Lessons Learned from Great Leaders — Part 2

Sivan Hermon
Women in Technology
6 min readMar 27, 2022


In the previous piece:

I shared 3 great lessons I learned from a great leader, Mark. Here are more lessons I picked up from other great leaders.

If you only take one thing away, let it be this:

Observe effective leaders and your favorite managers and analyze what are the actions that lead to your appreciation.

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Let’s meet Michael:

Michael worked at the same company for over ten years when he became my manager. He rose through the ranks from leading a team of five to running a large 150-person organization. He has a PhD in Computer Science and is an extremely logical human being, almost algorithmic.

My favorite thing about Michael was his ability to combine his high emotional intelligence (EQ) with strong logic skills to parse human behavior and navigate tricky situations. Michael taught me two additional lessons:

Lesson four

(4? first 3 lessons):

Empathy is the key to human beings — people are rational beings to decipher their behavior: assume the best intent and apply empathy. Michael would frequently say: If someone behaves in a way that seems irrational to you, pause to think: “What might they see/know/experience/consider that you are unaware of?”.

This lesson was hard to learn and took time to practice. Hearing Michael repeat this message, “People are rational”, made sense to me. But I just couldn’t understand why some people do what they do. I believed they were rational, but I just couldn’t understand their viewpoint.

On a few rare occasions in our busy work days, Michael and I had the luxury of time to analyze a situation or event I experienced. He coached me by putting myself in others' heads or shoes, adding context I hadn’t considered, and suggesting a few alternatives to what they might be going through. As a result, over time, my empathy skills have grown, and today I can do this on my own and even coach others.

Let me share an example: When John, a peer of Michael's and a person with whom I collaborated on several projects, came to visit our office in NY, we set up a 30-minute meeting with Michael, John, and myself. John visited our site infrequently, and I felt that we had a unique and limited opportunity to discuss a few topics in person. John spent about half of the meeting’s time discussing the stickers on his laptop and his past experience on prior teams. That meant we didn’t get a chance to discuss the work topics. I was furious, I felt he had no respect for our time and labeled him as crazy and a hot mess. Michael offered a very different viewpoint. He suggested that John must have so much on his plate if his head is so scattered. In a million years, I wouldn’t have come up with this evaluation, but I could see how this theory will yield the behavior I’ve witnessed. My instinct would have been to back off from John, frustrated by his lack of respect for my time. Instead, I was able to approach him with a fresh perspective, which allowed us to build a constructive and cooperative relationship despite the occasional odd behavior.

Take action:

Practice combining empathy with logic to challenge your intuition about a situation. Leverage trusted peers to collect alternative viewpoints, present the situation as objectively as you can and shift to listen to how they parse the same interaction. I do this often these days and am frequently surprised by new viewpoints I failed to consider.

This approach is extra helpful to address negative emotions on your end, if you feel mistreated, get others’ viewpoints to know what’s really going on.

I found this to do a good job of showing how to empathize

Lesson five:

Many of a leader’s interactions are a form of negotiation. Michael frequently recommended reading popular negotiation books (“Getting to Yes”) and taking negotiation classes. He specifically and repeatedly shared these practical tips when you are negotiating with what seems like opposing sides:

  1. Start with the areas of agreement. Humans are more prone to collaborate when they find common areas with their peers.
  2. Shift the focus from positions to goals. Instead of talking about positions: “Should we go left or right?”, focus on each side’s goals: “What are you trying to achieve by going left?”. Understanding the goals will give you an opportunity to find common ground and designing win-win solutions (thus expanding the pie).

Take action:

Upgrade your thinking and identify negotiation elements in work interactions. Many cross-team collaborations are a form of negotiation. Test out the above practical tips and invest in building and improving your negotiation skills. For example, in meetings with heated debate, I often take a step back and rephrase the areas of agreement I can identify. That reminds people of their shared views and makes it easier to resolve some other opposing opinions.

Introducing Kate:

Kate was a seasoned software and business leader. Starting as a software engineer in companies like Microsoft and Amazon, she later played key roles (VP and C-level) in a few companies and even started one of her own.

Kate took over as my manager after Michael. By that time, I was comfortable managing managers and was at a more senior stage in my career and organization.

Lesson six:

The best way to scale yourself is through investing in others. As Kate and I started working together, she often said, “Let me know how I can best support you”. I was taken aback, no prior manager spoke like that, and to be honest, it sounded like an empty promise. What does it even mean to support me? What can she do for me?

During the next months, Kate offered great advice on how to deal with a challenging employee, and like Mark, she taught me: how to represent my performance in writing and which influential tactics to use for achieving desired results. As I felt more supported, I occasionally opened up to Kate, venting and sharing negative emotions. Kate’s support not only persisted, but she helped me shift my focus from negative perceptions to productive ways of parsing situations. Her credibility, responsiveness, and actual support made me happier, more driven (with support), and more capable (by teaching) and led to me taking on more and delivering stronger results. As silly as it sounds, she nurtured me. And as a result, I grew bigger and stronger.

Today (many managers later), Kate is still someone I reach out to for advice.

Take action:

Invest in the long game, and nurture your people. The good ones will flourish. Practice shifting from “Here’s what you should do” or “Here’s what you need to do” to asking, “What do you want to do about this?”, “How can I best support you?” and “What do you need to be successful?”. Listen to them and do your best to follow through on that support. Follow up next time you meet — show you mean what you say.

Photo by Vero Manrique on Unsplash

My time with Kate offered even more lessons, I plan to share those.

Turns out you can (and should) also learn from the worst managers/leaders — read all about it here:

What have you picked up from a great leader near you? Hit the comments :)



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