Learning faster than the pace of change is your #1 priority with Stephen Bailey, Co-Founder and CEO of ExecOnline

“If we’re going to compete in the learning economy, we need leaders that are constantly being upskilled.”

– Stephen Bailey

Only 5% of leaders have the full capability set that’s going to be important for leading in this new world of change. That’s really disheartening. On this episode of the On Work and Revolution podcast, Debbie talks with Stephen Bailey, an academic and co-founder and CEO of ExecOnline, about the essential skill of adapting quickly as the workforce changes rapidly.

Debbie & Stephen discuss:

✓ Top 3 things leaders need to learn right now in order to keep pace with all the uncertainty & change.
✓ How to evaluate the hybrid readiness of a leader.
✓ What is multimodal leadership and the value in learning to lead well in many modes.
✓ Transitioning leadership development training from a metered landscape to a democratized access landscape.

About our guest, Stephen Bailey:

As co-founder and CEO of ExecOnline, the pioneer of online leadership development for enterprises, Stephen Bailey oversees the organization’s strategic vision and broader efforts to engage with corporations to drive equitable access to career-enhancing development opportunities. A passionate advocate for diversity and inclusion in the workplace and society, Stephen built ExecOnline with an eye toward helping leaders at Fortune 500 and Global 2000 companies further understand the importance of developing an inclusive culture and leadership pipeline.  

Stephen was named “EY Entrepreneur of the Year”. Under Stephen’s leadership, ExecOnline was named a Forbes “Technology Company to Watch” and “America’s Best Startup Employer.” Stephen earned his bachelor’s degree from Emory University and received his JD from Yale Law School. He is the board chair of the Truman Center for National Policy, on the Board of Directors of Match Group, and a member of the board of Prospect Schools, a charter school network in New York City. 

Helpful Links:

Follow Stephen on LinkedIn

Open for Full Episode Transcript

Open for Full Episode Transcript



leaders, organizations, world, leadership, people, capabilities, engage, development, talent, individuals, strategy, training, readiness, hybrid, company, leadership development


Debbie Goodman  00:04

Welcome to On Work and Revolution, where we talk about what is shaking up in the world of work right now, and how we can make work life suck less. But for people who know me, they always know I’m aiming for a slightly higher bar than that – I’m aiming for amazing workplaces. Suck less can feel like quite a feat on some days. So I’m your host, Debbie Goodman. And today we have Stephen Bailey as our guest. Steven, as I said, I love making introductions of my guests. And you’ve got a fantastic resume. So Stephen is the co founder and CEO of ExecOnline, which provides a range of leadership development programs actually solutions, through partnerships with the world’s best business schools, such as Stanford, MIT, Yale, Wharton, I mean, it’s all it’s all of the big, big names out there. Prior to Exec Online, he was CEO of Frontier Strategy Group, which he grew from early stage, to a company that serves nearly half of the Fortune 500 across a range of international markets. He has his roots in venture capital and private equity, preceded by an exceptional academic track record. I don’t usually talk about my guest’s academic credentials, because by the time they’re doing amazing things in the world, nobody really cares about that. But it’s rare that I have the Phi Beta Kappa and a summa cum laude from Emory University and a JD from Yale Law School in the house. So welcome, Stephen.


Stephen Bailey  01:41

Thank you so much for that wonderful introduction. And even though no one else cares, my mom cares. So that it’s really important to mention that she still has my Phi Beta Kappa pin.


Debbie Goodman  01:51

So today, we’re going to be talking about leadership development programs and leadership learning in the context of a world where management and leadership as we know it, which is we’ve been pretty much doing the same thing, since like the Industrial Revolution. Leadership, as we know, it has been completely turned upside down. It’s been completely disrupted. And I want to hear from you the expert, where we are at this point, with leadership learning. So let’s get into it. What is your take on what leaders mostly need to know or learn right now in order to keep pace with all of the change that’s taking place?


