How to tell if you’re headed to the top

While Generation X did not give a crap about building corporate America, Generation Y defined its own paths through corporate life, all largely non-linear, family-centric, and gold-star focused. If an achievement can’t be conveyed through social media then it doesn’t exist. The Organiziation Man is no more.

History is the study of the cycles of human development: war and peace, the rise and fall of civilizations, and the ebb and flow of generations. So history predicts how the tone and tenor of Generation Z will resemble most closely the Silent Generation. Which means they will construct a new version of The Organization Man.

“Each era has its own executive profile,” says Peter Cappelli, professor of human resources at Wharton, who has made a career of studying the differences among executives across generations. This month he released a long-term study about the trajectory of careers at the top of Fortune 500 companies.

The study notably predicts what you must do over the next ten years to get to the top. While the bottom and middle tiers of senior management show varied paths to get there, top ranks have a more prescribed path to success.

Ten years from now Generation Z will be the team to beat at work. Because Generation Z will have a love of strong institutions and organizational stability that is unequaled by anyone else in the work world, and they will start climbing quickly through corporate ranks.

See the photo of the escalator? Someone sent it to me as a great example of user interface. But every time I look at the photo I think of it as a great illustration of how preceding generations will languish one side while Generation Z marches upward on the other.

Here’s how to get a safe spot at the top of that corporate escalator before Generation Z passes you. 

1. Get an Ivy League degree or stay at one company. An astounding 24% of senior leaders in the Fortune 500 have Ivy League degrees. (And the percentage is on the rise over the last ten years.) Those who did not have degrees from the Ivy League had a more difficult time moving from company to company and had to work their way up, usually over two decades, within a single company.

2. Move around within general roles instead of staying in one functional role. Capelli says those at the bottom and middle ranks of management were more likely to have developed their career in “functional silos” like legal, communications, and human resources. Whereas people at the top were more likely to have have a wide variety of operational experience – including P&L responsibilities.

3. Gain international experience while you and your children are young. Most senior executives have international experience, but a survey from Harvard Business School finds that both men and women are unlikely to relocate when their kids are pre-teens because it’s so hard on the kids’ emotional and social development.

4. Create a solid support system at home. Top executives don’t always have kids (most women executives don’t) but they always have a supportive spouse. That same survey from Harvard Business School found that for men, this means emotional support and the ability of their spouse to sacrifice the short term for the long term. For women a supportive spouse meant “willingness to free them from traditional roles at home.” Also, most top-tier men have a stay-at-home spouse, but only 10% of similar women do. Which means the women have household help to make up for it.

 5. If you need to go to therapy, do it early in your career. Emotional intelligence is more important than ever for top-level executives. A key aspect of emotional intelligence is the ability to have negative thoughts without dreading them. This thought pattern allows you to make decisions based on your values rather than the wish to get rid of negative thinking. Susan David, psychologist at Harvard, provides a blueprint for building emotional agility.

Her blueprint includes a list of values for people to choose from. You just go through the list quickly checking off what matters the most to you. I took a picture of the list because I like it so much, but I did my own checks before I took the picture—sorry.

The list shows how clarifying your values helps you make faster and better decisions. It seems too simple to be true, but you know what? It’s true for me. I checked all the stuff that makes me love writing blog posts. And the checks also show me why I love doing webinars at Quistic —because in my videos the focus is so clearly on achievement but also on honestly, authenticity, and openness.

I have been worrying that spending too much time on videos is too much of a diversion from my blog. Now I see they are aligned. And the decision to make lots of videos seems easy and obvious now.

But the other thing this revelation shows me is why I’ve never been on my way to the top of corporate America. I value things that disrupt and challenge an organization rather than things that build an organization. Which means I definitely won’t be able to keep up with Generation Z as they race up that escalator to the top. Instead, I value the process of describing what it’s like to be standing on the slow side.

33 replies
  1. Nuria Costa
    Nuria Costa says:

    It is interesting to see the analogy of the picture with generations. I’ve never though it that way. But it is as simple as that.

    As you mention in your second point, nowadays, having an holistic and general view is better than specializing. Though we all end up specializing into something at some point of our lives.
    But in Europe, we have these “Graduate programs” for students who just graduate from business school and they get the chance to sign a contract for three years in a multinational company and they get to rotate to every department they wish each year. For example, they can work the first year in sales, the second in marketing and the third one in strategic marketing.

    So at this point I wonder if culture and trends are what shape us or we shape trends. Or maybe both happen at the same time. It’s like the vicious circle Nietzsche wrote on his books.

    And you may feel as you are standing on the right line. But to me, you’re leading the line of Generation Z by motivating them (or at least, motivating their parents who are reading your blog and motivate their kids).

  2. Beth
    Beth says:

    Ok – now I’m totally confused.

    I’ve read SOOOO many times on your blogs how important it is to specialize, specialize, specialize (which, of course, I have not).

