Stay on Top of Your Work With Cheryl Cran! [PODCAST EPISODE #19]

  • April 25, 2018
  • by Kate Borucka
  • No comments

Another Wednesday, another episode of our podcast! Are you ready for another dose of great tips?

Direct, on point, sense of humor and intuitive insights are just a few of Cheryl’s personality attributes. Her style is ‘let’s get things done – while having some fun’. She is fast, responsive and completely committed to helping others succeed. She is the author of the 6 books including “The Art of Change Leadership – Driving Transformation In a Fast Paced World”, and the best seller “101 Ways to Make Generations X, Y and Zoomers Happy at Work”.

Listen to #19 episode to learn the everything about Millennials, Gen Z’s at work and why we are unstoppable together!

Keynotes of this episode:

  • An evolutionary approach to work and people makes a phenomenal leader.
  • Millennials and Gen Z rule the business world… only with all other generations.
  • All generations are unstoppable together!
  • Everything a leader should not be.

Enjoy and let us know in comments what are your thoughts on today’s episode

Are you an iTunes user? Listen to the podcast here

Podcast Transcript

Kate: Hello, this is Kate, your podcast host and today my guest is Cheryl Cran, an award-winning international consultant, best-selling author and highly sought-after keynote speaker. So if you are looking for tips on how to be a good leader, you are in the right place. 

 Cheryl, thank you so much for joining me here today, I’m so happy!

Cheryl: Thank you for having me.

[00:00:36 – 00:2:09]

Kate: So I’d like to begin with, to tell our audience a few words about yourself and what do you do because I think everyone is different and all my guests have different stories and everyone is inspiring. So tell us something about yourself.

Cheryl: Oh my gosh, that’s a tough question, tell something about yourself. You know, you think that for me as a speaker I would be able to easily do that, right? So I am an author, I have written 6 books, I have a new book coming out this year. I’m a keynote speaker. I’ve been an advocate for understanding why people do what they do and specifically leaders in the workplace. So my background, I came from an insurance and finance, I was a very young leader. I was promoted to my first leadership role at the age of 23 and I had 10 people reporting to me and all of them were older than I was. And I had zero training or experience to be a leader.

But I had some natural abilities, you know, as far as taking charge and handling myself well under pressure. I was in a series of bank robberies when I was in the bank and I took control. I just was able to take control and I didn’t have a lot of trauma with them. It was more like, “okay, let’s do what we can with this situation.” So my background is really being a leader and always seeking to understand why people do what they do, how do we motivate people, how do we engage people? How do we lead in a way that causes us to make a big difference in the world? Those have been my driving sort of passions if you will for the last 20-30 years.

[00:02:10 – 00:04:59]

Kate: That sounds really inspiring. So when we talk about leadership, what are the good skills a leader should have?

Cheryl: Yeah, you know, I think there are… I’ll answer that in two parts. I think there’s a mindset and an approach that a leader has to have for themselves and then I believe there are strategies that a leader can use to have more success with people. So when we look at leadership really you have to lead yourself first. Which means you have to have a really high level of self-awareness, your personality style. What angers you, what pushes your buttons, how you are able to handle yourself well under pressure, your creativity abilities. All of those, you know, the best leaders have a really high level of self-knowing. If I think of leaders, for example, such as Sheryl Sandberg, the COO of Facebook or Richard Branson, the CEO of Virgin or Elon Musk. One thing that they all have in common is they’re very self-aware. They know who they are, they know their strengths, they know what they need to develop themselves. So I think those are like fundamental self-awareness skills that a leader has to have. As far as a strategy to inspire people, I think if you’re a leader that’s integrated those self-awarenesses with then appreciating other people. First of all, if you don’t like people, you can’t be a leader. So anybody listening to this, if you think that people are a pain in the neck or you know, a problem, then you never ever gonna succeed at leadership ’cause you’re always gonna feel like it’s a burden to have other people do things for you. But if you truly are interested in people and understanding people, you will want to find ways to inspire and engage and motivate. And I said earlier in my introduction, I’ve always been fascinated with people, like, even when people are really angry or they’re different than me, I’ve always found it fascinating, like what makes that person be that way? Or, I wonder, what they have gone through in order to be that kind of a person? So as a leader, I think when we can connect one on one and really, really see that person for who they are and for their potential, even if they’re completely different from us, I think that makes a phenomenal leader. And I think a phenomenal leader is always looking to increase their self-growth but also find ways to help other people succeed. And if you’re a leader who helps other people succeed, you will always have people be loyal and inspired by your leadership because it’s not about you, the leader, it’s about as the leader you’re helping other people succeed and grow.

