Tag Archive for: authenticity

Your Leadership Development Partner in 2026: How Executive Coaching Transforms Your Career Journey

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leadership development partner - executive coachingThe workplace in 2026 demands more from leaders than ever before. Hybrid teams still require some new management approaches to engage those in the room and on the screen. An understatement is that AI is reshaping how work gets done and will get done in the future. The result is a leadership landscape defined by ambiguity, fast-shifting expectations, and relentless productivity pressure.

Against this backdrop, choosing to engage an executive coach gives leaders the opportunity to think more deliberately about how they lead and how they grow. Research suggests that executive coaching supports improvements in leadership effectiveness, self-awareness, goal clarity, and resilience. Behaviorial flexing to learning, thinking styles and task styles are capabilities and can be learned as skills and have become increasingly important as roles expand and complexity increases.

To offer a comprehensive view of executive coaching, this three-part series explores not only its potential benefits, but also what executive coaching is, how it works, and how leaders can make the most of the investment. Whether you are an executive paying for your own development or an HR professional looking for leadership development coaches and team coaching in an offsite format, we want to hear from you.

Part 1 focuses on why executive coaching matters. It reviews the evolving demands on leaders, and the concrete outcomes associated with a high-quality coaching engagement.

Part 2 looks behind the curtain at how executive coaching actually works — what happens inside a coaching relationship, how the process unfolds, and how to evaluate and select the right coach for your goals, style, and context.

Part 3 turns to how to make the most of your investment, exploring how to actively engage in coaching to accelerate growth and practical next steps to move forward.

Why Executive Coaching Matters

Corporate training budgets today remain heavily weighted toward technical skills, systems training, and compliance requirements. Leadership development, when it exists, is often episodic rather than sustained. Traditional mentorship programs have largely disappeared in remote and hybrid environments. The informal learning that once happened through hallway conversations and after-work gatherings has changed in quantity and also was never a completely consistent practice by or for all.

Meanwhile, leadership complexity has intensified. Leaders are managing teams across time zones, navigating constant technological change, making decisions with incomplete information, and doing it all while maintaining work-life integration that often feels elusive.

Engaging with an executive coach helps leaders chart a path through the complexity. It provides personalized development when organizations cannot, strategic guidance when you are facing novel challenges, and accountability when it is easy to deprioritize your own growth.

This personalized approach matters because leadership is not one-size-fits-all. The skills that make you effective are deeply connected to who you are: your values, your strengths, your communication style, your life circumstances. Coaching helps you develop leadership that is both effective and authentic.

What Executive Coaching Actually Delivers

Let’s move beyond abstractions to concrete outcomes you can expect from a quality coaching engagement:

1. Clarity That Drives Action

Given the many demands on leaders today, it is no wonder that many feel like they are operating in perpetual reaction mode: responding to emails, attending meetings, and putting out fires. Coaching creates space for leaders to step back and ask fundamental questions: What am I actually trying to achieve? What matters most? Where should I focus my limited time and energy? What does success look like for me personally, not just professionally?

This clarity becomes a decision-making filter so that when opportunities arise, you can evaluate them against your actual priorities rather than defaulting to yes or getting swept along by others’ agendas. Research shows that working with an executive coach increases goal clarity and goal attainment, helping leaders move from urgency-driven behavior to intentional, strategic action.

2. Self-Awareness That Transforms Effectiveness

You cannot see yourself the way others see you. You can’t observe your own patterns, blind spots, or the gap between your intentions and your impact. This is where coaching becomes invaluable.

Through powerful questions, reflection exercises, and sometimes formal assessments, coaching builds the self-awareness that distinguishes good leaders from great ones. You discover how your communication style lands with different people, which strengths you’re overusing or undervaluing, what triggers cause you to react rather than respond, and where your assumptions limit your possibilities. Of note, leadership research consistently links emotional intelligence, of which self-awareness is a key component, to leadership effectiveness, team cohesion, and motivation, which executive coaching helps leaders develop over time.

3. Strategies for Your Specific Challenges

Leadership challenges are often maddeningly context-specific. How do you give difficult feedback to a high performer who has behaviors that negatively effect team culture? How do you influence senior stakeholders when you lack formal authority? How do you manage your energy when your role demands constant availability? How do you make the case for promotion without seeming entitled?

Books and training programs offer general principles. Your coach helps you develop strategies tailored to your specific situation, taking into account your organizational culture, your relationships, your constraints, and your goals. Generic advice rarely moves the needle; specific strategies do.

4. Accountability That Drives Change

Knowing what to do and actually doing it are entirely different challenges. We’ve all set goals only to abandon them when the daily grind takes over. Coaching provides structure and accountability that transforms intentions into actions.

Your coach holds you accountable not through judgment but through partnership. Between sessions, you implement agreed-upon actions, experiment with new approaches, gather feedback, and track progress. They then return to reflect on what worked, what didn’t, and what to adjust next. This cycle of action and reflection is where lasting change occurs.

5. Resilience to Navigate Setbacks

Every career includes setbacks: projects that fail, promotions you don’t get, relationships that sour, or reorganizations that derail your plans. How you respond to these moments often matters more than the setbacks themselves.

Coaching builds resilience by helping you process challenges productively, maintain perspective, develop coping strategies for high-stress situations, learn from failure without internalizing it as identity, and sustain motivation over time. Leadership coaching has been shown to increase leaders’ confidence in navigating their roles and improve trust in their direct reports, both critical factors in bouncing back from challenges.

6. Skills That Compound Over Time

Some professional development delivers immediate returns but little lasting value. Coaching is different. The skills you develop, like emotional intelligence or communication effectiveness, compound throughout your career.

A feedback framework learned today remains useful for decades. Increased self-awareness carries across roles and organizations. Communication shifts ripple through every future relationship. This compounding effect explains why coaching continues to deliver value long after the formal engagement ends.

7. Permission to Lead Authentically

Many professionals feel pressure to conform to leadership stereotypes that do not fit who they are. The charismatic extrovert. The tough boss. The relentless competitor.

Coaching offers a third option: developing a leadership style that is both effective and authentically you. This means honoring your values while building influence, leading in ways that energize rather than drain you, using your natural strengths rather than trying to eliminate weaknesses, and building teams that complement your style rather than compensate for it. Coaching helps you lead from a place of integrity and self-knowledge rather than imitation.

8. A Thinking Partner for Complex Decisions

Senior leadership can be isolating. The higher you rise, the fewer people you can speak with candidly. Your direct reports need confidence. Your boss evaluates judgment. Your peers may compete.

An executive coach becomes a confidential thinking partner, someone without agenda or judgment, providing a confidential space to think out loud, test ideas, and consider implications before acting. Having this thinking partner is not a sign of weakness; it is a strategic advantage that many effective leaders leverage intentionally.

A Deliberate Investment in How You Lead

Executive coaching is about supporting leaders at moments when complexity increases, stakes rise, and familiar strategies no longer suffice. In a workplace defined by constant change, coaching offers something increasingly rare: time, perspective, and partnership focused entirely on how you lead and how you grow. If you are ready to be matched with one of our coaches, please book a free exploratory conversation with our Founder and Head Coach, Nicki Gilmour here: BOOK SESSION

By Nicki Gilmour, Founder and CEO, theglasshammer and Evolved People Coaching

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Nicole Young: Head of CRE Portfolio Management, Wells Fargo

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Nicole Young“At the end of the day, the impact I care about most is on people, helping them achieve what they didn’t think was possible and elevating the organization to new levels,” says Nicole Young. “The efficiency, output, and success that result from bringing out their best work are just byproducts of that focus.”

Young is a leader whose passion lies in transformation: unlocking potential in people, teams, and entire organizations. She shares how this mindset has guided her career, from CMBS to consumer lending and back to commercial real estate, where she now leads Wells Fargo’s portfolio management organization.

Building from the Ground Up

With nearly thirty years in commercial real estate at Wells Fargo, Young has navigated multiple facets of the business, from underwriting and origination to credit approval and even workouts during the Global Financial Crisis. Each role sharpened her expertise and resilience, but more importantly, it revealed her talent for building and shaping something from the ground up.

