Mentoring Millennials with Lindsey Pollak | Podcast

Lindsey PollakLindsey Pollak, often called a “translator” among the generations, shares her insights, opinions and the latest research about today’s 20-somethings in this 30-minute recording of her recent teleclass.

Listen below (or read the transcript) to pick up some actionable strategies to harness the power of your Millennial workers.

Key Takeaways:

  • There are 76 million Baby Boomers approaching retirement age, but only about 45 million Gen Xers to fill their leadership roles. This means younger workers will have to develop and train faster to be ready.
  • Millennials often lack the confidence to lead. They should realize that no one is 100% prepared for leadership, but remember also that there is always room for improvement.
  • The shift from rock star employee to manager is huge – Millennials will have to learn to put their team’s success ahead of their own, to make sure they are effectively communicating with everyone they manage, and to enable others around them in a way they perhaps haven’t before.
  • Keep your personal brand/ reputation in mind. Give all of your profiles a makeover when you step into a leadership role. (e.g., On LinkedIn, choose a professional photo, make your headline descriptive as people might not read below that, update your summary— your elevator pitch—to ensure your leadership credentials are very clear.)

Lindsey Pollak will be speaking on “The Secrets for Succeeding in a Multigenerational Workplace” at the 2014 Pennsylvania Conference for Women.

View Transcript

Conferences for Women 

“Managing Millennials”

Guest: Lindsey Pollak 

Interviewer: Karen Breslau

Karen Breslau:      Welcome to the Conference for Women teleclass, “Mentoring Millennials.” Our guest today is Lindsey, bestselling author, keynote speaker and one of the world’s leading experts on training, managing and marketing to the Millennial generation. Lindsey is the author of “Getting from College to Career, Your Essential Guide to Succeeding in the Real World.” Her newest book, “Becoming the Boss, New Rules for the Next Generation of Leaders,” will be published today and focuses on leadership for Millennials. Lindsey serves as an official ambassador for LinkedIn, as spokesperson for the Hartford’s “My Tomorrow” Campaign, and as chair of the Cosmopolitan Magazine Millennial Advisory Board. We’ll be sharing highlights from today’s call on Twitter, you can follow along and join the conversation @PennWomen, @TexasWomen and @MassWomen, and you can find Lindsey on Twitter @LindseyPollak. Lindsey, welcome to the Conference for Women teleclass.

Lindsey Pollak:     Thank you so much for having me, it’s an exciting day!

Karen:                   Yes it is. Before we start I want to define Millennials. Can you tell the audience, for those who don’t know, what is meant by Millennials?

Lindsey:                Absolutely, Millennials is the generation born approximately 1982 to 2000, although those are always fluid dates, could be a little earlier or later, depending on the person. And it’s a synonym for Generation Y, so if you hear the terms “Gen Y” or “Millennial,” they both refer to that generation and they are very significantly the children of the Baby Boomers.

Karen:                  Great, thank you. You refer to yourself as a Millennial workplace expert. Can you describe what you do, and how and why you started your business?

Lindsey:                Yeah, it’s not one of those careers that you see on assessment tests, is it? To be a “Millennial Workplace Expert.” It has very much evolved… I really trace my career beginning to being an RA, a Resident Advisor in college and mentoring the students and classmates who were younger than I was and also liaising with their parents, and professors, and administrators and so forth. So I’ve always seen myself in this role of mentor, trainer to the younger generation, and also somewhat of a translator, so to speak, for the older generation. So I started my career at a magazine called, “Working Women”—which promptly went out of business 18 months later—and that’s when I started my own consulting, speaking and writing business. And at the time, in 2002, we weren’t even yet referring to the Millennials as Millennials, I remember my first business card said, “Entry Level Career Expert.” And then this term Millennial was invented by two gentlemen, William Strauss and Neil Howe, who have a business called, “Life Course Associates,” and this concept really took off. And I had really always seen myself as a mentor and teacher to the Millennials—you noted my first book was “Getting from College to Career.” I was primarily a college campus speaker and what started to happen about five or six years ago, is companies started to approach me and say, “We know that you connect with this younger generation, they seem to listen to you. We’re really struggling with managing them, marketing to them, really succeeding through them,” so now my business is about 50% still on campuses and dealing with needs career-wise and so forth, of the Millennials as students, and also doing a lot of orientations, once they get into the workplace to be professionals and manage their careers. And then the other 50% of my business is really working with leadership of organizations to attract, retain, develop and market to the Millennials so that they don’t really see them as this problematic generation, but very much as an opportunity. So hence lots of marketing people and brainstorms later, the term “Millennial Workplace Expert.”

