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Entrepreneur Jennine Heller: "Embrace Self-Awareness And Figure Out Who You Are"


"I spend a lot of time asking probing questions. When I was a software engineer, I was really good at testing. I could always sniff out the issues. And in my coaching I rely on the same sense of intuition to identify what's at the heart of a person's challenge. I do a lot of exploring, questioning and I find out where a person may be out of sync with what they say, what they want or how they think they're coming across."

Meet Jennine Heller, entrepreneur, former software engineer and now leadership coach at her own company JHeller Coaching in San Francisco. Jennine enables executives, managers and entrepreneurs to achieve success and fulfillment in their professional lives. RocketHub got a chance to talk with Jennine about her business, work, vision and entrepreneurial goals.

Psychologist vs. business coach
For Jennine the most essential part of coaching business leaders is that the clients need to know that they can be completely open and honest with her. She really wants to get to know the client and understand what makes them tick. Understand them as a whole person, what's working, what's not working and have no expectations or judgment about the clients. "You have to take them as they are. And for high achievers, who are used to succeeding and measuring up and always having to have the right answers, this often is very liberating."

She confirms it entirely depends on the person. Is he or she able to open up to her. "Some people come in ready to go. All they want is to just start getting into what's inside there. Others can be much more guarded. I think of them as a tough nut to crack. It can take a while before they're ready to open up. Some people never do, and that's just the way it goes." It almost seems like Jennine is more of a psychologist than a business coach. A comparison she doesn't draw herself. "A psychologist spends a lot of time figuring out why you are the way you are. A coach is very forward-oriented. All I need to know is your point of view on the world and then we move forward from there." She adds: "I don't think my clients are confusing me for a psychologist. They're looking for a business coach, they're looking for results."

In fact, figuring out what the purpose is for the engagement and determining what clients exactly want to achieve is what coaching is all about for Jennine. "I get every kind of entrepreneur and manager in my office." She worked with first time entrepreneurs trying to put a company together, experienced managers and senior executives of large companies. "Most of my clients are in tech, but not all."

Balance makes it fun
After successfully selling her software company CourseNet Systems, Jennine started JHeller Leadership Coaching in 2012. Being a longtime successful entrepreneur herself, Jennine brings years of business and management experience to her coaching practice to help leaders achieve the success they're capable of.

She founded her company CourseNet Systems in 1993. CourseNet Systems was a software business that developed web-based training tools for higher education institutions and Fortune 500 companies. As COO, she oversaw all operational functions. Including project development, finance, and human resources. In 1999, Jennine led CourseNet to a successful acquisition by Technology Solutions Company. After the sale of her company, Jennine ran operational, management and human resources as Senior Director of Operations at DHAP Digital, a leading digital services provider.

During her career Jennine worked at a number of startups, as well as large technology companies. Including Hewlett-Packard and Digital Equipment Corporation. "You know, when you come from the same environment and background as your clients, there's a sort of instant recognition that you have for each other. My work experience contributes to that sense of familiarity and trust. Even for clients outside of tech, the fast-paced corporate environment is one that we can always connect on."

Being an entrepreneur herself is an essential part for Jennine in her work as a business coach. She's a business coach and entrepreneur at the same time. She says combining both parts of the business is challenging and fun. "On the one hand you're guiding and helping people. On the other hand you're running your own business. It's about finding the right balance. My background initially is very technical. Later I moved into management roles where I spent most of my career. So running a business is something I love to do. Managing my own company is fun and it also gives me something when I'm just at my desk and working. It helps me concentrate on what I'm doing. Then on the other side there's the work with the clients which is completely different. I absolutely love that variety."

Become the leader
Jennine helps entrepreneurs by relying on her own experiences facing challenges her clients come across now. "I also draw on my formal training as a business coach. And at the same time I learn a lot from my clients themselves. Every time I coach somebody, I learn something new. For example they come up with the most creative, amazing things and sometimes that just surprises me. It's like well, they really know themselves and they really know what it is that they need to do to transform their own behaviour."

As a coach, it turns out you always have to be open for opportunities to learn yourself. "One of the basic principles of being a coach is to really stand back and be neutral. You should be completely listening all the time. Not only does it help you in your own understanding of people, but it's a gift you give to your client as well. It allows them to completely explore what they need to do." An example of the most interesting result Jennine booked during her work was a hardware engineer who ended up as president of a company for a number of years. "He was very reluctant to step in as a leader. He kept thinking, 'Maybe I need to hire a different person to come in and be president.' We first started working together two years ago, and now he's a really energetic step-up leader. Believe it or not, even the revenues have doubled in the last year. It's all because he decided to be a leader and he figured out how to do that."

She explains that when you decide you want to be a leader, you can. But what are the tricks to become one? "It depends on who you are, your experience, and what your thoughts are. A lot of this boils down to what people think about themselves. It's interesting. I find a lot of people having what they call 'Impostor syndrome'. Where they think, 'I can't be a leader. It's just me, someone is going to find out that I'm just completely faking it.' She adds: "Figure out who you are and be comfortable with it. Only then you can really begin working from a place of honesty and acceptance of yourself."

"You see it a lot with business leaders. A lot of their self-esteem is wrapped up. The higher you get on the corporate ladder, the smarter all of your peers are and the more you look across at other leaders of companies. You could start to feel like 'this is a club I don't belong to'. 'All those people have their act together and I just got here sort of by some hard work and luck'. The reality is that everybody gets there on their own path. Nobody has it together more than anybody else. If you can really understand what your strengths and weaknesses are, you can successfully work from there. The leaders who have it together are the ones that are most honest about who they are, and thus the most authentic."

Keep on pushing
Jennine emphasizes it's absolutely essential to embrace self-awareness and figure out who you are. "But it's the hardest part." She adds: "I've seen some people who just really enjoy the process and they can't wait to get into it. It depends on who you are, whether you're willing to take that on. I think the hardest part is really committing to changing reactions, attitude and behaviour." She stresses that in her training as well. "The whole point of coaching is that it has to lead up to something. You're paying me. You said you want this change and now you're not doing it. I care enough about you to hold you to what you said you want, and I'm going to push you. It's really easy for people in an uncomfortable position, to kind of go back and say, 'well, I can't', 'there's a reason' or 'it's too hard'. I don't buy any of that. I push them."

As said, Jennine launched JHeller Leadership Coaching to enable executives, managers and entrepreneurs to achieve success and fulfillment in their professional lives. To what extent is she happy herself. Is JHeller Leadership Coaching the company she has always wanted to start? "I feel like I'm finally in the role I was always meant for. I get to draw on my experience and a lot of aspects of what I love to do. I get to help people succeed. It's the most fulfilling work I've ever done. However, I couldn't have done this without all the other stuff. The fact that I had my own startup for seven years really influenced me. A huge part of who I am today, what I'm interested in now and how I connect with people is because of that entrepreneurial learning experience."

Some crucial moments in the past four years of the company determined where Jennine is right now. "There's a phase in your career where you keep moving forward. I got to a point where I felt like I was pretty senior and I was enjoying what I was doing. But it wasn't as fulfilling as it had been in the past. I noticed that the part I really enjoyed was not the projects and the processes we put in place, but watching my clients themselves transform into these great leaders. That's what people call coaching. Once I realized that, I got really serious about coaching. That's what brought me to where I'm right now."

You can get to know Jennine and learn more about her upcoming projects by connecting with her on her RocketHub profile.

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Jennine Heller
Executive Coach @ J Heller Coaching