    Then I read this paragraph:

    “Move around within general roles instead of staying in one functional role. Capelli says those at the bottom and middle ranks of management were more likely to have developed their career in “functional silos” like legal, communications, and human resources. Whereas people at the top were more likely to have have a wide variety of operational experience – including P&L responsibilities.”

    I dont get it – what am I missing here?

    Oh and this one..

    “Instead, I value the process of describing what it’s like to be standing on the slow side.?

    Except for moving to a farm, since when are you on the slow side of anything?!? LOL

    • Penelope Trunk
      Penelope Trunk says:

      That’s a great question.

      You need to specialize in order to get into senior management. There will be an opening, and you will have to have proven yourself as capable in the arena where there is a need for a senior manager.

      To get to the top of senior management you need to be able to manage all the high-performing specialists, which means you need a broad understanding of what each area of the company does. This comes from having hands-on management experience in a range of areas.

      In general, you can tell when someone is being groomed for very high positions because they are deliberately rotated throughout the company. People who will never get out of the lower ranks for senior management tend to just stay put.


  3. Lune
    Lune says:

    I’m sure this shows that I’m a detail person (whereas a person looking to get to the top is probably not interested in them), but when I read this:

    “See the photo of the escalator? Someone sent it to me as a great example of user interface. But every time I look at the photo I think of it as a great illustration of how preceding generations will languish one side while Generation Z marches upward on the other.”

    I just couldn’t help but think… but wait…the marching footprints (on the left) are going DOWN, not up.

    • Inge
      Inge says:

      You’re not the only one who noticed. I blamed noticing it on professional deformation (I’m in the building industry) rather than being detail focused, though.

  4. Lucy Chen
    Lucy Chen says:

    I used to work in corporate Australia many years ago, but it is icon concern to me now. I still enjoyed your post a lot. And I remember I first read about Gen Y from your Yahoo Finance column. I’m not sure whether it is your writing, your insight, that old link to the corporate world, or something else that makes me interested.

    I think history always move in a zigzag path. At first, it seems it is wasting a lot of time and energy comparing to going in a straight line. But anyone who’s ever ride a bike uphill knows the zigzag path is the path of least resistance.

    This universal pattern is seen everywhere. History at large. And our stick markets, real estate markets, and what you’ve described here about the workforce. Are we heading away from Gen Y’s jumping from job to job, and back to staying within one company?

  5. Ann Stanley
    Ann Stanley says:

    Thank you, thank you, thank you. I’m in a transition and can’t resist engaging with every pang of uncertainty that comes up, thinking I have to stop and work things out, instead of letting time pass and live the day according to my values. Thank you for the rich content you provide in every post.

  6. the legal career girl
    the legal career girl says:

    I agree with your points about getting international experience (though, I think most young people have some kind of international experience these days – at the very least, through study abroad programs in college) and getting a degree from a good (Ivy – or otherwise well-known) school.

  7. Mary
    Mary says:

    I’m also confused with your first point.

    1. Get an Ivy League degree or stay at one company.

    I assume that you’re making this recommendaiton for prospective high school students? What about for masters degree, do you also recommend that it be an ivy league degree or nothing?

    In many previous entries you stated that getting a masters degree is most likely unnecessary; therefore, I feel like this recommendation somewhat clashes with what you’ve wrote in the past.

    I’m just at a loss because I know an ivy league (masters) degree will get me places, but the investment on this degree is intense. I’m looking at *minimum* 50k in student loans to get a degree from an ivy-league school. Although you have said in the past that a masters isn’t necessary, do you think a masters from an ivy-league school is worth it?

    As for the other option you mentioned (staying in one company for 1-2 decades), that doesn’t sound particularly appealing. It would also be difficult to get a wide range of experience if you did that as well, no?

    • Penelope Trunk
      Penelope Trunk says:

      An MBA from a top-ten school or an Ivy is useful if you are getting it in your mid 20s. The Harvard Business Review article that I linked to provides a list of the top ten schools plus Ivies.

      In general, an MBA is useless to do anything except banking and climbing a corporate ladder in the Fortune 500. For all other careers you can get to the top without an MBA.

      And for sure an MBA that is not from a top school is not useful.

      Biggest misstep that I see: People who lie to themselves and say the school they got into is a top program and then they pay to go.


      • Lucy Chen
        Lucy Chen says:

        Penelope, and am I right in saying that a MBA is useless for an entrepreneur? I’m asking this because my husband is now in her 4th year as an entrepreneur and he has always wanted to do a MBA. I think it’s useless. There’s more we can learn online, and with much less $$. Even more useless because if anything, it’s going to be an Australian school. He argues about the connections he can potentially make. But then I doubt how good those connections with middle management people from big corporates would be for him anyway.

  8. Sadya
    Sadya says:

    I can’t get past this line that you’ve written “emotional intelligence is the ability to have negative thoughts without dreading them”.

