Aileen Alexander Transcript
Clint Betts
Welcome to the CEO.com show. My name is Clint Betts. Today we're thrilled to welcome Aileen K. Alexander, the Chief Executive Officer of DSG Global, the world's largest woman founded executive search firm, and co-author of the influential bestselling book, Deliberately Different: 50 Years, two Generations Leading in a Changing World. Aileen, thank you so much for coming on the show.
Aileen Alexander
No, thanks, Clint. Thanks for having me.
Clint Betts
So tell us about how you came to become the CEO of Diversified Search Group and give us a sense for what you do.
Aileen Alexander
Well, thank you. And I want to just give a nod to my co-author, who's also the founder of DSG, Judy von Seldeneck, who founded the firm 50 years ago. So it was 1974, and for five decades, we've been challenging the status quo and have understood the importance of being grounded around a purpose and always being performance and impact-driven. And you asked me how I got here. I would not be here if it wasn't for Judy, who was breaking barriers over those last five decades but also saw something in me to be a successor here at DSG. So, again, I give a nod to our founder, Judy, who I hope is listening by the way. In terms of my path, I mean my path; I've heard different people describe it as a bit unconventional or non-traditional in some ways. Never thought about becoming and being a CEO, but I have been drawn to leadership throughout my career.
So early on after college, I spent some time serving on active duty with the US Army. I was a Signal Corps officer, very foundational experience for me, getting to learn from and work with soldiers, sergeants, and other officers who taught me a lot about leadership. I did make a pivot and went to graduate school after serving and then found myself working in Washington DC, moved into the policy arena working at the Pentagon, the Department of Defense, and then I moved up to Capitol Hill where I was on the House Armed Services Committee as a staff member. So, I got some exposure to the policymaking world during a very transformational time.
And then, about 15 years ago, we made another pivot into the business world, really into our industry executive search. Over the course of the last 15 years, I have been really fortunate to have opportunities not only working with clients but also within our industry, which has also been transforming like many over these last number of years to make my own mark with a colleague built out a cybersecurity practice, had other opportunities to lead different initiatives before, believe it or not, we recruit recruiters, Clint, in our space and had an opportunity for potential succession here at DSG, which is a firm that over the last few years has gone through growth but has always approached leadership in a way, from my perspective, that's always been on the cutting edge in terms of what's needed today. And so it's been a great trajectory to come here.
Clint Betts
What do people not know about executive search, or what misconceptions might be out there?
Aileen Alexander
Yeah, I mean, I think in terms of our industry, we've historically been viewed as fairly transactional, that we're in and out, and it's only about the recruitment of individuals. But from where I sit, we find ourselves in boardrooms, we find ourselves working with CEOs and other leaders, and before we even get to the recruitment, we're often taking a step back to really understand what's happening within that particular sector or industry or with that organization, whether that's from a strategic perspective, an operational perspective, it could be a financial perspective, a cultural, and really taking a step back to think through what's needed in terms of the leadership bench or what's needed in terms of the profile of that next leader. So, one, I think we go beyond recruiting to truly being consultative in terms of the work that we do.
We also tend to not just be in and out. Again, there's that perception because once, particularly here at our firm, once we recruit a leader, we tend not to go away. We can be that coach, that counselor, and just that trusted go-to to help one get not only positioned, but perhaps get ramped up in terms of a new role, in some cases, a new industry.
Clint Betts
What had you decided to become the CEO, and what was that process like?
Aileen Alexander
Yeah, I mean, it was about probably five years ago that I was having my own reflection. I talked about my earlier path and really reflected on where my core drivers sit and my motivations. I love doing client work and problem-solving and advising those clients, but I missed being in that leadership seat. And so, like everything, you can't perfectly map out the exact course or what's going to happen next, but as I was in that reflective state, I got a call about a potential opportunity to join a firm, again, that was at a really interesting inflection point in terms of its own growth trajectory, transformational opportunity, and quite frankly, a firm that I admired. I mean, I mentioned Judy early on, which I knew for actually throughout my career in executive search, but really, really admired, not in terms of what the firm does but how they did it. A very values-based organization that we are.
