HR Tech Interview with Stephen Bailey, Founder at ExecOnline

Building a strong company culture takes a lot of time and consistent efforts from all across the team and leadership levels, Stephen Bailey, Founder at ExecOnline dives deeper in this chat while sharing a few pertinent thoughts on the need to establish better D&I practices in tech today:


Tell us a little about yourself Stephen…we’d love to hear about the idea behind ExecOnline.

I was born and raised in New Orleans and grew up with two parents who understood the value of education, particularly as Black Americans looking to advance in a society that doesn’t always make that easy.

Having worked at a large law firm  for a couple of years  after receiving my JD, I decided to try my hand at entrepreneurship, first as part of the founding team of Frontier Strategy Group and then as the founder and CEO of ExecOnline, which was the first startup to digitally transform enterprise leadership development. During my time as CEO of FSG, I noticed a gap in how large organizations cultivated and developed  their next generation of leaders and I used this insight to build a company that helps the world’s largest corporations develop truly diverse, equitable and inclusive succession plans and leadership pipelines. We partner with elite business schools to deliver business learning experiences that combine the engagement of on-campus study and role-based applied learning, with the convenience and scale of an online solution for all levels of leadership. Through tailored online offerings, global leaders at all levels now have access to top-tier business education programs from the most reputable business schools in the world, all at their fingertips.

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What are some of the biggest business and tech leadership trends that you feel businesses need to strengthen in 2021?

Looking ahead I think it will become even more important for US-based and global corporations to think deeply about what they want their brand to represent to customers, employees, stake- and shareholders.

This includes examining key workplace culture elements like recruiting, training and development, advancement and promotion, employment policies, clarity of mission, employee wellness and work/life balance, communication practices between management and staff, and even company traditions.

Particularly as we approach one year in “lockdown,” and a primarily work-from-home environment, business leaders need to be more broadly reflective than they’ve been before. Last year was challenging logistically, socially, economically, emotionally and politically, and the restrictions that resulted from COVID held us captive to realities many people had not faced before. That’s why it will continue to be critical for leaders to think about the ongoing effect these combined stressors–some of which would not have intersected so significantly with our working lives in the past–are having on employees.

How have your staff truly handled this past year? In light of industry shifts and demands for new skills, have they been able to take advantage of any professional development opportunities? Do they feel valued, supported and heard? A brand is only as strong as the people building it. If this past 10 or 11 months has taught leadership anything, it’s the importance of examining the foundation for cracks before it’s too late.

Another key area in which business leaders should invest in 2021 is measurement and benchmarking of their DEI initiatives related to hiring, compensation and leadership mobility. Consistent measurement will allow global leaders to fully gain an honest view of where their organization stands versus their inclusion goals. We cannot effectively manage what we don’t effectively measure, and too often organizations are unwilling to hold themselves accountable for progress against specific quantitative diversity, equity and inclusion metrics. When organizations do hold themselves accountable, the results can be quite powerful.

Given the events surrounding 2020 – what are some of the biggest best practices you feel global workforces and HR needs to inculcate to help create better measures for crisis management in future?

While the events of 2020 threw everyone for a loop, most large companies at least had some practices and processes in place that allowed their employees to transition to a work-from-home environment when that time came last March. That said, some of the biggest challenges were lurking in the corners just waiting to become more visible, including disruptions to productivity, employee wellness and work/life challenges, technology needs and capabilities, and internal communications practices.

For HR leaders, patience can be  a virtue, but speed and agility  are a must. When it came to managing their staff, some HR teams had to stop on a dime to assess the impact this pandemic would have on employees. And while it’s easy to assume that technologies like Zoom and WebEx would have made it easy to carry on with somewhat “normal” operations, the truth is there are millions of people who never experienced web conferencing before COVID. This was a crisis in itself.

Looking to the future, it is essential HR leaders learn from 2020 and realize 2021 is bringing forward continued challenges and struggles for leadership. If there was no “playbook” for 2020, there certainly isn’t one for 2021, a year that now entails what most have accepted as their new normal.

2021 will be defined by several themes for business leaders, including work/life balance and employee’s well being–  with an astute focus on mental health–remote work improvements or adjustments, the post-pandemic economy, an altered workforce and, of course, meaningful and purposeful action to fight racism at work.  All of these themes place HR at the center of the C-Suite agenda in the most progressive, forward-looking organizations.

