Your Virtual Mentors - 7 Crucial Lessons from F500 Women CEOs

May 29, 2024

TLDR: Not all of us have the mentors we need, that's why having F500 women CEOs as virtual mentors matter. Scroll down for the 7 crucial lessons we can learn from them.

Sometimes We Need a Little Help

Early in my career I had the best mentors - for my professional brand! They elevated my confidence, connected me to the development and networking resources I needed, gave me straight feedback and encouraged me to accept opportunities. I  hope you've also had the gift of having people like that in your corner.

But when it comes to Business Savvy, I pretty much taught myself using virtual mentors...among them the Fortune 500 CEOs.

You can accelerate your career by using them, too!

Asking Conventional Questions

Most women are inundated by conventional advice for career success - as are managers, coaches, HR Talent pros, Leadership Developers, etc. This means that when it comes to professional/leadership development, the hammer we use is assembled with advice like: be confident/deal with imposter syndrome, get mentors (and sponsors), speak up, develop executive presence, be more assertive, network, self-promote, etc.

Feedback we hear, self-assessments, 360º assessments and other development tools  often over-emphasizes these important, but incomplete pieces of advice.

And, because conventional advice is prevalent, it's embedded within AI. To illustrate how prevalent, I used Investopedia's list of the Top 10 Women CEOs as virtual role models and mentors. With a little help from* (an AI assistant created by Anthropic) and edits by me, it's easy to discover information about these women related to 8 familiar areas:

  • Confidence: All the CEOs are described as exhibiting self-assurance, decisiveness and instilling confidence in others. This points to the importance of self-confidence in leadership.

  • Mentors: Most credited mentors with providing guidance that boosted their confidence and leadership abilities early on. Mentorship is crucial for career growth. 

  • Communication: They are all praised for clear, direct communication skills - an essential competency for executives.

  • Executive presence: They project credibility, expertise and inspirational leadership, blending gravitas with approachability. This balance is key.

  • Career advancement: Taking risks by volunteering for challenges was a common theme. Willingness to step outside comfort zones aids career growth.

  • Assertiveness: Their steady rise into top leadership implies consistently asserting themselves to attain opportunities.

  • Imposter syndrome: Overcoming self-doubt was likely required to progress into the CEO role, as they took on increasing responsibility. 

  • Self-promotion: Tactfully promoting their vision and achievements was likely needed to reach the heights of corporate leadership.

But what if we ask ourselves even better questions? If we dig deeper, what else can we learn from the careers of these accomplished women and then use to advance in our careers? Surely, these F500 women CEOs didn't advance on the basis of this advice alone?

Ask About Business Savvy

To consider these remarkable women's careers in light of Business Savvy (business, financial and strategic acumen), I asked to discover what he could about how they developed and demonstrated business, financial, and strategic acumen. Here are the resultant mini-bios.

1. Gail Boudreaux (Anthem)

As a veteran of the complex healthcare industry, Gail Boudreaux has cultivated sharp business instincts leading organizations through dynamic change. She leverages her business acumen to make bold moves, like acquiring competitor Cigna's Medicare Advantage business to expand Anthem’s footprint.

Boudreaux also applied financial acumen to optimize Anthem’s performance by divesting less profitable units to focus resources. Her strategic acumen is transforming Anthem into a broad healthcare enterprise, expanding into areas like data analytics. Boudreaux is a case study in acquiring and activating diverse business skills.

2. Carol Tomé (UPS)

When Carol Tomé was named UPS’s CEO, she drew on decades of honing financial acumen as Home Depot’s CFO. Her business instincts come from managing huge volumes as an executive at a retail giant.

As UPS CEO, Tomé used her financial acumen to initiate a cost-cutting program to make operations leaner. She also enrolled in delivery worker training herself to gain strategic insights!

Tomé’s strategic and business savvy is leading UPS’s evolution into an integrated logistics provider. Her varied acumen is a blueprint for translating financial discipline into strategic growth.

3. Jane Fraser (Citi)

Citi CEO Jane Fraser is a example of leveraging specific financial acumen into broad business success. Her background in investment banking provided strong financial grounding to lead a major institution.

As head of Citi’s investment bank, Fraser sharpened her M&A expertise while strengthening returns. This demonstrated her strategic instincts for smart growth.

As CEO, Fraser is now applying her acumen to a banking giant, optimizing profits while positioning Citi for the future. Her journey shows how targeted financial experience can elevate strategic business thinking.

4. Corrie Barry (Best Buy)

Corrie Barry’s 19-year tenure at Best Buy allowed her to progressively build strategic and financial acumen. As CFO initially, she developed financial rigor crucial for a retail operation.

