The Benefits of Flexibility: Cali Williams Yost

Cali Yost, Founder and CEO of the Flex+Strategy Group

Photo Credit: Jordan Matter

This post is part of a series in which we put the spotlight on prominent Girl Scout alum and their achievements.

Cali Williams Yost is an internationally recognized flexible-workplace strategist and futurist. She is the founder and CEO of the Flex + Strategy Group, a solutions company that helps leaders unlock performance and engagement by reimagining how, when, and where work is done. For more than two decades, Yost has foreseen many early flexible-workplace trends. She’s used those insights to help organizations build dynamic, future-ready cultures that attract and retain an engaged and diverse workforce; increase productivity and innovation; enhance employee well-being; and maintain operating continuity when faced with unexpected disruptions. She is based in New York City.

CircleAround: What aspect of your experience as a Girl Scout has had the most significant impact on the woman you have become? Are there skills that you were able to develop and hone that you still utilize today?

Cali Williams Yost: My experience as a Girl Scout provided motivation, pushing me to try new things and to be goal-oriented. Each badge was another activity you could master. Through earning badges, I became self-directed and could explore different facets of life in an organized way that was safe and structured. I was a very aggressive Girl Scout cookie salesperson. I would get up early and I devised a whole system. Girl Scouts was also a place to go to feel happy and supported at a time when my home life was not great. It can provide things and structure that kids may not get from home life.

I was a very aggressive Girl Scout Cookie salesperson. I would get up early and I devised a whole system.

CA: How did you make the transition to commercial banking? How did you become passionate about transforming the way work is done to benefit both businesses and people?

CWY: I started in the early 1990s in commercial banking. I was a junior-level manager in training at a bank. The relationship between banker and the owner of a business was important: Lose a banker and a business could become vulnerable. I became interested in the emerging field of work flexibility, but there was no infrastructure or understanding to support it at the time. After meeting a forward-thinking CEO who had an aligned vision of new ways people could work, I was inspired to leave my job to pursue an MBA to become a work-flexibility strategist.

CA: Do you have advice for people who might be considering career “quantum leaps?”

CWY: Take a leap, but do it in a deliberate and thoughtful way. Save money, manage your lifestyle, and have a backup plan. On a deep level, we all know what we should do, so develop a practice — like meditation — to help you consistently check in with yourself. It doesn’t come easy and you have to put in a lot of effort. Be guided by what you are sensing for your life, and trust it.

CA: Do you think there is enough emphasis on how workplace culture affects employee happiness and well-being, hence business performance? If not, what do you think are the biggest barriers to prioritizing it?

CWY: A lot of organizations struggle with this because it is somewhat ephemeral and requires a constellation of factors that can be difficult to align. Traditional organizations don’t take the time because they have been constrained by an outdated model of what work should be. This moment is important to shift that mindset. Why don’t more organizations reimagine work? Because it’s hard. You have to stop and rethink how the organization operates, and it usually requires a visionary leader who says we need to do things differently. It’s not just about giving people a new technology. How to plan and execute differently? The current destruction of the traditional work model [due to the COVID-19 pandemic] is an opportunity to go forward in a smarter way regarding leadership and management. Let life merge into work and stop pretending they are separate. When organizations figure out how to fit the two together, it unlocks an amazing amount of potential. Don’t go back. Go forward in a better, smarter way.

CA: Attracting and retaining a diverse workforce and creating inclusive environments have become increasingly hot topics. What are some of the common pitfalls for organizations that lack diversity and have not-so-inclusive cultures? What is a hallmark of an inclusive workplace

To succeed in the marketplace and economy of today, organizations have to have a diverse and inclusive workforce to help them understand how to reach and serve their customers in a compelling way.

CWY: Leaders have to be willing to take an extra step to get different perspectives around the table and pull them all together. It requires more effort, but the return is much greater. To succeed in the marketplace and economy of today, organizations have to have a diverse and inclusive workforce to help them understand how to reach and serve their customers in a compelling way. Because of the pandemic, a lot of issues are coming to the fore: gender issues, child care, etc. Leaders have to be willing to do the extra work. And a simple hallmark of inclusive spaces: Do people feel heard? Are they being judged based on their performance and does it feel fair

CA: In the context of the COVID-19 pandemic, do you have advice for how people can increase their productivity while trying to work from home under challenging conditions, for example, managing child care, social isolation, etc.?

CWY: Be intentional about what you are trying to get done, and be thoughtful about how you are going to get it done. Make a detailed, shared calendar for both work and life. Do not simply focus on habits, but create key moments you want to prioritize.

CA: If there is a piece of advice you would give to your younger self, what would it be?

CWY: Trust yourself and trust the journey. It will all ultimately make sense.

CA: Any final thoughts on your Girl Scouts experience?

CWY: The Girl Scout ethos and culture is worthwhile to step back into as an adult to ask, "What did that mean to me?" You can really see how it helped shaped you and you can be grateful for it. Shout out to Girl Scout leaders who volunteer and the impact they have made.


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