Wonder Women: Cy Wakeman, leadership expert

Wonder Women: Cy Wakeman, leadership expert

By Jill Vitiello

Cy Wakeman
Cy Wakeman, New York Times bestselling author, keynote speaker and global thought leader

Wonder Women is a blog series that lets me introduce you to amazing businesswomen doing remarkable work. Meet Cy Wakeman, founder and president of Reality-Based Leadership, a company that trains organizations to “ditch the drama” and restore sanity to the workplace.

Nadine Green, Chief Operating Officer of VTLO, introduced me to Cy Wakeman’s work after she heard the dynamic keynoter at the 2017 Work Human conference. Both Nadine and I attended Cy’s meet and greet event following her speech at this year’s Work Human conference. Cy welcomed us with her characteristic warm smile, twinkling eyes and big hug. We caught up with Cy again after the VTLO team interviewed her for our podcast on change readiness. We continued the conversation to ask Cy about women and leadership.

Q: Is women’s leadership still a relevant issue – or has it passed its prime?

A: That is a big question! From my perspective, anytime we divide people into groups it leads to judgment and story. I believe that any leadership philosophy that leaves a group of talent behind or has to have a remedial class based on a whole gender is broken from the start. Women aren’t broken – traditional leadership philosophy is broken. We need to call for a modern philosophy for leadership that goes beyond ego and judgment. Some women are more natural at no-ego leadership, which is about operating from a higher level of consciousness.

Most leadership programs leave people in lower states of consciousness and then try to lead them. If you’re a female going up against an ego, because of our system and world, you’re already one down. If you are a male going up against an ego, you’re maybe going to hold your own, but not get results. So, we believe in modern leadership where you call people to a higher level of consciousness first and have them evolve and you meet them as an evolved person and then together you create great stuff. So, I would go beyond women’s leadership and just say why don’t we get into some evolved leadership? There is room for everybody to participate.

Q: What do you think is the most exciting challenge that you have in front of you today?

A: For me the most exciting challenge I have is making sure that the personal brands I have and the things I’ve developed turn into a legacy that sustain a knowledge base beyond me, the personality. In the past, I listened to the experts who advised building the brand of the business so that my teammates could continue that work 100 years into the future. But, I found out that in order to truly make that happen, I have to take a very counterintuitive approach. Today, I am building up my personal brand rather than the business brand so that I can lend all my credibility to the business. My biggest challenge is ensuring the work I’ve created, which people find helpful and valuable, is easily consumable and lives on beyond me.

Q: Think back to when you got started in your career. Who supported you at the beginning, and who has sustained your growth throughout?

A: People have come into my life at just the right time at different times. The people that have supported me throughout, and it sounds cliché, have been my sons. They’ve grown up with a mom that’s traveled; I ended up being a single mom. They were able to support me because they saw my integrity and passion around what I did so they never really felt slighted that they were missing out. I have a couple of friends who have supported me from day one. I learned over time that the universe always was supportive; it’s whether or not I said “yes” to what was in front of me.

No Ego by Cy WakemanQ: What is the one piece of advice you give to ambitious women?

A: Don’t confuse ambition and confidence with ego. Ambition and confidence is, “I’m convinced I have something of value to bring to the table.” Ego is, “I am the way; I know.” Once you get ambitious and confident, you have to be careful not to believe everything you think. That’s when your ambition takes hostages, imposing your will on others, leaving you thinking the only way to succeed is hustle and hard work and winning. I’ve found when you work on your own evolution the work is actually pretty effortless. A lot of ambitious women work on trying to change reality. I would say if you are ambitious, work on changing yourself and your view of the world.

Q: In terms of communication, what can we do, in alignment with your philosophy on leadership, to help people be the best communicators that they can be?

A: Good communication comes from silence. I’ve been fascinated with Japanese brush painting for a long time. I went to a brush painting class and we didn’t even get brushes or paint at first. The first two hours we got a cup and we were told to see the cup and figure out, with just one line, how to paint the cup with the fewest amount of lines possible. Then we got a brush and were given one minute to capture the cup with that one line. It is all about getting contemplative enough to boil the message down to the essence of the message.  The essence will live on after the noise dies down.  Don’t add to the noise, add to clarity.

I think if you’re not self-reflecting, you can’t capture what you want to say. But if you are self-reflecting in silence you can really boil it down — not thinking, but self-reflecting, which is different. Thinking is: “How can I say something to change the behavior and manipulate others?” That’s advertising; selling. Communicating is: “How can I boil something down to its essence and instead of elaborating on it just repeat it.” This invites others to self-reflect on the simple message and make it their own.  A lot of people want to take something and elaborate on it. Great leaders know they’re leading when they’re super tired of saying the same thing over again. When I communicate something, I don’t want to explain it to you because that takes your experience away. Instead, I want you to self reflect on it and find meaning in it. We want to listen to how people express the idea you’ve shared; to hear them echo it back in a way that is usable to them.

Q: What can women do to boost each other in business and generally in life?

A: Provide space for others’ self-reflection. Don’t feed into the ego of another by collusion. My mother always loved the song “Amazing Grace,” and one day, I asked her why. She said if you surround yourself with enough amazing women, and your life will be graced.  Amen to that!

Do you have a question for Cy or me about how to communicate with confidence? Ask it here in our comments, or reach us on Twitter: @CyWakeman; @JillVitiello.

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