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Creating a Culture of Courage

On How to Create a Culture Where People Feel Safe to be Authentic & Why That Helps the Bottom Line


In today’s fast-paced world, authenticity in the workplace and in our personal lives has become more crucial than ever. Yet, fostering an environment where individuals feel secure enough to express their true selves remains a challenge. The importance of authenticity cannot be overstated — it is the foundation of trust, innovation, and strong relationships. However, creating such a culture requires intention, understanding, and actionable strategies. As part of this series, we had the pleasure of interviewing Victoria Cumberbatch.

Victoria is a transformation leadership coach in Denver, bringing people from living in states of TENSION to living in states of INTENTION. She’s neuro friendly, trauma informed and supports people through coaching, breathwork and communal events. You can find everything she offers at her website,

Thank you so much for joining us in this interview series. Before we dive into our discussion our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

The true start would be when I was cheated on and in a state of full devastation when I was 21 and at the U of Maryland. Somehow, I found my way out of that nightmarish moment by following little pulls by the universe that led me to the spiritual, self help and psychology sections at Barnes & Noble. I would devour these topics for hours and learning about myriad ways people support themselves out of despair, gave me hope. Bit by bit, over the next few years, I found myself traveling incessantly, building community around the world, and learning about various cultural and religious traditions.

My eclectic experience ended up being well suited for positions like program leader at Remote Year and community manager at, for example. Although I was seen as the community maven, making a bit of a space by speaking at conferences and building a following on LinkedIn, it was leadership that people often came to me for. I have been coaching peers, managers, and more from an early age [if I actually look back]. As an only child, I always had a seat at the adults’ table and therefore, my capacity for understanding and taking on responsibility was grounded in me since I was in the double digits. After a few stints leading affinity groups, hosting honest conversation series and more; I decided to pivot from community specific work and into coaching + facilitation. Which is where you now find me!

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

One of the more interesting ones is when I was co leading a group of 50 digital nomads around the world and a seriously unfortunate event occurred to a few of our community members, while living in Lisbon. Seemingly, a fight broke out in the wee hours and there were lots of stories, blame, and fear being bandied about the following day. Although many of the staff from our home company were in Lisbon at the time, I was asked to speak in front of 75+ people that were affiliated with the company at the time and happened to also be in town. It was nerve wracking!

I wasn’t at the scene, I didn’t have all the facts, it seemed like many people wanted something official to happen and there was quite a bit of “american mindset” on race relations occurring within our group that I felt I had to address. I’d never spoken on anything like this before and I was honestly scared. It was month 2 of 12 full months and it felt very much like everything was at stake.

Turns out, it instigated a flurry of excellent outcomes. Tighter knit community, an open door to deeper conversation, and our group reached out to all the tourism books [think: Rick Steves] and were able to have the offending location removed from those books! It was a big deal and all because our group got together to create real, lasting change. It was an infinitely proud moment for me.

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

A tendency toward action is by far one of the most ingrained traits I have that has allowed me to experience so many things and become a Jane of All Trades, Master of None. In 2018, I had been chatting with some friends that asked “why don’t you just start filming these conversations you have and see what happens?” As a Capricorn, Enneagram 1 with ADHD; I can do nothing half way. So I decided to create a whole company in NYC, enroll a few friends of mine that were better suited at things like filming & editing, found a space to film and began a series called Anderson Street. It was fun, challenging, and opened my eyes to business for the first time. We raised funds and even won two web series awards! You can still find it on YouTube!

Just ask the question, instead of wondering endlessly. I’m a believer that, if you don’t ask, you won’t receive. When I saw the rampant ads on social media in 2016 for joining something called Remote Year, I immediately knew I wanted to lead those trips and not just partake in them. It was easily THE dream job for me; traveling as my work. I couldn’t find a careers area on their page or anywhere, so I went to LinkedIn to find people that worked there. I found an email and sent any/all information I could to have them see what a catch I’d be [having traveled to over 40 countries by then on my own]. It took a year, a full year, but someone got back to me and I went through 6+ interview rounds until I finally began my trip in Spring of 2017.