“I was fortunate to be asked to start from scratch and lead our small loan CMBS (Commercial-Backed Mortgage Securities) program, which focused on loans between 1 million and 15 million,” she recalls. “I started the group, structured how it would work, hired the people, developed the process. That was really fulfilling…it’s where I got the taste for building something from the ground up.”

After fifteen years in CMBS, Young made a pivotal decision to move to Wells Fargo’s consumer side, leading underwriting for the home lending group. The transition required scaling her leadership from 20 people to more than 1,700 while transforming the organization to be more efficient and effective. “That was a steep learning curve,” she says. “I had to really learn to lead with data… and understand how standardized processes are critical to making an organization of that size run efficiently and effectively.”

When Kara McShane, Head of Commercial Real Estate, asked her to return five years later to take on a role that demanded both large-scale leadership and efficiency shaped from the start, the decision was an easy one.

“I had always admired Kara’s leadership and knew I would love to work for her. When she contacted me about coming back to CRE, I was thrilled.” She continues, “Wells Fargo had recently consolidated its commercial real estate lines of business, but no one was managing the portfolio as a whole and making sure those businesses were acting and making decisions as one. There was a huge opportunity to create efficiencies through standardization, and I got to build the new Portfolio Management organization from the ground up.”

Today, Young’s group of nearly 400 professionals oversees capital strategy, underwriting, closing, and portfolio management, bringing consistency, efficiency, and risk mitigation across the organization.

“Kara’s vision of bringing those groups together and leading them as one unit has really paid off given that we are rated the #1 Global Real Estate Bond Bookrunner, #1 CMBS, #1 Bank Agency lender, #1 Construction lender, and #1 in Loan Syndications.”

Learning to Lead at Scale

As Young progressed into senior leadership, she quickly realized that success required developing new skills, most notably, learning how to lead at scale and communicate effectively across large, complex organizations. When she transitioned to leading a team of 1,700, she remembers her boss giving her valuable advice that fundamentally shifted her mindset.

“He said, ‘I need you to lead the people, not the work’…it really shifted me from feeling like I needed to be the subject matter expert to recognizing that I’m here to lead the people. They can be the subject matter experts. My job is to guide them, give them the vision, and make sure the organization is moving in the right direction.”

Young notes that another key part of leading at scale is mastering communication in many directions: down to the team, out to the organization, and up to executive leadership.

“With my team that means ensuring they understand the vision, are aligned around the priorities and the mission, and are inspired to do their best work to deliver for our clients. To do that, I spend a lot of time with the team individually and in groups.”

In communicating up and out to executives, regulators, and the board, Young explains, “It’s about taking the complex and making it simple, understanding your audience, and tailoring your message with the right level of detail.” For Young, effective leadership at scale depends on both connecting with her team and translating that insight for the broader organization.

Authenticity and Grit

Young’s experience learning to lead at scale also reinforced a few key traits that have consistently supported her success. Young attributes much of her leadership growth to a willingness to embrace new challenges and learn continuously. “I’ve taken on different roles throughout my career where I didn’t necessarily have deep expertise,” she says, “but I was always willing to dig in and figure it out. That willingness to learn and to tackle hard challenges is important.”

Young also points to authenticity as foundational to her approach. “I don’t put on a façade…I’m direct and frank, which some people like and some may not, but this is the real me. I lead my team that way, and I try to always be honest and transparent.” That straightforward approach, combined with high expectations, has helped her bring out the best in the people she leads. “One of the things I’m most proud of is the team I build and what I can help them achieve.”

Finally, grit and drive are an important part of the mix. “You can’t underestimate the power of hard work,” she notes. “It has served me well throughout my career.”

Believing in Others as They Believed in Her

While Young’s drive, authenticity, and willingness to take on challenges were essential building blocks to her career progression, she is quick to credit the support she received from both Wells Fargo and the people around her. Early on, she balanced career ambitions with family responsibilities, working part-time as a young mother while continuing to excel in her role.

“People saw my potential and believed in me—Wells Fargo believed in me—and were willing to wait until the time was right for me to step into bigger roles…I appreciate that I was given the time and space when I needed it and I try to do the same for my team.”

Now, Young pays that support forward. “When I see someone’s potential, I bring them in, help them develop, and give them a platform to grow. Sometimes that even means helping them move to other parts of the organization where they can expand their skills.”

Bringing Out the Best

The commitment to lifting others up naturally extends into how Young leads her own team. A defining principle of her leadership is written clearly on her whiteboard: What did I do today to make the team better?

“I spend time really trying to figure out what motivates people individually and collectively as at team to bring out the best in them. I give stretch assignments that get them to do more than they think is possible,” she explains. “When they’ve done the work, I make sure they’re the ones presenting it. They deserve the visibility and the access to other leaders.”

That people-first philosophy is both Young’s leadership signature and her source of fulfillment. She finds meaning in seeing her team grow, whether it is employees she once hired fresh out of college who are now thriving across the organization, or former team members who choose to come back and work for her again. “That to me is amazing,” she says. “Seeing people’s success and knowing you had a part in getting them there is truly fulfilling.”

Even after building multiple teams and functions, Young remains motivated by challenge and transformation. “We have a few more years before this group is a completely well-oiled machine… but it’s exciting to see the impact. Ultimately, success isn’t just efficiency—it’s the growth and fulfillment of the people I lead.”

By Jessica Robaire

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Latinas in Leadership: Self-Empowerment And a Steep Ascent

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Latinas in LeadershipDespite the fact that the U.S. Latino GDP would rank as the fifth-largest economy globally, Latinas still face the steepest climb up the U.S. corporate ladder in 2025, hindered by systemic bias, cultural taxation, and lack of meaningful support.

Amidst a disconnect between the growing economic impact of Latinas and their stalled advancement in corporate leadership, we highlight the culturally grounded and self-empowering strategies that Latinas can take to rewrite the narrative that corporate culture is lagging to recast.

Latino GDP in the U.S. Is an Economic Force

The Latino population is a force within the U.S. economy that isn’t slowing down anytime soon. According to the 2025 U.S. Latino GDP Report, Latino economic output in 2023 was $4.1 trillion.

Were it a country, the U.S. Latino GDP would rank as the fifth largest GDP worldwide, growing 2.7 times faster than non-Latino GDP in the U.S.

From 2010 to 2013, Latino real consumption also grew 2.9 times faster than non-Latinos, proving to be a real economic engine.

Latinas are also the fastest growing group of entrepreneurs, starting businesses at six times the rate of other groups.

The Steepest Climb Up the Leadership Ladder

Latina’s face “the steepest climb up the corporate ladder” according to The State of Latinas in Corporate America 2024 report by Lean In, based upon 2019 to 2023 data.

Latinas are the most underrepresented of any group at entry level jobs (5% vs 9% of general population) and have the greatest drops (78%) in representation on the way to the C-Suite.

Only 1% of C-suite executive positions in Corporate America are held by Latinas. The data showed two broken rungs on the pipeline ladder: one is at the initial promotion to manager and the other at promotion to VP.

Despite the barriers, Latinas continue to demonstrate the ambition and talent for leadership. Latinas are more likely (71%) than the average woman (63%) to be interested in becoming leaders and to indicate it’s increasingly important to them.

Professional Neglect: A Retention Issue

In her research among Latina leaders, Dr. Zaibis Muñoz-Isme, of American University, explores aspects of “professional neglect” for Latinas in leadership—a phrase shared in conversation by Dr. Sofia Pertuz, workplace cultural strategist.

  • Tokenistic inclusion – representing diversity at the table without meaningful support or inclusion in decision-making processes
  • Cultural taxation – the burden of being positioned as the lone representative of an entire group
  • Lack of mentorship/sponsorship – navigating leadership without the support networks, advocates and guidance that peers have access to
  • Dismissal of expertise – having ideas dismissed or co-opted by individuals who lack the lived experience informing them
  • Micro aggressions and bias – subtle forms of discrimination that undermine belonging and confidence

Indeed, the Lean In report showed that Latinas do not feel as supported as peers in the corporate world—neither by managers or peers. They are less likely than overall women to report managers ensure they get credit for their work or show interest in their career advancement. And less likely to say that senior colleagues praise their accomplishments or advocate for compensation raises.