Karen:                   Great. Now you mentioned you’re the author of, “Getting from College to Career, the Essential Guide to Succeeding in the Real World,” and your new book out today is, “Becoming the Boss, New Rules for the Next Generation of Leaders.” Why did you write this new book and can you tell us more about it?

Lindsey:                Absolutely, thank you, yes. It comes out today, my second baby, I call it. [Laughs] “Getting from College to Career,” was very much everything I wish I had known when I personally graduated from college. So the book has 90 tips, really soup to nuts of everything you want to know about getting your first job. And I’ve been able to communicate a lot through campus visits and social media with some Millennials who read that first book. I always kind of had my ears open to what the next opportunity might be to write a book for this audience. And what I started to hear was, “Okay we’ve got jobs, but now we’re realizing that we want to be leaders. We don’t know how to make that next step in our careers, from individual contributor, to really a leader of the organization.”

And at the same time, what I’ve learned from my work with organizations is that Baby Boomers are retiring in droves: there are about 76 million Baby Boomers here in the United States. And my generation, Generation X, we’re only about 45 million. So there’s going to be a huge gap in the number of people available to take on leadership roles as Baby Boomers retire.

And this was really supposed to happen several years ago, but because of the global recession, it’s been pushed back. And so what organizations have said is, “We don’t have enough people in the pipeline to promote into leadership, we’re going to have to train and develop younger people in our organizations, much, much faster than we have in the past.” And we’re starting to see people get promoted into leadership and management really five to 10 years earlier than previous generations might have, particularly Baby Boomers. So it was kind of this dual meet of Millennials realizing they were ready for the next step and organizations saying they absolutely had to be prepared for that next step. So the book is for Millennials, it’s for young people, but I’ve also had a lot of really nice sales and opportunities with organizations providing the book to their Millennials to help them make this step up into leadership and management.

Karen:                   So we’re saying people in their 20’s and early 30’s, it sounds like, being promoted into positions of higher responsibility.

Lindsey:                That’s exactly right, and just to give one example, I was being interviewed by an editor of an insurance publication and he said, he had just finished their “30 Under 30” issue for the publication. And he said, “Normally it’s kind of middle managers, directors, maybe some assistant vice presidents, and he said, for the first time he could remember in his career, on the 30 Under 30 list, and this is a big corporation, it’s not just entrepreneurial ventures, but at big companies there were people under 30 who were in senior vice president roles and in regional manager roles and even occasionally, in the C suite. And you only have to point to Mark Zuckerberg as the first Millennial CEO of a Fortune 500. We also have many Millennials in Congress now, so a lot of things are happening a lot younger and it’s really throwing a curve ball to companies that expected people to be in management after maybe 30 years of working at the organization.

Karen:                   Wow, wow. So how is leadership different today for Millennials than for previous generations?

Lindsey:                It’s a great question and I don’t want to imply or have anyone take away that the reason for this book is that we should throw out all the old rules. There is so much good management; it’s like too much good management and leadership advice out there. I certainly read the classics and the first chapter of the book is really about understanding Stephen Covey and Peter Drucker and even as far back as the, “Art of War,” understanding that this is not a new science. But at the same time, there are a lot of factors today, I think, that are different for Millennials and certainly everybody wants a book that’s customized to their needs.

So first of all, is this issue that people are tending, as a general rule, to step up into management with a lot less experience. Doesn’t mean they don’t have the confidence or the brain power, but they just don’t have the deep levels of experience. So how do you compensate for that, or keep your skills up or train yourself to be a leader? The second thing is obviously technology. This generation is going to have to lead virtually; they’re going to have to lead globally.

Millennials are often referred to as our first global generation; they realize that the world is their opportunity, but also their competition. So how do you lead a team that’s on multiple continents? And I think the last issue kind of goes back to this generational aspect that for the first time we have four generations in the workplace together. So I heard a lot of Millennials ask me things like, “How do I manage someone who is my mom’s age, or my grandpa’s age?” So you kind of see that issue that could’ve been occasionally there before, but is much more prominent. So again, I think a lot is the same, but there are certain nuances of leadership and management that are unique to Millennials and I didn’t really feel that they had been addressed before.

