The Gatekeeper Blog
Insights into the chief of staff role

If you’re a female chief of staff, then you’re probably already familiar with the elephant in the C-suite.

Despite years of effort to close the gender gap, male executives still outnumber female executives seven to one.1 And male CEOs outnumber female CEOs by a whopping seventeen to one.2 What’s worse, according to a recent Morningstar study, more than half of all companies do not have a single female executive officer. Not one.3 And the numbers are even more dismal for Black women and women of color.4

Despite all our best efforts it seems we’re going backwards not forwards.

Caroline Pugh, Chief of Staff to Aneesh Chopra, President of Care Journey and former US Chief Technology Officer, offered a new solution. In a recent interview in Forbes, she argued that female chiefs of staff may be our last best hope for closing the gender gap in the C-suite. 5

“More and more women are the right-hand women to CEOs of major Fortune 500 companies. They are being positioned as the next wave of C-suite executives themselves which is really exciting. The chief of staff role could be the very role that finally evens out the gender disparity in boardrooms.”6

While I share Pugh’s hope that a new generation of women might finally enter the C-suite in significant numbers, I’m worried that we’re still waiting for a male CEO to open the door.

Pugh isn’t the first person to suggest that women get a powerful male mentor or sponsor if they want to break into the C-suite.7 In this top-down model of mentoring, the all-knowing (typically, white male) CEO teaches his female mentee everything she needs to know to succeed in business.

To be fair, research shows that women who are mentored by men make more money, receive more promotions, and report greater satisfaction with their career path, especially in maledominated industries.8

Facebook COO, Sheryl Sandberg, who once served as Chief of Staff to former Secretary of the Treasury Lawrence Summers, comes to mind. As does Amy Cheetham, VP at Costanoa Ventures, who previously served as Chief of Staff to Zuora’s head of North America and Asia Pacific sales.9

But there’s a problem with this all-knowing guru model of mentoring.

Unless there is a clear sharing of power, the female chief of staff can end up as “the most overpriced executive assistant ever” according to Dex Hunter-Torricke, former Chief of Staff to Sir Alan Parker, chairman of Brunswick Group.10 The result is, “You have people who actually could be there to make leadership decisions, and instead they’re picking up sandwiches.”11

So instead of being positioned to become the next COO, you end up a glorified sandwich girl.

This is why I believe we need a new model of mentoring that avoids this trap…

Because research shows the old top-down view of mentoring no longer serves women in our diverse and fast-moving business environment.12

First, a good male mentor is quite literally hard to find. In the aftermath of #MeToo, LeanIn.org/ McKinsey reports that fewer men are willing to mentor women.13

I was shocked when good, decent men I work with, suddenly started asking me if I could join them for dinner with their female mentees, as if I was some kind of Victorian chaperone. They tell me they are afraid of being falsely accused.

When you factor in the 17 to 1 odds that the CEO is a man, this unintended backlash means that women have even less access to high-level mentors.

Second, even when good men are willing to mentor women, these men often see themselves as the “white knight” riding to our rescue.14 As Jennifer de Vries points out in her research, this just reinforces the stereotype that a woman needs a powerful man in order to lead and that we cannot succeed on our own.15

Third, the top-down all-knowing male guru model of mentorship just isn’t scalable.16 It might work for a few key women, but it leaves the majority of us without a mentor and without the support we need to succeed. 17

Finally, even if you are lucky enough to find a high-level mentor, it’s unreasonable to expect that one person will be able to address all your mentoring needs both personally and professionally. Especially when that high-level mentor is already overcommitted with other duties and responsibilities. 18

So, what does work?

Two new mentoring models have emerged that, when combined, provide a powerful alternative to the old top-down guru-based model – especially for women.

The first is called network-based mentoring. It was developed by Dr. Kerry Ann Rockquemore, Founder of the National Center for Faculty Development & Diversity. She created it to help women and people of color transition better toward tenure. 19 And it can help female chiefs of staff transition better into their new role too.

In network-based mentoring, the female mentee works with her mentor to identify the specific skills and connections she needs to succeed. Then her mentor helps her to build a broad and deep network of mentors to meet those needs. 20 The result is more like a mentoring roadmap than a white knight on a horse.

Network-based mentoring encourages all of us to take responsibility for our success and to ask for what we need from the mentoring relationship. This can be uncomfortable at first because many of us were not taught to network. 21

Men teach other men that mixing business and friendship is how you get ahead. As a result, men tend to network with a clear goal in mind and they are not afraid to ask for what they want.22 Women have a harder time asking.

