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Power Women: Sierra Hampton-Simmons of Project Management Institute On How To Successfully Navigate Work, Love and Life As A Powerful Woman

An Interview With Candice Georgiadis

Boldness and bravery. It is critical to lead and operate through this lens of being bold in all you do. Operating in a passive manner will not yield the results you desire. Whether it’s raising your hand to lead a project, adjusting your plans in the event something isn’t going right, or suggesting a new business proposal to help lead your organization to success, positioning yourself as someone who isn’t afraid to take risks and who yearns to lead with passion will put you on the path to true success.

How does a successful, strong, and powerful woman navigate work, employee relationships, love, and life in a world that still feels uncomfortable with strong women? In this interview series, called “Power Women” we are talking to accomplished women leaders who share their stories and experiences navigating work, love and life as a powerful woman.

As a part of this series, I had the distinct pleasure of interviewing Sierra Hampton-Simmons, Vice President, Products, Project Management Institute (PMI).

Sierra Hampton-Simmons has nearly two decades of experience as an expert in Certification Management with a track record for transforming and developing lucrative brands to include relevant performance-based testing and training. She joined PMI in 2013 and currently serves as Vice President, Products. At PMI Sierra is responsible for the entire portfolio of Certification Products including the PMP credential-the gold standard in project management credentials.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your childhood “backstory”?

An interesting part of my childhood that led to who I am today is that I was adopted by my grandparents. I was raised by people who were several decades older than me, which probably contributes to me having a bit of an old soul. They were raised in the rural South, and we had quite a garden in the backyard where we grew vegetables and fruit. Growing up with them taught me the value of hard work as they both worked well past retirement while caring for me and their home. My grandparents always encouraged me to pursue higher education, which they didn’t have the opportunity to do. It was ingrained in me from a very young age.

My grandfather was born in 1898, so he saw America change so much throughout his life. I remember I was maybe eight or nine, and my grandpa asked me, “What do you want for Christmas, baby girl?” I wanted the full series of the Nancy Drew books, so that’s what he bought me. He was so proud that I wanted books — not a doll, not a toy, but some books. We spent time together reading and discussing the plot. Through those pivotal moments with my grandfather — the man who raised me — I learned that while my grandparents never had a formal education past the fourth or fifth grade, they were very smart. And much of what I know now I attribute to them and the many life lessons they bestowed upon me.

Can you tell us the story about what led you to this particular career path?

One of my first jobs was as a teacher. I was a K-12 teacher, and I taught English in Japan. When I came back from living in Japan for several years, I taught Japanese to American kids. The way I taught was less about doing things by the book and more about giving students practical skills. How do you order food in a restaurant? How do you call and make a request to a customer care agent?

After that, I took that same philosophy I had employed in those previous teaching jobs and applied it to teaching people how to code using Java programming and HTML. This was when that technology was relatively new. I didn’t necessarily agree with how the information was presented in textbooks, so I employed some nontraditional teaching techniques to help students think more critically about the information they already knew, the information presented to them, and then how to merge all of that together to learn the technology and skills we were focusing on. At the time, this was called project-based learning. This way of teaching told me who actually learned the information and what we needed to reinforce — in other words, the effectiveness of the overall learning experience.

Teaching others taught me so much about myself: that I have a passion for empowering people to do big things, to make an impact, and to gain skills and expertise in their chosen fields. My role now has expanded from certifying people to include helping them train and learn beyond the four walls of a classroom and apply their knowledge, skills, and passions to new opportunities. And beyond that, it’s about product development. A major component of my role is understanding customers, the psychology of business, and the intrinsic values that drive people and their decision-making. All of my previous experiences have molded where I am today, and I don’t take a single moment for granted.

Can you share the most interesting story that happened to you since you began your career?

When I was a teacher, I had my students email me their assignments. One student decided to email me a job listing he thought I would be interested in. He said that while he enjoyed learning from me and having me as a teacher, he thought this job would be a great fit for me. I decided that since this student had taken the time to think of me and my skills and abilities, I would check it out. I ended up getting the job that my student sent to me — which focused on training adults in technology — and it ended up being a great job for me. That job opened up the door to the path that led me to where I am today, and I am forever grateful to my students for seeing something in me that has ultimately led to more than I ever expected. The moral of that story is that we have much to learn from younger generations, just as much as they have to learn from us

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

I call myself a “frustrated artist,” and that has been very important for my professional journey because it speaks to the creativity and innovation I bring to work every day. There are things I obsess over until they are exactly as I imagine they should be — that iteration process lends itself to getting an idea, a product, whatever it may be, just right so that whoever is at the receiving end of that innovation gets the best work or product possible.