Muñoz-Isme also found that Latinas in leadership roles were not as supportive of other junior Latina women as she expected, perhaps due to Queen Bee syndrome. When the culture is not inherently and structurally supportive, it creates strain on those Latina leaders who do manage to break through.

Belonging and Flexibility Matter

Lean In shares that 37% of Latina women report having the “only experience—being the only person of their group identity in a room, compared to 13% of all women. Compared to overall women, these Latina “only’s” are twice as likely to hear insults towards their culture (15% vs 7%), twice as likely to feel they are expected to speak on behalf of their cultural identity (20% vs 9%), and nearly three times as likely to deal with other’s comments on their language skills (21% vs 8%).

Experiencing these micro aggressions more than doubles the odds of feeling burnt out, feeling unable to advance as well as others, and considering leaving the company for a different work culture.

Additionally, while many Latinas remain highly committed to work and community, they do not feel they have the flexibility they need to balance their diverse commitments.

Six in ten Latinas feel pressure towards both family obligations and to succeed at work. According to Lean In, Latinas reported being less able to work remotely, set their own hours, step away from work, or take family time off compared to women overall.

As written by Nathalie Darras in Hispanic Executive, motherhood and professional work are often seen by many Latinas as two divergent paths, a dichotomy that need not exist, but results from the lack of support to balance out life.

Four Self-Empowering Actions for Latina Leaders

With the force that the Latinx population represent in the U.S. economy, it’s inevitable that Latinx leaders will change the composition of leadership, but changing the character depends upon authenticity.

Each Latina leader who brings her whole self to the workplace is going to help drive that change, because it’s people who hold the power to change culture and call organizations to a greater collective accountability.

1) Carve a self-directed career path.

Muñoz-Isme recommends that Latinas embrace a self-directed career path and take initiative in their own goals and advancement wherever possible, leveraging cultural assets.

Latinas can own their relational strengths in finding mentors and sponsors, seeking out allies, and putting your name in for opportunities. Being self-directed also means advocating for yourself, despite cultural resistance around self-promotion, leveraging existing networks of support and building new ones, as well as defining your terms of success.

It’s also important to discern your capacity to thrive in different environments, because not all work cultures are cultivated equally.

As Johanna Diaz, Global Head of Alternatives Product Strategy at Goldman Sachs, recently told us, “In facing challenges or change, I always go back to the questions: Am I in the right place? Am I surrounded by the right people? Am I learning? Am I growing?”

2) Be aware of and leverage cultural scripts and drivers.

For many Latinas, internalized cultural drivers shape behavior and decisions, often in ways that go against the grain of what is being rewarded in corporate culture. Some of these drivers are:

  • familismo: the importance of close and extended family relationships as guiding parameter for decision-making
  • marianismo: gender beliefs in which women are expected to be selfless, self-sacrificing, and nurturing
  • personalismo: creating personal and meaningful relationships
  • colectivismo: the importance of belonging to a group and recognizing the needs of that group
  • respeto: respect granted to others because of formal authority, age, or social power, without questioning
  • simpatía: promoting pleasant interactions and positive relationships, while avoiding conflict and disharmony

Embracing culturally relevant leadership means becoming aware of how these drivers influence you, as well as how they can be leveraged as assets within your leadership.

For example, Latinas must challenge the inhibiting influence of respeto and marianismo when it comes to sharing their voices and perspectives. Equally, they can leverage personalismo and colectivismo in building influence through collaboration and strong relationships.

Leveraging the strengths of cultural scripts can help Latina leaders to foster cultural pride, leadership skills, and empowerment.

3) Stay authentic.

Many Latinas have reported checking aspects of self at the door in order to fit into corporate cultural norms. But as the composition of the workforce and leadership changes, slowly and inevitably, so will culture. People ultimately create and influence culture.

While it requires courage and true resilience for Latinas to move in authenticity within a corporate context designed on different values, nothing will compromise your vitality and wellbeing more than contorting your authentic self while trying to fit in.

True belonging hinges on authenticity. It’s important that Latinas let themselves be felt in the workplace and in leadership, so that eventually, the corporate environment responds.

4) Leverage cultural wealth.

Latinas can flip the narrative by owning their cultural wealth: “an array of knowledge, skills, strengths and experiences that are learned and shared by people of color and marginalized groups; the values and behaviors that are nurtured through culture work together to create a way of knowing and being.”

Six forms of community cultural wealth, outlined by Dr. Tara J. Yosso, that Latinas can leverage in leadership include:

  • aspirational: the ability to sustain and work towards a vision for the future amidst both real and perceived barriers
  • navigational: the ability to maneuver through systems and contexts not historically designed to support you
  • social: the ability to leverage community resource and connections in building a network of support
  • linguistic: the sum intellectual, social and communication skills obtained through multicultural history, bilingual or multilingual capacity, and experiences
  • familial: the cultural knowledge and nuance obtained from family and community experiences
  • resistant: the cultural legacy of challenging inequalities and the status quo, and ability to resist stereotypes

Despite structural barriers, cultural bias, and underrepresentation, Latinas are ready to lead and are leading.

By embracing cultural strengths, carving self-directed paths, and showing up authentically. The future of leadership will be shaped not just by who gets a seat at the table, but by how leaders redefine the table itself. Latinas have the vision and the voice to lead in ways that are authentic, inclusive, and transformative.

It is no longer a question of if Latinas will lead, but when. And with every step upward, they expand the definition of leadership for everyone.

By: Aimee Hansen.  Alongside years of writing on leadership, Aimee Hansen is the founder of Storyteller Within and leads the Journey Into Sacred Expression women’s retreat on Lake Atitlan, Guatemala. Follow her at thestorytellerwithin.com, on instagram, and via Linked In.

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Nicola Free: Managing Director, Head of CRE, EMEA, Wells Fargo

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Nicola Free“It’s hard to teach determination, but if you’ve had setbacks, and you’ve had to fight to get to where you are, it is built in you to keep going,” says Nicola Free. “It’s how quickly you bounce back, what learnings you take away, that can make you even stronger.”

With a career shaped by determination, hard-won resilience, and a commitment to leading with integrity, Free does not just navigate change — she drives it. She reflects on how embracing risk, learning from inspirational leaders, and trusting in both her existing skills and her capacity to grow have been central to her journey.

Taking Risks and Having Faith in Herself

From an early age, Free learned to be a self-starter. She reflects, “I came from a very working-class background and went to the worst school in Warwickshire. I had to teach myself my GCSEs because the classes were so disruptive.”

Determined to “do something with my life and make my parents proud,” Free was the first in her family to attend university, where she pursued law. However, it did not take long for her to realize that the legal path, while hard-earned, was not where she wanted to stay. When a client she had supported on a major securitization project invited her to help launch a CMBS platform, she made a decision that would completely change her career.

“It was definitely a big risk,” Free admits. “I would never have anticipated that I would have left the law a year after qualification, but this new opportunity sounded really interesting.”

Jumping into a completely new environment, Free recalls that “a third of it was in my comfort zone and two-thirds I was learning from scratch.” Free leaned on what she knew: her work ethic and resilience.

“Have confidence in the skills you bring, work hard to learn what you don’t know, and don’t give up at the first hurdle. Be willing to take a leap of faith. Ultimately, it’s about believing in yourself; that you’ll get there, and that you can do it.”

That mindset has carried her through ever since. Today, Free is a recognized leader in her field. As Head of Commercial Real Estate (CRE), EMEA for Wells Fargo, she is driving the firm’s CRE strategy across Europe, strengthening its capital markets capabilities, and deepening client relationships in the region.

“It’s a hugely exciting time to be a part of this business and the opportunity ahead of us…this is the year that the strategy is all coming together.”

Leading with Humility and Authenticity

When reflecting on her leadership approach, Free emphasizes the importance of clarity, humility, and authenticity.