Karen:                   So these new managers are less experienced, although they are highly educated and very capable. What are some of the biggest mistakes that new leaders make?

Lindsey:                I think one of the mistakes is, I guess there are two that kind of relate to the question. The first is not having the confidence and maybe overly believing that you’re not ready. Once you get promoted to leadership or once you start a business, or a division or in any way leading other people and certainly I don’t define leadership as having to manage a huge team. You could see yourself as an individual leader, certainly. But one, I think, is that lack of confidence, that feeling that I’m not ready, I can’t do this, why is anyone listening to me? And hurting yourself as a leader, putting yourself down, even if you really are very capable, so I think confidence is a big factor and a mistake is not trusting that you are able to do it, even if you’re not 100% prepared, as really nobody is for leadership. And then I think the second is being overly confident, so not realizing that your skills may not be as sharp as they need to be. One of my favorite tips from the book actually was from an interview I read while I was writing the book, with Josh Sweden, who’s a director, and really prolific writer, and artist, and videogame designer and so forth.

And he said, “I’m constantly filling my tanks, I’m always learning, I’m always studying, I’m always trying to get better.” And that was one of the key messages of the book that, as a leader, you can’t rest on your laurels, particularly in this world today, you really have to keep filling your tanks. And just to add one more, a lot of the experts that I interviewed, psychologists and leadership gurus, said that, a classic mistake, not unique to the Millennials, but a classic mistake is forgetting that once you are in a leadership or management role that’s now your job, so often it’s really hard, for instance, if you were in sales, and become a sales manager, to realize that your job now is to help your other salespeople succeed, not to be the number one salesperson yourself. So kind of letting go of what made you a star individual contributor, maybe giving your best clients to somebody else, or letting your secrets be known to your team, because it’s not just about you anymore, it’s really about the success of your team. And sometimes it’s hard, I refer to it, in the terms of Millennials, it’s kind of like going from a senior in high school to a freshman in college. You were the highest on the totem pole, and now you’re back to being a beginner again and that can be very challenging whether you’re a Millennial or of any generation.

Karen:                   What are some of your other top tips for new leaders or managers?

Lindsey:                I talk a lot about communication and the importance of communicating, not always the way you think you should communicate or you feel would be best, but really understanding that different people hear your message in different ways, whether that’s by email, or a formal presentation or in a meeting and realizing that you have to adapt your style to different people and different situations. So as an individual contributor, you often didn’t have to think about it that much, but as a leader, I really talk a lot about over-communication and realizing that some people hear in terms of numbers, some people hear in terms of emotions, some people need visuals to understand what you’re talking about. And if you really want to get your messages across, which is crucial as a leader, you absolutely have to think about how your message will be received. And nowadays that, of course, includes face to face, telephone, instant message, Skype, international borders, there’s so many different ways to communicate now, even have a guide. When you should pick up the phone, because I think a lot of leaders just don’t intuitively know that anymore, so communication is huge.

The other piece is personal branding, it’s really thinking about your own brand as a leader, your own reputation, both in person and online. So as you mentioned in the introduction, I’m a spokesperson for LinkedIn and have been for five years, an ambassador. And I talk a lot about what a LinkedIn leadership profile looks like, how it needs to be different from maybe what your profile was before. If you’re going to Tweet, what’s the line between appropriate and inappropriate? How are you going to represent yourself in person and on the internet, I think is an issue that’s very, very relevant to today’s’ leaders? And particularly because, it’s likely you won’t always lead in the same organization, you might be looking for a job at some point, or get headhunted, or start your own business, and you have to manage how you’re going to look, just beyond the walls of your particular organization.

Karen:                   Let’s talk about LinkedIn for a moment, you’re an official ambassador for LinkedIn, and you say that LinkedIn is the most important social network for the majority of industries, because it’s completely professional. Can you talk a little bit about the LinkedIn profile and your top tips for making the most of LinkedIn in general? I think this is a huge issue for a generation that’s come of age with social media and may not know those boundaries.