And so having that opportunity to lead the firm during this next phase of growth, this next phase of transformation, while also staying true to our foundation was exciting to me. It was also a bit daunting. It also wasn't just about me. I do want to say that. We build out teams for a living, and so being able to be part of an executive team that would be doing that together is what really drew me ultimately.
Clint Betts
And what led to you and Judy writing this book now? Why is this an important time for this book?
Aileen Alexander
Yeah. Well, so I mentioned that we celebrated our 50th last year, an incredible milestone, and we wanted to recognize our clients and our colleagues past and present, but we also wanted to reflect on what we've seen in terms of leadership over these last five decades. It gave us an opportunity to really step back and really reflect upon and share with others what we've seen in terms of those enduring leadership principles, as well as what the evolving practices are. I think we could all agree that the broader environment in which people are leading is changing. I think it's been said by many others that the one thing that is certain is uncertainty right now. And so we had that opportunity to reflect and share some insights and perspectives with those leaders who are, in some cases, leading for the first time.
It was also us reflecting generationally. You mentioned that at the onset there. Judy and I had two very different career paths. We started at different times, Judy in the '70s with the backdrop of civil rights and coming through Vietnam, my career starting in the sort of late '90s onward. And so we had this opportunity to reflect on our careers as well and what we've learned from them, but also what we're learning from one another.
Clint Betts
You talk about these unconventional paths of leadership in the book. Give me a sense for the unconventional paths and your path to leadership and what people can learn from it.
Aileen Alexander
Yeah, I think when you look back a few years ago, it was more common for one to stay in one industry or to stay within one company or organization. In fact, just 10 years ago from a recruiting perspective, if we saw too many pivots, too many moves, we started to second guess that. Fast-forward, nowadays, not only are we seeing executives move from one industry to another, from for-profit to non-profit, but we're also seeing executives move from public to private companies. We're seeing individuals in terms of their own path to leadership or to the CEO ranks come from HR, come from technology, come from marketing, come from digital. And so a lot has changed, and I think there's become more of an acceptance that that variety of experiences is what's needed to really stay nimble and bring fresh perspectives to organizations today. So, a lot has changed.
I want to be clear, Clint, I didn't start out thinking I was going to pursue some unconventional path. I just always followed my path or what I thought was my true north. But even I reflect back and think about some of the learnings, some of the scar tissue, so to speak, that looking back was preparing me for this role in business.
Clint Betts
So, thinking about today's environment, which is expected to be unexpected, and no one knows what's going to happen next, AI adds a whole other layer of complexity beyond even just the political geopolitical, all that type of stuff. AI is crazy, and who knows what's going to happen tomorrow with it? That adds an interesting perspective to this. What do you think it takes to lead successfully in today's environment?
Aileen Alexander
In terms of AI or just in general?
Clint Betts
Just generally. Given everything, I just mentioned AI because of the uncertainty, but given the uncertainty of everything that's happening and we don't know, expect the unexpected, like you said, right? What does it take to be a leader in today's environment?
Aileen Alexander
Yeah, I mean, I think there's a few things. One, I think, in terms of leadership today, it starts with somebody who's highly self-aware and humble. You have to operate with a bit of humility, and you're not going to know everything. And again, having that self-awareness around not just what you know but what you don't know. So you're surrounding yourself with team members and really creating a team that brings a variety of experiences and perspectives. So starting there.
Also, just being able to maintain that high level of, we talked about adaptability, but really being comfortable with that adaptability, being able to stay nimble, being willing to pivot and not stay static. Really, really important. The third thing is this has sort of stood the test of time and trends, but being strategic, being forward-looking, being able to rally others around your vision, and bringing a bit of inspiration, I think we all could use some inspiration each day also is really, really important. And you mentioned AI. I'm one of those Gen Xers that's really wrapping my head and my arms around AI, and it's my teenagers who they keep me on my toes to stay more technical and digitally savvy, but also not letting go of the human skills. The human skills still matter in this environment.
Clint Betts
So, what does a typical day look like for you?
