterns and making sense of it);
  • Implement a solution and test ( changing my ways to adapt to what I now believe is what he expects of me and if I failed here and there, quickly adapt);
  • Continuous testing and measuring ( I achieved great results but I’m continuously paying attention to any friction points and adapting quickly).

Thankfully I didn’t give up and made an effort.

This could have gone differently if I had just given up and gone to a company that I thought would have “appreciated” me more and that was more involved in UX design culture. I think that would have been the easy thing to do, but it was worth trying to address these issues because after all, I loved the company, and the projects were very interesting and fun to work on.

Some tips, based on my experience:

  • Make sure you manage expectations, no matter what work you do, agency work, freelance, teamwork, a situation like mine, some other totally different industry or line of work, you must always make sure you know from the very beginning exactly what is expected of you. What is your boss’s notion of success? When your work is “finished” what will success look like to them?
  • Communicate often, don’t be afraid of this. If you have doubts, if you’re not sure what you need to do or get stuck, ask questions, I can’t stress this enough. My boss is so busy he doesn’t even have time to validate important design sometimes, but I try my best to always communicate with him (in person or via email) if I’m not sure of something or if there is something important he needs to be aware of.
  • Be patient because the changes will not be apparent overnight. It took me a little over two years to find the right balance and now I can confidently say that I have mastered my job at this company and even then there is always room for improvement and going the extra mile.
  • Focus on the good qualities as your starting point. Try to appreciate your boss a bit more by focusing on what they bring that is actually valuable to the company, the team and even you, especially you. There’s always something we can learn from people. Your boss has a lot of good qualities, there is a reason your company hired them to manage products, projects and/or teams. They must have good traits that qualify them for the job, for most cases I can imagine.
  • Empathize with your boss. We’re all just humans! Neither you or your boss know what it’s like to be in each other’s shoes. In busy work environments and especially when you’re in a position of heightened responsibility, stress can be a major driver of your actions. If you are able to look past this filter, it can help you a lot in empathizing with other people, your boss included!
  • Quitting might not be the answer. Of course, one quick solution to resolve this problem would be to quit and find another job. However, if the problem is that you weren’t able to get along with your boss for lack of making an effort to do so, there are no guarantees you won’t just fall into the same situation in your new role.

Life is a video game — a fun strategy you could apply to challenge this head-on.

I am a (former hardcore) gamer and I approach this situation, and many others, as if it were a video game. Imagine you are the main character in a strategy game and you have an objective to complete which is the end of the game.

Let’s say the goal is to launch a product and depending on how successful it was, you will be ranked accordingly on an online leaderboard. The challenges you face in the workplace are the trials you have to overcome to get to the end of the game. Your boss’s personality, your colleagues and the conditions of the company itself will define the level of difficulty you are playing at.

If your boss is very easy going and like-minded then you are playing at a low level of difficulty, congratulations (I think?!). If not, then it adds more of an element of challenge to the game and if you’re like me, a person who loves challenges (especially if you’re a UX designer), then this should be something positive and not necessarily bad.

Of course, these guidelines do not apply to bosses who are regularly disrespectful or in any way harmful to you as a person. These are serious offenses and need to be dealt with accordingly.


Created by

Samantha Da Silveira

Experience designer based in Luxembourg. Curious about everyday problems and how to resolve them.







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