“I always try and bring people along with me,” she says. “Give them a vision of what the strategy is, what we’re trying to achieve…make them feel like they’re part of something really special.”

She continues, “it’s about leading with integrity, humility, and doing the right thing for the business, the clients, and the strategy we’ve set for ourselves.”

Mentoring and feedback are important elements to how she leads. “The only way I managed to make a success of my career change was having good people around me who were prepared to coach and teach me,” Free says. “It’s incumbent on us all, particularly as leaders, to be that player-coach where you take the time to give people feedback and help them develop.”

She recognizes that it is also about holding oneself accountable when things go wrong and ensuring others are recognized when they go right. “When things are going really well, make sure people are getting the credit.”

Find a Culture that Aligns with Your Values and Leadership who Embody It

While Free is unquestionably guided by a strong internal compass, she also highlights the vital role that external factors, particularly an organization’s culture and leadership, play in shaping meaningful career development.

“One of the things I’ve learned throughout my career is to ask: What’s the culture? What kind of institution do you want to work for? At Wells Fargo I enjoy working for a bank that has a strong culture that I can relate to while being guided by truly inspirational leaders.”

Free is particularly inspired by Kara McShane, Head of Commercial Real Estate at Wells Fargo, “who is seen as one of the most influential women in finance.”

“To be able to work for somebody like her is really inspiring…and when you have leaders you trust and respect, you want to do your best for them.” It’s a dynamic she now pays forward to her own team. “I want them to come in and feel they’re part of something great, and that they want to succeed because they believe in me, in the business, and in the leadership above me.”

Be Bold. Own It.

Surrounded by leaders she respects, and serving as one herself, Free is acutely aware that leadership is not just about results; it’s also about presence. For women in real estate finance, that presence is still too rare at the top.

“If you’re a woman running a lending business in this industry,” she recalls reading in Real Estate Capital, “then you’re pretty extraordinary.” The line gave her pause, not out of self-congratulation, but reflection. “I come in and do my day job because I love it and want us to succeed. I don’t think of myself as any different than any other leader. But seeing that made me realize there’s a responsibility that comes with being one of the few.”

It is a responsibility that Free takes seriously. As she has risen through the ranks, invitations to speak and serve on panels have increased, and she uses them to push for broader representation. “I’m always conscious about making sure there are other women at the table, that the panels are diverse, and that we’re holding ourselves and others accountable.”

Her visibility is intentional. Instead of blending in, she embraces standing out.

“There’s a big real estate conference I go to every year,” she says. “You queue to board the flight, and it’s just a sea of men in navy suits. I make a point of wearing something bright and own the fact that I’m not the guy in the navy suit. I’m the woman in the bright red dress. It’s an opportunity to be seen.”

She emphasizes, “Being different can make you more memorable. It’s not just about gender. You might be younger, newer, or from a different background. Whatever it is, don’t be afraid to be visible. Have confidence and own it.”

Outside of work, Free applies the same conviction and focus to her personal life. She’s a mother of two daughters, and a competitive CrossFit athlete.

“I’m a strong working mom, and it demands a lot of my time, but I’m showing my girls what working hard and loving what you do can lead to and I’m not apologetic about it.” CrossFit is her outlet, her reset. “When I am training hard, I’m not thinking about anything other than being in the moment… it’s a really good way of switching off.”

That thread of determination runs through everything she does, whether it’s qualifying for a legal career, shifting into finance, growing a business, mentoring a team, or lifting a barbell.

“When things get really tough, don’t give up,” she says. “If you keep digging in, you’re going to feel so great at the end of it.”

By Jessica Robaire

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Sam Rapoport: CEO, Blue80

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Sam Rapoport“In this work around gender equity, I know I may never see the full fruits of my labor in my lifetime. But I want to be the one who plants the seed,” says Sam Rapoport. “If others can water it and sustain it, then I’ve done what I came to do, and I’m okay with that.”

Sam Rapoport knows that there is value in playing the long game. When it comes to change, she knows that you have to put in an intentional effort. As an out LGBTQ professional, Rapoport also knows that being yourself means betting on yourself.

As a high school and college quarterback growing up in Canada playing tackle, touch, and flag football from a young age, Rapaport honed the ability of making rapid decisions under pressure.

“You have three seconds to get rid of the ball, and you are making a hundred decisions in those three seconds,” she says. “You have five people in your face trying to attack you. I taught myself at a young age to become calm in those moments.”

The instinct to remain focused, fast, and forward-thinking shaped not only Rapoport’s playbook on the field but also guided her career at the NFL (National Football League). Over two decades, she rose from intern to changemaker, pioneering trailblazing work in gender equity. More recently, she made the fearless decision to step away from her full-time role, choosing to share her hard-won lessons more widely as a consultant and keynote speaker.

“I want to help organizations around the world achieve progress more quickly,” she explains. “Because this work is so much bigger than the sport of football.”

Learning to Shoot Your Shot

Rapoport’s emergence as a changemaker in professional football began with an unconventional pitch. “In 2003, I submitted a resume to the NFL with an actual football. On the football I wrote, ‘What other quarterback could accurately deliver a pass 3,806 miles?’ which was the distance between my university and the league office. That stood out to someone in HR.” It earned her a coveted internship and foot in the door of a historically male-dominated league.

However, Rapoport’s proudest achievement was not just breaking in, but helping other women do the same.

“For the last 10 years at the NFL, I created a program that served to introduce women into coaching. I took on the Boys’ Club. I took on an establishment that had done things the same way for a hundred years, which was putting men in coaching roles, and I questioned it and then I created a platform that changed the game for women in coaching.”

She continues, “now as of this past season we have 15 women working in full time coaching roles, which is more than double any male professional sports league in the world.”

Rapoport emphasizes that the program’s success didn’t happen by chance. It was the result of years of focused effort and a deliberate strategy, or “a blueprint for accelerating change”. A key element of that blueprint is a framework she learned along the way: the 20/70/10 Rule.

“I have found that 20% of any organization understands what needs to be done to make the change – they’re bought in. 70% want to do the change but have no idea how. And 10% wants nothing to do with it,” she explains. “Focus your energy on moving the 70% into the 20%. Ignore the 10%. The ground moves from under the 10% statistically anyway.” For Rapoport, it’s about shifting the focus from fighting resistance to fueling momentum.

Today, Rapoport continues consulting to the NFL Women’s Forum and is helping build the league’s first professional flag football league, one of her childhood dreams. She is also advising organizations like the USTA (US Tennis Association) on engaging more women in coaching. And one of her latest accomplishments includes working with USA Flag Football on creating a path to the sport being featured in the next Olympics. Finally, she makes sure to leave time for keynote speaking, which she describes as, “probably my favorite part of my job because I can deliver a lot in a short period of time on how to create change.”

On Being Yourself – Truly

As she worked to open doors for others, Rapoport also navigated what it meant to “be herself” in the workplace.

“I wasn’t out in the first decade of my career at the NFL…Everyone always says, ‘Be yourself,’ but that’s easy when you look and act like the default person at an organization,” she reflects. “It’s a lot more challenging when you are a member of the gay community, or the Black community, or the Latinx community.”

She continues, “when I felt confident enough to make the change to come out and be myself unapologetically…I started to thrive.”

Beyond being out at work, Rapoport defines being herself as, “finding the middle ground between professional you and weekend you. It’s about dropping the act, ditching the corporate lingo, the need to sound like a textbook, or mimic your boss, and just being real.”

However, Rapoport is quick to acknowledge the privilege required to let one’s guard down. “There’s a privilege in seniority to be able to do that. Younger people have a harder time.” She emphasizes that safety is paramount, both in professional and personal spaces. “It’s up to the environment. The environment owes it to you to make it safe to come out. I came out when it was safe, and before, it didn’t feel that way.”

Betting on Yourself

When it comes to navigating moments of self-doubt, Rapoport is clear: it’s not about faking it until you make it. “In my opinion, that’s the worst advice you could give anyone. If you fake it, then imposter syndrome kicks in.” Instead, her mantra is “publish and iterate.” Try something, learn from it, refine it, and keep going.

