About This Episode
In this episode of Reimagining Company Culture, we’re chatting with Sarah Lacy, Founder and CEO of Chairman Me. Sarah Lacy is the Founder of ChairmanMe, a 20-year award winning investigative journalist, author, serial entrepreneur, and a divorced mother to two phenomenal kids. Lacy’s previous startup, Pando, was renowned for calling out bro culture in Silicon Valley years before the rest of the media did. Tune in to learn Sarah’s thoughts on defining and practicing inclusive leadership, promoting accessibility to information for women, advocating for that promotion, and more! DISCOUNT CODE: For anyone interested in participating in the inclusive leadership course called "Be A Better Leader”, use the discount code ALLVOICES for 20% off.
About The Guest
Sarah Lacy is the Founder of ChairmanMe, a 20-year award winning investigative journalist, author, serial entrepreneur, and a divorced mother to two phenomenal kids. Lacy’s previous startup, Pando, was renowned for calling out bro culture in Silicon Valley years before the rest of the media did. Her most recent book is A Uterus Is A Feature Not A Bug: The Working Woman’s Guide to Overthrowing the Patriarchy (Harper Business; 2017). ChairmanMe is an educational platform where badass women learn, support, and connect with one another through our award-winning online courses.
Episode Breakdown

When Sarah Lacy joined us on Reimagining Company Culture, she had spent the previous decade running media companies and writing books about women, power, and the structural forces that hold both back. Her view of the working women conversation was sharper than the one most HR leaders hear at conferences. The career advice industry has produced a generation of self-help frameworks and not nearly enough structural change inside the companies that employ women.

Sarah's argument was direct. The retention problem with senior women is not a confidence problem. It is a structural problem. The companies that lose senior women are the ones whose policies, manager training, and ER processes have not changed enough to support the actual lives those women live. Pretending otherwise has produced a coaching industry that profits from the gap rather than closes it.

Why Senior Women Keep Leaving Companies That Say They Value Them

The data has only sharpened the case. Catalyst research found that more than 455,000 women left the US workforce between January and August of 2025, with caregiving pressures cited as the top driver in 42 percent of voluntary exits. McKinsey's Women in the Workplace research found that for every 100 men promoted to manager, only 81 women are.

These numbers do not improve when companies offer more women's leadership programs. They improve when companies fix the policies, the manager behavior, and the ER infrastructure that determine whether senior women can actually keep building their careers. The shift Sarah was pointing to is from individual development to structural change, and most companies are still investing in the wrong half.

What Structural Support for Working Women Includes

How Do You Redesign Parental Support to Actually Retain Women?

Generous parental leave is the floor. The retention work is in everything that surrounds it. Returnship programs. Manager training on bias and workload around pregnancy. Flexible scheduling that survives the first year back. A documented re-onboarding plan. The companies retaining caregivers are the ones building this surrounding infrastructure rather than relying on leave length alone.

What Does Real Pay Equity Look Like in Practice?

An external pay equity audit run annually. Statistical controls for role, tenure, performance, and location. Public methodology and high-level findings shared internally. The companies that publish results see fewer surprises and stronger trust. The companies that hide the work are usually hiding gaps that show up in the next round of senior departures.

What Actually Works for Retaining Senior Women

Fix the Broken Rung at First Promotion

The single biggest leak in the leadership pipeline is the first promotion to manager. Closing that gap requires structured promotion criteria, calibration sessions across business units, and explicit attention to demographic patterns in promotion velocity. The companies that fix this rung see compounding gains across senior levels over five to ten years.

Train Managers on Bias That Activates at Pregnancy

Bias against working mothers activates the moment a pregnancy is announced. The bias shows up in performance ratings, project assignments, and promotion timing. Manager training that addresses this bias directly is one of the most cost-effective retention investments a company can make. Maternity leave protections are necessary but not sufficient on their own.

Make Senior Women Visible in Decision-Making Forums

Senior women who are present in decision-making forums but rarely heard or attributed face one of the most exhausting forms of inclusion failure. The fix is structural. Meeting facilitation that rotates speaking time. Attribution discipline that credits ideas to the people who raised them. Sponsorship rather than mentorship as the development model. Sponsors give senior women the air cover that mentors cannot.

Where Employee Relations Fits in Retention of Senior Women

The single fastest way to lose a senior woman is to mishandle a complaint she or someone in her network raises. The ER function is where the company's stated commitments meet the hardest cases. Patterns of harassment, retaliation, or discrimination cluster around specific managers and specific decision points. The companies tracking those patterns can intervene early. The companies that are not tracking them lose senior women they will not be able to recover.

DEI work and ER work overlap most clearly here. The same structured intake, anonymous reporting, and pattern analytics that support DEI also protect the senior women whose continued presence depends on whether the company handles cases consistently.

How Does Connected Case Management Show Up in Retention of Senior Women?

