The Community Company with Ryan Paugh and Unleashing The Entrepreneur with Debbie Wooldridge

It’s not just entrepreneurs who struggle with making connections, but any ambitious professional. Ryan Paugh created the Community Company to help these professionals make connections in whatever industry they are in. He believes that there are communities around us in different ways and you can leverage those communities with the kind of value you offer to the people involved in them. Company managers need to be open to the idea of unleashing the entrepreneur in every member of the organization. By doing this, Debbie Wooldridge they can attract millennials to come work for them and stay working for them. The idea of providing a google-type work environment to pull them in isn’t true. What you should do is focus on professional development opportunities that will help you help them mature and grow in the organization.

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We’ve got Ryan Paugh and Debbie Wooldridge here. These are two of the top experts on millennials aka Gen-Y, and they’re going to share their knowledge. You’ve probably heard of Ryan Paugh. He has led so many companies and he is a cult legend in the online community-building world by Mashable, at least for being an expert in this area and so is Debbie Wooldridge. She has written books and has been scheduled as far as creating all kinds of content for MentorBox. Between the two of them, we’re going to find out everything you need to know about millennials in the workplace.

Listen to the podcast here

The Community Company with Ryan Paugh

I am here with Ryan Paugh who first Co-Founded Brazen Careerist, a career management site for high‑achieving young professionals and ambitious college students. He then Co-Founded Young Entrepreneur Council (YEC) in 2010 with Scott Gerber, an invite-only organization for top entrepreneurs, 40 and under, that Entrepreneur noted, “has quickly become one of the most elite organizations of its kind.” Ryan and his team are building on their vision of the future of professional organizations with The Community Company, a company poised to launch dozens of vetted communities engineered to help ambitious professionals grow their network and expand business opportunities. Called a cult legend in the online community-building world by Mashable, Ryan is focused on creating a strong membership experience and positive business outcomes for thousands of successful executives, thought leaders, business owners, and entrepreneurs across the country. It’s so nice to have you here, Ryan.

Thanks for having me. This is going to be fun.

You’ve been busy. That’s a lot.

It overwhelms me a little bit but it’s awesome.

I got to list it all because this is awesome and fascinating. I want to start at the beginning because I want to know what led to your interest in doing all this. Give me a little background before you started the first company.

I’m 34. I became an entrepreneur right out of college. I’ve always been a community builder at heart. Going through my teen years and then to college, I’ve always been the kind of person who was curating and convening the people around me to do fun stuff, to collaborate and have fun, and create more joy in our lives together. When I graduated college, I got my first job, a typical Corporate America style gig and I didn’t like it. I felt very unfulfilled and I wanted to do something about that. I ended up reconnecting with my freshman year roommate also named Ryan, and we both felt that we were in this position where we weren’t very happy with our jobs. We started reading online about other Gen-Y-ers who were having similar frustrations about the workforce and we’re reading from the Boomer and X-er perspective, the people who were managing us at the time, about how annoyed they were at us, too. We said, “This is an interesting phenomenon.” It was our first dive into blogging and social media. We thought that we could be the voice for Gen-Y speaking up from our perspective as to why the workforce wasn’t set up for what we wanted to achieve from our professional lives. We started a blog called Employee Evolution, which was a sounding board to connect with other people like us, not just Gen-Y-ers who are going through similar frustrations, but also X-ers and Boomers that wanted to better understand us and wanted to bridge that generation gap so we could come together and be a more effective workforce.

Through that experience we met our Co-Founder in Brazen Careerist, which is now called Brazen Technologies, Penelope Trunk and started a community to help bring the generations together and to talk about some of these workforce issues. That community is still alive in a sense. It has pivoted into a service play, which helps young professionals going into the workforce connect through online speed networking types of conversations with hiring managers and recruiters. We also do a lot of cool other styles of AB connections. We’ve done white label products for universities and colleges that are helping bridge the gap between students at universities and their alumni that want to help them as they enter the workforce. Any creative AB type of situation that you can think of is a great community platform to get people talking. When we became more of a software company though, the thing that I am great at doing every day, the community creation and curation piece went away and I started looking for new opportunities.

I did what any community-minded person would do. I went out and started talking to my network about things that I was looking for. One of my long-time friends that I had met and built a relationship with through my days at Brazen connected me with Scott, my partner in YEC. We started building a new community from the ground up to help entrepreneurs make their daily lives and everything that they’re going through. Through that experience, we learned that it wasn’t just entrepreneurs that are lonely and that have a problem with making connections, it’s any ambitious professionals. That’s what led to us expanding the business into The Community Company and starting to build over a dozen now of professional communities to help ambitious professionals connect in whatever industry that they’re in. That brings you up to speed.