Seeing feedback, as a gift. This is leadership 101; giving and receiving feedback is a gift. It’s also best served with a framework in mind and a few suggestions at the ready. When I was young and coming up in the professional world, I had tons of feedback but gave none. I’d call my dad [a former police captain, first responder for 9/11 and has a MS in HR] to vent all of the things I wanted to share that would make the workplace a more seamless situation for all. He’d listen and inevitably, one he just said, “it’s time to open the doors at work to permitting feedback. I’m over these calls, I love you, and you know what to do.” Sheesh.

It took me until my second job to muster the courage to request time from my manager to have a two way conversation, where I can share what’s up for me and how we can work better together and also open up space for that manager to actually give me constructive feedback. If you work in the west or the USA, it’s uncommon for genuine feedback to be given even under the guise of ‘360 reviews.’ In my view, feedback is a two way discussion that takes time; not a tell all and the door is closed until the following year. I was able to make a dent in our workplace culture at that place because my manager saw how pivotal this could become across all teams.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. Can you share a pivotal moment in your career or personal life when being authentic made a significant impact on your success or well-being?

In the USA, the day that George Floyd was killed was an immensely memorable day. Social media flew off the rails, everyone had an opinion, divisions were bolstered, and the overall tenor of the day was deep, visceral dissatisfaction all around. After about five colleagues reached out to me asking whether I was okay, if I needed support, or if I wanted to take the day off; I was confused. This catalyzed a deeper internal conversation for myself, reckoning with being biracial in the working world, again. I was surprised to find myself requesting whether I could lead an open, honest Zoom conversation for those that wanted to join to simply be together.

I envisioned a space where, albeit facilitated, it would be primarily a time for people to share what was coming up for them, good bad or otherwise. It was a time where many of us were isolated already, working from home, and mental health woes were beginning to take up more visible space in the professional world. It ended up being a vital balm during that time, it became something that the company could return to when the Ukrainian war & Israeli/Palestinian conflict reemerged and many of our community members were in those regions. I wrote a heartfelt piece to my colleagues that received a lot of love. Once again, a door for authenticity was opened and yes, it had a few rules to keep things PG, but moreso, it opened a lot of eyes to the fact of “hmmm, maybe I can be my whole self at work?”

What strategies have you found most effective in fostering an environment where employees or team members feel safe to express their true selves, including their ideas, concerns, and aspirations?

I’ve found that simple, often beats everything else. Keep it simple! Things like ‘they did what they said they would’ or ‘my manager asked me if I was planning to celebrate my upcoming cultural holiday, which was surprising because I didn’t think they knew about it!’ are examples of simple, yet not easy ways to foster authenticity at work. My strategies are simple: be exactly who I want to be perceived as. This is a personal exercise I’ve done, year after year, in determining who I want to be seen as when I show up to any room. I want to be seen as reliable, honest, compassionate, energetic and boundaried [as of today]. Once I have my guide posts [the ways I want to be perceived] it makes all relationships and situations easier to deal with.

Here are a few examples:

  • John seemed to stay unusually quiet in our all hands today, I better check in and see how he is.

  • Vivian let me know abruptly that she’s taking the rest of the week off, let me see if there’s anything on her plate that I can take off.

  • I know I’d be great at speaking at that conference, let me see if I can get some time on my manager’s calendar.

  • I recently read that a lot of professionals are on high alert, experiencing burnout and total stress; let me put ‘urgent’ or ‘not urgent’ with every Slack/email/message I send so that I don’t add any undue stress to my colleagues.

How do you navigate the challenges that come with encouraging authenticity in a diverse workplace, where different backgrounds and perspectives may sometimes lead to conflict?