[00:05:00 – 00:07:19]

Kate: So when we talk about working with people, how can a good leader manage a group of people? How to be successful in that because so many people fail at this and I think this is something really important.

Cheryl: They do fail at it, you’re right. I would say the main way to lead is your communication skills. And included in communication skills is your ability to have a really clear vision of where you wanna go as a leader and where you want the team to go. And if you can set that vision and if you can communicate it in a way that’s exciting but also truthful, because a good leader tells the truth, you’re honest. You don’t say, “hey, come with me and it’s all gonna be wonderful in six months!” You basically say, “hey guys we’ve got this big challenge ahead of us, it’s gonna take us six months to get there, here’s what I know we can do, here’s some of the challenges we’re gonna face and here’s how I’m gonna support you as we go through these challenges.” So I think communication skills are foundational.


I think second to that is understanding personalities, the ability to understand who is on your team. Do I have aggressive type people on my team and what do they need in order to just go and do their job? Do I have people that are more sensitive and caring about people? And how do I nurture them in a way that helps them recognize that we do value the people aspect of the team. Do I have people highly creative and they’re looking for ways to do their job in their own way rather than follow the rules or the way I’m telling them to do it? Do I have people who are very analytical? And they want proof before they take action on a task. And so those are questions as a leader that you want to ask yourself as a leader and then you wanna make sure that you’re customizing your approach to each of the people on your team rather than just trying to get everybody to do what you want them to do, which is what I see commonly leaders do and that’s why they fail is a leader just expects everybody to do what they’re telling them to do instead of seeing themselves as part of the team and seeing their role as engaging, motivating, inspiring people on an individual basis that’s really the key in my opinion. So communication and customization I think. I mean, there’s way more to that question but I would say those two things could definitely set a leader up for tremendous success.

[00:07:20 – 00:10:12]

Kate: And how can we make a good workplace where people feel comfortable. Do you think that what you just said applies to that or maybe there’s something more to that?

Cheryl: Well, I think what definitely applies to a good workplace is the openness and the honesty. I see in a lot of organizations and I have been consulting and coaching and working with leaders for many years, is they don’t tell the truth, they kind of sugarcoat the truth, that’s an American term I’m sure you know what I’m saying. So sugarcoat the truth in that they sort of… I had a lot of CEOs who’ll say to me, “oh, you know we don’t need to tell them everything, we just need to tell them ‘this’ so that they’ll go and do what they need to do.” And my response to them is, you wanna tell them as much as you can and as much truth as you can because people know anyway.

You know, people gossip, they are able to understand that something’s going on and so better to just tell the truth rather than try to sugarcoat is as I said. I think as a workplace culture, openness, transparency, encouraging that with everybody else is very important. A lot of my research has shown that in the future of work we’re really heading towards less of a higher archival culture and much more towards shared work or shared leadership culture.

And so the workplace of today’s, specifically with Millennials and Generation Z, they’re not interested in having an autocratic leader, they don’t respond to it, they find it almost comical. Because for one person to hold all the answers, Millennials and Gen Zs are smart enough to know that that’s just not true. Which is why Millennials and Gen Zs are so good at social questioning, asking on Twitter and social media to say “hey, what do you think” and getting a lot of input. I think culture today needs to be like Twitter and Facebook in that we’re asking everybody for their input. That doesn’t mean everybody’s input will be taken but at least if everybody’s voice gets to be heard, then we’re creating a culture of shared information. And there’s more trust. So what happens is, the more that we ask for everybody’s input, the higher the degree of trust.

Again, if you look at organizations, newer organizations, like a Twitter or, Snapchat, or any of these organizations, because they’re built by Millennials, they are already built upon these culture things that I’m sharing with you, they’re open. The workplace, workspace is open. People work remotely, they work from home, they work in other countries. That is the future of work. And so culturally what we need to have is leaders who can share their power and people who can feel like they can speak up and that they can make mistakes and they can fail, knowing that that leads to the company’s innovation and that it leads to the company success and growth.

[00:10:11 – 00:15:33]

Kate: That sounds great because I am also a remote worker and I know how it is. And I’m also a Millennial, kind of so this is just amazing for me. So let’s talk about the future of work. I think that we have to have that evolutionary mindset to think about the future of work. What do you think about that concept?

