Chief Change Officer - #338 Jennifer Selby Long: Personal Change First, Tech Change Second

Episode Date: May 3, 2025

Jennifer Selby Long has spent 30 years helping leaders navigate change—long before “change management” became a buzzword. In this episode, the Gen X executive coach reflects on how she stumbled into her calling during the early days of IT transformation, and why emotional intelligence—not just operational efficiency—is what drives successful digital change. Drawing from her own career pivots and coaching experiences, Jennifer explains how change must be mastered on a personal level before it can be led across an organization. For Gen Xers who’ve seen multiple waves of tech disruption and economic downturns, her story reminds us: experience isn’t old news—it’s the operating system for modern leadership.>>The Accidental Change Manager“I became an accidental change manager in the early 90s.”Jennifer shares how a basic IT training request exposed a deeper problem—one that launched her decades-long journey into change leadership.>>Coaching Tech Leaders Through the Chaos“We help leaders win at change.”From digital transformation to cybersecurity to user experience, Jennifer explains why leadership—not just management—is the biggest missing link in most change initiatives.>>A Gen X Career Rooted in Both People and Process“I kept trying to do stable things, but the change kept coming at me.”She describes how she went from resisting change to becoming its strategic champion—shaped by trial, error, and real-world messiness.>>The Power of Performance Psychology“Coaches aren’t therapists. They’re here to help you win.”Her earliest coaching experience came from a sports psychologist—and that mindset still guides how she supports high performers today.>>Understanding the Natural Process of Personal Change“There are three stages: endings, transition, and new beginnings.”Jennifer walks us through Bill Bridges’ model of change—and how leaders often forget their teams are still at the beginning when they’ve already moved on._________________________Connect with us:Host: Vince Chan | Guest: Jennifer Selby Long  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.15 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>150,000+ are outgrowing. Act Today.<<<

Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Oshul is a modernist community for change progressives in organizational and human transformation from around the world. Today, I'm sitting down with Jennifer Selby Long, who has spent the last 30 years helping tech leaders navigate the waves of tech evolution, leading and managing organizational change. In recent years, her focus has been on cybersecurity, digital transformation, and user experience. But don't tune out just yet.

If you're not in those views, what Jennifer shares is relevant to anyone looking to thrive in today's fast-changing world. Give me 30 seconds, and I guarantee you'll find something valuable in this conversation. This episode and the next is all about how to guide yourself through personal transformation and step into your next opportunity. A leader cannot successfully drive organizational change without first mastering their own personal transformation. So we'll dive into why understanding the natural process of personal change can help you fast-track your transformation. How to manage self-doubt, avoid sabotaging your own progress, and how to make career moves that truly work in your favor,

instead of simply running away from one undesirable situation to the next. Let's get started. Jennifer, tell us a bit about yourself. I know you've been in coaching for a long time. You specialize in coaching tech leaders manage and navigate change. Can you tell us more about that? I always say my practice and the focus of this coaching practice was not something that I determined it found me. And by that, I became an accidental change manager in the early 90s when I was just Jennifer from the IT training department. And I would get contacted because someone would want some technical training. And the very first project that I did at this company, I was so excited because

they said they're not adopting, storing their work on the servers and they need some training, so I showed up ready with my pencil sharpened and I was waiting to hear the process and the manager driving that project listed the first three steps, which I wrote down, and then he stopped because that was the whole process. Vince, it was three steps long. Anyone with an engineering degree

can execute a three-step process. And training really only helps you with learning how to do things that you can't do. And so with that, my colleague and I began digging into why on earth are they not executing this simple three-step process? And that was really the first change management type of project that found me. Now, over the years, as I shifted back into my primary interest, which is really around people and organizations and the development of those, I kept finding that the change related challenges kept finding me and they were exhausting

and I didn't wanna do them because I didn't like conflict and change always involves some conflict. And I wanted to get on a trajectory of doing something very stable and steady. And yet the things that came my way were all challenging changes where people were mad at each other, where people were feeling blue, where millions of dollars were sitting on the sidelines because large systems had not been implemented properly and were not really being adopted. And so it just kept coming at me and somewhere along the line, I came to recognize I've now been coaching leaders on change for so long that it's actually my specialty. And so the whole firm aligned around that.