It’s high time that leaders budget funding for cross-cultural understanding, more than simply DEI, especially if you’re hiring outside of your own country. A lot of my knowledge comes from the excellent book, The Culture Map by Erin Meyer, and it’s evident through her experience that there are deep enough differences between cultures that it becomes necessary in the 21st century and beyond to have a wider awareness of who is in your space. Besides holidays and time zone options [although very impactful to be aware of], I’m talking about having an inkling of the conflicts around the world that may be seriously affecting your staff. Adhering to ensuring that there’s no work communication on weekends, where many cultures practice a day of rest or no tech. I could list several examples but the gist is this, be pliable! Be willing to recognize that your way is not the only way and that every person has something worth sharing. Open up the space, consistently, for real discussion, real brainstorming, real ideas exchange or don’t be surprised when your place of work becomes an echo chamber.

Two women and one man sitting at a round table in discussion
Anderson Street Episode

Based on your experience and research, can you please share “5 Ways to Create a Culture Where People Feel Safe to be Authentic?”

  1. As I mentioned earlier, it’s imperative to have guiding principles that dictate how you want to show up. For a manager or CEO, that company mission and values are most likely tied to their own. Taking on a coaching leadership style means that modeling is vital, modeling around the appropriate time to wait for latecomers to a zoom meeting, modeling that weekends are actually taken for family friends and fun, modeling that single tasking is more effective than multitasking, even modeling that no one uses caps lock when messaging. Again, these things may seem tiny, but I assure you they are impactful, simple and can be made to be easy. It would be a delicious company-wide practice to have everyone, instead of a vision board, curate their guiding principles as workers & teammates and have those be front and center. A collaborative, team building exercise that is built upon the foundation of individual autonomy.

  2. Today, safety can not be guaranteed by one person [manager, facilitator, host], it gets to be co created. In transformational leadership, autonomy is crucial. How can I support you adequately, if I have no idea what it is you need? Having the courage to climb the difficult mountain of direct communication and honesty with a peer or manager, must first be modeled and then consistently upkept. If we give it a shot and it doesn’t seem to stick and quit, then it’s no surprise when the whole work culture continues to deviate from the real, necessary, oftentimes hard conversations. A client of mine wanted to walk through how she’d initiate a conversation with her manager due to his [seemingly] aggressive behavior on their slack communications and its ripple effect across the department. She felt she had to be the one to say something because her colleagues were from a culture where sticking one’s head out in this way was the complete opposite of what they’d been raised to believe would be helpful. Inevitably, she created her own light framework of how she would compassionately share what her manager was doing, how it was affecting her, a few suggestions for the manager and then opening up for conversation. Not only was my client thanked profusely by this manager, but now she’s become the de facto go to person for people wanting to engage in hard conversations but not quite sure how. She’s slowly yet surely, adjusting the culture of her workplace one department at a time.

  3. Back to simple yet not easy are tea times, or unofficial work togethers. We are in the midst of becoming a work culture that no longer has watercooler chat, happy hour, or really, any other sort of getting together with those from work. If you’re unable to connect in real ways, even over the internet, how can trust, belonging or inclusivity be built? In a previous position, we tested the idea of tea times which was a weekly hour block in the middle of [most] peoples’ work day, where they’d grab a beverage of choice and we’d simply catch up on real life things. Who was moving, whose parents were flying in from another country, who was dealing with grief, and so on. It humanized each person we worked with and shocker, the regulars became closer over time. Often going to each other for advice, feedback on work outcomes and so on. My suggestion would be that top level leaders do not attend, if it’s a western led company, but honestly, as long as parameters are clear and people can be honest without fear of retribution or reprimand, then it can work.