“I have a lot of things, but I don’t have imposter syndrome,” she says. “I’m okay with putting something out there and maybe running away after I do, but I’ll fix it from there.”

She and her wife even have a motto: “We’re betting on ourselves.” Whether it’s stepping into a new gig or turning down one, the calculus is simple: “We’re literally putting all our chips on us. And if it works, great. If it doesn’t, we learn.”

A Pragmatic Path to Meritocracy

With years of experience in gender equity, Rapoport offers an informed perspective of what’s falling short in DEI and what has the potential to move it forward. “We need to stop with these massive pendulum swings,” she says. “It has to be apolitical.” She believes real progress is possible and meritocracy is about removing barriers so that everyone has the same access to opportunities. Rapoport is also adamant that true equity work must be intersectional stating it to be critical to ensure access to all women.

At the heart of her work is a long-term vision that stretches beyond any single organization or lifetime. “I think ahead 100 years, and I think of what the NFL can look like with all genders being ubiquitous,” she says. “With half of the head coaches being women. Half of the general managers. Half of the owners.”

Rapoport is not pushing for dominance, but for balance. “I don’t believe the future is female, I believe in balance, and I believe the future is everyone – equal representation of great people. That’s how you start to take down very destructive structures that hurt marginalized people.”

Outside work, Rapaport is “massively into plants,” plays three instruments, cooks, paints, and has a list of future hobbies she is excited to learn. But her greatest joy, she says, is her family. “I am so proud of how functional and healthy and happy my family is,” she laughs. “And I’m very passionate about putting my energy there over anything.

By Jessica Robaire

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Jennifer Doyle: Managing Director, Co-head of Structured Products Group, Wells Fargo

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Jennifer Doyle“Life is about picking yourself up when you get knocked down. Those who do that the best are the ones who tend to be the most successful, however you might define success,” says Jennifer Doyle.

Tenacious in the face of challenge, Doyle is a leader who does not quit. She shares how this mentality of perseverance and optimism has helped build her career and shaped her life.

Moving Forward for Success

Starting as a temp more than twenty years ago, Doyle describes the opportunity of getting in the door working on the trading floor as “winning a lottery ticket” and paving the way to the career she has today. Being surrounded by intelligent people in a fast-moving, competitive environment that is also relationship-focused felt perfectly aligned with her personality and strengths.

“As a former college athlete, I like to compete, I like to win, and I like to be part of a team. I also enjoy making decisions and operating in a fast-paced environment. It was a fit from the beginning.”

Fast forward to today and Doyle is a Managing Director and co-head of the Structured Products Group at Wells Fargo’s Corporate and Investment Bank. However, she will be the first to tell you that success does not happen overnight.

“There is a certain tenacity and grit that is required to be successful in this business. If you can cherish the highs and reinvent yourself and pick yourself up when things get hard, that resiliency in time will keep you moving in the right direction.”

Doyle approaches her life outside of work with the same mentality of persevering when the going gets tough and recognizing that she has agency in the process. It served her well in dealing with the shocking experience of being one of the passengers whose plane crash-landed in the Hudson River 15 years ago while on a business trip.

She reflects, “If you went into that experience an optimist, I think you came out even more of an optimist. If you went into that experience as a pessimist, I think you came out even more of a pessimist. We all experienced the same thing, but everyone had a different interpretation of what happened and how it affected them.”

For Doyle, her optimistic outlook and belief that she needed to keep moving forward meant that she got on a plane the next day because she “did not want fear to rule my life.” She adds, “I tell my children happiness is a choice. I choose to be happy, and if I was unable to make that choice today, then I’m going to try to make that choice tomorrow.”

Sponsorship and Speaking with Authenticity

Beyond resilience and determination, Doyle points to having the support of others as integral to her career. She shares how the kind of support she needed shifted over time as she continued to build confidence, finding there is strength in speaking with authenticity.

“As I developed in my career, the sponsors that I acquired would later tell me that the reason they took an interest was because I brought a different perspective and opinion to the table.” She continues, “People wanted to hear what I had to say because they recognized that I didn’t have an ulterior motive, I was genuine.”

As a leader, Doyle mentors and sponsors others in both formal and informal capacities, often finding her calendar full of people interested in connecting to get her advice or opinion. Being sought after for her point of view is a direct reflection of others seeing she genuinely cares and takes an interest in their growth.

“My mission is to lead in a way that balances the needs of the business and our employees – and ultimately drives positive outcomes for both. I’m always thinking about what’s best for our team and what’s best for our clients. That approach has cultivated a desire for people to want to talk to me and get advice.”

Doyle has twice been the head of Wells Fargo’s WomenGoFar network, as well as its executive sponsor. She also is a sponsor for BOLD, a program designed to provide mentorship and sponsorship to high-potential talent at the firm.

Challenging the Norm

As determined as she is to persevere in the face of obstacles, Doyle is also unafraid to challenge the norm stating, “I do think I am a change agent. It probably took me 20 years to have the courage to say that.” She speaks to the recent experience of being a woman in a leadership role playing in the Wells Fargo Pro-Am Golf Tournament and what it meant for her to participate.

“I was blown away by the response that I got from women, so many of whom pulled me aside afterwards to tell me how inspirational it was seeing me play in what was publicly a field of men.”

One comment that was particularly touching to Doyle was a woman who said, “you’re breaking the mold.” Intentionally participating in the tournament to prove that a woman could do it, Doyle is thrilled by the response of her colleagues – both men and women.

“As a leader, I now have the opportunity to challenge and change what people consider to be the norm, and I actively do so.”

Using a Passion for Golf to Connect to Community and Family

Taking her passion for golf beyond breaking molds at work, Doyle is on the board of First Tee of Charlotte, an organization that provides opportunities for youth who would not otherwise typically have the opportunity to play golf.

“It integrates the game of golf with character-building learning experiences and emphasizes values such as honesty, integrity, confidence and perseverance. And of course, they have fun.”

Doyle is also passionate about bringing the game of golf to more women, not only because it is typically a more male-dominated sport, but because she herself has gained so much from the sport.

“It provides an opportunity from a business connectivity standpoint to play with clients or colleagues. I love being outside and in nature, getting exercise by walking the course, and it’s a chance for me to spend time with our children.”

Doyle admits that one of the reasons she got into golf was because her spouse and children enjoyed the game, and she didn’t want to be left out. Now that her children are teenagers, she is thrilled to have the opportunity to be active with them outdoors for an extended period without distractions like smartphones. It also ties into her approach of managing a successful career and time with her family.

“I am really present. It’s not about quantity, but about the quality in everything you do, whether it’s at work or being with your family.”

By Jessica Robaire

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Dania Shahzad: Business Manager, Client Advisory Group, PGIM

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“Over the years, I’ve not always felt confident walking into certain scenarios as a brown, Pakistani, Muslim woman,” says Dania Shahzad. “When I reflect on my previous self, the same things I was nervous about are now what make me feel the most confident and empowered.”

Shahzad speaks to finding inspiration in her family, building confidence in the face of adversity, and how she lives her life steadfast in her conviction that women can do anything.

Finding Her Footing

Shahzad was inspired by her father’s successful career in the financial industry when she chose to major in business during her freshman year of college.

“My dad and I have similar personalities – we are both bold, confident, personable people. I used to go to ‘Take Your Child to Work Day’ and the New York Stock Exchange as a child, and it was so exciting. I was always interested in his world.”

As much as she found her father’s career in the financial services industry compelling, Shahzad recognized that, depending on the role, it could come at the price of long days and working weekends. However, she was determined to find a position and company that encouraged and supported a strong work/life balance while giving her the opportunity to learn, grow, and explore various facets of the financial services industry.

After interning at a variety of firms while in college, she was excited to land at PGIM upon graduating. She says the culture, the wealth of knowledge and breadth of opportunity at PGIM is what’s kept her at the firm.

“It’s a great company for somebody who wants to explore different aspects of the financial services industry,” Shahzad says. She shares that networking opportunities and business resource groups have been particularly enriching for her, as they bring together people from all different backgrounds.