And that is really where we have our attention now. We always say our motto is we help leaders win at change. And today it's not really so much about the management of change, which I believe has come a very long way since I sat down with that technology leader and his three-step process that no one would adopt. It's come a very long way since I sat down with that technology leader and his three step process that no one would adopt. It's come a long way, but the piece that is still a huge gap and a struggle for so many leaders is the leadership aspect of that change. How on earth do you get people to come along?

How do you get your peers who you're not the boss of to come along. How do you get your peers who you don't, you're not the boss of to come along? How do you influence the leaders above you to support and embrace and get on board with the change? And at the most deeply personal level, how do you bring yourself through change? Tough stuff. So basically, you're helping a leader who sits at the center of a complex situation. They may have senior people above them, perhaps a CEO reporting to a board of directors, or they may be the CEO themselves. Below them, they have a whole team of people, some more senior, some at operational or junior level. This leader has to engage, convince, and motivate

all these people to buy into the change and act on it. But each of these stakeholders has their own agenda. And that's not even touching on the emotional aspects involved. So you're helping this person in the middle, managing everyone around them, while also guiding them on a more personal level, helping them find peace and balance, while navigating change. Is that a good summary of what you do now? Absolutely, yes. A leader is at the center of any project that we're working on and we're working closely with that leader. We're often working with that leadership team that reports to them and even sometimes all the way down to the individual

contributor level to help all of them embrace and enable a critical change. Technology is such a huge and evolving field. I'm sure when you first started back in the 90s, as you said, the project found you. And now here we are in 2024 going into 2025, so much has changed in the tech space over the years. Could you be more specific about what areas of leadership you focus on today? And maybe educate us a bit on how this evolution in technology and leadership has played out over the years? I think it's a great question. It has, technology has changed a great deal across time.

For example, one of the biggest problems that we had in the past was the technology didn't always work that well. And so a lot of resistance to change was founded, and it's not working better than what's already there. And in some ways it's worse. But today technology actually works pretty darn well. And so that's no longer at the root of the challenge. Initially, we worked most closely with IT functions because that's what I'd come out of. And that's who was really driving some of the initial change that had to come across an organization that had to change who people worked with and who they trusted and had to involve people letting

go of a certain amount of control. And so that is really where we initially were working, but it costs time because our practice has grown entirely by referrals and repeat business. We would have business leaders who would go, I need to lead a lot of change in my business. For example, perhaps we've acquired another firm and the two leadership teams have not formed into one. And so they're struggling with that change of integration and being part of one and moving as one. And so now I would be working with the business leaders. Across time, IT split off.

And so today we have information security or cyber security as typically a separate practice from IT in many organizations. And we also have digital transformation, which again, can be part of the IT leader's role, the CIO, or it can be a separate role depending on how the company's organized. One of the more recent areas that we've gotten more deeply into is that aspect of technology that drives the user experience across both consumer, business, both ends of the spectrum. That's been a real interesting space for us to work in because those chief experience officers have often end-to-end processes that include a great deal of technology driving the change, but it's all about getting the people to change how they work, how they think.

In some cases, it radically alters and uplevel jobs such that a whole new set of soft and personal skills are required for people who used to spend all day making magic with the Excel spreadsheets. We really cut across the spectrum of leaders who are leading something that either is directly technical or technology has become a huge component of the business that they lead or the part of the business that they lead. Before we dive into your own experiences working with these leaders, sharing examples and stories. I'm curious, have you ever been coached yourself? Maybe through leadership training or personal coaching along the way?

Enough to hear about your experience as a learner, as a student being coached, and how that experience student being coached and how that experience has shaped or enhanced your abilities to help your clients today. So it's a great question. The answer is yes, absolutely. And when I began coaching, it just barely existed. As they say, it wasn't a thing. There was a very small number of coaches in the world and many of the great ones worked at an organization called the Center for Creative Leadership.