Network-based mentoring pushes us to get better at asking. If you are a new female chief of staff, you can use this network-based mentoring model to create a list of your key mentoring needs. Then you can sit down with the CEO and identify other senior executives who can help you fill in these gaps. That way you’re not waiting on the CEO to provide everything you need to successfully transition into your new role.

In addition, as a key connector between the C-suite and the rest of the staff, you’re in a unique position to help other executives create their own mentoring roadmap and connect them to potential mentors across the entire company.

Instead of waiting for the perfect unicorn of a mentor to appear, everyone can start filling in their own mentoring gaps one conversation at a time across a broad network of experienced leaders. As a result, the company moves forward faster.

The second alternative to the old-school top-down mentoring approach is co-mentoring or reciprocal mentoring. 23

In reciprocal mentoring both the mentor and mentee bring their own insights, life experience, and skills to the table. Reciprocal mentoring isn’t about a bunch of mentees sitting at the feet of the mentor guru. Instead, it’s about humility, shared power, and a willingness to listen. 24

The payoff is worth it. Research shows that reciprocal mentoring boosts productivity, increases fulfillment, and provides opportunities for growth for both partners. 25 It also has greater lifelong impact than traditional top-down mentoring. 26

Reciprocal mentoring can also help men and women get comfortable with co-ed mentoring in the wake of the #MeToo movement because co-mentoring is about shared power, not hierarchy. Both men and women who participate in reciprocal mentoring are more resilient, have clearer priorities, and enjoy more satisfaction in work-life balance. 27/28

Reciprocal mentoring can lead to greater gender equality in the C-suite as well.29 30That’s good for the bottom line. Because organizations with greater diversity and support for all staff, enjoy a statistically significant boost in profitability and performance.31

For female chiefs of staff, reciprocal mentoring can help you avoid the “sandwich girl” trap. It creates a strong partnership with the CEO and makes it easier for you to use your power and influence to lead from behind.

As a female chief of staff, you’re also in a unique position to use your influence to create mentoring programs and initiatives that benefit all women. Because before we can close the gender gap in the C-suite, we must first close the gender gap when it comes to mentoring.

A survey from Development Dimensions International, a global leadership consulting firm, discovered that less than 4 in 10 female executives have ever had a formal mentor. 32

And it’s not that women aren’t willing to be mentors, they are. Over 70% of women said they would be willing to mentor women at work. 33

So why aren’t they?

Women are not asking for a mentor and often they don’t see themselves as a mentor to other women. 34 One of the reasons men typically have more mentors and also mentor more, is because they ask, and are asked. 35

One way you can encourage more women to engage in mentoring is to use your position to create a formal structure that promotes these relationships. You can also help to build a culture that encourages seeking help and giving support.36/37

As a female chief of staff, you can also reach out to more junior women in the organization. It’s critical that these women have access to the organization’s more powerful women, particularly in male-dominated fields.38 As Sian Beilock, President of Barnard College and a cognitive scientist, explains, “Research shows that when women are exposed to powerful female role models, they are more likely to endorse the notion that women are well suited for leadership roles.” 39 In other words, when women see you as a leader, they begin to see themselves as leaders.

The ultimately helps to close the gender gap in the C-suite. In fact, organizations that encourage or require senior executives to mentor women report the highest percentage of women at the executive level.40

There is one final critical connection women need in order to close the gender gap in the C-suite

. And it’s not what you might think…

Recently a group of researchers followed a bunch of brand new bright-eyed MBA graduates. They looked at their networking skills and then they compared them to their job-placement results. 41 They were shocked at what they discovered.

For men the secret to landing the best jobs with the biggest paychecks and greatest authority was being super connected to a lot of other highly connected people.42 But for women, being central to a highly connected network wasn’t enough. The most successful women also needed something else.

Women needed an “old girls’ club” in order to succeed at the highest level in business. 43

According to the study coauthor Brian Uzzi, that’s because men and women need different information to succeed. Men need access to more public information like who is hiring and what you need to know to apply.

But women need more.

Women need a second women-only peer group that can provide insider information about a company’s culture and attitude towards female executives, as well as advice about how to survive and thrive in a male-dominated industry.44

“You need that private information to understand how to negotiate within a world where you’re being held to different standards.”45

That private information is worth its weight in gold to women looking to break into the C-suite. In fact, women in the study who had a second female-only inner circle went on to land jobs with nearly triple the salary and authority than women who relied only on their co-ed network.46/47

If you want to succeed in what is statistically a male-dominated C-suite environment, you need to build your own women-only inner circle. Then you can use that female network to help recruit other women to the chief of staff role. In fact, that’s exactly what many female chiefs of staff are already doing today.48

While I have never been a female chief of staff, I have spent most of my career as a woman in male-dominated industries. First as a business manager for an international contemporary art gallery in the early 90s, then as a venture capitalist in the early 2000’s, and finally for the past fifteen years as a copy chief and copywriter for some of the largest online marketers.