Cheryl: Well, the evolutionary is a word that I use a lot. In order to get to the future of work, we have to be constantly evolving. And I do feel that, from a generational standpoint, Millennials and Gen Zs have born into that reality. You know, the fast change of technology. Those generations have just recognized that they have to be on the leading edge of what’s happening technologically because that’s part of the culture. I think older generations, and when I say older I mean with all due respect because I’m also in that grouping, I’m a Gen X/Zoomer, you know, a Zoomer is a Baby Boomer who refuses to age. So Gen X, Zoomer, and then even older than that, the traditionalist, which is like in their late 60s and older. I think those generations have adapted well, I mean, when you think of how much change we’ve had in last 10 years, it’s more than we had in the previous 40. So there’s been a lot of rapid change which is driving us to the future of work.

But if you’re not willing to change your mind, and you’re not willing to flex with the realities, you will struggle. And I think that’s what I’m seeing with a lot of organizations where, you know, a lot of Gen X, Zoomers, traditionalists, they know that they need to be changing and a lot of times they push back because they’re focused on what’s worked in the past. And I’m not saying we ignore what the past is because I actually believe the future of work is an integration of the success of the past with looking towards the future. I also believe that everybody needs to be a futurist, which mean they have to be looking at the future and they have to be looking at how do I upgrade my skills? How do I upskill? How do I reskill? So you’ve heard a lot about robotics and AI, and all those things that are happening, a lot of people get scared and think: oh, robots are gonna take my job.” I’ve actually found research that says that’s actually not true, there’s gonna be new jobs created.

So the new question needs to be, “how do I reskill and upskill so that I’m future ready?” And I think that’s where most people get challenged, is they’re so busy dealing with today and putting out fires and worried about today versus looking at what can we do to prepare ourselves for the future, which means let’s prepare every single leader with the future of work skills so that rather be the reactionary, we’re actually ready for these changes. Rather than be afraid of these Millennials and Gen Z’s that are going to be running companies and taking over, how do I think more like a Millennial or a Gen Z so that I understand where they’re coming from and I can work well with them.

Because also research has shown that, in addition to remote working which you and I mentioned earlier, more and more Millennials and Gen Z’s are going to be entrepreneurs. The Gen X’s, the Zoomers will be working for those companies or working with them as a contractor. So in order to successfully work with Millennials or Gen Z, you’ve got to be inspiring, flexible, open-minded, willing to work as a team. And I think that’s the opportunity in an evolutionary way is for us to look at our skills, again it comes back to self-awareness. If you look at our skills and go “okay, where are my opportunities to really shift?” And I can actually make an example of myself. I am quite flexible, I consider myself more a Millennial, you know, when I look at the generations because I’ve been an entrepreneur for 20 years, I’ve been on a leading edge of technology because I’ve had to in order to keep my business alive and thriving. So I feel like I’m very in touch with the Millennials and the Gen Z’s. On a personal level, I have a Millennial daughter, I’ve got two Millennials stepsons and I have Gen Z granddaughter.

So in my personal life I’ve got these people around me and I really recognize that I can either be negative about…you know, and a lot of people say, “oh, you know, Millenials, they just wanna do it their way and they only wanna work 4 hours, they wanna work from home” and all these things. And my answer to that is, well yeah, they’re actually onto something because that’s what we all want. And so they’re actually leading the future in my opinion. Millennials and Gen Z’s are revolutionary. They’re saying “there’s better ways to work so that we can have a life and work fits in with our life.” So from an evolutionary standpoint, I think the opportunity is for all of us. And, by the way, I’m not saying Millennials have it figured out, I actually believe Millennials and Gen Z’s have a lot of work to do around grounding the ideals they have with practical application. And Millennials have to really understand what Zoomers and Gen X’s had to do in order to get to their success. And really work with them as partners and respect that time and effort and I think together we’re unstoppable.

I mean if you think of all the skills and talents that we each bring, from a personality level and a skill level but also from a generational level, we’re unstoppable together.

So the future is about all of us really honoring each other and respecting the skills and coming together and saying, “okay, let’s build a future that’s great for all of us.” I get really excited about it to be honest.

[00:15:34 – 00:18:49]

Kate: Because it sounds exciting. So when you’re talking about, what I am thinking about is how to make a positive change, a positive impact also as a leader? Do you think there is a certain way to do it?