Still in existence today, originally focused on helping leaders and nonprofits come together and grow as leaders and then expanded beyond into business. And my last boss in real job, as I jokingly say, said, I need you to go off to this leadership school because we report up to HR. You have a career trajectory upward here, but frankly, you don't get along well enough with HR people and you need to work on that. And so I'm sending you there to work on that.

And it was an absolutely eye opening week. And so the coach who led our group was a coach of Olympic champions. She was a sports psychologist. To this day, I still incorporate a great deal of sports psychology, or what's now called performance psychology, into my practice. Because athletes engage a coach because they want to win, and leaders engage a coach because they want to win. Both of these people want high performance in themselves and in others, and that's why

the coach is there, right? Yes, coaching has a little bit of a therapeutic feel to it, but a coach is not a therapist paid for by the company. The coach is there to help you win at your goals. And in our case, those are largely goals that revolve around their capacity to continue to lead and change and transform businesses. So that coaching was absolutely instrumental to me.

It was eye opening because a good coach helps you face yourself and look at those flat sides and not just the ways in which you're great. When you think about it, it's largely high performers and people who are successful, who get sponsored for coaching. And so it becomes super important that the coach helps you see that what got you here won't necessarily get you where you want to be next and to really face yourself and how you might be caught up or getting in your own way of that. And by extension, getting in others' ways.

Another type of coaching that's been extremely valuable to me, because I had absolutely no background running a business or having a small business, was hiring a business coach. Someone who was more of an advisor in their style and who specializes in small practices that are advisory and coaching, such as my own. So they have tremendous depth. And I think part of my takeaway from that is to some extent, a good coach can cross

a lot of different areas from life coaching to leadership to specialized industries. It is helpful when your coach has experience relevant to what it is you're trying to do and where you're trying to do it. Because that particular organization's ability to specialize in the type of business I lead has been enormously helpful to me. And it was one of the reasons that I decided to continue staying focused on leaders and particularly leaders who are leading change. Often change that exists in part because technology is now available that enables things that couldn't happen before. It is very helpful to have your coach be specialized.

Great. Now let's explore your experience coaching others. You have a lot of depth. And one of the key topics we discussed was the process you call the natural personal process of change. Could you well assure what that is, the do's, the don'ts, and some of the dangerous myths around it? And if it helps, give us examples, show us how it works in practice. There is a natural personal

process of change. This is a little bit separate from organizational change. Organizational change is about how the company needs to change. But there is every person in it going through their personal process of change as part of this. And this is where we often don't get people across the finish line as leaders. And that's where the changes get stalled and hung up. Because there are these perfectly natural but often very painful stages that we go through with change. And Bill Bridges was one of the early writers on this. I have actually gone back to Bill Bridges' model

after trying many others since then because it is beautiful in its simplicity. He says there are fundamentally three stages that we go through. The first one is losses and endings, the recognition of what we are losing, what is ending. The second one is the big long transition stage. It is the big one. It is very substantial. And the third one is new beginnings, where that change starts to get integrated into our new sense of identity. And where leaders often

struggle with this, I find, is they are either thinking of the change themselves or privy to the change much sooner than the people who are on their teams. And so I had a leader who was getting quite impatient with her team because she had moved through losses and endings, through a transition. She was really starting to transition into new beginnings. Some of them were still struggling with losses and endings around what would they lose that was familiar to them, even though they agreed that what was coming was going to be better for them, was in fact going to address a lot of the problems that they complained about a lot.

And so for a leader, it can be really challenging because you're off in a stage ahead or further ahead within the same state over the people who you lead. And so being patient and just reminding yourself you need to be patient with others and that impatience does no one any good is a pretty vital self-awareness and other awareness skill to have. We do find that those stages hold whether you're the leader initiating the change, right?

So it's your choice, or you're in control, or whether it's a change that's forced upon you such as say an unexpected layoff and suddenly you no longer have that job. The stages that your brain goes through are what they are, and you go through a period of loss, you go through a period of transition, where as Bridges says, it's as if you're on a ship and you look back and suddenly you can no longer see the shore, but you're looking out ahead and all you can see is water. So when my client was getting impatient and her team was getting a little uncomfortable with that impatience, it was because she could start to see the shore on the other side, all they could see was water, right?

