The failure of leadership, and how to get better from here

There are many great leadership/management books, articles and tips to help people develop leadership skills, and yet this article is something different — I am not giving tips on how you can become great leaders, but rather an observation when leadership fails in my own experience. If you could learn one thing or two, I hope to help you see red flags in your company’s leadership or a potential company you want to work for, but let’s hope you will never encounter what I had encountered. In addition, this is not an exhaustive list of bad leadership out there, since I’ve only experienced a handful in my 10 years’ design career. However, I think some of them might be common enough that anyone can tap into. And when you do, I hope my experience can be a lesson to you to get out of these situations with some damage control.

(Note: all stories are in chronological order. If you want a TL;DR ver, just jump to The Lesson in each story.)

Story 1: No leadership, lack of communication and chaotic management

I got a job offer as an Art & Production Director right after my grad school in Chicago. The company is a magazine startup, and had 3 designers in house at the time. I met the founder, passed interviews, and got the offer in email. Everything went well, until my first day at work:

I arrived at the office early before the scheduled company meeting. I first met some designers on the team. One designer introduced herself to me as the “Art Director” on the team, and told me my job responsibility was to “find images and photoshop them”. I was confused as I was supposed to be the art director and manage the team. I didn’t confront her, as I thought this must’ve been some confusion and misunderstanding. I’ll wait for the company meeting to clarify things.

And then the company meeting started. The three designers showed up. The administrative assistant showed up (who gave me the offer btw). The founder and CEO showed up, with a couple other operational staff. He announced me as the “Art & Production Director” of the design team. Immediately, the design team flipped. They argued they had never heard of any new hirings of art directors, and the designer who talked to me earlier said she was the real art director, and other designers said the team didn’t need another designer, it was a waste of money — Yes, this really happened in my welcome meeting. The administrative assistant pointed out that the other designer was not an “Art Director” since she claimed so by herself, and then there’s just more finger pointing and people arguing. Finally, all designers stormed out, and threatened to quit, left me in shock… The founder & CEO guy apologized for their “rudeness” and then told me that’s the team I had to manage.

And the following story should be no surprise — the design team held a grudge against me for everything I did, even I tried to communicate how I understood their feelings — didn’t work. And one after another, they quit the job.

The lesson: How the company communicates changes internally can reflect how chaotic and non-transparent they are. Some obvious red flags: 1 designers didn’t know the company was hiring; 2 designers didn’t weigh in on any interviews, and didn’t feel respected; 3 there was a confusion on job titles and job responsibilities; 4 there’s no support system for new managers or onboarding training to deal with situations like this. My suggestion: try talk to the team if you can before accepting any offer, so you know what the real culture is like.

Story 2: The patronizing boss that belittles others

This is probably the worst working experience I had in my entire career. I got this trial offer to work for a marketing agency for a month, and if they see me as a good fit they’ll hire me as a full-time employee. The job title is the same as last one — art director, and same structure of a startup, with me reporting to the CEO directly.

The CEO was nice to me at first, and I was referred by a friend, so I loosened my guard. One of the first projects I got was to refresh a logo for a client. I worked hard on it, starting from some basic sketches, and then tried around 50 different font, layout, color combinations, and then sent to the team to review internally. After sending my pdf through, the assistant sent it directly to the client without asking me first. And the client thought these were final design and got upset and called the CEO.

Of course I didn’t know any of this until I got a call from the mad CEO. The first thing the CEO said to me was: “Do not ship anything that you’re not proud of!” And then she went on attacking me personally “How can you be an art director for so long and didn’t know these basic protocols?” I didn’t feel I did anything wrong, but it was just a misunderstanding, so I said well maybe we should focus on how to solve this with the client asap, instead of blaming each other. And the CEO got more upset, with me not backing down, and screamed: “Why are you so tough? Do you never apologize to people?” Ultimately we clarified to the client that the pdf we sent was for internal first draft and not final design, and I was pushed to create at least three concepts in a week to present to the client as a remedy.

After this incident, whenever the CEO talked to me in meetings, she’d always belittle me in front of others. She once said in a meeting “I think this design intern’s work is better than Jany’s. Yeah maybe we should switch them…” If I didn’t need the work visa, I probably could’ve quit onsite, but I had to endure all the humiliations for a whole month. By the end of the month, I felt so free like I can finally breathe again.