Lindsey:                Absolutely and this is a tip for any generation. I think we often think about Millennials; that they’re going to have college party photos or bikini beach photos, but I’ve seen so many professionals of all ages have pictures or statements online that they really shouldn’t. So first and foremost, is to remember that as a leader you are always building or harming, potentially, your reputation. And I don’t want to scare people, but if someone is going to meet with you, or interview with you or do business with you, they’re almost always going to Google you first. And what they find is going to reflect on how they perceive you. And often that might be Facebook photos, or Instagram photos, or Google Plus or wherever you happen to hang out, even if you have very tight privacy settings. In my opinion privacy settings are like Whack-A-Mole, they’re always opening up new ways for people to see information about you. And you might be your husband’s sister-in-law who happens to actually be connected to you or see you on Facebook, so just be careful that anything you post on the World Wide Web, remember its worldwide, anything you post on there, could potentially be seen. And it doesn’t all have to be super buttoned-up, but you just want to make sure that it’s appropriate. And what I like about LinkedIn and the reason I’ve worked with them for so long, is it’s entirely professional. It’s a place for you to just put that professional foot forward, so make sure that your photograph is professional, wear what you would to a job interview, or to a very important meeting or presentation.

Look the way you would look to people, not your wedding photo, not a picture of you with your boyfriend with his head and shoulders cut off, not you with your pet, the image that you put is really important. I think it’s important in the headline, the words under your name, to show your leadership role, to talk about some key words related to the role that you have. So a lot of people will put something like director at IBM, that doesn’t tell me anything about you. Director of what? What are you passionate about? What do you offer people? What is your skill set? I would really recommend making sure that all of that is visible in the headline, because people are so busy, they may not read below that. And then in your summary statement, which is the professional bio, make sure that the very first sentence of that is your elevator pitch. If people read nothing else on your LinkedIn profile, what would that be? And it’s amazing to me how often leaders have never even updated their LinkedIn profile, once they get promoted, to talk about the fact that they’re managing people or managing a large project.

Make sure that your leadership credentials are very clear, right at the beginning of your LinkedIn profile. So those are just a couple of tips, but really giving your profile a makeover when you step into a leadership role, so that if someone were to come across you on LinkedIn before they meet you, which is entirely possible, if not probable, make sure that they’re getting the very best leadership version of you, just as they would if they met you in person.

Karen:                   Great advice. In general, how would you say that organizations benefit from hiring Millennials?

Lindsey:                I think there’s an epidemic out there, and I’ve seen it for probably the past five years of what I call Millennial shaming, which is saying, they’re so entitled, they’re so coddled, this generation has grown up in affluent times and yeah I know the economy has gone south, but they seem to feel like they should be CEO on day one. And they just have their devices in front of their faces all day, they don’t want to work hard. And I think that people have sort of decided that that’s going to be the image of Millennials, and they often don’t give individual Millennials a chance. And sure there’s some duds out there, there are of any generation. But I think Millennials are energetic, I think they’re smart, I think they’re creative, I think they want to succeed and help their organization succeed. So I think there really needs to be a mind shift in leadership of companies that your young talent is an enormous asset to you, it is going to make your company more productive, and it is going to make your organization more money or whatever it is that drives your organization, if it’s good work or whatever your goals are. And really align Millennials with that, so let them share their big ideas, let them bring their technical knowledge.

I think companies that have Millennials as customers, which today is pretty much any organization, Millennials being in their 20’s and early 30’s today, let your internal Millennials be focus groups for you of what the Millennial market wants. People say, “Oh, it’s so confusing and hard to market to Millennials,” but they don’t tap the greatest resource they have, which is their own young talent. So I have a rule with all of the companies that I work with through corporate training, and keynotes and consulting, we always have to have at least one or two Millennials in the room for any meeting, because we cannot talk about this generation without them being present and sharing their thoughts and ideas.

Karen:                   Great. Now you talk a lot in becoming the boss, about the need to manage generational differences in the workplace. Why is that so important and what is your advice?

