Jes Osrow of The Rise Journey: 5 Steps We Must Take To Truly Create An Inclusive, Representative, and Equitable Society

Authority Magazine
Authority Magazine
Published in
12 min readAug 30, 2021

I am entirely optimistic, or else I wouldn’t have worked so hard to launch a startup that works to bring awareness and change to our current workplace cultures. It really is about people, and people are changing. The world is changing. How do you keep up? How can you pivot? You need to be able to shift, talk about it and have that flexibility. Society, culture, and the workplace are intrinsically linked for the rest of time. I know it is going to take time, and I know it is not going to be an easy journey, but even if it is only one organization at a time, together we will rise.

As part of our series about ‘5 Steps We Must Take To Truly Create An Inclusive, Representative, and Equitable Society’ I had the pleasure to interview Jes Osrow, Co-Founder and DEIBA Specialist, The Rise Journey.

As a no BS kind of person, Jes’ goal is to create fundamental change in People Operations. As Co-Founder of The Rise Journey, Jes works to operationalize DEIBA (diversity, equity, inclusion, belonging, and accessibility) strategies as part of building foundational and sustainable organizational culture. As Head of Learning and Development at Quartet Health, she empowers organizational culture to be inclusive, diverse, equitable, and accessible for all employees.

Thank you so much for doing this with us! Before we dig in, our readers would like to ‘get to know you’. Can you tell us a bit about how you grew up?

I grew up as an only child in rural New Hampshire. My mother was a college professor, and when I was 16, she wanted to take a sabbatical and move to the island of Grenada in the Caribbean. We were the only white people living on the island who were not passing through from cruise boats. People would point fingers at us and want to touch our skin, etc. People knew us all over the island. We were celebrities, and at 16, it was really unnerving for me. I just wanted to live my own life. I wanted to do normal teenage things without being scrutinized.

At the time, I did not realize this, but it ended up being probably one of the most influential times in my life.

When I went back to school in New Hampshire, I was able to see all of this privilege I had. I was able to appreciate the education that I was so spiteful about. I was able to appreciate really basic concepts like hot water, etc. I went on to study art and theater where I wrote my college essay about my neighbors in Grenada who were four year old twins. I painted pictures of them and took endless photos of them. They inspired me every day. The fact that I could write a college essay about my experiences signified just how tremendously impactful this part of my life was.

This experience growing up really changed my perspective on a lot of things in life. I directly attribute this to the work I do in DEI. When I think about being an HR professional and how it impacts me today and what I would advise, it comes down to being able to bring your full selves even in the professional setting. The good, the bad, the ugly, and the everything in between. It’s not about a specific trait you possess, I am most definitely not perfect on paper, but it’s about knowing yourself enough and knowing that you constantly are evolving to know yourself more, and how you bring that to impact the people you’re serving. If you can’t know yourself and can’t reflect with yourself on these issues, how are you expected to support them? Whether it’s a singular person or through consulting with a number of different organizations, HR has the potential to have so much impact.

Is there a particular book that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

Biased by Jennifer L. Eberhardt, PhD.

Mitigating bias plays a significant role in the work that I do. In this book, Dr. Eberhardt explains how bias develops, and suggests it’s something to manage vs. overcome, given how deeply rooted it is in our environment. A large part of working to minimize bias is in acknowledging it, and closely examining the situations where bias is most likely to occur. When we can better plan for and manage these situations, we can mitigate the most negative outcomes.

A few years back I took Harvard’s Implicit Bias test around disability to see if I had a preference for able bodied vs. disabled bodies. As an invisible disabilities advocate, I was upset at myself that I lean toward able bodied people and therefore open myself up to bias against the disabled. It takes a lot of chutzpah, or faith in oneself, and willingness to do better and to listen to those kinds of examples of where you could be doing wrong for others — but that is vital to growth. No one expects you to change overnight, but there should be a better expectation of growth as a human.

Do you have a favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life or your work?

“A rising tide lifts all boats.” My mother repeated this phrase countless times (and still does to this day). These words have always resonated with me and applied to the work that I do. DEIBA work, HR work, anti-racism work, and the base of intersectionality needs to be based on how we can do good for all — not just a small few.

How do you define “Leadership”? Can you explain what you mean or give an example?