    My takeaway from the HBR article: The best way to deal with negative thoughts is to just have ’em, not beating up yourself for having ’em.
    But it seems very simplistic. Negative thoughts can feel as rational thoughts. The analysis is always in retrospect

    • Angie
      Angie says:

      I’ve been in therapy for years and the most effective tip I got from it was “It’s normal to be anxious sometimes. Just feel it, acknowledge it, and move on.” Before that, I would use tons of energy to figure out WHY I felt anxious so that I could get rid of the cause–a process that only increased the anxiety. Once I started saying, “Oh, I feel anxious. Look at that,” the anxiety dissipated much more quickly. So, although it does seem simplistic, in my experience the best way to handle the negative thoughts is to have them and move on, as you say.

  9. Gretchen
    Gretchen says:

    Why are we listening to a book published in 1997 telling us Generation Z “will have a love of strong institutions and organizational stability”…? I question that “prediction” a lot.

    • Penelope Trunk
      Penelope Trunk says:

      The book is the gold standard for studying history in terms of cycles. The authors go back to Egypt and show how human nature produces generations in cycles that react to the generational cycle that came before them. Once you understand the theory you can see how history is predictive in terms of very large trends — like, are we in an age of stability or instability, for example.


      • Thomas Hill
        Thomas Hill says:

        Penelope, I love what you’re doing on here. That’s for writing these blogs.

        WRT your post, I’ll have to check it out. I still think that external forces can throw things out of kilter in a big way. I work in the sustainability sector, for example. It sounds rather dramatic, but I fear that James Lovelock speaks correctly in his predictions (see below). If so, then I suspect that a lot of these cycles are going to be highly disrupted?

      • Terry
        Terry says:

        To say this article is the gold standard of studying cycles in history is like saying it is the gold standard for studying astrology. The definition of ‘generation’ by a pair of dates is completely arbitrary. In terms of career guidance for any individual, it is at least as bad as ethnic stereotyping.

        This was a fun post to read, however.

  10. Jeff Putz
    Jeff Putz says:

    This prediction seems to be at odds with the idea that massive percentages of people will be freelance contractors. That seems like the opposite of organization building.

    • Gretchen
      Gretchen says:

      Yes…and I also thought it kind of went against PT’s penchant for home/unschooling…unless these Gen Z people love organizations and structure so much because they missed it when they were homeschooled (?) It also goes against the whole establishment idea discussed in Twighlight of the Elites where everyone’s lost faith in the institutions and the whole Ivy thing…

  11. YMKAS
    YMKAS says:

    This was helpful for me because I have helped my husband get to where he is. I’m one of the wives being described in #4, and it requires a tremendous amount of flexibility in your thinking, being supportive even on the worst of the worst days when he is gone for work for 3 weeks at a time getting to travel and see the world, stay at nice hotels and eat gourmet meals every night; and I’m homeschooling and have three kids under 7 years old (wouldn’t want it any other way). The payoff is great, and he gets to be the leader he is. It’s a mental game, get the right perspective and it makes all the difference.

  12. Laura Hamilton
    Laura Hamilton says:

    Interesting post, Penelope.

    But what makes you think that what’s worked in the past will continue to work in the future? I think we’re seeing an increased focus on finding tech-savvy, entrepreneurial-type execs — especially those who have a strong personal brand.

    • Penelope Trunk
      Penelope Trunk says:

      I don’t think Gen Z will use these steps for getting into leadership positions. It’s what you need to do now to get into leadership positions before Gen Z comes into the picture and changes things up.

      Gen Y is great at teamwork and totally changed the workplace to be collaborative, supportive and team oriented. But there is a dearth of leadership because Gen Y doesn’t lead, and really, Gen X doesn’t either.

      Gen Z will fill that leadership gap in a flash. So you need to be in position before they get there. This list tells you if you’re on track to get a leadership position before Gen Z comes in.


  13. Chrissy
    Chrissy says:

    I was confused by the post as well. Penelope has been preaching that degrees aren’t useful and that you should specialise. But the more I think about it, I think this post actually relates to those who want to make it to the top level in a Fortune 500 (or equivalent company that has been established for quite some time). It seems people in Fortune 500 companies may play by different rules than those who would like to start their own business (or grow a start-up). I would like to see an equivalent study done on those who would like success as an entrepreneur.

  14. Stress Manager
    Stress Manager says:

    In my experience there are not pre-determined ways to get to the top. It’s more a question of making the right decisions based on your current situation. One eye looking towards the future and it’s options and one to the present moment – doing a great job where you’re at.
    Don’t try to do or be something you´re not – it will not work in the long run.

  15. Helen Carroll
    Helen Carroll says:

    I’m confused. I’ve been following Penny for a long time. She has lived on a farm for years, right? It must be at least a decade now since she actually worked in genuine corporate management (not just a 3 person start up like Quistic).

    So why should I pay any attention (any longer) to someone whose not actually embedded in the cultures she talks about? In fact, temporally and geographically speaking, is light years from this culture?

    I just thought of this today, and the words that popped into my head were “Qualified” and “relevance”

  16. Matt
    Matt says:

    Wow, that picture at the top of the escalator hit me in the face! It’s the answer to the title of the post.. and it’s so true. Are you taking your sweet time, or are you pushing forward with desire to get to the top?

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