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Chessa Eskandanian-Yee: “Build for your consumer, don’t just assume what they want”

Build for your consumer, don’t just assume what they want. There’s the idea, and then there’s the execution. Get the basics done, and then start asking questions about what people want to see in your product. You might not end up taking their advice, but that outside perspective helps immensely in fleshing out your ideas As […]


Build for your consumer, don’t just assume what they want. There’s the idea, and then there’s the execution. Get the basics done, and then start asking questions about what people want to see in your product. You might not end up taking their advice, but that outside perspective helps immensely in fleshing out your ideas


As a part of our series about strong female leaders, I had the pleasure of interviewing Chessa Eskandanian-Yee. Chessa is the CEO of LeaderEQ. LeaderEQ is Artificial Intelligence-Based Executive Coaching led by Mother-Daughter Duo Chessa Eskandanian-Yee and Katherine Eskandanian-Yee. Leader EQ aims to inspire constant improvement for business leaders and their organizations.


Thank you so much for joining us Chessa! Can you tell us a bit about your “backstory”? What led you to this particular career path?

My co-founder (and mother) is a serial entrepreneur and I grew up watching her create her last venture, which was a recruiting agency, Agency360. I remember being 7 or 8 in the backseat of the car going to school and reciting her prep calls to her candidates and clients and coaching them through the entire process. When I was in college I finally realized, why isn’t coaching like this accessible to all companies, no matter their size? And so, LeaderEQ was born a few months later.

Can you share the most interesting story that happened to you since you began leading your company?

The most interesting story is probably how I have become a coach in the process of starting this company whose main goal was to simply connect leaders with the right coaches. I have found myself utilizing the wisdom and skills that my coach has taught me, and coaching my employees and clients in the same way. I think the beauty of the coaching industry is that it’s really just about uplifting the people around you.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

The funniest mistake I made early on was in an email communication that I thought was with my co-founder with a funny picture, but I had really sent it to a coach with no context. I learned to ALWAYS check the sender before sending an email!

Ok, thank you for that. Let’s now jump to the primary focus of our interview. What is it about the position of CEO or executive that most attracted you to it?

I don’t think it was necessarily the position that attracted me to the role, but more of having this dream and idea and bringing it to life. What I love about what I do is meeting all of the incredible people I get to meet every day and learning so much from everyone around me. It’s a truly humbling process.

Most of our readers — in fact, most people — think they have a pretty good idea of what a CEO or executive does. But in just a few words can you explain what an executive does that is different from the responsibilities of the other leaders?

It’s a lot of juggling and becoming well-versed in almost every aspect of your business. From juggling the present goals and then turning them into actionable items in order to obtain your future ambitions. There’s the dream of what you want your company to be, and the job of a CEO is finding out and creating a plan to make it that reality.

What is the one thing that you enjoy most about being an executive?

I have so many different interests that being an executive lets me jump into every aspect of my business and exercise all parts of my brain. From marketing to product development to sales, I get to learn and grow every part of myself every day.

What are the downsides of being an executive?

I wouldn’t say there are downsides to being an executive. It’s a lot of stress management and finding balance. Other than that, I don’t see much of a downside.

What are the “myths” that you would like to dispel about being a CEO. Can you explain what you mean?

I think the biggest myth is that CEO’s have all of the answers. At least speaking for myself, I don’t have all of the answers, but I’m willing to explore and take risks on what I think is right, and then also listen to my team and brainstorm ways to approach problems. It’s not about knowing all of the answers, but knowing how to find the answers.

In your opinion, what are the biggest challenges faced by women executives that aren’t typically faced by their male counterparts?

I think it’s just primarily all of these assumptions that society has accepted to be true about women executives such as having a family or personal life and not being able to have both. Plenty of male executives have both and that isn’t a barrier to entry, but for female executives it is. Really, it’s the myths that are put out there. A person’s ability to lead should never be judged by their gender identity, but by their capabilities, and that is different from person to person.

What is the most striking difference between your actual job and how you thought the job would be?

I think I thought the job would be a lot more stressful than it is, but it’s really the mindset that I have that has changed my perception of it. Instead of placing mental barriers on myself, I take every opportunity and learn from it. Stressing about the uncontrollable never helps a situation, so I have learned how to switch my mindset to be more proactive over the things I can control, and worry less about what is out of my hands.