I also consider myself to be transparent. I think oftentimes people are wary about sharing or thinking out loud with leadership for numerous reasons. I was cut from that cloth for a very long time, but I found that operating in that way led to a lot of confusion and scramble. So, something that I learned over the last decade is that oversharing to some extent and building trust — basically, being a transparent leader — is one of the most important leadership attributes a person can possess.

Lastly, I consider myself to be reflective. In many aspects of my life and career, I have paused to reflect on people and experiences that have shaped where I am today, whether in a positive way that has caused me to want to emulate certain leadership qualities, or in a negative way that has led me to do things differently than I have experienced in the past. I didn’t always have the best leaders in my previous experiences. But I have used those instances of negative leadership to learn how I should lead differently, and it has resulted in me managing people the way I would want to be managed — with interpersonal skills (we call them “power skills” at Project Management Institute) at the forefront, such as empathy, communication, and collaborative leadership.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. The premise of this series assumes that our society still feels uncomfortable with strong women. Why do you think this is so?

Women have made massive strides in the workplace and in society at large over the past few decades. But in doing so, they have challenged the status quo. They have challenged the ways things have always been, resulting in discomfort amongst those who wish for the world to remain static. Anyone who has ever gone against the grain knows how difficult it is to effect change on a large scale — understanding that change doesn’t happen overnight. So, it’s this idea that there are pursuers of change and forces for good out there who won’t stop until this change is normalized, resulting in women — in everyone — being viewed through the lens they deserve: as powerful, resilient changemakers.

Without saying any names, can you share a story from your own experience that illustrates this idea?

When I was first starting in my career, I worked on a very large-scale innovation project using simulations and emulations in a certification exam. While this wasn’t new for the IT industry, we created some new types of emulations that indeed were different and got the attention of people in the testing industry. However, this project came with multiple risks, involved tons of internal and external stakeholders, and as a result also came with many individuals who challenged the concepts and openly fought against wanting the project to move ahead. These parties would stop at nothing to cause delays and lend criticism to the efforts during the development. They would often ask, “Why can’t we just do a normal multiple-choice exam?” or “Is this investment worth it?” Despite these objections, I continued with this project and succeeded in bringing cutting-edge learning and testing experiences to the market. The resulting product was a game changer because it enabled people to demonstrate their skills in virtual environments thereby proving they were the best job candidates. And as a result, people who traditionally struggled with old fashioned tests and theoretical learning, found these new products delightful. This resulted in my company at that time making this new way of learning and testing standard throughout their products.

What should a powerful woman do in a context where she feels that people are uneasy around her?

The most important thing a woman can do in this situation is remain true to who she is. Rather than shy away from the situation to make others feel more comfortable, she should remain steadfast in leading and inspiring those around her to be their most genuine and authentic selves, while knowing that there will be times that she’ll face moments of doubt — both from internal and external forces. Whether it’s standing in front of a crowded room, leading a presentation or meeting, or working one-on-one with a peer, authenticity in these moments is critical, which can lead to more support from those around her as they witness this authenticity in action.

Additionally, in these moments a woman should focus on utilizing her power skills — interpersonal skills like empathy, communication, active listening — that come naturally to many women. Because these skills are becoming more of a priority in the workplace, women can lean into them as a competitive advantage.

What do we need to do as a society to change the unease around powerful women?

Simply put, we need to support women in their endeavors and elevate and promote women in the workplace. Diversity of all kinds, including gender diversity, leads to better business outcomes. Similarly, we need to appreciate and uplift women in these moments of greatness and recognize that it is normal for women to succeed, to prosper, to lead. And for women who are in positions of power, they should work to uplift other women, whether their peers or those who are just starting their careers, to prove a commitment to this growth. We are all where we are today because of the women who came before us, so putting this collective mentality at the forefront of effecting change will ensure that the generations of women who follow us will have the same access to opportunities that we have today, and hopefully, in even better and more prosperous ways. When I was working on the simulation project I mentioned earlier, the detractors were often times men who were in roles much higher than me. However, I was fortunate to also have the support of very strong women who were experts in the field, believed in our project vision, and leaned in to assure we met our objectives.

In my own experience, I have observed that often women have to endure ridiculous or uncomfortable situations to achieve success that men don’t have to endure. Do you have a story like this from your own experience? Can you share it with us?

We have all found ourselves in situations that make us uncomfortable, oftentimes having to prove our resilience through that discomfort to overcompensate for preconceived notions about who we are and what we bring to the table, all thanks to stigmas and stereotypes women face in the workplace.