A leader is someone who will always step up to advocate for their team with humility and authenticity. As a leader, especially white leaders (or any leader who represents the demographic majority), when you learn that you are not doing something correctly, own it. You should not be afraid to not know something — you should be excited to learn and have light shed upon your blind spots. There is nothing wrong with having an error or misjudgment as long as you acknowledge it and recognize the impact, regardless of your intent. Make space for the error, talk about it, pivot your thinking and move forward with action.

In my work, I often talk about how to release and relieve stress. As a busy leader, what do you do to prepare your mind and body before a stressful or high stakes meeting, talk, or decision? Can you share a story or some examples?

Prioritize your mental health. As hard as I preach the hustle, I equally recognize the toll it can take on you mentally and physically. I take the opportunity to shed light on the invisible disability awareness as often as I can because I have personally struggled with anxiety and depression. Therapy has made a huge difference in my life.

You will face challenging moments. Make space to press pause, take a breath, take a walk. Give yourself permission to decompress and decipher the best path forward.

Working in a space where doing good and providing good for the world is everything. At the end of the day, I know I am making an impact, and that makes everything worthwhile.

Ok, thank you for all that. Now let’s move to the main focus of our interview. The United States is currently facing a very important self-reckoning about race, diversity, equality and inclusion. This is of course a huge topic. But briefly, can you share your view on how this crisis inexorably evolved to the boiling point that it’s at now?

We aren’t at a boiling point, we’ve been at a boiling point for decades. We’re at a particular inflection point, but the anti-racism work has been building in multiple communities globally — people just have better access to the realities of racism (and other isms) that many face every day. The rise of social media has allowed an influx of experiences to be in the palm of our hands rather than relying on other, often strongly biased, media.

The systems in which our world runs are broken for the majority of folks, but it earns a small group of individuals trillions of dollars every year. Greed is a powerful motivator, and that small majority doesn’t just work diligently to keep the broken system intact, but lobbies and takes action for continual decay.

Can you tell our readers a bit about your experience working with initiatives to promote Diversity and Inclusion? Can you share a story with us?

I’ve been working in HR, L&D, recruitment and DEI for 10+ years now. My business partner and I founded The Rise Journey in 2017 with the ethos that all businesses deserve equitable HR and DEI practices — even if they are small businesses, have lean HR teams, or have limited resources. We met at a ‘Managing Diversity and Inclusion in the Workplace’ mini-masters program at NYU. Every class ended with us talking for 3–4 hours afterwards about DEI, operations, HR, and how much foundational change was needed across so many industries. We also wanted to leverage the knowledge and expertise of our peers, colleagues, and of those we connect with along the way. Our model uses those experts to join us and our clients on a project by project basis so we have business and niche expertise that pertains directly to the client’s pain points.

The driving force behind The Rise Journey is a firm belief in accessibility and action: all organizations have the power to create empowering workplace cultures, driven by diversity, equity, inclusion, belonging, and accessibility (DEIBA).

This may be obvious to you, but it will be helpful to spell this out. Can you articulate to our readers a few reasons why it is so important for a business or organization to have a diverse executive team?

I think, just like everything in our society, we have to go back to how it was built, and it was built for old white dudes. I’ve got some great old white dudes in my life, so no shade to them, but when a system is built for able bodied, cis-gendered white males between the ages of 23 and 63, you’re leaving out a lot of people. And with founders, whether they did or did not make the decisions, it’s playing directly into the system that benefits them.

The reality is that if your leadership is entirely white, you will have blind spots. Representation matters. I am white. I am female. I consistently ask myself, ‘whose perspective am I not hearing?’ It’s important to have leaders that can relate and share different perspectives, seek diverse perspectives, and amplify diverse voices. Being an ally is a verb regardless of what your demographic markers are.

Ok. Here is the main question of our discussion. You are an influential business leader. Can you please share your “5 Steps We Must Take To Truly Create An Inclusive, Representative, and Equitable Society”. Kindly share a story or example for each.

While I mainly work with building inclusive, representative and equitable workplaces, the ideas and actions translate when it comes to society as a whole.