Stephen Bailey  02:35

That’s a great question, Debbie. And I particularly love the fact that you mentioned the Industrial Revolution, because in many ways, it’s an analogy for the change in work, the change in the leadership environment, the change in how businesses operate, that’s underway. Now, you know, if you think about many of the things that we take for granted about work, that were rooted in the industrial revolution, that was pretty revolutionary at the time, hence, industrial revolution. And now we kind of fast forward, and we find ourselves at this moment where work has been totally up ended. And there’s a lot of discussion of, can you put that back in the bottle, and can we just go back to the way things were, and much as you couldn’t put the Industrial Revolution back in the bottle, you can’t really put this moment back in the bottle. So ways of working are changing across a variety of different vectors, obviously, the one that’s discussed the most is the move to virtual work. And that has significant implications. That’s the field in which we’re now playing as opposed to everyone being next to us in the office. But there are also some other big changes. And we sort of call it our future ready leaders framework that will define the success of leaders as we move forward. So one is the ability of leaders to consistently manage change. And in particular change to business models has happened at a pace that’s never been faster. And so leaders have to be able to understand the market around them how it’s changing how you stay ahead of the competitive landscape, communicate that to the teams and organizations. So one is managing business model transformation. The second is how do you lead empathetically in a world where change is really uncomfortable for people, and where you’re now in this virtual or hybrid world where people are not having as much day to day contact with each other. And so individuals that are facing personal challenges, professional challenges, grappling with change, need to be engaged in different kinds of ways that prevent burnout, prevent despair, and prevent them from disengaging with their work. And then thirdly, we’re and I think this is a welcome change, but one that still comes with a set of challenges for leaders, we now are leading in more diverse environments than ever before. And one of the things that’s really interesting about diverse teams and diverse organizations is that diverse teams are both the highest performing teams, and the lowest performing teams at organizations and the difference is inclusive leadership. And so leaders also need to be inclusive in their posture. And so when we think about those three buckets, we think vo Let’s define in many ways what a future ready leader will be, and whether organizations can develop those leaders at scale will determine whether organizations are ultimately successful.


Debbie Goodman  05:11

Okay, so as I heard, just to summarize, it is about PACE, needing to learn quickly and keep abreast of all the changes, number two, leading with empathy, which just feels so hard because leaders themselves are probably equally burnt out. And if they have to add one extra thing to their list of things they need to do that also feels overwhelming need as a human to. And then thirdly, leading well in diverse environments, and figuring out new ways to do that are the keys to the kingdom, or the queendom. Well said. So one, I guess then can understand why there’s a desire in some what I hear certainly from leaders is can’t we just go back to the way things were and you alluded earlier to the genie that’s just popped out the bottle, and he’s never, never, never going back in? Why do you think the reluctance aside from the daunting task,


Stephen Bailey  06:11

so I think a lot of it is that unsurprisingly, these are for many leaders are challenges of first impression, they haven’t had to do these things before. We survey 10s of 1000s of leaders a year and evaluate their readiness for these types of skill sets and capabilities going forward. And our research suggests that only 5% of leaders actually have the full capability set that’s going to be important for leading in this environment. Now, you can look at that and say, That’s really disheartening. However, our view is that that’s actually kind of the new normal, the pace of change is so fast, that you’re always going to be needing to develop new capabilities in order to keep up with the pace of change. And so the era that we find ourselves in is what we call the learning economy. So we’re in this world now, where success is a leader, we talked about the different capabilities. But as those capabilities shift, the thing that’s going to be consistent is the ability to learn faster than the pace of change. If leaders and organizations can learn fast and the pace of change, there’s tremendous opportunity for competitive advantage. If leaders and organizations alone in slot in the pace of change. That’s why it’s so much risk since in both organizations and individual career trajectories. And so what’s exciting is that as long as leaders are willing to embrace continuous learning, designed to stay ahead of the curve, and create opportunity for differentiation, there’s a lot of upside, but leaders that believe that they could just be static in their approach, or try to put the genie back in the bottle and have the environment shaped to their capabilities will find significant challenges in the world we’re in and the world will be in going forward.