At one point early in my career, I was struggling to get to a formal managerial title, and I didn’t understand why because I had been working really hard, fostering relationships with colleagues and managing a team of young rising professionals, all while proving I had what it takes to be in that role. Finally, I got promoted, and my direct manager at the time told me I needed coaching on my professional appearance. After asking for an example, I was told, “Maybe it’s your shoes. Have you ever thought about wearing heels?” I wondered what my shoes had to do with whether I can be a good manager. It was so frustrating that this person believed that the shoes I chose to wear should hold me back. But rather than getting upset or shying away from the conversation, I explained why my choice of footwear was necessary to perform my job, a technical role that required walking around and inspecting equipment. However, the fact that this person’s perception of what was “professional attire” for a woman included high heels and make up was something that brought delayed progress to my career. This was not a roadblock for my male counterparts.

And through all of this, I have learned that I am much more than the labels and stereotypes placed upon women, and I will continue to push that boundary for myself, for the women around me, and for future generations of women.

In your opinion, what are the biggest challenges faced by women leaders that aren’t typically faced by their male counterparts?

Women have had to overcome many hurdles in society and in the workplace over time that men have not had to face — from overcoming the stigma that women shouldn’t work, to the time it’s taken to accept that women can lead at the very top, to how women have been disproportionately affected in the workplace by the pandemic. There’s much work that has been done to ensure women are heard, seen and valued in the workplace.

But at the same time, what we’re witnessing now is no longer whether women belong in the workplace, but where do they belong? The answer is everywhere. Industries that have conventionally been more male-dominated are seeing women fill new roles in droves, proving that not only can women succeed in roles that have historically gone to our male counterparts, but that they will succeed. And it’s thanks to the women who have come before us and the women who are alongside us now that we can continue to elevate women in the workplace today and for future generations of female leaders.

Let’s now shift our discussion to a slightly different direction. This is a question that nearly everyone with a job has to contend with. Was it difficult to fit your personal and family life into your business and career? For the benefit of our readers, can you articulate precisely what the struggle was?

To some extent, it was difficult to fit my personal and family life in my career. Early on in my career, I made a choice to become a single mother. I wanted to be a mother, and I wanted to advance in my career, and I felt like I could do both. My son was a very rambunctious little boy. He had a lot of energy, and he wanted to spend a lot of time with me. I was working on a very big project and spending some time on the weekends in the office. I made the decision to bring my son with me, and I encouraged my team to bring their kids, as well. We all had to make it work, and I encouraged my team to do what they could to make it work, too.

However, there were some instances that I will never forget the disappointment on my son’s face. He was older, maybe second or third grade, and he was attending a summer camp. He had a softball game, but the game was in the middle of the workday, and I wasn’t in a position where I could say, “I’m not going to such and such meeting because my son has a softball game on a Tuesday at 10 in the morning.” I didn’t feel comfortable actually making that decision, and I wish I had. It’s important that your family realizes they are more important than the job, and it’s something I’ve been working on as I balance home and work even to this day.

What was a tipping point that helped you achieve a greater balance or greater equilibrium between your work life and personal life? What did you do to reach this equilibrium?

As a mother, I know the toll that burnout takes on the person experiencing it and on those they love and work with. And I know that I cannot give my best to my family if I am not taking care of myself and prioritizing things that bring me joy and allow me to re-center my priorities. Anyone who has the important job of caring for someone else — whether children, elderly family members, or a friend who may need a little extra help — understands the importance of advocating for yourself in these moments of burnout when work-life fulfillment isn’t being achieved, because there are people who are counting on you in various ways.

Something I have found to help me in these moments that I struggle with balance is prioritizing family time. For example, at one point, I had to take off work when my son was sick, and I felt the need to take a picture and show my boss to ensure they knew I really did have something going on at home that was keeping me from work. I received a positive note back saying, “I don’t know why you felt you had to share me the picture. I’m sorry your son is going through this, but please know that we support you, and please put your family first.” It was the wake-up call that I needed — the permission to be human, the permission to be a woman and a mother. I have to prioritize everything accordingly because I may not have this job next week, but my family, if I’m lucky, I’ll have for the rest of my life. I think that was a pivotal moment for me career-wise. It allowed me to recenter my priorities, restore my sense of calm, and manage my priorities as I moved forward as a mother and as a professional.

I work in the beauty tech industry, so I am very interested to hear your philosophy or perspective about beauty. In your role as a powerful woman and leader, how much of an emphasis do you place on your appearance? Do you see beauty as something that is superficial, or is it something that has inherent value for a leader in a public context? Can you explain what you mean?

While I’d like to live in a world where appearance doesn’t matter and that in the workplace all are judged fairly by their accomplishments and contributions. However, the reality is we all have some level of internal biases that are oftentimes cultivated around what society has defined as beauty standards. And while this is never something that should have bearing on a woman’s career, things like ageism, sizeism, and even how a woman dresses can become a blocker for women. Sometimes those inflicting these standards are not even aware of their biases and unconsciously tie a woman’s value to their appearance.