The lesson: You should never work for someone that belittles you or makes you feel you worth nothing. A boss never listens to your side of story and just blames you when something goes wrong is the worst. Plus all the personal attacks? Respect should be the bottom line.

Story 3: When the boss doesn’t have any domain knowledge of what you do and has to manage you

In 2017, I was in a special task force as the solo Sr. designer on the team, reporting to an editorial director and the VP of creative. The ask is to redesign the whole website of the flagship brand I was responsible for. The VP of creative was from a marketing and editorial background, and not a designer. He asked me to wrap up the design assets in 3 months so I can send to developers for production. I knew it was not gonna work, so I had 1–1s with him on what a good UX process should be, and why we should stick to a good UX process, and presented design thinking to the whole creative department, and finally persuaded him to make the project a year-long project starting with some solid user research.

The lesson: It’s hard when the boss doesn’t know anything about your domain. They set unrealistic timelines for you and expect wrong things from you. It could be harmful to the project and also to your morale. And like I did, you can seek alignment from: Advocating for a good process from your domain; Educating the boss on what he doesn’t know; Showing ROI and metrics to convince him (if he’s into data); Asking crucial questions to help him see the gaps; Aligning others on the team to advocate for you. And most importantly, don’t be arrogant and think “I’m better than you” — this won’t get you anywhere. If the boss is smart enough, he will know he doesn’t have to know everything, and especially things outside of his domain. And that’s when he will rely on your expertise to solve the problem. But if he’s not, then you deserve a better boss.

Story 4: A boss that can’t embrace authenticity & vulnerability

In the same company, I was reporting to another editorial director lady at one time. At the time the editorial department was understaffed so she had to jump in for some IC work. She was on the brand I was responsible for, and did editorial work while I did the design. It was right before thanksgiving (one of our busiest time), and she had several days scheduled for vacation. Before she left, I had a chat with her to make sure we were on track for shipping our mags to production, so the prints can come out and get delivered to our clients on time. She reassured me all her editorial edits were done, and just needed some final oversight and then I can send for print. And she pointed another editor to work with me in her absence.

When the new editor went through the mag with me, she found at least half of the stories (300+ pages for the mag) were not edited — meaning they were still just drafts without any fact check. I was concerned and reported to the VP of creative (a different guy from story 3) right away. To my surprise, the VP told me to “not let anyone on the team know our project can’t make the deadline”, and we probably have to postpone the print schedule secretively. This is ridiculous logic to me as I think we should focus on getting all the help to make it happen, instead of covering it up from other teams. And the temporary editor was under tremendous pressure to “finish as much as she can”. So I made a bold decision — I called other editors on different teams, explained the situation, and asked them for help. People were very empathetic and jumped in right away, even this was outside of their responsibilities. Ultimately we finished all edits in time and I sent the mag to production.

Well, the story is not really about how I saved the print schedule, but what happened next. I saw this gap of communication and misaligned expectation, which needs to be addressed. So after the editorial director came back from her vacation, I gathered her, the VP, the temp editor and some other folks on the project team to have a post mortem meeting. I wanted the meeting to be constructive and not finger pointing, so I started with what happened and how we solved it and what we could’ve done differently. Before I can finish my points, the editorial director got very defensive and said “Why are we talking about this, since the mag is already sent to production? Can we just drop it?” and after I pointed out why reflection was important and so we can prevent it from happening again, she got emotional: “Can I beg your forgiveness, because I was overworked, I worked till midnight everyday, and I just couldn’t get all things done!” And the VP helped: “Yeah I don’t think there’s anything to discuss, if it’s just a shortage of resources”. I disagreed and shared my point of view: 1 we are not accusing the director for not getting all stuff done, if she’s overwhelmed, but we weren’t informed; 2 we acknowledge we’re understaffed, but still, there are things we could do to help prevent this from happening, like a better communication. The director should be empowered to share with her subordinate and boss that she’s overworked. And she should not have lied about how much progress she had made in the edits. And the VP should’ve not asked us to “cover up”, as we are a team, and we’re in this together.

The lesson: Some people believe being in a leadership position means they are the authority, they are the know-it-all, and they should appear “on top of everything”, otherwise they might be seen as incompetent. The truth is, everyone is only human, and everyone can feel overwhelmed or off track at times, and there’s no shame to admit that to your manager or peers or subordinate. To hide it or cover up will only cause more negative impact and jeopardize trust.