What is The Community Company? Explain what that looks like to people.

What’s important for people to recognize, especially today, is that we all have a community whether we know it or not. It can be something structured like YEC, a very traditional professional community of entrepreneurs or it can be something amorphous, like your customer base, the fans of your product, your employees. There’s community around us in many different ways. How effective those communities are depends on how successfully you leverage the value that they can bring to your lives and the value that you can bring to theirs. We build a community as service programs to help all of these different types of community become more engaging, to help them be higher-retaining and to help them increase the lifetime value of everyone who’s involved in those communities. That can look like a more human touch service-based program with our internal team who are expert community builders and that could also include technology that we’ve built, systems, processes, and platforms that help people take their amorphous sense of community and turn it into something more tangible for the people involved.

We also do a lot of contributor network programs, so we work with brands that have content strategy, but it’s not quite as powerful as it could be. We turn their community as the curator of the content, which makes that content much more powerful and also creates a stronger sense of cohesion between people in the community and the brand that they’re associated with if that makes sense.

I’m curious what you thought of being called a cult legend when you read that.

I try to be as humble as I can. I’m definitely not the kind of guy who likes to be on center stage. For someone who wrote a book called Superconnector, you’d be surprised to know that I’m incredibly introverted and I don’t like being the center of attention. That being said, I think that introverts are much more set up for success to be superconnectors than some extroverts, but it was nice, I’m not going to lie. It certainly is nice for someone to look at your work and think that it’s legendary to be a colt legend, but it’s not something I went out seeking or looking for. What’s important to note there is today more than ever, it’s so difficult to decipher who is legitimate and great at what they do or who is just a huckster presenting themselves online as something that they’re not. I don’t go looking for those definitions and other people shouldn’t either. They need to be true to themselves and be themselves and others will label you and create that opportunity for you to be “legendary.”

You mentioned your book and I want to talk about that because you co-wrote it with Scott Gerber. You had worked with him and you’re a Co-Founder at the Young Entrepreneur Council. Your book is called Superconnector: Stop Networking and Start Building Business Relationships that Matter. It came out this year. Tell me a little bit about this book. What is different about this? Give me a little background on that.

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Superconnector: Stop Networking and Start Building Business Relationships that Matter

Scott and I have spent ten-plus years together and building community and I’ve spent many years prior to that through Brazen doing community work. One of the things that I’ve seen is a lot of great people who want to build strong communities using terrible networking practices that don’t work and don’t get the jobs job done and actually make them seem like transactional used-car salesmen. More than ever in the social media era, it’s important to develop techniques for yourself and develop strategies that help you do real human connection.

Social media has been a blessing and a curse in a lot of ways. It’s a blessing because we’re connected more than ever before. Case in point is through writing the book. I’ve done podcast interviews with people all around the world who I never would have connected with and it’s been amazing. However, it’s been a curse because most people have developed a more quantity over quality mentality to building connections. We’re more concerned with vanity metrics like the amount of followers or likes or re-tweets we have and less concerned about the actual quality of those connections. If you look at some of the most successful people in the world, they’re more concerned with a very small, close-knit group of individuals, their inner circle, their spheres of influence than the masses. If you look at any successful business person, you would find that they have a close inner circle of relationships that have been a part of their success over the years and it has nothing to do with a massive amount of quantity in terms of followers and people that like their content online. That’s not what it’s all about. It’s about building real human connections with a very curated group of people that over time are going to help you be more successful and you’re going to help them in return.

That would be a good example of what you would say is a terrible networking practice to reach out to so many people and have no real depth to it. Would you have any other examples of what you gave as terrible networking practices?

One of the things we talk about in the book that I like is the importance of asking great questions so you get to know people. One of the questions that you’d be surprised that I don’t like, in fact I’ve banned people on our community team at The Community Company from using it, is the question, “How can I help you?” The question “How can I help you?” is a terrible question because most people that you’re getting to know and you’re talking to aren’t prepared to answer that question in a meaningful way. They might not know you well enough to know how you could help and you get surface-level stuff that doesn’t help you make connections for them. If you’re a great connector, you ask questions that allow you to collect a lot of meaningful information and then you’re responsible for doing the work to help figure out how you can help that person.

A good example of a question that you should ask instead of “How can I help you?” would be, “What’s something that you’re working on that you’re excited about?” If you’re talking to the right people, passionate, driven human beings, they’re going to have something that they could talk to you about for hours and you’re going to be able to collect so much more meaningful information with depth that you can then collect and put the pieces together, connect the dots. If you’re a great connector, you will enjoy that part more than anything else.

