Jim Ryan, the CEO of Flexera, is my guest on this episode. Jim has moved up in his career with intentionality and a great deal of self-awareness. He shares with us what it takes professionally – and personally – to step 100% into that next level of responsibility.

About the Guest:

Jim Ryan leads Flexera, a global, privately-held $400M+ software company headquartered outside of Chicago. He has been with the company since 1998, in roles that included Chief Operating Officer, SVP of Global Sales, and Managing Director of EMEA, where he lived in the United Kingdom for seven years.

Jim has served as an Operating Advisor to the Private Equity Firm Thoma Bravo since 2014, specializing in the area of sales. Jim also sits on outside Boards leveraging his experience and track record of delivering results at Flexera. Jim started his career at IBM in sales and remains passionate about the sales profession. Jim was instrumental in forming Marquette University’s Sales Program, which is designed to help students excel in their career as salespeople and currently acts as an Advisory Board Member to the program.

He is frequently asked to speak on business topics, including Technology Value Optimization, private equity, M&A, sales strategy, leadership, and culture. Jim holds a BA from Marquette University, where he studied Political Science and French.

https://www.flexera.com/

About the Host:

Amy L. Riley is an internationally renowned speaker, author and consultant. She has over 2 decades of experience developing leaders at all levels. Her clients include Cisco Systems, Deloitte and Barclays.

As a trusted leadership coach and consultant, Amy has worked with hundreds of leaders one-on-one, and thousands more as part of a group, to fully step into their leadership, create amazing teams and achieve extraordinary results.

Amy’s most popular keynote speeches are:

The Courage of a Leader: The Power of a Leadership Legacy

The Courage of a Leader: Create a Competitive Advantage with Sustainable, Results-Producing Cross-System Collaboration

The Courage of a Leader: Accelerate Trust with Your Team, Customers and Community

The Courage of a Leader: How to Build a Happy and Successful Hybrid Team

Her new book is a #1 international best-seller and is entitled, The Courage of a Leader: How to Inspire, Engage and Get Extraordinary Results. 

www.courageofaleader.com

https://www.linkedin.com/in/amyshoopriley/

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Teaser for next episode

Tune in next for “How to Fearlessly Focus Your Team to Truly Make a Difference” with Barbara Best, Founder of Cap Strat and Cap Strat Women’s Forum

Jim Ryan, the CEO of Flexera, is my guest today, Jim has moved up in his career with intentionality and a great deal of self awareness. And in this episode, he shares with us what it takes, personally, and professionally, to step 100% into that next promotion. And that next level of responsibility, I'm glad you're here to learn from Jim's experience and candid sharing.

Welcome to the Courage of a Leader podcast. This is where you hear real life stories of top leaders achieving extraordinary results. And you get practical advice and techniques, you can immediately apply for your own success. This is where you will get inspired. And take bold, courageous action. I'm so glad you can join us. I'm your host, Amy Riley. Now, are you ready to step into the full power of your leadership and achieve the results you care about most? Let's ignite the courage of a leader.

Jim, I talk with leaders all the time about the challenges when they're transitioning into a new level of responsibility. Maybe it's initially stepping into a leadership role. Maybe it's stepping into a regional right or now I'm now I'm running this part of the business. There is a shift that takes place in our own personal capabilities as leaders. What advice would you give to leaders who are stepping up in their responsibility?

We see this all the time when when we go through this AMI at flex era. And I think like like anything that you embark on in your personal or professional life, I think you've got to really step back. And first of all, reflect and reflect on what is your ultimate picture of success. And I'm a big believer in visualization. And, you know, unfortunately, far too many times a lot of people that are candidates for promotion into a management or a leadership position at a variety of different levels. They're action oriented, and they're problem solvers. And their knee jerk reaction is to want to dive into the fire and start fixing things and that's admirable. But I would encourage everybody to step back and really reflect upon what is it that they want to be what is that future and that reality that they aspire to be their future. And it's only after you get a clearer picture of success in your own mind as to what you're trying to accomplish. And the ways that you're going to do that by leading other people, I think that you can then start to put together the discrete goals, objectives, action plans, whatever you do to motivate yourself to go and make that success a reality.

Yeah, well said, that slow down to be able to speed up, because I see exactly what you're speaking to, I gotta get an action. There's all these things I can do. How quickly can I do them? And stead of really visualizing what what do you see possible? What impact do you want to have in this role you're at now. That's right.

