7 Skills Every Business Icon Has in Common

June 25, 2016, 3:00 PM UTC
Businessmen discussing paperwork in office
Photograph by Hero Images via Getty Images

The Fortune 500 Insiders Network is an online community where top executives from the Fortune 500 share ideas and offer leadership advice with Fortune’s global audience. Mike Guggemos, chief information officer at Insight Enterprises, has answered the question: What can 20-somethings do to set themselves up for success?

Be curious. Twenty-somethings should do as much as they can to learn as much as they can. Don’t be quick to specialize. Rather, immerse yourself in your business as a whole. Once you learn one area, move to another. Have an insatiable appetite for knowledge, and challenge yourself to take on tasks and responsibilities that scare you. Then build basic competency in them.

Take every opportunity to watch and learn from people around you, and don’t be intimidated by tenure or title. Just because senior executives have higher titles than you doesn’t mean they know everything. What they do have over you is experience and diverse context when it comes to overcoming problems. So look for the traits, skills, and tools they use when making decisions. It’s likely you will notice some common behaviors among them. Executives encountering obstacles, for example, tend to quickly explore how to best mitigate negatives, expand positives, and adjust course rather than complain, stop, or quit.

See also: What This Fortune 500 Exec Wants Millennials to Know About Success

Know what you know, and know the areas you don’t know. Ask questions and get comfortable not knowing all of the answers. When you look at business icons—millionaires and billionaires—don’t doubt for a second that they have made an art of asking questions.

Experienced and confident folks don’t pretend to have all of the answers. They focus on asking questions that matter.


Embrace ambiguity and seek out different points of view. I have been fortunate in that I’ve served in most major business functions. This cross-functional view taught me that most successful leaders and managers, regardless of function, are those who ask thoughtful questions and possess broad knowledge more so than deep expertise. They:

  1. Behave as participants in conversation more than judges
  2. Strive to ask open and probing questions that provoke thought (it’s harder than you think)
  3. Understand that teamwork is critical to success
  4. Embrace collaboration with cross-functional teams
  5. Understand that giving definitive answers is easy, but asking questions that cause experts to questions themselves is not
  6. Know there is usually someone with greater knowledge, about most everything, than they have
  7. Realize substantive behavioral changes come more through insightful questions than definitive answers


In addition to curiosity, pushing yourself, and knowing what you don’t know, there are a few other things to consider:

  • Googling doesn’t supplement experience. Experience gives context for understanding and recognizing real-life experiences.
  • Failing is as important, if not more so than succeeding. Think of the tech greats—Robert Noyce and Gordon Moore, Bill Hewlett and Dave Packard, Steve Jobs, Bill Gates, Michael Dell, Larry Ellison, etc. Was it always smooth sailing for them? No. They failed, succeeded, failed, succeeded, and learned with each step.
  • Psychological safety matters. Lead by example in discussing issues, ideas, and experimentation in open forums and giving credit for trying—promote those who do.


Mike Guggemos, CIO at Insight Enterprises, a Fortune 500 provider of hardware, software, cloud and service solutions