Think about the questions you’re asking and make sure that they are questions that put you in the driver’s seat of collecting valuable information so then you can figure out the best way that you can help someone. The other thing to recognize is that a lot of people don’t even know what they need help with. They’re not thinking about that or they’re thinking that they need something that they actually don’t. Putting yourself in the driver’s seat is the best thing that you could possibly do as a connector to make sure that you are in a position to help other people in the most meaningful way possible.

I’ve worked in sales for decades and the mistakes salespeople make is they sell at people without even knowing what their pain points are. You’re bringing in all the questioning that is important. Introverts are good at listening and I am not surprised that this fits right into your introverted personality, which we’re seeing a lot more value in sales. When I was in sales in the ‘80s, you were supposed to be an extrovert, that would be the only salespeople you’d want. But that’s changed with your generation and with books from Susan Kayne and about quiet and different introverted abilities. Did you read that book?

I did. I love Susan. She is someone we interviewed and featured in the book when we talked about introverts and her work is phenomenal. It empowers introverts to understand that they have a lot of powerful qualities that can help them succeed in any role. Salespeople have always been this extroverted thing, but some of my favorite salespeople, on our team even, are more the type of people that sit back and listen and they let the potential customers do the talking and it’s amazing how well they convert because they know more information about them to tell a story about the benefits of all of our products and services that they would need to know versus regurgitating the same old script and hoping people buy. I find the same thing to be true when I’m in a crowded room full of people. I get a lot of value out of sitting back and listening and asking good questions, and later on I’m able to create more meaningful connections because I know more about the people that I was talking to. Introverts are in a position now where they have a leg up in a lot of ways because they know when to shut up and they know when to be more thoughtful and listen and find opportunities versus having to be the one on the megaphone all the time.

I interviewed Ken Fisher, who’s the billionaire genius behind Fisher Investments and he is a huge introvert. He said that Susan Kayne’s book impacted him. What’s interesting about the dynamics of introverts and extroverts, since I’m a Myers-Briggs qualified instructor, is that there’re so many people that are on the border, in the middle between the two. That’s a helpful quality, but for people who are extreme one way or the other, teams have changed so much. In the past, when I was in sales, I was it. There was no team, it was, “Here’s a phone book, dial for dollars,” or “Here’s your territory, drive for dollars.” There was no one else. If I was a complete extrovert or introvert, that was all I had but I’ve seen a lot of changes. My daughter, Toni Rothpletz, works for Tealium and I’ve watched how at Tealium they have these teams and different ways that they connect with people with their products. I love watching the interactions of how they all help support each other that it helps to have a balance of introverts and extroverts when you’re talking sales. What do you think about that?

You need a balance on any team. Scott and I are such good partners because we even each other out. Scott is definitely an extrovert and we’re great partners because of the fact that we come to the table with different strengths and weaknesses and then we face challenges in very different ways. The reason why I love the book we wrote so much because you will get strategies that work for both a very extroverted personality and a very introverted personality and everything across that spectrum. That’s one of the most important things that we’ve been trying to tell people through the interviews that we do. It is that this book is not gospel.

This book is designed for you to get inspired to think about building relationships in more meaningful ways and to throw out all the bad habits that you had been trained to use throughout the years and come back to building real meaningful relationships. Read this book, get inspired by the people that we’ve showcased, the super-connectors that we find are doing some great stuff, and to pick and choose what works for you, steal some of these ideas, but if something doesn’t jive with you, don’t do it. This is about figuring out a strategy that works for you because we’re all incredibly different. The person you need to listen to is yourself more than anyone else. The literal first or second chapter of this book is all about self-awareness because before you read this, you need to know yourself and know who you are before you can decide what strategies for building relationships you’re going to adopt and which ones you’re not going to.

I’m glad you brought that up because that’s an important part. My dissertation was on emotional intelligence. One of the biggest factors in emotional intelligence is self-awareness. And to understand others, you have to begin at the beginning, which is understanding yourself. If you understand your own emotions, you’re more able to grasp those in others and that’s so important. My research now is on curiosity. You obviously seem to be a very curious person. You said you didn’t like corporate America. It didn’t fit you that well. Have you always been a curious person to try and reinvent yourself and to help others? Is this something that came to you naturally? Where did you get this?