Debbie Goodman  08:01

Wow. Okay, so that’s a statistic that I had not heard before, that only 5% of the 10s of 1000s of leaders that you’ve evaluated, are actually have all the components of readiness for this new world that we’re in the brave new world of work work, in post pandemic world of work, but Okay, so 5% are ready, that’s 95% of leaders who just not equipped and are, they would potentially be equipped, but they need to be willing, ready and open to learning more and to this continuous learning process? How do we evaluate that because for example, you know, I run an executive search group, and companies constantly, I’ve mean, our job is to find leaders who are ready to take on new roles. And, surprisingly, we’re not getting as many requests for readiness around hybrid leadership, I would have expected this to creep into the job description and the job brief, very much more like fundamentally by now already, but that should, should surely be an interview question that very least are in their part of the evaluation, how ready are you? What skills do you have? And so I want to know, for my benefit, how do you guys evaluate the readiness?


Stephen Bailey  09:19

Yeah, so we look at each one of those buckets of future ready leader capability. And we break it down into different, you know, sort of sub capabilities. So if you think about managing business model transformation, for example, there are several components, but that sort of fall into that. So you need to be strategic. You need to have some level of business acumen to kind of understand how your business model operates in order to figure out how to evolve over time. You need to have some financial acumen to understand how to set targets, how does this all manifest in your financial envelope, and you could go through each one of those categories and you can sort of break it down into constituent parts and so when we when we ask For leaders, what their level of confidence is, in those particular areas, there are usually multiple of those areas across those three sort of core buckets, where a leader say, I’m not up to the task at this moment, right. And if you really think about our own personal experience with leaders, it’s not that surprising. You know, typically, as a leader, you have leaders that really over index on on business acumen and financial capability and operational capabilities, you have other leaders that are often termed charismatic leaders that over index on empathy and ability to connect, how often do you find that in the same package. And then when you overlay the need to lead increasingly diverse teams, across both of those two areas, in a virtual and hybrid world, it’s really not that surprising that very few individuals possess everything. Now, that doesn’t mean that those individuals don’t possess any of those capabilities, they have some of the skill sets right out of the box that are ready to you know, sort of be implemented as leaders. But what’s really important is for leaders to be willing to embrace what they don’t have, and then get up the curve as quickly as possible to round out there leadership capabilities that and that’s important for them individually, as they’re thinking about advancing their careers. But it also has implications for organizations, because organizations that have the best laid plans, from a strategy perspective at maybe the C suite level, will find it increasingly difficult to execute against those strategic imperatives, if they don’t have that broad based leadership capability that can actually put strategy into action effectively.


Debbie Goodman  11:40

Okay. And then to add to that, when we spoke earlier this week, you use the terms, unintentional leadership, to refer to a style that we would have used in the past, versus intentional leadership, which is what is needed in order to operate effectively in our hybrid or virtual world. And I loved some of the analogies that you had, once you once you expand on that, I think there’s, there’s so good.


Stephen Bailey  12:07

Yeah. So I mean, I think when so we talked about the capabilities, leaders need to be successful. The environment in which those capabilities need to be expressed and executed against is this hybrid world that we’re in. And, you know, I’ve heard a lot of leaders say, Well, when you’re in a hybrid world, or you’re in a virtual world, there are just certain things that you can’t do as effectively. It’s hard to innovate, it’s hard to engage people, it’s hard to get people aligned to your values. And my response to that is always I agree with you, if you add in our current leadership model, so based on the way we lead today, that is true. But can we evolve our leadership model to take advantage of the benefits of virtual and hybrid work. So for example, you now have more global talent pool. So you can tap into individuals from many different markets, as opposed to be limited and get the best talent no matter where that talent sits, you can actually gauge talent in your organization that might have been hampered by having to come into a physical office. So for example, think working mothers, you can engage them at different time ways. So the obvious benefits, but the disadvantages I typically hear tend to revolve around an approach to leadership that in a lot of cases, lacks intentionality. So folks will say, Well, you know, it’s easier for me to be able to engage folks if I can see them or you’re at the watercooler and you have different idea. And that’s the serendipity that often comes with being in person. Now, that also has a lot of disadvantages. It can be very exclusionary, who happens to sit next to you who you happen to bump into, right, as opposed to, you know, sort of something that’s much more intentional. So when you move into a virtual or hybrid world, it requires more intention around how you can beam people, how you communicate, how you engage with folks to ensure that you’re touching all the members of your team and leveraging all of their capabilities and skill sets appropriately. So intentionality in a virtual world more of that, yes, so it’s different. But if you do it well, you can actually be more inclusive, and more enabled at a team level because everybody’s skill sets are being leveraged, then what often happens in an office which is much more serendipitous and focused on who you happen to be comfortable with, or who happens to be close to you.