They were just not quite caught up with her yet. Now, I do think that there are some do's and don'ts that help move yourself and others through these stages. There are a number, but a few that anyone could put in place. The first, obviously, Vince, you want to secure your basic survival needs. Those are going to help to ground you. Go take a look at your bank accounts. Go cut your expenses if you're worried about that. Do what you need to do to have a sense that your basic survival needs are met.

This is really going to help to ground you in the moment. Now, a second one that sounds totally woo woo is to build hope. And the way that we build hope is by envisioning what your life will look like, say 12 to 18 months from now, if the change turns out in the best possible way. And if you're a leader, this is often a gap that I see. So I'll take this same client as an example. She had very much envisioned what the future would look like for the organization. She's a business genius.

She's on the short list of clients who when she was doing a 360 and I contacted the EAs of the senior most team. Man, those guys couldn't call me fast enough. Oh, she has something that she needs for me? I'm in, right? So, a super business genius with a challenge was that she needed and didn't realize she needed her people to actually envision what their lives would look like if this change turned out in the best possible way. Not just their work, right? Not just what is best for the business, but who are you with?

What's your life like? What are you doing? What are you saying? Where are you? How do you feel when you look back? That builds hope and interestingly a lot of leaders will want to mix this up with planning and road mapping. That's not what this is. This is connecting the change that you want to lead to the individual's reasons. Their big whys. Not yours. Not the company's. A couple others that are important dues are to strengthen personal bonds. We instinctively go in when change comes and think we have to power through it alone, but we do not. And the more you're going through it together with others, the stronger.

So reach out and strengthen those personal bonds. And I think also one that can be difficult, but so vital, is to look for that hidden gift in what seems like a bad situation. As you were sharing, it brought back some personal memories for me, both in terms of personal change and organizational change I experienced during my time in the corporate world.

You mentioned personal change, the do's and the don'ts, and I can see how those applied even to individuals making major transitions like leaving a corporate job to become an entrepreneur or starting a private practice, much like you did. Yes. As you mentioned the do's and don'ts in personal change, I can think of some specific examples like controlling your expenses while investing in your own new venture. It's important to generate hope, hold on to it, and get some quick wins.

But what happens 12 or 18 months down the road? The process is challenging, especially when you're still building your practice. You're uncertain, and then you look at your friends, formal classmates. They are getting promotions, landing new jobs, as the big guys, the CEOs of big companies. And they seem to be doing so well. Meanwhile, you left a six-figure income to pursue something on your own, something unknown, something unproven, and you start questioning yourself. Self-Doubt sneaks in, which can lead to what I call Self-sabotage.

Could you share your thoughts on this situation? It's something I've personally experienced and struggled with. It's not easy. I love to hear how you help your clients navigate this, whether they're facing personal change or dealing with external changes that they're part of but can't fully control. Regionally, they may want to move forward, but emotionally, it's a different story. It's such a great question and as you were talking about this experience of you leave, you're starting a business,

you see your colleagues get promoted, they're still sitting in their six figure incomes. Oh, believe me, that one resonates with me personally. And it's not a straight line. When I started this business, which is actually my second business, a few years after it started, we hit the dot com bust and the business sank, right? And really struggled. And then again, we got hit in 2008 when the economy collapsed in the United States. And it is so easy to fall into the self-sabotage. And I want to really convey the important message that when you start to feel yourself

self-sabotage, that's not you. That's the saboteur neural networks in your mind firing up. That's all that is. And they're sitting in there and they jump out when they get a signal that indicates that there's a threat to survival. Earlier we talked about the natural personal process of change and touched on self-doubt and self-sabotage with the help of neuroscience and explore how to make career moves that truly work in your favor instead of just escaping one undesirable situation after another.

Be sure to check back in the next 48 hours. The next episode will be ready for you. Thank you so much for joining us today. If you like what you heard, don't forget to subscribe to our show, leave us top-rated reviews, check out our website, and follow me on social media. I'm Vince Chen, your ambitious human host. Until next time, take care.