It was probably in a lot of ways. I am naturally curious about new things, trying new things, having new experiences. That has always led me to be curious about other people and how I can be a part of their lives and how I can make tiny impacts that allow me to support them and help them continue to grow, but also allow me to learn and be a part in some tiny way about what they’re doing or what they’re creating. My favorite part about building YEC and all these other professional communities is that in some tiny way, I’ve been able to be a part of all their businesses and learned a lot from them in the process. It’s inherent. For those where it’s not inherent, that’s a challenge. I don’t have the answers for fixing that challenge, but if you are naturally curious where you can find a way to become more of a curious person, you are going to be more successful at connecting and building meaningful relationships with people. Some ways that you can exercise that brain muscle is to read a lot, to ask yourself questions about the things that you read, to watch the news a lot, stay up to date on current affairs and what’s going on in the world and to have opinions about those things. Those are the types of exercises that might help create curiosity where otherwise might not exist.

There’re a lot of people that don’t know where to start. A lot of people have fear or technology can be an issue as well because technology does everything for us more now than in the past. Do you think that your generation is any different than any others? Since there’s so much technology now, does that help you or hinder your curiosity do you think?

It helps than hinders. We are different, but only because we grew up with specific technologies and specific resources at our disposal that have become second nature. That’s not to say that there aren’t Gen X-ers and Boomers and those that have been a part of previous generations that haven’t adopted and gotten very savvy with the same stuff, but there are fewer just by the nature of how my generation has grown up. It helps in the sense that when we are curious about something or do want to learn something, it has become so easy for us to go out and find information and to be able to learn about things that otherwise we would have to go miles to get access to, to a library, to meet with people in person before we can absorb information and satisfy curiosities.

It’s a hindrance because there is so much out there. There’s so much noise. It’s very hard to determine fact from fiction, who is legitimately an authority and who is faking until they make it or outright lying to you. It also brought so many more people inward that they’re not going out and having that tangible experience of going to a museum of, of picking up an actual book and reading it, sitting down and having a cup of coffee with someone in person where you get to make a more intimate, trusted connection. There’s a balance that needs to be had and unfortunately, a lot of us have fallen into what’s easy, which is to stay at home, surf the web, and learn from technology and that creates much less well-rounded person at the end of the day.

You made some important points. It’s interesting because I give a lot of talks on the generational differences and why people misunderstand some of the millennial issues and things and maybe they’re harsh on different generations when it’s not necessarily the truth. In my generation, if we weren’t fifteen minutes early, we were considered late. That impacted why Boomers are so expecting certain things because we were so ingrained with some of that Mad Men mentality of what was going on. What do you think is the biggest misconception about millennials?

There are so many. What I’ve learned over the years, because I’ve spent a long time fighting for Gen‑Y, the earlier millennial packet, is that we’re not all that different. We all want the same things. We all want stability in our lives. We all want happiness in our lives. How we get to that end goal is just different because we’ve had different resources and different societal barriers in place when we came to that age where we went out into the “real world” to start forging it for ourselves. One of the big things that a lot of people peg Gen-Y and millennials as narcissistic and I don’t think that’s true.

There are narcissistic people across the spectrum. Now that I’m a little bit more established in my career, I deal with narcissistic people at the age of 60 all the way down to the age of 21 and it’s like a personality type, there is an equal opportunity. There are a lot of people that are pegged with that stereotype that aren’t just because of the way that they approach challenges, the way that they are more willing perhaps to put their opinions out there, to share their ideas. Frankly because of social media and the access we have, it’s easier to do that and that is a good thing that we should embrace. At the end of the day, we need to all get off each other’s backs, give each other the benefit of the doubt, get to know each other a little bit better beyond the surface level of crap that we see online, and then make decisions about whether or not someone is the right fit for you to work with. We’re a lot deeper than our social media habits and what we put out there online than you give us credit for.

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Unleashing The Entrepreneur: It wasn’t just entrepreneurs that are lonely and that have a problem with making connections, it’s any ambitious professionals.

I agree with everything you said and that’s important. A lot of people are going to find this very fascinating and they will want to buy your book and want to know more about you. Can you share how people can reach you?

I am incredibly findable online. I love talking to people about community-building projects that they’re working on, I love getting out of my day-to-day picking out on someone else’s work, so feel free to reach out anytime. The best place to get started is Ryan Paugh on Twitter. I share ideas there. If you want to learn more about the book, is a great place to go to understand what it’s all about and then you’ll find links to all the different places where you can buy. If you’re an Amazon person, you look at the Amazon, Audible. Whatever you need, we’ve put it all there in one convenient place. If you want to learn more about The Community Company works, go to and that’s a great jumping off point to learn about what we do.

Thank you, Ryan. This has been so fascinating. I enjoyed having you on the show.

Thanks for having me. I had a lot of fun.

You’re welcome.