Cheryl: Well, I think of a positive impact in my experience, I think of the leaders who had made a positive impact on me, the qualities they had were they were tough, yet inspiring because they helped me to a high standard. And they were truthful, so they would honestly tell me, “Cheryl you’re good at this but you need to work on this, this, this, and this.” So the best leaders are coached and they’re able to… I’ll tell you, my worst leader, his name was Hall, and it should have been Hell because we was such an arrogant, overbearing, he thought he knew everything. He was sexist, he thought all women were useless, he was just the worst leader you could possibly have.

But you know what? I very much was happy to have him as a leader because he actually showed me what not to do as a leader. He was everything that a bad leader is. He thought he knew everything, he was condescending, he didn’t ask for anybody’s input, he was rude, he was biased. All those things that make a lousy leader. But right after working with Hall I went to work with a leader named Ron, and the first thing Ron said to me is, “my goal for you Cheryl is to one day far surpass me in your career.” And when he said that to me, first of all, I had been in banking as a woman, young woman. And I’d never had a male leader say to me, “my goals for you is to one day be better than me.” And that was so inspiring because I actually worked really hard for him because he saw my potential, and so what he modeled for me, he was a revolutionary leader before that was even such a thing, which is over 10 years ago.

And what he modeled for me was, he had so much self-confidence and he was so sure of his own abilities that he wasn’t threatened by anybody else’s talent or ambition or ability. And to me that’s a phenomenal leader is a leader who they build so much strength and confidence that all they wanna do is help other people succeed. And the best leaders, they’re not worried about losing people, they actually wanna help people go on to be their best version of themselves. And so I feel like a phenomenal leader that I’ve worked for has done that. For me as a leader that is always my goal. Whether I’m working with the CEO or I’m coaching or consulting or I’m speaking in front of the group, my goal is to say, “look, you’re already smart, you already know what needs to be done, let me give you a few resources, tools, ideas, and support, and let me help you sore so that you can go and be the best you that you could be.” And to me, that’s what we’re lacking in leadership today. I feel like there’s only a certain percentage of leaders who really model that, who really model the desire to help other people grow. And, wow, if more organizations had leaders like this, we would see a transformation, honestly, we would because we would have more people eager to make a change through their work versus just see it as a job.

[00:18:50 – 00:20:15]

Kate: That sounds really inspiring and when we talk about inspiration, I’d like to change the topic to your books. Can you tell us a little bit more about your books? And your latest book which you mentioned?

Cheryl: Yeah, so I’ve written six books. My best selling books are the ones.. the first one was “101 Ways to Make Generations X, Y and Zoomers Happy at Work.” That has been a bestseller, that was published in 2010 and it’s still very, very popular. And the book that I wrote in 2015 is called “The Art of Change Leadership: Driving Transformation in a Fast-Paced World.” That book too has been a bestseller and all of my books are available on Amazon and where booksellers offer books. My most recent book that I’ll be publishing this year in the fall is in alignment with the brand that I’ve launched in March 2018 and it’s called “Next Mapping: The Best Way to Create Your Future Is to Map It” And it’s all about what we’ve talked about today. About being a leader who creates an inspiring feature. And in that book, I talk about the impact of robotics and AI and technology and how it’s forcing us as leaders to be more human than we’ve ever been before. And that means increasing our ability to connect, communicate, collaborate, lead in a way that has us working together collectively to create a better future.

[00:20:16 – 00:23:19]

Kate: That sounds good and I’m definitely going to read that book. So can you tell us what inspires you in your work?

Cheryl: Honestly, the people that I work with. Just before I answer that to you, I think, you know a lot of times people ask “are leaders born or made?” And I think it’s a combination. I think there’s some people that have, that come up with naturally innate leadership ability. And then I think also that leadership can be learned with a true desire to want to be a great leader. And for me, I have had an opportunity in my life, I’ve had a very difficult childhood in life and I can either look at that as a victim and say these circumstances made my life horrible or I can use them to leverage my leadership and that’s what I’ve chosen to do is look at my life as an opportunity to help inspire other people.