Moving forward, HR leaders need to examine what data they have available around their 2020 response, not only existing metrics, but new surveys of employees to gain feedback on areas of success, concern and ongoing improvement opportunities. As the keepers of the organization’s talent, HR leaders also need to have open conversations with corporate leadership about strategic goals. Armed with all available information from all levels of the organization, they can then evaluate their crisis management plans to see what worked, what was missed and what contingencies need to be drafted to address potential future disruptors while moving toward the organization’s goals.   

As HR trends shift in light of today’s evolving workplace culture – what are some ways in which companies in tech can strengthen their diversity cultures?

When it comes to corporate culture and addressing the need for more diverse, equitable and inclusive workplaces, it is up to today’s leaders to uncover the unconscious biases that exist within their organization in order to truly address issues in their culture, talent acquisition, retention and succession processes. I’ve always said diversity flounders without adequate support, and today’s evolving workplace needs that support to come from the top.

That is why we have pioneered the concept of “Development Equity” – or “equal access for underrepresented minorities and women to formalized, career-enhancing development opportunities.” As such, we have also created a Development Equity Council of progressive organizations that we work with to help companies across the world better understand how to substantially increase the trajectory of women and underrepresented minorities into positions of leadership.

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Leadership development is an under-utilized tool for increasing the mobility of diverse talent into leadership positions, and equity in leadership development will lead to equity in leadership. Research shows that companies that invest in developing diverse leaders achieve 19% growth in revenue, so it’s easy to see why investing in an equitable workplace is also good for business.

But knowing the numbers and setting intentions won’t be enough. Here are a few ways organizations can “walk the talk” when it comes to leadership development and equitable initiatives that address both internal disparities and increasing expectations for corporate social responsibility:

  1. Focus on the “E” in DE&I. The concept of workplace equity demands that employees have equal access and opportunities to pursue and be considered for promotions, advancements and professional development. If leaders work together to identify and eliminate barriers that have prevented women and underrepresented employees from seeking advancement, not only will this improve the processes and policies set within HR, but it will also boost employee morale, add to a healthy workplace culture and help move our society forward in a positive way. HR and other senior management must find the courage and energy to invest in creating a truly equitable workplace.
  2. Conduct a thorough inclusion and diversity audit. Lectures, trainings and “digital badges” can only do so much to educate people about racism and inequality in corporate settings. The conversations must go deeper. That means not just having a diversity and inclusion officer at the table. It means actually examining the current work culture–how inclusive is it and what changes need to be made to provide a base of support for the kind of diverse population you want to attract and retain? It also means investing in developing the skills and career paths for the diverse talent you already have before pulling talent from other places for appearances’ sake. Making a difference tomorrow can be as simple as supporting the right people today.
  3. Get off the seasonal bandwagon. Martin Luther King, Jr., reminded us that “the arc of the moral universe is long, but it bends toward justice.” And that change takes a long time, but it does happen. There will still be challenges with inequity this time next year, and the year after that, but, if the wealthiest organizations around today can commit to that change year-round and not just after an injustice or during Black History Month, we can start to see real change. This means investing in causes that employees value and actively partnering with Black business owners and organizations that complement or enhance your own mission for greater real-world impact.

Can you talk about some of the biggest brands today that boast of strong D&I and related policies?

One brand that comes to mind is lululemon, a well-known healthy lifestyle inspired athletic apparel company. Under their CEO’s leadership, lululemon took action in 2020 and created ‘IDEA,’ their commitment to creating real and lasting change through Inclusion, Diversity, Equity, and Action.

By the end of October 2020, more than 100 lululemon leaders participated in our “Fostering Inclusion and Diversity” course, a three-week program in partnership with Yale School of Management. Included in the group of leaders enrolled in the program – the CEO himself, Calvin McDonald.

We ended up naming lululemon as the recipient of our 2020 Inclusion & Diversity Impact Award, which recognizes an organization that is going beyond unconscious bias training and is committed to taking real action to create meaningful, lasting change within their organization and broader community.

We’d love to hear about your top people culture and most successful company culture programs…over the years: some of the top strategies you’ve driven?

Building a positive company culture takes time and effort from every single staff member, the HR team and senior leaders, and I am extremely passionate about ensuring my entire team benefits from a healthy, happy and progressive culture.

As for what we’ve done at ExecOnline, at least in the past year, we are fortunate that we had a successful remote culture before COVID, so we have focused our support on reducing the impact of COVID-specific burnout challenges.  Even more importantly, we were able to lean on cultural values of passion for our mission, collaboration and intelligent risk-taking.