Unleashing The Entrepreneur with Debbie Wooldridge

I am here with Debbie Wooldridge, who has built an outstanding reputation at ttcInnovations over the past thirteen years with their clients by assisting learning organizations to elevate perceived value within their companies. They do this by demonstrating that successful training solutions enhance on‑the‑job performance, impact business results, and improve customer satisfaction. I saw that Debbie was featured on MentorBox and her work is all over the Internet. She’s written books, A Manager’s Guide to Unleashing the Intrapreneur, Unleashing the Intrapreneur, and different versions of that. I am curious to find out more about you. Welcome, Debbie.

Thanks so much for having me, Diane. I’m excited to be here.

I’m very interested in this MentorBox, how you got interested in being part of that and how did they find you to do that? You teach a course with them or you did, and you were writing about intrapreneurs and millennials and that type of thing, is that correct?

Yeah. I have written two books. The first book was called Unleashing the Intrapreneur: Changing the Face of Corporate America One Millennial at a Time. That book is targeted for millennials themselves and how they can work their career in such a way that enables them to take that entrepreneurship experience and idealism and take it risk-free inside of a corporation, and so how they build their careers inside of companies and feel successful in that manner. In order for that to work well, they need managers in companies to be open to the idea of intrapreneurship, so the companion book is A Manager’s Guide to Unleashing the Intrapreneur.

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Unleashing the Intrapreneur: Changing the Face of Corporate America One Millennial at a Time

I met with the folks at MentorBox. There is a subscription service that takes a lot of unique and leading information books that CEOs should be keeping track of and reading but may not have all the time in the world to do that and they put them in condensed versions, then give them some working guides to help them get through the materials very quickly, but then they also take some books and build these one-hour workshops that walk you through the process of the book. They kindly reached out to me about my book, the Manager’s Guide and asked me to come in and talk about the different techniques that managers can use to embrace the idea of intrapreneurship. I got to go to San Francisco, meet the MentorBox team and worked with them to build out the workshop. It was a great experience.

I’ve written some courses and workshops, so I’m always fascinated how everybody does it. The techniques are so important for managers. We don’t want to give away the free class. Is there any that you can share?

I walked through the book, the Manager’s Guide and highlighted some of the most important things that managers can do. One of the biggest challenges is that everybody thinks that millennials themselves are looking for these Google-type experiences where you have this massive campus and you get to play games and all this excitement and managers think to themselves, “I don’t have the dollars for that. I can’t even put a ping-pong table in my break room, so that’s not happening.” What I try to do with this is to help managers realize that why that’s all fun and great and not a bad thing to offer if you can, that’s not the most effective way to attract millennials and to attract intrapreneurs to want to come work in your organization. I take it back to reality and the number one that millennials are looking for and the number one reason they want to join an organization is if they feel like they can truly grow within that organization. The first thing managers can do is focus in on professional development opportunities and “How can I help you come into my company where you’re at today and then find ways to help you mature and grow in the organization so that you want to stay here?”

You said that by the year 2025, millennials will make up 75% of the global workforce. I’ve gone to a lot of these events where a lot of the leaders are on stage and they talk about how millennials like to job hop, so they try to keep them as long as they can through development-type opportunities. Some of them are even saying they’d keep the door open, yet they realize that they don’t offer everything they need at their company, but if they want to go get something at other places and then come back, they keep the door open for them. When you say that you want to help them grow, do you think that they’re able to keep them in the companies? Are you seeing that giving them more development opportunities while they’re there, will they stay longer? How does that look in your eyes?

Here are some scary statistics for companies. A recent Gallup poll suggested that 21% of millennials say that they’ve changed their job within the last year and that’s three times higher than any other generation in the workplace. It’s a dramatically high number of millennial to say, “I’m not getting what I need here. I’m going to make a switch.” If you think about it, back in 2009 when we had the world’s worst economy, there were 6.6 individuals applying for every single open job. In January of 2018, Labor statistics came out with data that it’s 1.1. That is a huge decrease of workers looking for jobs. If you have 21% of millennials saying, “I’ve left my company,” it’s a huge problem because who are you going to fill it with? You don’t have very many options. Companies do not have the luxury at this point to say, “What if we lose a couple of people. It’s fine, because I will refill this position.” The reality of it is there aren’t very many job seekers. In fact, there are 6.3 million open jobs at the end of January 2018. That’s the highest number in years.

Companies do not have the luxury of waiting around and saying, “Maybe we should make some changes,” or “Do we even care whether our team comes and goes?” Unless you plan to downsize your organization, you’ve got to find a way to keep millennials and keep employees in your organization. To give another statistic, there’re 10,000 Baby Boomers retiring every single day in this country. It’s a lot, and so the job openings are getting larger and larger. Whatever companies can do, they need to start doing today to be attracting millennials. They need to be working to finding ways to retain their employees.