“At PGIM, asking questions, making connections, and taking calculated risks are all encouraged—that helps employees maximize their potential and make the most of their careers.”

Since joining PGIM, Shahzad participated in a two-and-a-half-year rotational program, giving her exposure to several parts of the business and the chance to adapt to new challenges and build her skills. Now, as the business manager for PGIM’s Client Advisory Group, she enjoys handling a variety of responsibilities while leveraging her problem solving and project management skills, such as working on strategic priorities and business reviews, and making connections across the organization, which helps her make progress on the firm’s strategic initiatives and get work done more efficiently. This role has also pushed her to discover her voice, particularly as she is often the most junior person in the room.

Believing She Belongs in the Room

Oftentimes being the most junior person, woman or minority in the room can be intimidating under any circumstances. Shahzad notes that her resilience and courage have grown alongside her belief in the value she brings to the table because of her experience and the encouragement of mentors.

“I’ve grown through advice and mentorship. When entering rooms with senior stakeholders, I remind myself why I belong, why I should be there, and embody that. In the past, I would almost physically make myself disappear, taking more of a passive role in group discussions, but I have gained the confidence to show up more fully.”

One of the leadership positions Shahzad stepped into is as co-lead of the Asian Global Network, an employee affinity group at PGIM. The experience has given her the opportunity to make connections and form peer mentorships across the organization, building her network of support and influence beyond her own group.

“It’s exciting that despite being the most junior of the co-leads, people look to me for recommendations and leadership – and I get to build all these connections. The group has been invaluable to me.”

Shahzad reflects that finding her voice has not only impacted how she sees herself, but how she is viewed by senior leaders.

“It changed how my leadership team sees me. I’m considered someone who can lead and assume bigger responsibilities.”
Shahzad’s personal and professional growth have also influenced how she manages challenging working relationships. “I’m generally a very positive person, but at the same time, I’ve come to recognize and accept that not everyone is going to connect with me, and that’s okay.”

“I’ve learned that you can deliver your opinion, your voice, your vision to a project in a professional way, even when you’re not seeing eye-to-eye with someone. You can still work together productively.”

Embodying the Belief that Women Can do Anything

Shahzad credits her strong female support system as a significant contributor to the confidence she exudes today.

“I believe women are incredibly strong. I have learned so much from the women in my personal and professional life and their experiences. I look at what we’ve accomplished collectively and think, ‘We really can do anything.’”

She hopes to be an example to her two nieces, teaching them how to courageously show up in the world as their authentic selves.

“They are two South Asian females who are going to grow up in the U.S. I want to be able to help them navigate that experience, while also showing them all the powerful things that a woman can do.”

Shahzad notes that part of setting that example is demonstrating her commitment to giving back to the community that has supported her. Serving as the VP-at-Large for the New Jersey Institute of Technology (NJIT) Alumni Board of Directors, her alma mater, she engages with students and actively contributes to the university where she once held a full scholarship.

“Inside, I feel deeply privileged to have such a great life in America. I am passionate about wanting to spend more of my time giving back, and the Alumni Board is one way to do that.” Another important part of Shahzad’s philanthropy ties to her faith – spending time engaged with her local mosque and affiliated community organizations, such as supporting children in need.

Authenticity as an Influencer

Shahzad’s message of empowerment reaches more than the people she works with. In fact, outside of work, Shahzad has gained a following on social media, sharing beauty tips based on her cultural traditions, fashion trends, her adventures around the globe, and more. The success of her platform is evidence of the positive impact that can be achieved by having the courage to stick to your convictions.

“I was bullied as a child for having these beauty rituals, but I persisted because I believed in their benefits and cherished the bonding moments they created with my family. Today, the same hair and skincare secrets and ingredients are becoming popular and normalized in the beauty standards and industry in the U.S. I’m proud of these rituals and passionate about using my platform because I’ve worked hard to create a safe space for women to learn and ask questions while sharing tips from my family and our heritage.”

Shahzad also attributes the success of her platform to the skills she’s attained through her work at PGIM. Applying her project management experience and organizational expertise, Shahzad continually receives positive feedback from brand owners and CEOs about her high level of professionalism.

“I’m really grateful for the experiences I’ve had. I feel empowered that I can have this meaningful career in finance and get to express my more creative side—I can be myself all the time.”

By Jessica Robaire

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Graciella Dominguez: Vice President of Investment Operations, Operations and Innovations, PGIM

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Graciella Dominguez“Lean into all experiences, professionally and personally,” says Graciella Dominguez. “Find the opportunity to grow from everything you experience, channel those lessons, and then use them to do good.”

From Numbers to Relationships

Dominguez was drawn to accounting due to her love of numbers – concepts like credits and debits that felt concrete and measurable. She began working for Ernst & Young while in college, and then joined Prudential a year after graduating. After switching to a smaller firm for a few years to try out auditing, she returned to PGIM, Prudential’s global asset management firm, where she has been for 23 years.

“That brief experience in auditing really challenged me and gave me a lot of confidence in going to different places, interacting with different people and tracking with different levels,” she says. “It was pivotal for my career, but it wasn’t for me long-term, so I brought what I learned back to PGIM.”

PGIM has grown tremendously during her career, and so has she. Although Dominguez went into accounting because of a love for numbers, her work focused just as much on supporting people as she stepped into leadership.

“You really have to push yourself in areas of unexpected growth. When I started as an accountant, I didn’t realize that interacting with people and building relationships was going to be more central to my experience,” she says. “I have been able to grow my relationships, and they are so important – and rewarding – in accomplishing greater things.”

Facing the Toughest Experiences as a Mother

“What has been most pivotal in my career, and truly in my life, was when I became a mom,” says Dominguez. When it comes to the challenge of dividing your energies between work and home as a working mother, nobody understands what that means more than she does. She lost her 11 year-old son, Alexander, five years ago. Throughout her son’s life journey, Dominguez worked, mostly full-time. One of her key motivators was providing for her son and his needs.

“I think we as women have to lean into all of our experiences. For me, that included leaning into being a mom of a child with special needs. It shaped me both as a person and as a professional,” she says. “I learned from his great strength, determination and courage in his short life.”

Alexander was born medically fragile, immunocompromised, hearing impaired, legally blind and ultimately unable to walk. While parenting a child with several medical needs, Dominguez had to find her voice in advocating for what was important when it mattered most.

“Being a mom to a child with so many medical complexities gave me the confidence to speak up and say, ‘No, I don’t agree with that. I don’t agree with how you’re going to treat my son,’” she says. “And that same confidence to speak up for what I believe crossed over into my work.”

Her motherhood has also inspired her to be a more empathetic leader. “As a leader, I’m more compassionate now,” she says. “Because I understand that people have so much more going on than you see at work. You don’t know the challenges people are facing day in and day out. Everybody has a story.”

She continues, “But at the same time I also expect a lot from people, because I saw my son, who was completely disabled, and his friends who faced the same conditions, show up for school every day with a smile and ready to work. That inspired me and really shaped me. Witnessing that has given me the courage to face anything. That is how I honor his legacy to make him proud.”

Dominguez describes her son as a social butterfly with a sparkling personality and smile that shone through no matter what challenges life threw at him. Knowing him has pushed her to get out of her comfort zone – as an introverted person – and show up more with her own voice to share her story and her son’s legacy.

“I hope sharing my story can inspire people to learn how both amazing and fragile life is,” she reflects. “We all have these gifts and abilities to do good things, so never take that for granted.”

Working with Integrity as a Core Value

Being detail- and research-oriented has supported Dominguez throughout her career, as well as her principle of doing due diligence for the work and her clients. Integrity is the most important value to her – being who you are, being true to yourself and leaning into your experiences.

As such, Dominguez is inspired by leaders who show openness and truly embody their words and what they stand for. “I admire the leaders who truly act and behave from who they say they are and who show up as their authentic selves,” she says. “I respect integrity.”

When approaching any challenge, Dominguez emphasizes process – taking the necessary extra steps and knowing the why behind every decision you make. This comes to the forefront especially when bringing junior members on board – helping them learn processes in a way that helps them appreciate each step and helping them question each decision. She aims to always rise to the challenge to do the best, most complete job for the task at hand.