Story 5: A dictator boss

After I was hired, my original hiring manager resigned in my first week, and another manager took over the design team until he left too. So the VP of creative was trying to find someone to backfill the position. Just a little context: we had four designers at the time — two senior designers(including me) and two mid-level designers. There was one week I saw the VP had frequent 1–1s with one of the mid-level designers, and had other directors in the meetings too, and the next week I found the VP offered the mid-level designer a “Lead Designer” role. This came as a shock to me and the other senior designer as the promotion was skip-level and there was no communication to us whatsoever. The mid-level designer must’ve felt the same way that she rejected the offer.

The next thing I heard, after a few weeks, is that the VP has found the new design director for the team. He announced to the design team his start date, and told us about his experience, and his portfolio site. Everyone was caught off guard as we’ve never heard of this guy before, and he just suddenly parachuted. Now I really felt how designers in story 1 felt. After the announcement, the designers went to that new director’s portfolio site, and… let’s just say none of us thought he would be a good fit. Some got even upset, so we went back to the VP and explained why we don’t think he would be ideal for this job, and we should have a more transparent process, e.g to involve designers in the loop, and know the hiring criteria, etc. Of course the VP didn’t listen to our reasonings or feelings and insisted on his “executive decision”. I comforted myself to just give him the benefit of the doubt since I’ve never met him, and maybe seeing him in person would change everything. And fast forward to the ending of the story: designers left one after another (including me), the design director was fired for some misconduct, and the VP was laid off later too.

The lesson: Avoid a dictator boss that only does things his way. I’m not saying that all decisions should be a team vote. If we do so, we will never get stuff done. The boss should still be the decision maker, but it’s important to have a hiring process in place, transparent to others, and all decisions should be made against those criteria, not by the boss’ personal preference. That should be the same for UX design too. When there’s a conflict in design decisions, we should always hone in on the customer needs, and assess if the design helps users reach their goals, instead of yielding to whoever speaks the loudest in the room.

Story 6: A boss that doesn’t care about you

In one of the companies I worked for, we had a flexible work schedule and people can work from home a few days a week (that was way before COVID). Soon after a new boss came, he took multiple measures to make sure “we are productive” — he didn’t allow us to work from home on Monday & Friday, stating that “then people would combine the weekend with one of those days and not work”; he made us report to him everyday on what we did and show proof; and lastly he made us report time off at least 2 weeks in advance otherwise he won’t approve it. I remember the team fought him on some of his measures, and he explained “your salary is the best reward for your work, and you shouldn’t ask for more, just be grateful…”.

In another company, I was put on projects that didn’t fit my job description, and I had no interest in doing, most of the time. I tried to talk to my boss in our 1–1s, elaborated on what my career goal was, how I felt not growing and being stuck, and what I got was “it is what it is, but you should hang in there in case things change — of course things never changed.

The lesson: There are many signs when the boss doesn’t care about individual employees and just treat them as “replaceable resources”. And you will definitely know when that happens. When encountering those moments, try to acknowledge your feelings, emotions and needs, instead of feeling guilty of what you are asking for. Try to negotiate with the boss/company and if they really value you, they will figure out a way to accommodate your needs. And if not, it’s time to move on. It should be a no brainer: before you join a company, ask about all the benefits (e.g healthcare, dental, vision, 401k, hsa/fsa, free meals, career development funds, phone bill expenses, transportation stipend, pto days, paternal leave, daycare assistance, work from home policy, etc), but also ask how many people got promoted in the past x years to get a sense of the promotion rate, what is the churn rate, etc.

Of course to “care” about an employee doesn’t just mean all the benefits at a company level. It also means the boss cares about you on a personal level, acknowledges your needs, advocates for you when appropriate, motivates you when you’re stuck, and supports you so you can be the best self you strive to be. And that’s when you can finally substitute the word “boss” to “leader”.

On the final thoughts, I just wanna share some good leader traits I found from all the stories above:

A good leader:

1. communicates and over-communicates to make sure everyone’s aligned
2. always listens, and listens to different sides of the story
3. doesn’t make you feel you are worthless
4. is empathetic and respectful
5. shows their authentic and vulnerable self
6. supports you when you need help
7. challenges and motivates you to achieve more
8. never orders people to do things their way, but leads by example
9. admits that they don’t know everything and asks for help/feedback when needed
10. makes informed decisions, and not by personal preference
11. is transparent about the business, their job, and how decisions are made

Let me know if you have encountered other types of leadership failure and I would be interested to know as well. 🙂