It shows up because senior women, more than most demographic groups, watch how the company handles other people's cases before deciding whether to raise their own. A track record of consistent, documented case handling builds the trust that keeps senior women in the company through the hard moments. Inclusion is the cumulative effect of how the company shows up over thousands of decisions.

Frequently Asked Questions About Supporting Working Women

What is the single highest-return retention investment for senior women?

Manager training on bias around pregnancy and caregiving, paired with structural fixes to promotion velocity. The two together produce compounding effects. Either alone underperforms.

How do you measure whether a women's leadership program is working?

Promotion velocity by demographic. Senior-level retention by demographic. Pay equity audited by an external firm. If those three numbers improve year over year, the work is producing results. If only program enrollment is improving, the work is producing brand value but not change.

What is the role of sponsorship versus mentorship?

Mentorship offers advice. Sponsorship offers air cover, public endorsement, and access to high-visibility work. Senior women who get sponsored are promoted at higher rates than senior women who only get mentored. The companies producing real movement on the leadership pipeline have shifted their development models accordingly.

How do you handle a senior woman raising a sensitive case?

With structured intake, a trained investigator, a clear timeline, and follow-through that is documented and reviewed. The cases that go badly are almost always the cases handled informally. Caregiver advocacy often starts with the way a single sensitive case gets handled, and senior women are paying close attention.

How does AllVoices support retention of senior women?

Through structured, anonymous intake, multilingual support, and aggregate analytics that surface patterns by demographic. Employee engagement data and case data together tell the People leader whether the strategy is working in real time.

Sarah was clear that the path forward is also generational. The senior women who stay long enough to redesign the systems are the ones who make the next generation's path easier. The companies that retain them get a return that compounds across decades. The companies that lose them keep paying the same hiring tax with each new cohort, and the leadership pipeline keeps looking the same as it did ten years ago.

The Bottom Line for HR Leaders

Sarah's argument has aged into a structural blueprint. The retention problem with senior women is not solved by more career advice. It is solved by fixing the policies, manager behavior, and ER infrastructure that determine whether senior women can stay. Equity is what survives the audit, not what survives the press release.

The companies that do this work hold their senior women through difficult moments and produce leadership pipelines that look different from the industry average. The companies that do not keep losing the women they say they value, then commission another report on why.

See how AllVoices supports retention of senior women through structured intake and pattern analytics.

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Founder and CEO of ChairmanMe, Sarah Lacy- Invest in DEI from Day 1
Episode 220
About This Episode
In this episode of Reimagining Company Culture, we’re chatting with Sarah Lacy, Founder and CEO of Chairman Me. Sarah Lacy is the Founder of ChairmanMe, a 20-year award winning investigative journalist, author, serial entrepreneur, and a divorced mother to two phenomenal kids. Lacy’s previous startup, Pando, was renowned for calling out bro culture in Silicon Valley years before the rest of the media did. Tune in to learn Sarah’s thoughts on defining and practicing inclusive leadership, promoting accessibility to information for women, advocating for that promotion, and more! DISCOUNT CODE: For anyone interested in participating in the inclusive leadership course called "Be A Better Leader”, use the discount code ALLVOICES for 20% off.
About The Guest
Sarah Lacy is the Founder of ChairmanMe, a 20-year award winning investigative journalist, author, serial entrepreneur, and a divorced mother to two phenomenal kids. Lacy’s previous startup, Pando, was renowned for calling out bro culture in Silicon Valley years before the rest of the media did. Her most recent book is A Uterus Is A Feature Not A Bug: The Working Woman’s Guide to Overthrowing the Patriarchy (Harper Business; 2017). ChairmanMe is an educational platform where badass women learn, support, and connect with one another through our award-winning online courses.
Episode Transcription

When Sarah Lacy joined us on Reimagining Company Culture, she had spent the previous decade running media companies and writing books about women, power, and the structural forces that hold both back. Her view of the working women conversation was sharper than the one most HR leaders hear at conferences. The career advice industry has produced a generation of self-help frameworks and not nearly enough structural change inside the companies that employ women.

Sarah's argument was direct. The retention problem with senior women is not a confidence problem. It is a structural problem. The companies that lose senior women are the ones whose policies, manager training, and ER processes have not changed enough to support the actual lives those women live. Pretending otherwise has produced a coaching industry that profits from the gap rather than closes it.

Why Senior Women Keep Leaving Companies That Say They Value Them

The data has only sharpened the case. Catalyst research found that more than 455,000 women left the US workforce between January and August of 2025, with caregiving pressures cited as the top driver in 42 percent of voluntary exits. McKinsey's Women in the Workplace research found that for every 100 men promoted to manager, only 81 women are.

These numbers do not improve when companies offer more women's leadership programs. They improve when companies fix the policies, the manager behavior, and the ER infrastructure that determine whether senior women can actually keep building their careers. The shift Sarah was pointing to is from individual development to structural change, and most companies are still investing in the wrong half.