Using Her Voice as a Latina Woman

As the daughter of Cuban immigrants, Dominguez prizes hard work. “My family came to this country seeking freedom, and that’s not lost on me. My family left everything and sacrificed so much. Their experience instilled in me a strong work ethic,” she says. “My grandparents and my parents (who immigrated as adolescents) understood the importance of education and hard work to succeed amidst challenges, and that drives me. I want to honor their legacy, and my son’s, with how I show up in my own life.”

Dominguez appreciates working in a culture that also values high integrity and high standards, and emphasizes diversity and inclusion. She is also co-founder of the PGIM Operations & Innovation Latinx Networking group.

“Representation is really important to me as a Latina woman. Earlier in my career I used to observe women in more senior positions. I love working for a company that really values diversity of backgrounds and perspectives, and puts so much effort into their initiatives for diversity and inclusion,” she says. “It’s really important to me to use my voice and honor all the women who paved the way for me. I am also trying to pave the way for other women. I don’t take that responsibility lightly.”

For those beginning to make their mark in the professional world, whom she also learns from, she advises, “Be yourself. Hard work and integrity pay off at the end of the day. Be yourself and be open to possibilities.”

Reflecting back she says, “I wish I would have been kinder to myself as a young mom. Challenges can look so big sometimes, but you will climb them and be successful, and it’s going to be OK.”

Kindness, More Kindness, and Service

“The more I go through life, the more I realize we do not know what challenges people have every day,” reiterates Dominguez. “So above all, we need to practice kindness towards ourselves and others.”

Classically trained in piano, Dominguez has also returned to playing piano since leaving it behind in her early 20s. She is remembering how to read music again and starting out first with greatest hits.

Born and raised in New Jersey, Dominguez is passionate about volunteerism and giving back to the community. She is on the finance council and works with children at her church. In honor of Alexander’s birthday each year, Dominguez and her husband collect and donate books to Cooperman Barnabas Medical Center, the local hospital where their son spent so much of his time.

By Aimee Hansen

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Mikaylee O’Connor: Principal, Senior Defined Contribution Strategist, PGIM DC Solutions

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Mikaylee O'Connor “One thing that’s at the core of how I operate is a focus on internal versus external gratification. I tend to go above and beyond for my own satisfaction because I have very high standards for myself,” says Mikaylee O’Connor. “Everyone’s way towards internal gratification is different, but I feel that when you do things for yourself, you exude different energy and attract more of what you want.”

Moving From Her Comfort Zone

Growing up in a small Oregon town, O’Connor was put on the Montessori track with an emphasis on independent thinking and hands-on learning. She then skipped middle school, while being home-schooled and spending her time in the stables, riding horses. She graduated high school at 17 and was off to Portland State University.

As a finance graduate, O’Connor joined a local investment consulting firm, RVK, as an investment analyst. She stayed for almost 13 years, working her way up while advising clients on pensions, 401k plans, and endowment foundations, to eventually becoming Head of Defined Contributions (DC). In 2020, she craved a new challenge.

“When you feel like you’re in your comfort zone, it’s the right time to maybe see about getting outside of that comfort zone. I wanted to do more strategic thinking, be a little more creative and be part of a movement to help the DC industry forward and find better solutions for everyday people,” she says.

In the start of 2021, she joined PGIM as a senior DC strategist and, this past February, she became a principal. O’Connor enjoys the ‘think tank’ atmosphere of her team: “We’re always asking, ‘What is the problem out in the market and how can PGIM and Prudential as a company come together to solve these problems and deliver solutions?’”

Embracing the New Challenge

“In my experience, the consulting world is very much for people who like to be constantly challenged,” she notes. “Every client project provides something new – new content, new research, new ways of presenting materials, or simply, adjusting to different personalities.”

O’Connor finds that everything depends upon how you approach those challenges: getting frustrated or seeing each as an invitation to grow. Receiving the support of mentors and advocates has been critical to rolling with new challenges. As she’s become senior, providing that same support to junior associates has been essential and rewarding.

She’s also learned to stay open to what she doesn’t yet know: “If you’re constantly trying to learn new things, you have to be humble to the fact that you don’t know everything,” she advises. “It’s important to surround yourself with different voices and perspectives so that when you’re trying to solve problems or provide solutions, you have that 360-degree view instead of looking only right in front of you.”

Opening to More Possibilities

O’Connor is known to give an unfiltered view of what she is thinking and play her own part in widening the conversation in any meeting.

“I push us to think differently or to have a different view on what we’re trying to solve. I often bring the end-user to the table,” she reflects. “Let’s put ourselves in the position of the person that’s going to be using this product or solution. How would they go about doing this or that?”

Despite being in a predominantly white male industry, O’Connor had the opportunity to work under a female CEO at RVK and with many female shareholders throughout her career. But when becoming involved in industry organizations, the gender skew became salient. Her approach to being underestimated by male peers was simple: “I would feel compassion for them because, at the end of the day, that’s their own challenge, not mine.”

But mostly, she has leveraged being a unique voice in the room to help her challenge the status quo.

“I’ve always been one to point out that just because we’ve done it this way in the past doesn’t mean we need to do it this way going forward. What are we missing? What should we be thinking about differently?” she says. “Having both that fresh perspective and high conviction about thinking about problems and solutions differently doesn’t always make people feel good. But I like a good debate and being uncomfortable talking about things, because we are only going to grow more through it.”

Adapting For Your Audience and Your Team Members

“Whether it’s your boss, client or a prospect, reading the room and adjusting how you approach the situation and your communication style matters to being effective,” says O’Connor.

Being able to adapt to and apply different ways of learning and communicating has been a powerful component in her ability to meet people where they are and create the momentum that drives results. Equally, sitting on the extrovert-introvert cusp, O’Connor highly values adapting her approach to hearing all voices in the room, including considering the different ways they may need to be heard.

“You have extroverts and introverts. You have people who need more time to think and you have people who can come up with ideas right on the spot in the meeting,” she says. “In order to capture all of the different great ideas, concerns and considerations, you have to consider how to make sure that you’re getting what you need from each of them, and that you make them all feel included.”

Reframing for Confidence

Shifting her mindset to increase her confidence has helped O’Connor to take on bigger roles.

“In the past, despite being overly prepared for a client meeting or discussion, I would still feel nervous,” she recalls. “But one mentor in particular assured me, again and again, that I knew more about the topic than anyone in that room. Over time, it shifted my perspective from being the ‘victim of scary stares and expectations’ to a ‘person with important information to share.’ I shifted to see that I’m going in there as a teacher.”

Now she loves to speak in front of an audience and does so often. Another learning curve has been around the challenge of leadership.

“I can be a perfectionist and always want to do things correctly, but when you’re in charge of people and emotions, that’s a different skillset and a different realm of understanding how to deal with things,” she says. “It takes a lot of listening and stepping back to ask how you can best support each of these individuals. Ultimately, their success is also my success.”

She’s also learned to always ask for feedback and to create an environment where people feel comfortable giving it.

Meanwhile, O’Connor has recently been unlearning multi-tasking as a leader: “I’ve been working on mindfulness and there’s a huge benefit to focusing your attention on one thing at a time. I’m much more active and creative when I get rid of distractions.”

Focusing on Internal Gratification

“By focusing on internal gratification, I’ve naturally been given more opportunities without necessarily focusing on what I have to do to get to the next step or to get promoted, because those are external focuses,” she notes. “By doing what I want to do – to grow and to learn and to do it for myself – I’ve just had those opportunities come to me.”

For years, O’Connor has been doing a self-review after meetings to consider whether she could have done anything better or differently. While it can be exhausting, it helps her grow and creates internal gratification.

“I would encourage women to focus internally and not worry so much about external steps and getting to the next one,” she says, “because then you’re doing the work for someone else instead of yourself.”

Being Human, First

O’Connor appreciates how PGIM Quantitative Solutions CEO Linda Gibson shows strength in her role and humanness in her communications.