As CEO, Barry has combined this financial discipline with sharp business instincts to transform Best Buy’s store and online models. Her strategic acumen is focused on evolving Best Buy’s customer experience.

Barry’s ability to blend financial knowledge with visionary business thinking is key to Best Buy’s continued success. She represents broadening specific functional acumen into multi-dimensional leadership.

5. Tricia Griffith (Progressive)

Tricia Griffith honed strong financial acumen for leadership by serving as Progressive’s CFO for nearly a decade before becoming CEO. This gave her concrete operational insights.

Griffith applies this financial background to keep Progressive profitable and financially stable as it navigates a period of elevated claims. Her business instincts align with Progressive’s data-driven culture.

Griffith’s strategic use of her financial knowledge to expand Progressive’s lead in usage-based insurance shows how targeted acumen can enhance overall leadership thinking.

6. Mary Barra (GM)

Mary Barra leveraged her robust strategic and business acumen shaped by 30+ years at GM in engineering and operations roles. This provided first-hand understanding of the auto value chain.

As CEO, Barra applied this acumen to make tough calls like exiting unprofitable markets and overhauling production approaches. Her instincts align GM with future needs like electric vehicles. 

Barra exhibits using hard-won insider knowledge to transform strategic thinking. Her blend of focused operational experience and wide business vision provides a model for developing leadership acumen.

7. Thasunda Brown Duckett (TIAA)

Thasunda Brown Duckett gained specific financial acumen from high-level banking roles before becoming TIAA’s CEO. This acumen allows her to employ financial rigor in TIAA’s operations.

Duckett combines this with the strategic outlook to expand TIAA’s acquisition of investment management firms to diversify assets. Her business instincts drive providing differentiated client experiences.

Duckett represents leveraging niche financial expertise to elevate strategic thinking in a new industry context. Her journey shows transporting acumen across sectors to advance as a leader.

8. Safra Catz (Oracle)

Catz gained extensive financial acumen with senior roles in investment banking earlier in her career. This acumen enables her to make financially prudent decisions as Oracle CEO, like emphasizing cloud revenue growth.

Her strategic approach of expanding Oracle's capabilities through acquisitions demonstrates business instincts honed over time.

Catz exhibits leveraging deep financial expertise to inform wider strategic thinking and vision.

9. Rosalind Brewer (Walgreens)

Brewer acquired business acumen from senior operations roles at companies like Walmart and Starbucks. As Walgreens CEO, she applies this acumen to transform retail operations and strengthen digital engagement.

Brewer's background provides first-hand understanding of consumer experiences to inject strategic insight.

Her vision to expand Walgreens into a neighborhood health destination shows strategic instincts grounded in practical business knowledge.

10. Karen Lynch (CVS)

Lynch built strategic leadership acumen over years managing CVS's core retail pharmacy business. This provided intimate knowledge of industry dynamics to inform business moves as CEO.

Lynch demonstrates acumen by strategically shifting CVS's focus toward healthcare services.

She exhibits ability to leverage insights from specialized business experience to guide strategic transformation.

With their focus on the development and demonstration of business, financial and strategic acumen, these mini-bios reveal often invisible keys to success.

What's a Woman To Do?

When it comes to career options and progression, consider these 7 tips summarized from the experiences of the Top 10 F500 Women CEOs (with a little help from

  1. Take on international/global roles like Mary Barra did to build acumen in different business contexts.

  2. Seek out P&L management opportunities like Gail Boudreaux to connect finance and operations and like Carol Tomé working directly in operations for strategic insights.

  3. Obtain experience across business functions like Jane Fraser's journey from investment banking to leading operations.

  4. Fill non-traditional roles like Tricia Griffith taking on strategy as CFO to broaden perspective.

  5. Pursue cross-sector experience like Thasunda Brown Duckett’s financial background applied in new industry.

  6. Command the data like Rosalind Brewer leveraged customer analytics to sharpen business instincts.

  7. Take board positions. This isn't derived from these 10 women, but from my own research into earlier F500 women. Most of them were on boards before being elevated to CEO. Why? Because it prepared them for seeing the business through the eyes of the board.

To get to where they are now, these CEOs have passed through the career stage where you are. Taking guidance from them will serve you well.

Catch you next time!


PS Was this of value to you? Share the content with a colleague or friend so she can benefit as well.

PPS I refer to Claude as "he/him" - even though Claude can be a woman's name - because I like the non-stereotypical reality of having a male assistant. Here's what Claude thinks about this, "I'm an AI assistant created by Anthropic to be helpful, harmless, and honest. I don't have a gender identity."

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