For me at one point I was very overweight and noticed that many of those who entered their career at the same time as me were outpacing me in their advancements. I wasn’t aware of any professional accomplishments they had that exceeded my own. At first, I thought there was perhaps something I needed to do differently: work harder, take on more complex assignments, etc. But at one point I wondered how much my size and others’ biases were playing against me. So, while continuing to focus on my work, I began to focus on my health and over time lost a significant amount of weight. With this newfound focus on my physical health, I gained more confidence and began accomplishing more positive outcomes at work, but I recognize that the most impactful outcome was that I felt better — not that others felt better about me.

To me, true beauty is centered on wellness — both physical and mental wellness. When I feel like I am taking care of my body and mind, I feel that I am able to give my best to those around me and the work that needs to get done. Additionally, self-confidence is also a beautiful thing to witness. Women and men must look within to define what makes us who we are and find practices that cultivate this sense of well-being, leading us to being better leaders and colleagues because we see people for who they are beyond the unrealistic expectations society sometimes places on us.

How is this similar or different for men?

This can be similar for men because everyone has expectations for how leaders should look and present themselves. However, this does seem to be exacerbated for women simply because of the stigmas and stereotypes women in the workplace have had to overcome in relation to how they look and dress. But I think what we’re seeing more so now than we have in the past is this sense of allyship from our male counterparts — celebrating women on International Women’s Day and during Women’s History month (and year-round), uplifting female voices in the workplace, and shining a light on all of the change women are spearheading across industries and sectors. It no longer has to be us versus them. When we come together as allies for each other, that is when our best work gets done.

Ok super. Here is the main question of our interview. Based on your opinion and experience, what are the “Five Things You Need To Thrive and Succeed as a Powerful Woman?” (Please share a story or example for each.)

  1. A community who will uplift you. To me, this is one of the most important aspects of being a powerful woman in our personal and professional lives. We can’t do it alone. We must have a team of people both inside and outside of work who we can lean on when things get hard, who we can turn to when we need a helping hand, and who we can rely on to keep us grounded. I would recommend looking into both virtual and in-person networking communities, as I’ve seen firsthand through PMI’s chapter network that they can be a great way to connect with people who will both empower and challenge you.
  2. Time and space for resetting. We can’t be everything to everyone at all times, and this is especially true for the workplace. Furthermore, we can’t expect our people to give their all to their work if they aren’t taking care of their mental well-being, too. So, we must model what it looks like to prioritize mental wellness not only for ourselves, but for the people we lead, as well.
  3. Intellectual curiosity. We all know that learning and growth isn’t limited to a classroom. The key to being a powerful, impactful leader is committing yourself to lifelong learning and using that knowledge to drive better business and people outcomes in your respective industries. Whether it’s honing an interpersonal skill like collaborative leadership or obtaining an advanced degree or certification like our Project Management Professional (PMP)® at Project Management Institute (PMI), being a lifelong learner and finding joy and passion in curiosity will set you up for success in the long run.
  4. Empathy for yourself — and others. If we’ve learned anything over the past two years, it’s that we need to extend empathy to others and to ourselves if we want to be successful and collaborate in meaningful ways. Finding that right balance of expectations and empathy is key if you want to succeed as a leader in today’s workplace.
  5. Boldness and bravery. It is critical to lead and operate through this lens of being bold in all you do. Operating in a passive manner will not yield the results you desire. Whether it’s raising your hand to lead a project, adjusting your plans in the event something isn’t going right, or suggesting a new business proposal to help lead your organization to success, positioning yourself as someone who isn’t afraid to take risks and who yearns to lead with passion will put you on the path to true success.

We are very blessed that some very prominent names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US with whom you would love to have a private breakfast or lunch with, and why? He or she might just see this if we tag them.

I would pick Rihanna, specifically the business mogul version of Rihanna. She mastered inclusivity right away. Her whole focal point was creating a brand that catered to every woman. It even evolved because it wasn’t just about women — it was anybody who wears makeup, anyone who wears clothes. I love how in her fashion shows you see everyone, from who you are used to seeing on fashion runways to people who have different abilities, different sizes, different genders. It’s wonderful. She’s winning in this world where there are some pockets of hatred. People are buying her brand. I love how she’s gotten that and made it a universal mission of her company to be a brand for everyone because everyone can be beautiful. I love that.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.


Power Women: Sierra Hampton-Simmons of Project Management Institute On How To Successfully Navigate… was originally published in Authority Magazine on Medium, where people are continuing the conversation by highlighting and responding to this story.