Aileen Alexander
A typical day. I wish I had a typical day. I think we just talked about that uncertainty. But my day starts. I'm an early riser, and my team teases me that I tend to get up at O dark 30, so I do like to get up before others so I can ease into my day. It often starts with reading. I like to jump right into the news. I like to have a sense of what's going on in the world. I use LinkedIn. That is probably one of my favorite apps out there. It's a way I can really get a pulse of what's going on with my network. It's also sometimes a bit of a cheat sheet because connected to some great thinkers and thought leaders, particularly in the leadership space. So I start there, and then after that second cup of coffee, I usually rally those teenagers to get going, get out the door, and not miss the bus.
But then, for the rest of the day, I'm checking in with my team here. I've got a great team, great COO, CFO, and others who are leading our different practice groups. So just getting a pulse of what's going on with the business. I still love talking to our clients, so will spend some time with our clients as well. And then one thing I've really been working on and more intentional in '25 is making sure I take time to meet with other leaders and really have variety in terms of those leaders that I'm missing with to really get a pulse of what they're thinking about, what's top of mind, what are they dealing with, how are they navigating the constant change? And I think it's really important to have that connectivity.
Clint Betts
And how are the people you're recruiting, not to double-click again on AI, but let's do it because it's all anybody's talking about. Give me a sense of how people are thinking about AI, the people you're recruiting, and the leaders, how they're integrating it, and what you're seeing just in your own industry and how it's being used.
Aileen Alexander
Yeah, I mean, in terms of recruiting, we saw a couple of years ago that, and it wasn't just, I mean, some assumed people recruiting chief AI officers, or this would fall within the CTO realm. We definitely saw a pivot, not only in the CEO ranks, but with chief marketing officers or CHROs or chief people officers or even CFOs, the importance of embracing AI and at least having some sense of curiosity to understand what it is and what it isn't. Nobody's expecting you to be a technical expert by any means, but we did see that shift pretty broadly across industries.
I think in terms of our industry, we're like any other in that there's that application of AI that can perhaps be used in terms of more from a productivity perspective or generating some operational efficiencies or taking on some administrative tasks so others can put their energy more into the relational part of what we do. I mean, we are in the human business, so a lot of what we do is relational and human and aspect. So it's changed on that front. But yeah, we're like any industry looking at how to utilize AI.
Clint Betts
And I really want people to read the book. And I assume it's available everywhere there's books to be bought, right?
Aileen Alexander
It is. The team has done a good job here. It's out there at Amazon, I think Barnes and Nobles, and it's in a number of airports and train stations. So if you're on your commute, it's-
Clint Betts
Oh, that's incredible. That's very cool. So, in it, you discussed timeless leadership qualities. What are the enduring principles that remain essential for leaders?
Aileen Alexander
Yeah, some of those I mentioned just earlier, but one is, again, still having that strategic muscle, the ability to have a vision and to inspire others around a vision. So that's really the first. The second mentioned enduring principle is the willingness to adapt and pivot, and those that do so sort of quicker or faster tend to beat out the competition in terms of organizations. So those leaders who bring that forward are really important. And again, the third I mentioned probably didn't go as deep, but it is about those human skills. Those are timeless in nature. Being able to show a level of empathy and being able to communicate effectively is really important. I think the difference is when you fast-forward to today, we could have a conversation, I'm sure, in a podcast, around the different modes of communication and how leaders need to navigate that. However, the fundamental principle of communicating, being transparent, and maintaining that flow of communication hasn't gone away.
Clint Betts
Finally, we end every interview with the same question, and that is at CEO.com, we believe the chances one gives is just as important as the chances one takes. When you hear that, who gave you a chance to get you to where you are today?
Aileen Alexander
There's so many in my life, but I really do need to acknowledge our founder, Judy von Seldeneck. It is not lost on me the impact that she's had, the barriers that she broke, and that ripple effect in leadership, and also in particular, what that means for me as a woman and as a CEO. And she made a bet on me, and I'm incredibly grateful to her and for that.
Clint Betts
Aileen, thank you so much for coming on the show. Seriously, it means a lot to have you here. Everybody should check out the book. We'll make sure we link to it and promote it. Thanks for coming on, really appreciate it.
Aileen Alexander
All right. Thanks, Clint.
Edited for readability.