The 5 Top Unspoken Pain Points for Women CEOs

Woman with forehead leaned against the side of a bookcase

“Uneasy is the head that wears a crown.” -Henri IV, part 2.

If you’re leading an organization, whether your title is “CEO,” “Executive Director,” “President,” “Chancellor,” or “Founder” you know exactly what this means. But for clarity sake, according to No Sweat Shakespeare it means “those charged with major responsibility carry a heavy burden that makes it difficult for them to relax.” I’ve met a lot of women leaders of organizations who appear relaxed. What kind of image would you be projecting if the stress of your organization shown on your face at every meeting, conference, event, and interview. You wouldn’t show as confident and thus lacking. The stress wouldn’t be attributed to the functioning of the organization, it would be attributed to you. But…

Most women leaders can say they are anything but relaxed on a regular basis. I definitely could not say that during my time as a CEO. I was tremendously stressed. As with any organization, my organization had some big issues and extreme challenges. Often people assume that therein lies the issue…the organization as a business. If you can right the business then the stress will disappear. But there are greater pain points that women leads have to contend with that rarely get talked about publicly. That’s what this space, and specifically my newsletter discusses.

Let’s open pandora’s box…shall we.

Isolation

Not only is the head that wears the crown uneasy, it is lonely. Unless, you have a group of peers who are also friends you can trust deeply, there is no one to talk to about the burdens, issues, frustrations and even celebrations of what it’s like to run an organization.

I had a colleague whom became an appellate court judge. I asked him very early into his tenure what it was like. He had really wanted the position. He was extremely excited, as we all were when he was appointed. So I was expecting his answer to be a positive one. Instead he leaned into me and said very softly, “It’s lonely.” Feeling both compassion and curiosity I asked him “How?” And our conversation ensued from there. It wouldn’t be for many years later that I understood and experienced personally what he meant.

As a leader you can’t outwardly discuss the challenges &c.. you’re facing with your staff. You could go home and discuss things with a spouse, good friend, or parent. But unless they’ve actually led an organization during their careers, they can only empathize. Often times what a leader, like you needs is real business, emotional and mental advice from someone who has been in your shoes. There are very few people with whom you can admit fear or doubt, process mistakes, strategize politically, or be fully honest.

Board/Shareholder Management and Governance Politics

Boards and shareholders are tricky. They can love you one minute and literally hate you the next. In a less dramatic description, they can think you are perfect of the job and then suddenly question your ability to do the work they were so sure you were meant for. But most of the time operations is a smoke screen. There have been more women leaders than I can count who have come into organizations where the prior leader (often male) was abysmal at their job. Harvard actually did a study on why organizations keep hiring ineffective males.

Board/shareholder management is about understanding power, hidden agendas, personalities, influence, and gossip. Managing these groups of people is a full-time job in and of itself. No person can please everyone. When you’re a women CEO constantly trying to figure out who is the right person to “please,” it often results in you as contortionist if there isn’t true alignment. Even if there appears to be alignment, something can go terrible wrong behind the scenes unbeknownst to you.

The McKinsey Report “Double-Bind.”

Just because you’ve “shattered” the glass ceiling doesn’t mean that gender assumptions don’t exist. What’s the double-bind? Basically it the double standard. It’s the same attributes that make men great leaders but make you a questionable leader open to judgement, criticism, and oversight.

If you are decisive you are too harsh.

Strategic then you are too cold.

Warm then you’re not tough enough.

Collaborative? Then you reek indecisiveness.

I was new into my position and met with a donor. He asked my strategy for the organization. I told him. He replied, “You won’t be able to do that.” The table of other organizational guests went silent. I immediately thought to myself, he would never say that to a white male CEO sitting across from him.

I also had a male subordinate on my executive team request of me, that I provide him with my plan for engaging with this donor. I did not. Here is the kicker. This subordinate was not in development. He just needed to monitor my interactions as it was his “friend.” The double-bind or just basic patriarchy still exists, especially since only 29% of the world’s leaders are women.

Identity Crisis & Purpose Drift

I don’t believe that when a woman finally reaches the point of leading organization she’s prepared for the potential identity crisis and purpose drift that can come with it, especially if you’ve spent your life out-sourcing your identity and emotional stability (which most women have been conditioned to do, myself included).

When you reach the top of an organization you fail to realize that the chase to get there is over. “Yes.” You can go to the next organization. But many women have been working their whole careers, decades, to get to this one title. For driven women the chase is frustration and exhilaration wrapped into one. When you get “there”, the chase will never be the same. For some, that is extremely disorientating, because the next obvious rung doesn’t exist anymore.

Secondly, external validation slows way down. Women are groomed from a young age to find their source of identify through validation. It starts with. “Be a good girl.” “You’re such a good girl.” There is no foundation, outside of performance that anchors her. Additionally, when that validation of performance fluctuates (which it will because it comes from people) a excellent, good, okay or bad or unspoken performance “review” (not in the literal sense) will shake her emotional stability. When you become a CEO the external validation wanes. In fact, when things go wrong it’s the leaders fault, when things go right and well it’s with the work of everyone else. That reality can cause a severe identity crisis and depression if unchecked.

When one is in the throws of an identify crisis you can’t help but ask yourself “Why am I here?” “Is this even how I want to show up?” “Why doesn’t this feel as great as I thought it would?”

Decision Fatigue

I’ll be blunt. After I was done with working for the day as a CEO, the last thing I wanted to do at home was make another f&*! decision. Any decision. No matter how small it was, I did NOT want to make it. Why? Because I had decision fatigue and most women CEOs do as well. When you lead an organization you have what seems like a million decisions coming at you everyday. You start to wonder how so many capable, bright people in your organization cannot make a decision without your input. But every decision you makes seems and often times (but not all the time) is high stakes because every decision you make as a leader is high impact, it’s reputationally risky, it’s financially consequential, and it affects people. Add to this, most of the time you’re making these decisions with incomplete information. Therefore, for me making a decision about dinner, no matter how inconsequential, was something I wanted nothing to do with. The irony is that the decisions about my family are the most important decisions I wanted and needed to make. But I couldn’t do it most days, and most women leaders can’t do it as well.


Now that pandora’s box is open, where do we go from here? This blog will start parsing out the signs symptoms and effects of these pain points, and how to manage them, as well as the newsletter. They really require an on-going conversation.


What to do next

  1. Tell me what you think. Have you experienced any of the above pain points? If so, how are you handling it? Leave a comment below.

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