On Your Way to the Top, What Hurdles Will You Face?

Women who aspire to be a CEO should be aware of the hurdles they will likely face on their way to the top, said best-selling author Jennifer McCollum at the 2025 REACH Women’s Conference.

As CEO of Catalyst, McCollum oversees the strategic direction and global operations of this global

non-profit designed to accelerate progress for women. McCollum has chronicled her own career journey in her book In Her Own Voice: A Woman’s Rise to CEO. The book includes a wealth of findings and helpful advice based on more than 25 years of research on women’s leadership.

Early in her career, a male colleague described her as “a cupcake with a razor blade inside,” McCollum told the audience during her afternoon keynote and fireside chat with moderator and REACH member Tiffany Tate.

While her colleague meant it as a compliment, McCollum asked, “Would a man ever be called a cupcake?”

McCollum cited this as an example of the “double bind” women often face in the workplace. “People are conditioned to see a strong, aggressive, competitive man as their image of a leader. Women feel they have to meet that stereotype, but also there is the stereotype of a woman as a soft, collaborative, kind, warm person. And the challenge is, we find we are seen as one or the other but not both. So you spend time trying to figure out which version of a leader you’re going to show up with.”

Other hurdles women face include:

• The Inner Critic -- the “mega hurdle” as McCollum describes it. “It’s that annoying, soul-crushing voice of criticism that sounds like this: ‘I’m not good enough. I shouldn’t ask for that raise or that promotion.’ ”

  
  

  Her own Inner Critic roared to life when she was first contacted about the CEO job at Linkage, she recalled. Although she had served in major executive roles, her negative voice told her that she was not qualified, that she needed to hold the No. 2 position at a company before being a CEO, and that she would not have enough time for her family. Fortunately, before she talked herself out of seeking the job, she talked with three male colleagues who, without a moment’s hesitation, assured her that she was indeed ready to be a CEO. The situation taught her “the critical importance of allies – men or women – who can help you see what you might not see yourself.”

• Clarity. When women are struggling with career advancement and seek McCollum’s advice, “I say, ‘Tell me what you want’ … Because when you can articulate what you want, the world will conspire to help you get it,” McCollum said. “But many women will say, ‘Nobody’s ever asked me that.’ … Or ‘I’m too busy doing my current job that I couldn’t possibly imagine the next job.’ And then the saddest one for me is when they say, ‘I’m afraid to put it out there.’ ”

  
  

  It is important to have clarity in your own mind about what you are seeking, McCollum said. In Her Own Voice includes advice on writing your own clarity statement -- and personal visioning exercises to help you if you are having trouble.

• Proving Your Value: “This myth that we are going to put our heads down, and we’re going to work harder and harder and harder, and we’re going to say yes to every opportunity… and someday someone is going to notice and they’re going to give us that promotion, they’re going to give us that raise,” McCollum said.

  
  

  Closely related, she added, is your own “Internal Bias” – the belief that if you want something done right, you have to do it yourself, at work and perhaps at home as well. But insisting on doing everything yourself robs your colleagues – and perhaps even your spouse – “the chance to show their own excellence, even if their way of doing something isn’t exactly the way you would do it,” McCollum said. Looking back on her own career, she wishes she had engaged her those around her more instead of working so hard, she added.

• Making the Ask, such as for a promotion, raise, or more flexible work schedule – and expecting to get it. “Women have a tendency to make an equal ask as men, but when we’re told no, we tend to retreat faster and don’t come back. We also tend to ask for what we believe is possible, not necessarily what we want or believe we deserve.”

  
  

  The result, research shows, is that women are paid significantly less than their male counterparts over the course of their careers. Do your research ahead of time to make a business case for your ask, and start from the mindset that you deserve this -- something that men tend to naturally believe, McCollum said.

At a time when women make up only 29% of C-Suite positions in corporate America, it is important to understand the hurdles – and that they are surmountable with the right strategies and a dose of courage.