Launching Women Into Leadership Through the Chief of Staff Role




While many parents, women included, adjusted their full-time work schedules or took time off in the midst of the pandemic because of caretaking restraints, many will be returning to the workplace now that we’re digging out of the situation. One outcome of the pandemic was painfully clear: women deserve better support systems and flexible work models in order to thrive in their careers.


We hope that the collective experience of remote work will encourage more employers to offer flexible options that will allow them to balance competing priorities while building a successful career. In our focus on the chief of staff role, we’ve found it can help propel women into the highest levels of leadership. Women are often an incredibly good fit for the role because of their skills and approach, which provides them the opportunity to shine within the C-Suite and chart a path for success down the road.


A Good Fit

The core responsibilities of the chief of staff role oftentimes align well with the many responsibilities women balance in their professional and personal lives. These shared characteristics tend to fit the chief of staff role and indicate a signal of long-term success. It's almost like they were made for each other. Here are just a few examples:


  • High EQ: Women leaders tend to be more empathetic of those around them and are able to read a room quickly and accurately, an incredibly useful skill as a chief of staff. Women are also more adept at adjusting to transitions and leading calmly in times of crisis, making them an effective chief of staff.

  • Multitasking: The chief of staff role provides ample opportunity for “juggling,” whether it’s attending to various fire drill items all at once, dealing with competing priorities, or just generally taking on anything that the CEO or executive doesn’t have the bandwidth for. Have you ever watched a mom in action for more than five minutes? We were made for this.

  • Communication: Undoubtedly, women and men communicate differently. According to research presented in Forbes, women’s strengths lie in listening and reading body language and nonverbal cues. Chiefs of staff are often expected to communicate with various stakeholders in order to influence positive outcomes for the organization, so these communication skills come in handy.

  • Detail-oriented: Many women are experts at focusing on the details and creating systems of organization to keep them all straight. This is a key element of a chief of staff role.

  • Being the “second brain”: Since women are typically better listeners, more empathetic, and more aware of nonverbal cues, they are often more attuned to what’s happening above and beneath the surface, making them the ideal “second brain” of your organization.


Prepping for Leadership

While women continue to shatter glass ceilings and earn their rightful place in leadership roles, there is still much work to be done to achieve parity with men. We’d be remiss not to mention that the pandemic has taken down some of these gains as well (more on that later).


According to a McKinsey study on women in the workplace, at the beginning of 2020, the representation of women in corporate America was trending upwards, with the most pronounced gains in senior leadership. Between January 2015 and January 2020, representation in the C-suite grew from 17 to 21 percent. Women remained dramatically underrepresented—particularly women of color—but the numbers were slowly improving.


Likewise, during this period of time the chief of staff role has expanded its influence to the startup and entrepreneurial realms and the need for more qualified individuals continues to grow. A chief of staff role is an ideal starting block for women to gain a stronghold into the inner workings of an organization’s leadership. For many, the role is two years of prep work for the C-suite, a dynamic space where women can continue to build their career.


Here are a few notable chiefs who have moved on to leadership positions:

  • Sheryl Sandberg, chief operating officer at Facebook, was Larry Summers’ chief of staff when he was U.S. Treasury Secretary

  • Aileen Lee, head of Cowboy Ventures, a VC firm in Palo Alto, California, was chief of staff for Mickey Drexler when he ran The Gap.

  • Aretae Wyler, former chief of staff to Atlantic Media founder David Bradley, is now general counsel and chief administrative officer of the company.


Pandemic Pause

It’s no secret the pandemic has been especially challenging to women in the workplace, specifically those in active caretaker roles. The McKinsey study we referenced earlier cited as many as two million women are considering leaving the workforce due to challenges created by the COVID-19 crisis. Reasons women shared for why included:

  • lack of flexibility at work

  • feeling like they need to be available to work at all hours, or “always on”

  • housework and caregiving burdens due to COVID-19

  • concern that their performance reviews would be negatively impacted by their additional caregiving responsibilities during the pandemic

  • not being able to share honestly with their teammates or managers about the challenges they are facing

  • not being included in decisions that affect their day-to-day work

  • feeling pulled in all different directions, making work focus challenging

Women are especially prone to dual responsibilities of caregiving and managing their careers. Isn’t it time we started asking why that is? Why do women bear the brunt of “other” responsibilities, even when they’ve intentionally set up career goals for themselves? How can we break out of this cycle? Finding supportive partners who want to equally bear the burden of responsibilities is one step. Advocating for flexible and culturally-responsive workplaces is another.


It’s a fact that women are becoming impactful, powerful, smart leaders whose compassionate perspective and strong listening abilities can be a determining factor in successful organizations. We know from personal experience that women make exceptional leaders. The business world would do well to provide more opportunities for women to succeed in the workplace through leadership roles while also creating flexibility to attend to the outside responsibilities that are important to them. This isn’t rocket science, but it requires a bit of a culture shift and perspective adjustment, which we can certainly get behind.