Lindsey:                So, as I mentioned before Unique Generations, the traditionalists are only about 5% of the workforce, but in many ways set up the structure of many companies that Millennials will work in. Then we have the boomers, which have just been this massive economic, political, social force for 30/40 years, they tend to be in their 50’s and 60’s. You have my generation, the Gen X’ers, we’re in or 30’s and 40’s, and then you have the Millennials who are in their 20’s and 30’s and we’re going to blink our eyes and we’ll have the next generation, which unfortunately they’re calling Generation Z, which is obviously problematic, because I don’t know what you do after Z. But this mix of generations, we’re so very different, particularly in their use of technology, and their cultural touch points, so you’ve got this wild mix of generations. And then you throw in the fact that it’s a global workforce and there are different generations in different countries. The words I’m using are very American, and suddenly you’re not just dealing with your peers anymore, you’ve got to learn to communicate with people who maybe grew up with very different technologies from you.

And you don’t want to assume that a Baby Boomer doesn’t like technology, but you also don’t want to assume that a Millennial always wants technology. The biggest complaints I hear when I run workshops is, boomers say that, “I love technology, it’s totally fine to text me.” And Millennials say, “Everyone thinks all I want to do is text or Skype, please come talk to me at my desk, I like face to face too, I’m human.” So we kind of make these assumptions about generations that I think can be very destructive and unproductive in the workplace. I also think when it comes to generational differences, you have to think about the fact that different generations tend to behave in different ways and you always want to think about the individual before you think about the generation. But Baby Boomers tend to be a little bit more social, a little bit more outgoing, a little bit more optimistic, as a general rule. Gen X’ers like me, are a little bit more independent, maybe a little bit more pessimistic, we grew up in bad economic times, we were the baby bust, we’re a small generation, we were all latchkey kids with divorced parents playing our Atari at home. These are kind of the historical precedence that make a generation one way, and Millennials have grown up with technology, they’ve grown up in a customized world where they can go to build in their workshop, and create anything the way they want.

They get in the workforce and Baby Boomers say, “But you’re going to be one of 73 new associates.” And they say, “But, I want to express myself, I want to be different.” And so you have these kind of tension points, that I think, are very generational. And if you’re able to see them through the eyes of someone who understands generations, you can stop in that moment and say, “Oh, I understand when you came into the workforce, you wanted to be an associate like everybody else, I want something different, let’s talk about it.” So it kind of brings these unspoken issues out to the forefront and makes you realize it’s not that you don’t like somebody, or that they’re wrong, it’s that you have very different touch points, very similar to diversity training, very similar to Myers-Briggs personality types. There’s so many ways to splice and dice the workforce, I happen to see things through a generational lens, and I think at this particular moment in time, that’s a really helpful way to understand some of the dynamics in the workplace.

Karen:                   Got it. Now in the book you also say that career fear, and that can be everything from the fear of failure to the fear of success, is totally natural. How do you recommend that aspiring leaders move forward despite their fears?

Lindsey:                I’m really glad you brought that up. We’ve talked about Millennials as kind of confident, which they very much are, it was actually my editor at HarperCollins, who read the book and said, “So, when I got my first management role, I was really scared, can you talk about that?” She’d probably kill me for mentioning that to the entire conference room and audience, but I realized that I had to delve into that psychological feeling, that it’s scary to lead other people, it’s scary to have everyone look to you for the answers and the reality is everybody is fearful when they take on a leadership role. The most confident person is always going to, sometimes, wonder if they’re making the right decisions and the answer is not to ignore the fear, the answer is not to quote, overcome it, I think the answer is, and this sounds very therapy, but you have to go through it, you have to feel it and deal with it and say, “Okay, here’s what I’m going to do to get through my fear.” So for instance if you’re a very nervous public speaker, practice as much as you can, hire a coach to help you, ask a mentor to run through the meeting with you three or four times before you stand up in front of other people. If you’ve never done a profit and loss statement, Google it, see what people say about how to do it, again talk to a mentor outside of the office. You don’t have to stand up in front of everyone you manage and say, “I have no idea what I’m doing.”

But you can arm yourself with support, with ideas, with information and then because of the internet we just have so many vast resources, you know I’m an ambassador for LinkedIn, people ask me questions that I don’t know the answer too, and I look them up, up on the help page of LinkedIn, you have to kind of have support in this world, there’s so much out there to know. And I think, I was very conscious once I got that comment from my editor of interviewing even more extremely successful leaders of all generations and asking them about the fear and everyone admitted to having it and they gave some really interesting ideas for how to get through the fear and succeed anyway.