You made some important points. Going back to your developmental opportunities on how to keep them staying and growing, you look at the data, engagement is so low if only a third of workers feel engaged at all. We need to do things to get leaders to work on those kinds of situations.

When you were talking about the MentorBox, it made me think of all the books and all the things that they’re not reading about. I’m researching curiosity because younger generations want to know more for engagement’s sake. They want to know how they’re doing, they want that feedback, they want to know how what they do ties in the goals with the organization. They are curious and they want these things, but we’re maybe not giving them enough of it. Then we also have a lot of employees who maybe aren’t well aligned to what they could do best because we’ve not asked them and they don’t get a sense of developing their sense of curiosity because either they’re afraid or different reasons. Do you think that we’re developing these natural curiosities in our younger employees or even in any of them?

I do think that’s the problem because employees don’t leave companies. They leave their managers. If you don’t value what they bring to the table and if you can’t find a way to engage that in your organization in some manner, they’re going to walk out the door. That’s the reality. One of the things that we talk about in the book about how to increase that engagement is trying to talk with the employee about, “What things are important to you? What do you want to be doing?” and get away from that hierarchy. That’s one of the biggest challenges, especially in companies that are entrenched with doing business the way they’ve always done business. You come in and you’re at this associate level and then you may get additional training and prepare yourself to become the manager and then you may become a director, a vice president, and work your way up the chain. millennials aren’t looking for that. The chain of command means nothing to a millennial. What they’re looking for are companies that support them to have the opportunity to bend and flow and flex with their interests. If I come into your organization and maybe have a graphic design degree and you hire me to help update the marketing materials.

While I’m there, I’m starting to research and build all these great infographics and all of these numbers are being used and I’m making these beautiful visual pictures about the organization, and suddenly I realized I like numbers. I go to my manager and say, “I’d like to join the accounting department. I’m intrigued by this idea of how metrics impact this company. Can I do that?” If your manager says, “That’s interesting, but you’re a graphic designer. I need you to make this next marketing piece of paper.” Then the person’s not going to be very interested in wanting to stay with you because their interest has changed. If you can find a way to say, “You don’t have the accounting experience, but let’s see if we can get you an internship or a mentor from the accounting department. Maybe this is something we can do for you.” The excitement then and the you-support-me is there and you want to become part of the company that wants to grow you in those ways.

There’re advantages to flatter organizations versus hierarchy and vice versa and different reasons. The only issue I can see is if everybody does what they like to do, who’s going to do the bad stuff?

That is true. That is an important concept. We all have tasks that we have to do, but if you can make sure that you feel like you’re being appreciated for the things that you love to do, it’s easier to take on the things that aren’t as attractive because you realized that it adds value to the organization.

I don’t think that they do enough in the hiring process to find out what people are capable of. These job descriptions sometimes are vague or they’re not even accurate and you get into this job and it’s not even what you think it is. Do you find this happening out there?

If you are hiring for the role and not hiring for the person, you’re limiting yourself dramatically. A company has a job opening. We currently have a job opening ourselves for an HR specialist, so we’re definitely looking for somebody who has HR experience and has a passion around HR. Most importantly, I want to bring in somebody in our organization who has some vision and has some ideas of where we could go that I haven’t thought of in the HR realm. When I’m doing interviewing, I want to be finding out, “What are your outside interests? What things excite you? Where do you see yourself five years from now?” My vision of this organization is limited by what I come up with, but the vision of my organization is so much greater than me because of the people that work here in this organization. If companies can take that perspective and say, “All of us bring something unique and different to this company and yes, we have job skills. We’re bringing those skills and those skills are vitally important, but we also have other interests in life.” People are more than one dimensional and if you can embrace those different dimensions, you can find unique ways to grow your company in manners that you never thought of.

I’m thinking of your HR specialist type of a situation. I know I could think of somebody who would be perfect for that but a lot of people want to work virtually now and that can be a challenge. Do you offer virtual type of arrangements? Is that still too hard to do?

It’s so funny that you mentioned that because I opened my company in 2001 and we have been virtual since 2001.

All of your jobs are?

All of our jobs. In fact, I’m working out of my house. All of our teams are virtual and many of the clients that we work with have moved into a virtual world as well. We don’t even go on site with most of our clients with the work that we do because we can do it in a virtual environment. That’s one of the things that I talk about in the book as well about that whole idea of flexibility, allowing people to work in environments that make sense for them rather than limiting who you can have in your company because of where they are physically located.

It’s such a challenge but I know so many people that want to work virtually, but if you start looking for virtual jobs online, you get all the scams. I don’t know why they don’t have a better way to find good virtual jobs without getting sucked into those websites. Have you found a better way to list your jobs in real ways?