Debbie Goodman  14:30

Right, I’ve heard the term multimodal leadership, and although it’s applied in a slightly different context, to me, this idea of evolving the way in which we lead and evolving our leadership model is just that we can learn to lead Well, in many modes. Previously, it was you know, we had primarily one, I mean, certainly I used to love going into my office and walking around to everybody’s desk and checking in on them and Finding out how things are going and having the chat and it was just seamless and easy. And I didn’t really need to think about it. For many of us, same thing, you know, now I work remotely and actually have since even before the pandemic, and had to completely rethink how I was going to cultivate those connections, because I was no longer going to have the privilege and ease of walking into my office using my energy, my charisma, my you know, my vibe, the things that are my, you know, my superpowers to engage people. Now it was I really had to think about that completely differently. And we all had that experience during lockdown. And it was hard for a lot of people. And so I think for many people, they were kind of in this wait and see, yeah, we’ll eventually get back. And you know, I won’t necessarily need to upskill myself to learn how to do this thing. Well, and I think the moment is, here, we are post pandemic, and hybrid is a thing or fully remote is a thing. And we’ve got to get with the program of learning how to be evolved and multimodal in our style,


Stephen Bailey  16:01

Once you realize that you made that transition, did that excite you? Did you embrace it? Or did you feel more like, I’ve got to just sort of hope that the world changes and sort of comes to me.


Debbie Goodman  16:09

So when I actually worked with a coach for about six months prior because I moved from Cape Town to Los Angeles, it was not just a moving remotely, it was moving nine or 10 hours away from my main office at the time. And so I actually had the luxury of working with coaching team to help me and my team figure things out. And there was like this massive buildup to the day when I would log on remotely via zoom. This was in sort of first week of January 2019. And it was like launch day, you know, but I had all this, all this preparation, and then the fact that it actually worked, at least for the first day. And then the first week was sort of felt miraculous to me. And so I applied that to the thinking around my goodness, you had a world of leaders who had none of that preparation, not the figuring things out before you actually press go. And it’s a was a shock to the system for so many. But we’re through that now. And the new world is asking for, for something different. I wanted to get on to the point of access, because I know that is your big passion. It’s the mission of exec online democratizing access to leadership training, and creating more inclusive leadership pipelines. And you quoted some data 70% of the people who are selected for leadership development training are based on the referral of somebody who knows them. Is that an accurate? Did I get that?


Stephen Bailey  17:48

Close! I mean, so all organizations are not all but most organizations have traditionally had something called a high potential program, which is sort of where they identify these are the most the most not necessarily important in some organizations, that might be the right word, but but certainly the leaders that we’re placing our bets on in terms of the future leadership of the organization, and we want to give them special access to training and development and resources. And so that group to your point 70% of the time organizations make that decision based on a single subjective nomination from typically that person’s manager. And you can imagine what that means in terms of risk for bias and exclusion as those decisions would be made.


Debbie Goodman  18:28

So you said that L&D is shifting from a metered world to a democratized access world, which I love, because I hadn’t heard that raised in that way. share more about that.


Stephen Bailey  18:39

Yeah. So when you think about what a metered world for leadership development, and really for broader training and organizations has traditionally looked like, it’s been this belief that look at certainly by the time you get to leadership level leaders need to be engaged in a certain way. That, you know, 10 years ago, when I started the company with my co founders, the belief was leaders need to develop in person instead of online. And so we there’s a limited number of seats in a physical classroom, there is a limited amount of resource that we can put into bringing people to those seats. And so so much of l&d was a metering function, a series of assessments and evaluations to determine who are the individuals the lucky few, usually no more than a few percent of a company, that were going to get access to these really special opportunities. And when you overlaid that, with some of the bias and subjectivity and processes that were just discussing, you have situations where your future leadership pipelines don’t look particularly representative, right? disproportionately male, disproportionately white. And so when you think about a democratized world, which is the world that exact reminders created, our belief was organizations and individuals would be much better off if instead of having this metered approach to leadership development, you had an approach where every leader had access To leadership development from the world’s best institutions and schools, you named at the outset, some of the world’s best coaches that we also work with to supplement that those programmatic learnings. And that’s the world that exactly managed training, we’ve done that by taking the classroom and the physical classroom and moving it virtually so that a lot of inherent constraints of bringing people together in person, and the biases that are associated with those constraints can be addressed. And we then work with organizations to leverage this powerful digital medium to deliver what we call development equity, and that development equity think of it as as pay equity for development so much as we now measure, what is the extent that pay is equal across race, gender, other, you know, sort of identity lines, we can now also measure? What is the level of equality in the provision of development opportunity to leaders in organizations, you know, based on their on those different areas,