Karen:                   Yeah, we often learn more about people acknowledging their fears than being in the super confident winning role.

Lindsey:                Absolutely and…

Karen:                   When they admit their vulnerabilities I should say.

Lindsey:                Yeah I think vulnerabilities are so important to acknowledge and to read about other peoples’ and just the spoiler alert, the entire first page or first few pages of the book, is about what a horrible terrible manager I was when I got my first management role. So I try to start the book by saying, “I’ve gotten to a point where I’m writing on this topic, but let me tell you, I was awful when I started and I got through it.”

Karen:                   Now you also devote a chapter in the book to the subject of listening, you say that leaders use the word I, less than non-leaders. Dispelling the commonly held belief that leaders are self centered or egotistical and that according to your research the high status person is looking out at the world and at the low level person. And that the low level person is looking at themselves. Can you share your thoughts on that research?

Lindsey:                Sure. And the levels are just related to workplace, certainly not categorizing people as high or low. I love that research because what I think it points too is another way to get through the fear, is to stop thinking about yourself. And a leader doesn’t think, what am I going to do, how am I going to get through this, what does everyone think of me. The leader thinks, how are we going to handle this, what are we going to do, what does the team need to make us successful? And I also got a lot of questions, particularly from Millennials, but I’m sure it’s cross-generational, how do I be a good leader and let people know I’m a good leader without sounding arrogant or egotistical? And the answer that I gave is, I think you talk about we, you talk about the success of your team. You talk about the success of the projects you worked on. I think when you’re focused on your team, and your stakeholders, and your customers or clients, or donors or whatever is in your world, that, I think, is not only going to make you better liked by the people you work with and respected. But I think it also gets rid of that fear because you’re focused on the fact that you are…yes you’re the leader, but you’re also part of the group or the team, as well.

Karen:                   Got it. And your book also has a quiz that helps readers identify their own management styles. How can learning your management style help you to make decisions as a leader?

Lindsey:                Management style was something I hadn’t really thought about until I wrote the book and some companies are very interested in management style, and testing and assessments, and some aren’t. But what I learned in talking to really, really smart leaders, who I admired, is they’re very conscious of their tendencies. So maybe you’d tend to be a micromanager or you’d tend to be a consensus builder. If you know your tendencies, you can play to your strengths in some ways and say, “Wow, I’m really good at rallying the troops, if it comes to doing that, I know I’m going to do a good job.” If you are somebody who’s more of a consensus builder and a little bit quieter, maybe introverted, you might realize there are times when maybe you need to bring in a motivational speaker to do that while you build consensus a bit more quietly. So it’s knowing your management style or tendency helps you understand when you can play to your strengths. I think it also helps you understand the kinds of people you want to surround yourself with, whether as other people on your management team, perhaps people you hire, if you’re in that type of position.

Or the people that you choose as mentors, for example if you’re very introverted, you might choose and extroverted mentor to help guide you on things where that would be an asset. So it really helps you develop yourself and understand where your opportunities and challenges might be.

Karen:                   Great. Lindsey, we’re running short on time, but I would like to ask you, before we rap up, what are your favorite leadership books and blogs?

Lindsey:                My favorite part of writing the book was writing about my favorite books, I’m a huge fan of a lot of the classics. “Seven Habits of Highly Effective People,” Stephen Covey is fantastic, of course. “The Myths about Entrepreneurship” and working on your business not in your business if you are an entrepreneur. For women leaders, I love Lois Frankel’s, “Nice Girls Don’t Get the Corner Office,” I think it has some very tangible tips. And I wanted to share, I just discovered an app called “Blinkist.” Blinkist takes all of these nonfiction books and cuts them down into 10 minute summaries, kind of a cliffs notes or spark notes of leadership books. So I’ve started to do that on all of the new management books and I’m finding new favorites every day.

Karen:                   That sounds great. Well I want to thank you, Lindsey, for being part of today’s Conference for Women teleclass. And also to let our listeners know that if you’d like to hear more from Lindsey, she will be speaking at the Pennsylvania Conference for Women on October 16th and again at the Massachusetts Conference for Women on December 4th. To register for Pennsylvania, visit I want to thank you again, Lindsey and thank you all for listening to today’s teleclass.