When we post our positions, we do post out there that it is virtual. I do think the nature of the work that we do feels like it’s more comfortable for people virtually, but it will also tell you that in doing interviews, I have had people say to me, “What do you mean there’s no office that I come into?” The flexibility means that not everybody wants to work in a virtual environment. For us, I don’t have a way to bring them into an office environment because we simply don’t have a brick and mortar for them to come to, so this wouldn’t be a great match for somebody working virtually. There is an amazing person who lives in Great Bend, Kansas that could lead our company to be successful, but we’re located here in Carlsbad. The only way to make that work is to offer them to transfer here, which they may not be at all interested in or allowing them to work virtually. If companies can keep an open mind about what’s going to be best for both the company and the employee, then you have a lot more opportunity.

A good friend of mine lives on the border of Minnesota and Wisconsin in the middle of a farm and she’s probably the best HR professional I know. She wrote all the courses. I used to work with her, but she works virtually as an instructor, like I have worked virtually as an instructor. For her, a lot of it is where she’s located. There’re so many amazing people out there. I would like to see a better way for people to connect. Please create something.

I’m just thinking, that a growth opportunity for our company if we can come up with a database. I liked this idea.

I would love it because seriously I’ve worked virtually almost my whole career because I worked for twenty years in an industry for a company and fifteen of that was in pharmaceutical sales. You have a company but you don’t have an office. You work out of your home for that. This was in the ’80s and nobody was working virtually. It’s always been that way for me and it was interesting to go to an office setting after that.

TTL 192 | Unleashing The Entrepreneur
Unleashing The Entrepreneur: Enjoy being on their phones quite frequently, but that’s not how they want to learn and grow.

I can’t even imagine going in day-to-day into an office anymore. I am not sure that I would be willing to go to an office environment.

It’s fun to be around the people and I love that part, but it’s interesting to me because when I was in banking, I had a job that was 9:00 AM to 6:00 PM and you had to be in the office. I was so exhausted because it was in an office and it seemed like such a long day. Then when I worked at home, I’ll start work at 4:00 AM and maybe work until 6:00 PM and it seems like it goes by so fast, and I could work so much harder at home. There are a lot of people who find that challenging that they need to be held accountable and they like to have office settings. Do you find that millennials do better with the virtual or Boomers? Who likes the virtual? Is it across generations?

This might be a little bit shocking but millennials prefer face-to-face. We think of them being on their phone and be connected with the world, which they definitely are. In doing all of the surveys and the work that we did for development of the books, we identified that millennials, more than any other generation, want that connection with somebody. It’s not that it couldn’t happen virtually because you can use Skype and you can use a lot of the great tools that are available to make it possible to do it in different locations, but they absolutely want FaceTime with their managers and with the partners that they’re collaborating with. They want to be able to walk into the executive suite and talk with the CEO of their company and say, “I’ve got a brilliant idea.” They do enjoy the face-to-face. That’s one of the challenges that we’re having as my company builds training solutions for other organizations as our primary business. I’m trying to get our clients to understand that we know that millennials enjoy being on their phones quite frequently, but that’s not how they want to learn and grow. They want to learn and grow face-to-face.

Maybe we need more holodecks like Star Trek or maybe the Surrogates movie with Bruce WiIlis where you have a robot go to your office and you can still stay at home. There’re a lot of options now that Zoom and some of the other video options are getting bigger and better that eliminates that need. I worked on a virtual team when I was MBA Program Chair at Forbes where we would use the Skype or Zoom type of videos for our weekly meetings. We can all see each other, we can all talk and interact and it was so much better than the telephone call. I’ve had Tripp Crosby on my show. I don’t know if you’ve seen A Conference Call in Real Life where everybody’s talking over one another and put on mute and all the bad things that happen with audio only, but now that we have video, doesn’t that help a little bit?

It totally does. I do a weekly cadence call with my team and we go on Skype and everybody turns on their video cam. You don’t need to worry about putting on your makeup, your jewelry, getting gorgeous or anything. It’s that ability to look at somebody in the face while they’re talking and it’s such an easier way to have an understanding of what they’re meaning behind what they’re saying. Otherwise, we all know statistically that what you hear verbally does not necessarily reflect what’s being said. That’s such an important part if you are going to have a virtual work environment. If you are going to be flexible where somebody is in one location and somebody else is in another location, finding ways to do that connection that feels much more in real life is going to bring you forward and the ability to communicate effectively.

How are you holding people accountable in virtual situations without micromanaging and making sure that they’re working?