Seven years ago, I founded a female-only mentoring collective for marketers, entrepreneurs and copywriters. I have personally road-tested all of the advice in this article in the Titanides Mentoring Collective.

In the Titanides we use a combination of reciprocal and network-based mentoring to help more women grow and succeed in business. To help facilitate this process, I invested in a program called MentorCloud that links women with female mentors in key areas much like a dating platform and includes specific actions, steps and feedback loops proven to make the mentoring relationship more effective.49

The results have been extraordinary. Not only are women finding access to more jobs, but they are receiving mentoring on exactly how to apply for those jobs, how to negotiate pay increases, how to bid contracts, and much more. Our mentoring program is designed to help close the gaps between male and female entrepreneurs.

I’ve seen firsthand the results this kind of facilitated women-only mentoring and networking can have in the male-dominated world of internet marketing. And I believe it can have a powerful impact on female executives and women in the chief of staff role as well.

As a thank you to all the women who are currently blazing a new trail to the C-suite, I wanted to share some of our collected wit and wisdom from female entrepreneurs in the Titanides Mentoring Collective with you. You can download a free copy of our book, cheekily titled, “Why Didn’t Anybody Tell Me This Sh*t Before” at www.talesfromthetop.com. There’s no charge, this is a gift from our female-only network to you in the hopes it might inspire you to start your own. In the meantime, feel free to join us. We’d love to have you.

Marcella Allison is the founder of the Titanides Mentoring Collective, an organization dedicated to helping female entrepreneurs, marketers and copywriters succeed at the highest level in the direct response industry. She is also a top direct response copywriter herself who has generated over a hundred million in sales for her clients. And she is an in-demand mentor and copy chief for the next generation of copywriters.

Laura Gale is a ghostwriter and writing coach. She works with entrepreneurs from all over the world to publish stories that leave a legacy. Laura is also a bestselling author in her own right and is based in Europe.