  4. An immense issue with workplace culture is ego. When a leader believes that the way they do a task is the only way to do said task, it causes a ton of strife. Firstly, trust is obliterated because the leader doesn’t actually have trust in that persons’ innate capacity to get the result, and what often happens is hovering and micromanagement. Secondly, it nixes the idea that there is neurodivergent inclusion because, like me, I often do tasks in a completely different way than others simply because I’ve had to hone the ways that work for my brain over years. Without allowing one to get to the result in whichever way they can, within parameters, there is now no trust, little amiability, increased fear of getting ‘it’ wrong, some imposter syndrome may start to creep up, and so much more lives in that rabbit hole. By simply, letting go of a modicum of [in the weeds] control and allowing one’s team to innovate and creatively get to the result however they will, workplace culture can skyrocket. Trust, or lack of, is a major root in the tree of workplace culture functioning well. A leader may give direction, share parameters, ask if there are any questions and let the team go off and figure out how to get the thing done. Moving in sprints is often great for this as everyone is aware that we will all reconvene on this topic and review everything by a certain date and time.

  5. Boundaries are modeled & respected [work hours, urgent & not urgent messaging, for work only email or slack no texts, etc]

Finally, but certainly not last in an exhaustive list, is that boundaries are created, modeled, and respected. With the advancement of working from home, digital nomading, and millennials beginning to take on the dual roles of caregiving for aging parents as well as their own children; boundaries are imperative. Not to mention, when organizations are cross continental, you’re now dealing with time zones, holidays and so much more. Things like, creating job descriptions for remote roles with the inclusion of ‘must overlap with at least 4 of these hours’ or denoting that all work related communication only happens in slack, email, teams, or anywhere but your private cell phone number!

When a leader has their own boundaries, or it’s shared in onboarding documentation, then it subtly feeds the thought that ‘okay this is real and I will not be reprimanded if I actually have a boundary.’ Another excellent example is beginning every message, email, etc with ‘urgent’ or ‘not urgent’ to keep nervous systems lowered and inevitably, lessen the chances of burnout overall. Keeping all pertinent information necessary in slack/teams/etc profiles and simply, discerning what ways actually set you up for success!

In your opinion, how does authenticity within an organization influence its relationship with customers, clients, or the broader community?

It’s so evident when a company practices what it preaches. We live in such a review type culture, people go straight to Google, Yelp or Glassdoor to share their experiences, it’s just not worth it to spend zero time on improving workplace culture. From my perspective, the easiest, lowest hanging fruit to make that incremental change is through authenticity. BEing over DOing, as we say in the transformational coaching world, is the pathway to influence.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)

Open, outdoor plazas just like the ones you see all over Europe, South and Central America. By providing open outdoor space, it fosters actual connection, community and maybe even joy. Unless you’ve been living in a tree [I wouldn’t blame you], we are currently in a loneliness epidemic and it won’t simply go away. What else won’t go away as resultant factors are depression, anxiety, fear, and the rest.

How can our readers further follow you online?

Thank you for the time you spent sharing these fantastic insights. We wish you only continued success in your great work!

About The Interviewer: Vanessa Ogle is a mom, entrepreneur, inventor, writer, and singer/songwriter. Vanessa’s talent in building world-class leadership teams focused on diversity, a culture of service, and innovation through inclusion allowed her to be one of the most acclaimed Latina CEO’s in the last 30 years. She collaborated with the world’s leading technology and content companies such as Netflix, Amazon, HBO, and Broadcom to bring innovative solutions to travelers and hotels around the world. Vanessa is the lead inventor on 120+ U.S. Patents. Accolades include: FAST 100, Entrepreneur 360 Best Companies, Inc. 500 and then another six times on the Inc. 5000. Vanessa was personally honored with Inc. 100 Female Founder’s Award, Ernst and Young’s Entrepreneur of the Year Award, and Enterprising Women of the Year among others. Vanessa now spends her time sharing stories to inspire and give hope through articles, speaking engagements and music. In her spare time she writes and plays music in the Amazon best selling new band HigherHill, teaches surfing clinics, trains dogs, and cheers on her children. Please connect with Vanessa here on linkedin and subscribe to her newsletter Unplugged as well as follow her on Substack, Instagram, Facebook, and X and of course on her website VanessaOgle.


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