If you have tools like Skype, if you have tools like email, those are all great ways that you can quickly reach out and touch somebody. One of the things that’s most important is trying to focus in on what is being produced because that’s how you know that people are doing their job. It doesn’t matter whether they spent ten hours preparing this Excel report on the latest sales numbers for the company or whether I spend an hour. If I produce a report that’s effective, that to me demonstrates that I’ve done my job and that I’m being an effective, wonderful employee. In order to do that though is you have to, as a company, set up markers and key performance indicators that people know, “This is what I’m responsible for producing and if I know that these are my deliverables, this is what I’m supposed to be producing, then as long as I meet those, it doesn’t matter when I do my work.”

That rewards efficiency and I’m a big efficiency person. I’ve had people make a joke that I could do more in a half hour than people could do in a week. If there’re people like that who can do things quickly, and then I start to worry if you are that person and the more you do, the more they’ll give you.

That’s a great reward thing for being so efficient, “Here’s other people’s jobs.”

That happens a lot at least where I’ve worked. No good deed went unpunished. How do you get around that? There’s going to be people who are slow.

There are and the bottom line is that you have to establish accountability for those team members. Instead of rewarding the people who are being slow by taking the responsibility off of their shoulders by giving it to the person who’s being effective, hold that person accountable that’s being slow and reset their parameters and say, “The bottom line is you have this report. It is due tomorrow at 8:00 AM. I don’t care how long it takes you to get this done, but it has to be done by 8:00 AM tomorrow. You can either do it in one hour and be done with it or you can spend the entire day today producing it, but it’s still due at 8:00 AM tomorrow.” If the report doesn’t come in tomorrow at 8:00 AM, the manager has to be there and available immediately to take corrective action because all too often, it is easier to say, “I’ll do it myself,” and take that report over, so you are consistently rewarding this person for underperformance. Managers have this huge responsibility of being able to ensure that they are holding people accountable for doing the job and the task that they’ve been assigned to do.

That’s tough when you’re saying if this person doesn’t do it, you’ll get rid of them, but then you have nobody else to do it.

We’ve got these 6.3 million job openings, so if you get rid of this person, who’s going to fill their slot, but from a manager’s perspective, it may be better to have a smaller team and bring people altogether and say, “The bottom line is folks, we have a couple of performers on this team that are not meeting expectations. What can we do together?” You can partner people up with each other and they can help hold each other accountable as well. That’s the other thing. It doesn’t have to be the manager by themselves because oftentimes the manager feels, “I don’t have any time to do my own job because I’m micromanaging you because you can’t do your job,” whereas if you build a community within your division or your department and each other is holding each other accountable and making opportunities for, “I’ll help you this time but I’m going to need you to help me next time” and build this whole community of team members together, then it doesn’t fall all to the manager.

You’ve got good insights. There’re so many people that want to learn more about some of the things that you teach, either in your Manager’s Guide to Unleashing the Intrapreneur or all your work in general. Can you share how people can find out more about getting your books and reaching you?

On social media, I’m @DebbieWooldridge and that’s Facebook and Instagram or through my company which is @ttcInnovations. Both of my books are available on Amazon, A Manager’s Guide to Unleashing the Intrapreneur and Unleashing the Intrapreneur: Changing the Face of Corporate America One Millennial at a Time, available on eBook as well as actual books that they can order.

This has been so great, Debbie. Thank you so much for being on the show.

Thank you for having me. I enjoyed it.

Thank you so much to Ryan and Debbie. I enjoyed this episode. I do a lot of talks about generational conflict, so this was right up my alley of things I’m interested in and a lot of employers need to know more about. Please check out their sites and if you want to know more on my site about our show and what we can do, it is for millennials as well, go to

About Ryan Paugh


TTL 192 | Unleashing The EntrepreneurRyan Paugh first co-founded Brazen Careerist, a career-management site for high-achieving young professionals and ambitious college students. He then co-founded Young Entrepreneur Council (YEC) in 2010 with Scott Gerber, an invite-only organization for top entrepreneurs 40 and under that Entrepreneur noted “has quickly become one of the most elite organizations of its kind.” Today, Ryan and his team are building on their vision of the future of professional organizations with The Community Company, a company poised to launch dozens of vetted communities engineered to help ambitious professionals grow their network and expand business opportunities. Called “a cult legend in the online-community building world” by Mashable, Ryan is now focused on creating a strong membership experience and positive business outcomes for thousands of successful executives, thought leaders, business owners and entrepreneurs across the country.

About Debbie Wooldridge

TTL 192 | Unleashing The EntrepreneurDebbie Wooldridge has built our outstanding reputation at ttcInnovations over the past 13 years with their clients by assisting learning organizations to elevate perceived value within their companies. They do this by demonstrating that successful training solutions enhance on-the-job performance, impact business results and improve customer satisfaction.


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