Lessons Learned from Ineffective Leaders

How bad leaders add value without trying to.

Sivan Hermon
Women in Technology


Don’t miss lessons learned from great leaders parts 1 and 2 — I think it’s worth your time.

Is there anything to learn from bad leaders? Well, yes! Yes there is — a lot, actually. In all areas of life, you can learn:

  1. Recommended actions/strategies — proven things help achieve your goal.
  2. Discouraged actions/strategies — proven things that risk achieving your goal.
  3. Gray zone — things that haven’t been proven to be good nor bad.

Just as observing and analyzing how great leaders behave, inspire and make us want to follow them, observing and analyzing weak leaders teaches us what to avoid doing.

So while this story focuses on leaders who were ineffective in their role, I am genuinely (albeit in hindsight) thankful to them and grateful for those teaching opportunities. Without them, I would have likely made the same mistakes or, conversely, it would have taken me longer to learn what works and what doesn’t.

Ok, let’s get going:

Many startup companies hire the first technical person to design the product at the beginning, and then when the company expands, there is an organic evolution to that person taking on a manager role (sometimes based on skill, oftentimes due to necessity), even if they have no experience or desire to fill that role. So the first person we’ll learn from, was in a similar situation. Based on their leadership, I have to wonder if they even wanted that role. My guess is that they were asked and probably said “let’s give it a try”.

Photo by Sander Sammy on Unsplash

Lesson seven

(Read here and in the link below for lessons 1 to 6):

Sharing your raw (negative) feelings with your reports demotivates them:

This manager used to join customer video conference calls with me, and during the wait for the customer(s) to join, they’d often yawn, and literally say things like “work is boring”. Now this is an easy one right? It’s kind of easy to see why you shouldn’t tell your employees that your work is boring you. But this lesson (and advice) goes deeper. Sometimes, we (as leaders) are unhappy with something that is outside of our control; maybe it’s our company’s leadership ideology or specific actions that the company has taken. Hashing that out with our employees, in an unthoughtful way, might feel liberating for a manager as we might think we’re open/authentic/genuine with our team. But for them, it will likely discourage them or turn them against “leadership” or the company. I’m a big champion of authenticity, ask anyone I worked with. But as a people leader, it’s part of your role to thoughtfully bridge gaps between your organization and the company leadership. So you need to carefully consider both sides, and what will help your team to do a good job, mentally, knowledge-wise and professionally of course.

Take action:

I’m not saying “avoid sharing negative work-related thoughts and feelings with your peers/reports”. You are human, it’s ok to do so. What I’m suggesting is that before you do that, you should stop to consider your goals and motivation. Are you looking for an outlet to vent? Are you commiserating? Is there a benefit for them to be hearing your raw thoughts or is it just to take a load off of you?

There can be good reasons too. Maybe you want to prepare them for an upcoming change. Perhaps you want to help them understand that good leadership involves thought processes that differ from one’s usual thought processes.

Real like example:

When I was working for Google, I oversaw the meeting room booking systems. After 2 years where most of the company’s workforce was remote, we prepared for Googlers returning to the office. Google’s leadership asked all non-remote employees to come into the office 3 days a week. I knew that Googlers were unlikely to follow the guidance of a 9–5 Tue/Wed/Thu rigid schedule; they would prefer a flexible schedule. So, in light of finding our leadership guidance to be unreasonable and unrealistic — in other words: stupid and confusing — I guided my team to adhere to both requirements. I explained what our leadership is telling all employees, and I explained my prediction (based on years of experience with Googlers) and I asked them to ensure our solutions can accommodate more than a rigid schedule, but also support rigid schedules if/when needed. I could have bad mouthed Google’s leadership, whined, complained and whatnot. Instead I used it to teach my team how to deal with such a situation, how to deliver a great user experience, while accommodating company needs.

Photo by Kilimanjaro STUDIOz on Unsplash

Lesson eight

People wither without attention

Employees are people, and people like flowers without water, wither without attention. At the time I joined the team with the aforementioned manager, I was both new to the US.

I remember my first day coming to the office. I thought (read: expected) that my manager would set up a 1:1 for us, sit me down, welcome me to the team and office and tell me what I needed to do to hit the ground running. They didn’t. After about 3 days I set up time with them to figure out what I needed to do.

About 3 months later, I took a 2 week vacation. When I came back I thought my manager would ask me how I’m doing, how the trip was and maybe give me an update on my tasks/projects. Again, they didn’t.

You see, my manager loathed niceties — what they considered to be empty human interactions and chatter. They didn’t see the point of it; thus, they didn’t offer them to their employees. But… I craved some attention. I wasn’t given an option, I didn’t ask not to be bothered and I felt unimportant and alone. Even realizing that this person wasn’t a great manager didn’t eliminate those feelings for me.

Take action:

Remember employees are humans and humans thrive when being nurtured and tended to. I had a great quote comparing leadership to gardening as they both require creating a great environment and nurturing growth, which I sadly can’t find 🙁, but the sentiment does the job hopefully. Since that experience I learned the importance of seeing my team (and my peers), treating them as humans, showing interest in their needs, aspirations and also their personal lives (when shared of course). Treat your team as you wish to be treated by your leaders, and if you know you require very little TLC, then remember you are not the average person, and give them more than you yourself need. I promise you, they will appreciate it and be happier and more productive.

Weak leadership offers valuable lessons. Mistakes, poor judgment and bad behaviors serve as great demonstrations of things to avoid. Remember that no one is perfect, not leaders, nor are we. We all have shortcomings and strengths. So the next time you encounter a bad leader or manager, take a moment to reflect on what you can learn from the situation and channel it towards personal growth to improve your own leadership skills.

Eager to consume the next lessons learned? here you go :)

I ❤️ learning from your experiences, what did your bad leader teach you?



Sivan Hermon
Women in Technology

Leadership Coach, Speaker. ex-Google, Columbia MBA. Love helping humans through leadership, software and knowledge sharing. http://buymeacoffee.com/sivanhermon