“Linda has brought a sense of ‘we’re all just people.’ We’re all trying to do the same thing and nobody needs to be on a pedestal,” she says. “She can talk to you in the office just like anybody. It’s refreshing.”

O’Connor observes that since the pandemic and remote offices, more people are breaking down barriers and hierarchy, while seeing everyone as individuals and not just as employees.

“If we want to bring out the best in ourselves, we also have to show that we’re all humans and we all have things going on,” she says. “We can normalize that. But also, how do we take that change and use it to create a more cohesive and better company? Our relationships can be stronger because I can relate to you on something I didn’t know before.”

Speaking of which, O’Connor finds travel to be good for the soul, and enjoys seeking out AirBnBs and boutique stays with her husband while getting out of their comfort zones and taking in the cultures wherever they are exploring, most recently the Swedish Lapland in the forests of the Arctic circle, with saunas and cold plunges. Iceland is another favorite. Closer to home, she likes scouting out new atmospheric spots for a great meal in New York.

By Aimee Hansen

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Op-Ed: Breaking the Mold – How to Become Your Own Boss

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Amy PorterfieldThe meeting that catalyzed me to become my own boss feels like it happened yesterday.

I was working as the director of content development for peak performance coach Tony Robbins and was called into a meeting. Online education was just starting to take off, and Tony had invited some of the most successful entrepreneurs in this space to come in and share their experiences.

These men — and they were all men — had hugely successful digital courses, online membership programs, and mastermind groups. We were exploring how we could add this strategy to our business.

My job was to sit there quietly and take notes. And since women hold only 8.2% of CEO roles, this dynamic didn’t seem unnatural to what I was used to. But as I was taking notes, everything started to change for me.

I realized I wanted a seat at the table, not just near it. I wanted to be a part of changing statistics like the global gender pay gap – currently estimated to be 16%, meaning women earn an average of 84 cents for every dollar men earn.

And finally, I realized I wanted to be part of the 12 million women-owned businesses in the US that generate over $1.8 trillion in revenue and employ over 9.4 million people.

So I decided to start my journey towards these desires right then and there in the meeting. I paid close attention to what these powerful business owners were sharing, and today, I want to pass along three lessons I learned to help you build the business – and life – of your dreams, too.

1. It is possible to design your life on your own terms.

As I listened to those entrepreneurs talk about their businesses, I realized something that changed how I thought about my career path. These men were all in different industries but had one thing in common: freedom. They weren’t hitting the glass ceiling. They weren’t asking for permission. They were taking charge of their own destiny.

Without knowing it, women let outside forces shape their destinies all the time. Just look at the latest PitchBook data showing how startups with all-women teams receive a mere 1.9% of the 238.3 billion dollars of venture capital awarded each year.

But these men… in this meeting? They were calling the shots and not waiting for someone to give them a green light on their business ideas.

They were achieving business success while designing a life on their own terms. And I wanted to do that too.

For me, the answer was to build my own business and be my own boss. I wanted to do work I loved and do it how, when, and where I chose. That would be designing life on my own terms.

When I started exploring what life on my own terms looked like,
 I remember reaching out to a business owner and boldly asking:

 “I know you don’t offer this as a service, but could I pay you for an hour to ask how you built your business?” 



She said yes, and I spent that hour under my desk whispering into the phone as she broke down steps to get started, how to align a business with personal values, and how she brought her vision to life on her terms.

It wasn’t glamorous, but it was just what I needed.

She could have said no, and if that happens to you, I want you to look at that “no” as bringing you one step closer to a “yes.” Keep reaching out and asking people for advice. Eventually, a door will open.

And mentors like this don’t have to come in the form of a person, either. Books like Big Magic by Elizabeth Gilbert showed me how my ideas were a big enough deal that I could build a business around them.

The message she shares in the book about how you can either go all in and share your gifts with the world, or dismiss them, resonated with me and served as the kick in the pants I needed to get crystal clear on how I wanted to impact the world.

A life designed on your terms might look different than mine. That’s the beautiful thing: You have the power to choose your path. 

And once you do, I encourage you to find a mentor to guide you as you walk down it toward your dream life!

2. Your existing knowledge and skills are more valuable than you think.

As I listened to the men in that boardroom talk about the online courses they were selling, I took note of their success. Each one had taught hundreds or even thousands of students, creating a massive impact in their field. From dating advice to real estate investing, they were transforming lives. It was truly inspiring.

I also took note of what they didn’t say. None of them talked about investing years and years into certification and education before they created their first course. They didn’t go back to school to earn a business degree before they launched. They weren’t wracked with fear about staying on top of their game.

In fact, whether you’re starting your own business or applying for a new job, this seems to be a common theme. A Hewlett Packard report found that while men apply for a job if they meet only 60% of the qualifications, women tend to apply only if they meet 100%. That stops now – you know enough to take the first step!

Your knowledge today has enormous value if you share it with the right audience. Whether you are starting an online education business of your own or continuing a professional career, the key is to look for places where you have a 10 percent edge.

If you are at least 10 percent ahead of those you serve, you can lead the way. In fact, it’s sometimes easier to lead when you aren’t too far out in front.

3. Boss traps are a barrier to success.

The third thing I noted during the meeting was that these highly successful entrepreneurs had faced their share of problems. Yes, a professional career comes with challenges. But becoming your own boss isn’t always smooth sailing either.

As I started my own business, I discovered that many of the traps you fall into as a boss stem from “demoting” yourself and not embracing the full scope of your role. You may experience some of these in your career as well. For example, one of the most common boss traps is falling prey to superwoman syndrome and trying to do everything yourself.

A study by the U.S. Bureau Of Labor Statistics found that 20% of businesses failed within the first year, and I believe many are due to superwoman syndrome.

There are so many stories of entrepreneurs who had to learn this lesson the hard way, from Arianna Huffington, the co-founder of The Huffington Post, to Sophia Amoruso, founder of Nasty Gal.

In 2007, after launching the news site, Huffington became consumed by the demands of running the business and regularly worked 18-hour days. In 2007, she collapsed from exhaustion and hit her head, resulting in a broken cheekbone and stitches.

This experience prompted her to reassess her priorities and make changes in her life and work. She stepped down as editor-in-chief of The Huffington Post in 2016 and launched Thrive Global, a company focused on wellness and reducing burnout.

Huffington has since spoken about the importance of taking care of oneself and avoiding the trap of “superwoman syndrome” in order to be successful in business.

Sophia Amoruso is another example of a founder falling into the “superwoman syndrome” trap. She launched the online clothing retailer Nasty Gal in 2006 as an eBay store and grew it into a successful brand with over $100 million in annual revenue.

However, Amoruso took on too much work herself and ultimately experienced burnout. In 2015, Amoruso stepped down as CEO of Nasty Gal after the company filed for bankruptcy.

She has since gone on to start a new company, Girlboss, which aims to provide resources and a community for women entrepreneurs. Amoruso has spoken publicly about the lessons she learned from her experience with Nasty Gal, including the importance of delegation and self-care in avoiding burnout.

I tell you these stories not to discourage you, rather, to remind you that none of us magically wake up one morning feeling like a “boss babe” from Instagram. It takes time, experience, and a willingness to change to become a leader who can live life on her terms.

You absolutely deserve to get there. And along the way, don’t forget to take off your superwoman cape and ask for help so you can bring people along for this incredible journey you’re starting! 

It’s like the legendary leader John Maxwell says, “Leadership doesn’t involve being ‘lonely at the top.’ If you’re at the top of a mountain alone, you’re not a leader, you’re a hiker.”

Dream big, but don’t stop with a dream. As quickly as possible, take a step toward that dream. Action creates clarity, and clarity will propel you to more action.

Don’t wait. I know you’ve got this.

Amy Porterfield teaches eight best-selling courses that empower women across the globe to take their futures into their own hands. She hosts the top-ranked marketing podcast Online Marketing Made Easy and author of the new book, Two Weeks Notice: Find the Courage to Quit Your Job, Make More Money, Work Where You Want, and Change the World.

(The opinions and views of guest contributions are not necessarily those of theglasshammer.com).

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