Debbie Goodman  20:56

I certainly know that many organisations, this idea of access to world class leadership training has been something that has been very restricted to those very few fortunate view. And what you said is that with ExecOnline, this is now open and democratized. But it’s not just for people who are in existing leadership, it’s now companies have the ability to extend this beyond even their necessarily their high potential programs, but to many more people in an organization. So many companies, when when when I get to hear the conversation, is because there hasn’t been a succession plan in place, because they haven’t started to train their people internally. And they’re at the point where they have to go external to look for, for somebody to take on a key leadership role. It seems to me that this should be a strategy for retention, and for cultivation of talent, that every organization, it should be like a non starter, it should be in the no brainer of the talent management program. And yet, we are in a position now where with the economy being a little tighter? I certainly know, I’m not sure how you’re seeing things right now. But where budgets start getting tighter, the idea of discretionary line items, meaning training and development sometimes get the chop. And that seems weird. That’s something that should be so integral to a company’s lifeblood, should be considered discretionary. I’m interested to know how what you’re seeing in the current market?


Stephen Bailey  22:43

That’s a great question. And we’ve certainly seen the approach to that evolve. So if you think about it, when capabilities were more static, there was certainly this belief or training developments and nice to have. And, you know, if if we’re in a market that’s tighter, we can cut it. We’re seeing progressive organizations, a lot of organizations certainly not all recognize that. Talent Development, particularly leadership development has moved from discretionary to strategic, because leaders are going to be absolutely critical to executing strategy and the half lives on the skills that they that they have, are continuing to compress. And so back to that learning economy piece. Organizations are recognizing if we’re going to compete in the learning economy, we need leaders that have different kinds of capabilities that are constantly being upskilled. Otherwise, I shred yourself to get on paper will fail in practice. And then the other thing we’re seeing organizations recognize is they’ve got really unique talent challenges that require them to engage their talent in ways that may be in a downturn or an economic volatility, your belief is people will just be happy to have a job, you don’t really have to worry about engaging them, right. They’ll just do. They’ll just put their heads down. But we’re finding in this environment, folks are burnt out, they need that engagement. You obviously you hear a lot about quiet quitting right now. And what is the relationship between an employer and an employee and organizations that have what I would call kind of a social contract with their employees, where they say, We’re gonna help you not only you’re not only here to do your job, each and every day, you’re not only here for a paycheck, but we’re going to help you succeed in the learning economy. And that’s going to be good for business and it’s going to be good for you personally, we believe those are the organizations that are going to win over time and have the most motivated and successful talent, particularly at the leadership level.


Debbie Goodman  24:41

We’ve got a lot of listeners who are in the learning and development, HR, coaching, facilitation, etc. This is a community of interested and engaged people in exactly the topics we’re talking about. And so I want to refer people to aside from exec online.com Which is your the website of the company, but For L&D leaders, you’re offering a free program on managing budgets in a volatile market, I could not think of anything more useful and timeless. So we’ll actually put that in our show notes for anybody who’s interested in that. Steven, this has been such a pleasure, very engaging, and I am so keen to, I’d love to pick up this conversation and maybe six months time and hear how things are going. Because the markets have changed where post pandemic, leaders are going to have to step up the to the next step. And what we’ve been speaking about now seems the perfect opportunity to upskill and engage in our next round of what does the future hold?


Stephen Bailey  25:43

Well, thank you so much that it was a pleasure to sit down with you and have this chat and appreciate the perspective and invited me on. So looking forward to reconnecting in six months. We’ll let you know what happens.


Debbie Goodman  25:55

Thanks. Thank you so much, and bye.


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