Certainly, not everyone is cut out to be an executive. In your opinion, which specific traits increase the likelihood that a person will be a successful executive and what type of person should avoid aspiring to be an executive?

I don’t think a certain kind of person is born to be an executive, but a key trait of successful executives is high emotional intelligence. If someone is self-aware or is willing to work to become self-aware, they will succeed at being an executive.

What advice would you give to other women leaders to help their team to thrive?

I would say just stop worrying about what other people think and be authentic in the way you lead. Follow your gut and what you have learned, and be willing to fail. People respond incredibly well to authentic leadership, and in return, they, too, will be authentic and thrive.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

My mother and co-founder, Katherine. I don’t know what I would do without her. She has been my sounding board and coach since I was a kid, and my success is truly because of her. She always told me to follow my heart and do what I’m passionate about, and I’m so lucky that I get to do it with her every day. There’s also my best friend who has taught everything there is to know about empathy. She makes me believe that if this world has a little more empathy in it, we would all feel more safe and therefore have the freedom to fail and learn.

How have you used your success to make the world a better place?

Bringing emotional intelligence into the workplace also helps us all bring it outside of the workplace. Overall, I hope LeaderEQ is helping people be happier in both their professional and personal lives. Human connection is the most important aspect of life, and I hope we are helping leaders find more purpose in their every day lives.

What are your “5 Things I Wish Someone Told Me Before I Started” and why? (Please share a story or example for each. This answer will likely be a little longer than the rest.)

  1. You don’t need to know all of the answers. I was terrified of running a company because I had no idea what I was doing, but I had this dream, and a plan to make it a reality. The first step is just starting it, and not giving in to the fears of what can go wrong.
  2. You will fail. A lot. There are going to be countless number of wrong hires, bad decisions and mistakes along the way. But that’s how you learn. I took every mistake so personally at the beginning, as if I were a failure overall because of it, but in reality I learned SO much from these mistakes.
  3. Hire slow, fire fast. One of my advisors taught me this one, and it was the best advice I have ever received — just maybe a year too late. We had hired someone that was just not producing at the rate we needed them to in a fast-paced environment, and month after month and countless hours of coaching later, nothing changed. The second I received this advice, it became clear that what we needed to do to succeed was not to keep putting energy into a partnership that would never work. Recognize a mistake early on, and it will hurt everyone less if you correct it immediately.
  4. Listen. As an executive, you get so many things thrown at you that you get lost in the day to day of things and the voices around you start to become blurred. The key is to listen to your advisors, customers and employees. There is so much wisdom in everything they have to say.
  5. Build for your consumer, don’t just assume what they want. There’s the idea, and then there’s the execution. Get the basics done, and then start asking questions about what people want to see in your product. You might not end up taking their advice, but that outside perspective helps immensely in fleshing out your ideas

You are a person of great influence. If you could inspire a movement that would bring the most amount of good for the greatest number of people, what would that be? You never know what your idea can trigger.

The movement of empathy and to see life through another person’s eyes. If we all would become more empathetic and less self-involved, there is so much good that will be done from just harnessing that one quality.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

“Your scared space is where you can find yourself over and over again” — Joseph Campbell

I used to always be afraid of what scared me. So, I would avoid it. However, I soon realized that the things that scared me were the things that could bring me the most joy. This is what I have to remind myself of every day, whether it be with my company or in my personal life, when I am entering uncharted territory. I have a ton of fears myself. And anytime I give into them, I embody the “what if” feeling. On the other hand, if I acknowledge that the fear is present and I go through with it, I am free to fail. Failure isn’t going to be the reason that I don’t do something. The worst thing to happen is I fail, but at least I know that I tried. Most of the time, the fear is attached to the feeling that somebody will not accept me and I become afraid of rejection. When we give into our fears, we put walls and boundaries up for ourselves as we’re afraid of failing. But there is so much gratitude in trying something and failing instead of not following it and not knowing the answer.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them

Ryan Serhant. I completely admire his state of mind and how he is willing to harness any weakness to turn it into a strength. He’s an incredible business person, salesperson, and to be able to acquire some of that wisdom would be amazing.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

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