So truly what inspires me is other evolutionary so people like Peter Diamandis with Singularity University. He is a future-focused let’s change the world mind and I get inspired by people like that. Faith Popcorn is also a futurist. Sheryl Sandberg and her book “Lean In” and her newest book. I read a lot of autobiography and memoirs because I feel like other people’s lives are inspiring and help me sort of compare my life and say, “am I living my best life compared to these really amazing people?” Not in a comparison as in, am I wanting to be like them but more of an inspiring, how can I maybe learn of or two tricks from them in order to live my life in a more inspiring way.

I’m inspired by my husband who’s also my business partner. He’s been with me for years. There’s no way that I could be doing what I’m doing in my life without his support and his energy. My family inspires me, my daughter is an amazing young lady, an amazing mom. And then my clients, you know, whenever I work with a new client, I always am in awe of their desire to be better and that inspires me because I wanna work with people who are seeking to be better, to be more, to contribute more to the world. So, as long as I focus on those things, I’m constantly inspired.

If I get into a place where I feel frustrated or I feel like people aren’t changing fast enough, then I can get a little bit negative. But because my work is about changing the world, my work has always been inspiring which is, you know, often times I tell people I’m never retiring because I really do love what I do. And you know, when you love what you do, it’s a calling, it’s a passion. It’s not something that you have to wake up and do it, something that you feel you must do. And I really feel very privileged that that’s what my work is for me.


Kate: So I have one last question to you.  The podcast’s title is “Stay on Top of You Work,” how do you stay on top of your work?

Cheryl: Ah, the productivity question! You know, I think as a leader, in addition to what you’ve asked me, I think the most inspiring leaders actually lead by example. So I think you do really have to be focused and because I’m an entrepreneur and I’ve a very busy life and because I want my personal life to have as much value as my work life, I’m extremely focused. I plan out my week, I know what I have to accomplish by the end of the week, I believe you have to honor your commitments, so when I tell you I’m gonna do something, I do it and I follow through. So I stay on top of my work, I also have an office manager, Michelle, who I know you’ve connected with for this interview and she’s phenomenal! I mean, Michelle makes sure that my schedule is that I know what is happening and that I know what I’m doing. She keeps me very much on track and for years I worked with audit office manager and I would just tell you that that was just pure stubborn pride on my part because I felt like I could do it all and stay on top of it but since having an office manager which I’ve had for the last 10 years, it has completely transformed my business as an entrepreneur. It allows me to focus on the things that I’m good at versus trying to manage the administrative, you know, all those details side. Michelle’s very good at that. I’m also very, I use a lot of the technology tools so, we use shared collaboration tools like Google Doc, Time Calendar and salesforce and all sorts of technologies that allow me and my team to be on the same page at the same time. I think that’s crucial, like without that, you’re sort of guessing what everybody’s doing. But that shared collaboration tools have worked really well for my company. The times when I’m not on the top of my work is when I don’t put it into my calendar, or I… I also use my iPhone a lot like my iPhone 10, I use Hey Siri put this in my calendar or do this… So I’m using the technology to leverage my time and I’ve become very good at, for example, writing. I can write very focused and very tightly now because I’ve written a number of books and I’ve gotten sort of the process down. As far as my clients, preparing for keynotes and speeches, again, Michelle schedules all of that but I’m able to then show up and make sure that I get the most out of my client. As far as the travel and the speaking, that requires a tremendous amount of stamina and I have all sorts of mind things I do. I meditate daily, I visualize, I do a lot of things to keep my personal self very resourced and productive. So I exercise regularly, I do all sorts of bodywork, things like network chiropractic, acupuncture. So I think it’s important to have, in order to really contribute as a leader I think the self-care is really, really important. If you don’t take care of yourself, you’re gonna burn out. And by the way, in the past I had burnout and so it’s a tough lesson to learn because if you’re not on top of your things, and a lot of times people feel stressed by being on top of. For me, as long as I take care of myself, if I’m exercising, if I’m doing all those self-care things, then it’s fairly easy for me to stay in the flow and stay on top of my work.

Kate: That sounds really good. Thank you, Cheryl, for the interview, it was my pleasure to talk to you, it was really inspiring.

Cheryl: Thank you.

Kate: And if you guys want to know more, make sure to check out the information about Cheryl under this podcast. And don’t forget to let me know in comments what would you like me to talk about with my guests. Stay tuned for the next episode and I see you next time, bye-bye!

Thanks for listening!

Connect with Cheryl

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Kate Borucka

Kate is a freelance translator, copywriter, and a content writer specializing in time tracking software, time management, and productivity. When not researching new software, she's reading books, or spending time outdoors.

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