  1. DEI efforts in the workplace will never be sustainable without folding and embodying the concepts of belonging and accessibility. There is no silver bullet for activating allies in the DEI mission but I believe that bringing belonging and accessibility to the forefront is our next crucial step — potentially more so to have our society be representative of the people. To put it another way, diversity, equity, and inclusion are the instruments while belonging is the symphony those instruments play. You may ensure that the flutes, cellos, and drums are individually perfect, but it’s only when they work together that they can create art, have impact, and build into something that inspires people.
  2. To say that the DEIBA space is complicated would be an understatement. Part of being complicated means that it’s evolution has the ability to have tremendous impact at every step of change. Our first step with clients is having real, difficult, and honest conversations. Two core values that have run our business are ‘No Ego’ and “Transparency.’ We work to support clients to understand how big the DEIBA space is and that ego has no room to play; talking about our own missteps, errors, and how we’ve grown from them is vital to creating a space where clients can talk about their own past as it relates to DEIBA. By bringing ourselves to the conversations with no ego and showing behaviors that align, our clients are more at ease and more likely to bring less ego to the table. This means more productive work and stronger actions will take place. If you want to have a value-driven business, live by your values day in and day out — especially when it is difficult. Make sure your values are represented in all your materials, conversations, and processes with clients, customers, and employees.
  3. No matter the type of business, workplace, or ecosystem, there is always the ability to implement a DEI task force. Their work can be about many things, but at first should focus on how to diversify the voices and perspectives involved in DEI decision-making, and improvements toward becoming more inclusive and equitable. For organizations hiring, look at your career and about pages, job descriptions, and interview process. Make sure you’re looking with a DEIBA (Diversity, Equity, Inclusion, Beloninging, and Accessibility) lens. Don’t use tokenism in your photos and language — if your workplace isn’t representative demographically then own it and where you’re at in the process.. Think deeply about the people you’re looking to hire, why, and what makes them get excited about an organization or role.
  4. Pay Parity (across gender, race, and other demographic markers) is something EVERY organization must focus on as part of being a part of an equitable society. Equalizing pay and role levels is a huge part of getting equality and financially empowering those who historically have been financially marginalized. Ensuring that people are paid the same for the same work, given raises and promotions based on a clear set of guidlines, and that discrimination has no home within these structures is key for talent retention as well as an understanding of the process.
  5. In tandem, work on creating and cultivating safe (or brave) spaces. The term “safe space” and “physiological safety” are big right now — but what does that actually look like? At The Rise Journey, we differentiate between a safe space and a brave space. In the world, there aren’t many safe spaces that occur naturally. In our sessions (workshops, lunch and learns, conversations, committee meetings, etc) we ask that our clients and their employees challenge themselves to speak up and be vulnerable. It is the bringing and communicating with vulnerability that helps to create a brave space. We don’t expect these brave spaces to develop overnight, nor be sustained without nurturing. But it is within brave spaces that work gets done and real change occurs.

This allows individuals within an organization to have and facilitate difficult conversations as appropriate or needed. This isn’t just around DEIBA issues, but management, performance, interaction, ERGs, etc.

We are going through a rough period now. Are you optimistic that this issue can eventually be resolved? Can you explain?

I am entirely optimistic, or else I wouldn’t have worked so hard to launch a startup that works to bring awareness and change to our current workplace cultures. It really is about people, and people are changing. The world is changing. How do you keep up? How can you pivot? You need to be able to shift, talk about it and have that flexibility. Society, culture, and the workplace are intrinsically linked for the rest of time. I know it is going to take time, and I know it is not going to be an easy journey, but even if it is only one organization at a time, together we will rise.

If you want to make an impact, I feel that HR is the best place to be. In nonprofit, for profit, big or small, change is happening at a more rapid pace. Black Lives Matter has ignited not only a fight around systemic racism and other issues in society, but it has lit a fire under the butt of HR folks in a great way. Not all can see it right now, but there’s tremendous opportunity.

Is there a person in the world, or in the US, with whom you would like to have a private breakfast or lunch, and why? He or she might just see this, especially if we tag them. :-)

Jameela Jamil. Total badass. An authentic voice of our generation. To be able to support, empower, and galvanize the way she does is something I strive to do at The Rise Journey.

How can our readers follow you online?

Thank you so much for these excellent stories and insights. We wish you continued success in your great work!

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Authority Magazine
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In-depth interviews with authorities in Business, Pop Culture, Wellness, Social Impact, and Tech