What Structural Support for Working Women Includes

How Do You Redesign Parental Support to Actually Retain Women?

Generous parental leave is the floor. The retention work is in everything that surrounds it. Returnship programs. Manager training on bias and workload around pregnancy. Flexible scheduling that survives the first year back. A documented re-onboarding plan. The companies retaining caregivers are the ones building this surrounding infrastructure rather than relying on leave length alone.

What Does Real Pay Equity Look Like in Practice?

An external pay equity audit run annually. Statistical controls for role, tenure, performance, and location. Public methodology and high-level findings shared internally. The companies that publish results see fewer surprises and stronger trust. The companies that hide the work are usually hiding gaps that show up in the next round of senior departures.

What Actually Works for Retaining Senior Women

Fix the Broken Rung at First Promotion

The single biggest leak in the leadership pipeline is the first promotion to manager. Closing that gap requires structured promotion criteria, calibration sessions across business units, and explicit attention to demographic patterns in promotion velocity. The companies that fix this rung see compounding gains across senior levels over five to ten years.

Train Managers on Bias That Activates at Pregnancy

Bias against working mothers activates the moment a pregnancy is announced. The bias shows up in performance ratings, project assignments, and promotion timing. Manager training that addresses this bias directly is one of the most cost-effective retention investments a company can make. Maternity leave protections are necessary but not sufficient on their own.

Make Senior Women Visible in Decision-Making Forums

Senior women who are present in decision-making forums but rarely heard or attributed face one of the most exhausting forms of inclusion failure. The fix is structural. Meeting facilitation that rotates speaking time. Attribution discipline that credits ideas to the people who raised them. Sponsorship rather than mentorship as the development model. Sponsors give senior women the air cover that mentors cannot.

Where Employee Relations Fits in Retention of Senior Women

The single fastest way to lose a senior woman is to mishandle a complaint she or someone in her network raises. The ER function is where the company's stated commitments meet the hardest cases. Patterns of harassment, retaliation, or discrimination cluster around specific managers and specific decision points. The companies tracking those patterns can intervene early. The companies that are not tracking them lose senior women they will not be able to recover.

DEI work and ER work overlap most clearly here. The same structured intake, anonymous reporting, and pattern analytics that support DEI also protect the senior women whose continued presence depends on whether the company handles cases consistently.

How Does Connected Case Management Show Up in Retention of Senior Women?

It shows up because senior women, more than most demographic groups, watch how the company handles other people's cases before deciding whether to raise their own. A track record of consistent, documented case handling builds the trust that keeps senior women in the company through the hard moments. Inclusion is the cumulative effect of how the company shows up over thousands of decisions.

Frequently Asked Questions About Supporting Working Women

What is the single highest-return retention investment for senior women?

Manager training on bias around pregnancy and caregiving, paired with structural fixes to promotion velocity. The two together produce compounding effects. Either alone underperforms.

How do you measure whether a women's leadership program is working?

Promotion velocity by demographic. Senior-level retention by demographic. Pay equity audited by an external firm. If those three numbers improve year over year, the work is producing results. If only program enrollment is improving, the work is producing brand value but not change.

What is the role of sponsorship versus mentorship?

Mentorship offers advice. Sponsorship offers air cover, public endorsement, and access to high-visibility work. Senior women who get sponsored are promoted at higher rates than senior women who only get mentored. The companies producing real movement on the leadership pipeline have shifted their development models accordingly.

How do you handle a senior woman raising a sensitive case?

With structured intake, a trained investigator, a clear timeline, and follow-through that is documented and reviewed. The cases that go badly are almost always the cases handled informally. Caregiver advocacy often starts with the way a single sensitive case gets handled, and senior women are paying close attention.

How does AllVoices support retention of senior women?

Through structured, anonymous intake, multilingual support, and aggregate analytics that surface patterns by demographic. Employee engagement data and case data together tell the People leader whether the strategy is working in real time.

Sarah was clear that the path forward is also generational. The senior women who stay long enough to redesign the systems are the ones who make the next generation's path easier. The companies that retain them get a return that compounds across decades. The companies that lose them keep paying the same hiring tax with each new cohort, and the leadership pipeline keeps looking the same as it did ten years ago.

The Bottom Line for HR Leaders

Sarah's argument has aged into a structural blueprint. The retention problem with senior women is not solved by more career advice. It is solved by fixing the policies, manager behavior, and ER infrastructure that determine whether senior women can stay. Equity is what survives the audit, not what survives the press release.

The companies that do this work hold their senior women through difficult moments and produce leadership pipelines that look different from the industry average. The companies that do not keep losing the women they say they value, then commission another report on why.

See how AllVoices supports retention of senior women through structured intake and pattern analytics.

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