We have used regular town hall meetings to stay connected and address major issues head on in the context of our values.   Whether it was the stresses and challenges created by COVID or our support of Black Lives Matter in the aftermath of George Floyd’s murder, we have used this company-wide forum to encourgage employees to share their opinions, concerns and questions in a respectful and trusting safe space.

And when it comes to general employee wellness, we have sponsored virtual workout sessions for any staff who are interested in maintaining or improving their physical and mental wellness. Through Zoom video sessions organized so as to provide access to staff who may live outside the Eastern time zone, our training offerings range from yoga and Peloton rides, to high-intensity interval training.

We have also created a program that sponsors virtual company coffees, lunches and dinners so new employees could meet the team–bolstering employee morale. The virtual sessions are organized as cross-functional groups of 8-10 employees with a  “host” and a curated set of potential topics for the groups to discuss. They are designed to be low-stress, engaging events that keep tenured employees connected to one another while allowing new employees the opportunity to meet people they don’t interface with as part of their day-to-day.

A few of your biggest takeaways and tips on working effectively from anywhere….and adjusting to the new normal in 2021…

Some of the biggest challenges associated with managing a remote workforce often come from trying to manage the “intangibles,” such as employee morale, building and maintaining a healthy workplace culture, and, of course, relationship building.

Another critical component of effectively managing a remote workforce is the continuation of employee development.  HR leaders, even from their home offices, should continue to engage staff about their career ambitions. With a loss of office time also comes a loss of focus on professional development, and by extension, leadership development. Virtual personal and professional learning opportunities at all employee levels should be offered on a regular basis, and senior leaders should continue to educate themselves on how to be the best managers they can be.

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Additionally, corporate leaders managing a remote workforce need to consider a few other intangible practices to support a healthy, successful and happy workplace environment:

  • Offer clear and consistent communication. Uncertainty breeds unrest, and that kind of distraction negatively impacts productivity and health. Clarity and transparency are important in the best of times; in unfamiliar or uncomfortable circumstances they’re critical. Since employees are no longer able to stop by a manager’s desk to ask for clarity, leaders have to make an extra effort to communicate. That includes reinforcing/reminding everyone of existing procedures and project goals and, of course, detailing changes in policy, procedure or priorities.
  • Develop a support system for everyone, including team leads, managers and senior management. Company leaders are likely just as overwhelmed with the remote work situation as non-managers, maybe even more so. Many of life’s challenges right now are simply out of our control and when leaders try to manage these instances, they too are faced with the challenge of trying to be everything to everyone. HR needs to have an “open door” policy, as do the CEOs, presidents and other senior leaders. Checking in with each other is not only necessary, it could be a lifeline for someone in need.
  • Be intentional about promoting wellbeing. At ExecOnline I’ve made what I call “virtual empathy” a priority for every video meeting. Sometimes it’s as simple as letting employees introduce us to their children or pets if they’d like to, or doing a walk and talk where I encourage exercise WHILE working. HR teams should encourage leaders to focus on things that are constant such as company values, company mission and core objectives. Everything in between has to be fluid, such as challenges with child care and work hours. Focusing on the mission ahead can provide comfort when managers make it easier for their teams to simply do what they can, the best they can.


ExecOnline breaks the compromise between cost and quality through a dynamic and interactive online learning environment that scales across the enterprise and fosters collaborative skill building.

Stephen Bailey, JD is a regarded entrepreneur, leadership and workforce expert and futurist who works with corporate leaders within the Fortune 500 and Global 2000 to create memorable life-changing learning experiences.

Stephen is the founder and CEO of ExecOnline, the premier online leadership development enterprise platform that delivers tailored professional learning opportunities for tomorrow’s top leaders.

As a passionate advocate for diversity and inclusion in the workplace and society, Stephen built ExecOnline with an eye toward helping leaders at Fortune 500 companies further understand the importance of developing an inclusive culture and leadership pipeline. As CEO, Stephen oversees its partnerships with top universities and the organization’s broader efforts to produce unique, impactful and life-changing experiences for leaders across the world. Since its inception, Stephen has raised nearly $43 million, building the company into a leadership development powerhouse that works with over 300 leading companies, NGOs and government agencies.

Under his leadership, ExecOnline has grown to now include partnerships with 7 of the top 10 business schools in the country, including Stanford, Wharton, Berkeley-Haas, Chicago (Booth), Yale, Columbia and MIT (Sloan), and was named as a “Top Tech Company to Watch” by Forbes.

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