References

1. Jackie Cook. “The Gender Gap in the C-Suite: A Window on the Gender Gap at the Top of Corporate America and
the Case for Better Disclosure,” Morningstar. February 17, 2021.
https://www.morningstar.com/lp/gender-pay-gap.
2. Naomi Cahn. “Women’s Status and Pay in the C-Suite: New Study.” Forbes. February 19, 2021.
https://www.forbes.com/sites/naomicahn/2021/02/19/womens-status-and-pay-in-the-c-suite–newstudy/?sh=2ddd93d43762
3. Cook.
4. Cook.
5. Sarah Coury et al. “Women in the Workplace.” McKinsey & Company. September 30, 2020.
https://www.mckinsey.com/featured-insights/diversity-and-inclusion/women-in-the-workplace
6. Marcus.
7. W. Brad Johnson and David G. Smith. “Mentoring Women Is Not About Trying to ‘Rescue’ Them.” Harvard
Business Review. March 14, 2018.
https://hbr.org/2018/03/mentoring-women-is-not-about-trying-to-rescue-them
8. Aarti Ramaswami et al. “Gender, Mentoring, and Career Success: The Importance of Organizational Context.”
Personal Psychology 63, no. 2 (May 12, 2010): 385-405.
https://onlinelibrary.wiley.com/doi/full/10.1111/j.1744-6570.2010.01174.x
9. Anna Kramer. “Everybody Wants a Chief of Staff, Even When They Don’t Know Why.” Protocol. October 09, 2020.
https://www.protocol.com/chief-of-staff-tech-company
10. Kramer.
11. Kramer.
12. Kerry Ann Rockquemore. “A New Model of Mentoring.” Inside Higher Ed. July 22, 2013.
https://www.insidehighered.com/advice/2013/07/22/essay-calling-senior-faculty-embrace-new-stylementoring
13. Lean In. “How Men Can Support Women at Work.” January 2018.
https://leanin.org/mentor-her
14. Johnson. “Mentoring Women Is Not About Trying to ‘Rescue’ Them.”
15. J.A. de Vries. “Champions of Gender Equality: Female and Male Executives as Leaders of Gender Change.”
Equality, Diversity and Inclusion 34, no. 1 (February 09, 2015): 21-36.
https://www.emerald.com/insight/content/doi/10.1108/EDI-05-2013-0031/full/html
16. Rockquemore. “A New Model of Mentoring.”
17. Rockquemore. “A New Model of Mentoring.”
18. Rockquemore. “A New Model of Mentoring.”
19. Rockquemore. “A New Model of Mentoring.”William Ford. “Tenure Crusader.” Diverse. January 11, 2011.
https://diverseeducation.com/article/14598/
20. Rockquemore. “A New Model of Mentoring.”
21. Caroline Castrillon. “Why Women Need to Network Differently than Men to Get Ahead.” Forbes. March 10, 2019.
https://www.forbes.com/sites/carolinecastrillon/2019/03/10/why-women-need-to-network-differently-thanmen-to-get-ahead/?sh=58757594b0a1
22. Castrillon. “Why Women Need to Network Differently Than Men to Get Ahead.”
23. Johnson. “Mentoring Women Is Not About Trying to ‘Rescue’ Them.”
24. Johnson. “Mentoring Women Is Not About Trying to ‘Rescue’ Them.”
25. Johnson. “Mentoring Women Is Not About Trying to ‘Rescue’ Them.”
26. B.R. Ragins. “Relational Mentoring: A Positive Approach to Mentoring at Work.” Oxford Handbooks. August 2011.
https://www.oxfordhandbooks.com/view/10.1093/oxfordhb/9780199734610.001.0001/oxfordhb9780199734610-e-039
27. Ragins.
28. Reciprocal Mentoring Lab. “Equipping Men and Women to Mentor and Sponsor More Confidently through
Reciprocal Mentoring.” 2021. https://reciprocalmentoringlab.com/
29. Lean In. “How Men Can Support Women at Work.”
30. Johnson. “Mentoring Women Is Not About Trying to ‘Rescue’ Them.”
31. V. Hunt et al. “Delivering through Diversity.” McKinsey & Company. January 18, 2018.
https://www.mckinsey.com/business-functions/organization/our-insights/delivering-through-diversity#
32. Stephanie Neal, Jazmine Boatman, and Linda Miller. “Women As Mentors: Does She or Doesn’t She? A Global
Study of Businesswomen and Mentoring.” Development Dimensions International (Publisher). 2013. Source info
from email.
https://www.shrm.org/ResourcesAndTools/hr-topics/employee-relations/Documents/womenasmentors_rr_ddi.
pdf_ext=.pdf
33. Neal.
34. ResearchGate. “The Guiding Hands Mentoring Women.” September 2009.
https://www.researchgate.net/publication/291461108_The_guiding_hands_mentoring_women
35. Neal. “Women As Mentors: Does She or Doesn’t She? A Global Study of Businesswomen and Mentoring.”
36. Sarah Dinolfo and Julie S. Nugent. “Report: Making Mentoring Work.” Catalyst: Workplaces that Work for Women.
January 19, 2010 https://www.catalyst.org/research/making-mentoring-work/
37. Neal. “Women As Mentors: Does She or Doesn’t She? A Global Study of Businesswomen and Mentoring.”
38. Nilanjana Dasgupta and Shaki Asgari. “Seeing is Believing: Exposure to Counterstereotypic Women Leaders and
Its Effect on the Malleability of Automatic Gender Stereotyping.” Journal of Experimental Social Psychology 40.
no. 5. September 2004: 642-658.
https://www.sciencedirect.com/science/article/abs/pii/S0022103104000253?via%3Dihub
39. Siam Beilock. “Research-Based Advice for Women Working in Male-Dominated Fields.” Harvard Business Review.
February 13, 2019. Updated March 03, 2019.
https://hbr.org/2019/02/research-based-advice-for-women-working-in-male-dominated-fields
40. Neal. “Women As Mentors: Does She or Doesn’t She? A Global Study of Businesswomen and Mentoring.”
41. Yang, Nitesh V. Chawla, and Brian Uzzi. “To Land Top Jobs, Women Need Different Types of Networks than Men.”
KelloggInsight. March 01, 2019.
https://insight.kellogg.northwestern.edu/article/successful-networking-men-women
42. Yang.
43. Yang.
44. Yang.
45. Yang.
46. Yang, Nitesh V. Chawla, and Brian Uzzi. “A Network’s Gender Composition and Communication Pattern Predict
Women’s Leadership Success.” Proc. Natl. Acad. Sci. January 22, 2019. https://doi.org/ 10.1073/pnas.1721438116.
https://www.pnas.org/content/116/6/2033
47. Yang.
48. Marcus. “Are You Ready to Become Chief of Staff?”
49. https://www.mentorcloud.com/