And I think many people oftentimes give themselves permission to just just take that time and then what will invariably happen to quote the great Mike Tyson, you know, everybody has a plan until they get punched in the face. You know, that picture of success and how you're going to do that, and all the great things that you intend to do, you will be thrown a variety of different curveballs because human beings in what they are unpredictable, sometimes they're illogical. Sometimes they're highly illogical. And, and your, your, your visions of brand door and that people are just going to be inspired by you 24/7. You know, you come back down to reality. And you've got to continually reinvent, you know, retool, how are you going to do that? One of the common mistakes that misconceptions maybe that people make as you're leading a team of eight people, it's not a one size fits all management philosophy or leadership philosophy. There's eight individuals, and each and every one of them just like our children are going to require slightly different parenting and our leadership

techniques. Yes, yes. Yeah. You know, figure out what they need. And I think we're also as we're stepping into the next level of leadership. Who are we, as a leader at that at that level? Right. We might be taking the place Have someone who did a great job or not, there can be a variety of circumstances. But even if we're taking the place of someone who did a great job, we're not going to do it that exact same way. We've got to figure out how our style, our strengths are going to work in that new role.

Yes. And you know that that happened to me. So I replaced a highly successful and super effective CEO. He's a good friend of mine to this day mark Bishop. And, you know, Mark and I, and a variety of other the senior leadership team did a fantastic job and growing Flexera from 2008 until Mark retired, I guess it was in 2016 or so. And I think, what people need to understand I had a plan, I had a picture of success, I knew how I was different from Mark and the way that I interact with England, how I operated or how I roll to quote Flexera. But a lot of people didn't know me. And a lot of people didn't necessarily give me the chance on the front to prove how I was different. They just assumed that I was just like Mark and the way mark made decisions, the way Mark did things and the way things in general was not really going to change. Yeah, there was a new CEO in town, but things are just going to remain the same. And of course, you

are an internal candidate. Right. So you're from Flexera. So you're just gonna be like, Mark.

That's right. We're gonna be like Harkins. You know, I think I think you just don't always get the opportunity to define that for yourselves. I think that was one of the big challenges that I faced, I came up through the sales ranks made my way into general management. That was Mark's right hand person for many years as the Chief Operating Officer. I when I took over and was Mark success, or a lot of the engineers for example, some cheese how to choose a sales guy. Jim doesn't get us. And if someone just doesn't make any sense, Jim has been here 18 years, you know, me, I'm way more than a sales guy I was. I was a general manager for seven years running AMEA. develop different stereotypes and impressions on how how you are as an individual. And you got to understand it's not just a change for yourself, looking looking into the mirror, your role and capacity, it's a change for the hundreds or 1000s of people that are now ultimately reporting to you in some way.

Yes, we will talk more about that. I want to tell everybody Today, my guest is Jim Ryan, you've already is the CEO of Flexera. It's a global privately held $400 million plus software company headquartered outside of Chicago. Jim has been with the company since 1998. And you heard some of these roles chief operating officer as VP of global sales, Managing Director of AMEA, where he lived in the UK for seven years. In the five years, maybe it's been six years now since Jim has been CEO Flexera has experienced dramatic revenue, and Abida growth led to ownership changes with private equity, and completed over a dozen m&a transactions. He's been instrumental in growing the company's valuation by a factor of 15x, plus more than two now nearly $3 billion. You have to let us know if there's any updates to those numbers. It's such aggressive growth. Most importantly, the over 1300 employees at Flexera have recognized the company as Inc magazine's 2020 Best workplaces, and Flexera has been named a top workplace by the Chicago Tribune. For now. 10 consecutive years. Jim has served as the operating advisor to the private equity firm Thoma Bravo since 2014. specialized in specializing in the area of sales. Jim also sits on outside boards, leveraging his experience and track record of delivering results at Flexera. He's frequently asked to speak on business topics including technology value optimization, private equity, m&a, sales strategy, leadership and culture. Jim holds a BA from Marquette University where he studied political science and French, a law new proven product of raasay. But we are going to speak English and we're gonna talk about leadership. Thanks for being here, Jim.

Thanks for having me. Amy. I appreciate it.

Yeah. So you were talking about the expectations of Flexera employees, as there was the transition from Mark to Jim in the CEO role, what they're so there was obviously changing person effectives of the employees, but what work did you need to do? Personally, Jim being put into that position, and then seeing the variety of reactions from the workforce?

Well, you again, I, in my case, I felt like I needed to step back and really try to formulate a picture of success for what, what I wanted the company to look like, in five years time when I wanted to look like not physically, but you know, what would I be doing? And, you know, I worked with an outside code that really helped me put clarity to that, you know, we talked about, what would the investors be saying, what would I hear the investor saying a board meeting in five years time? What would the employees be saying? What would the analysts or the press, what would a variety of these different stakeholders be saying in five years time, and then I think once once you get that picture of success, you're better able to step back and start to work on the things that you know, that you need to do, or in my case, I needed to do as an individual CEO to, to enact some changes to get to that picture of success. I'll tell you, the place that I struggled, and I have no problem admitting that I struggled. And I would venture to say that well over 90% of every individual struggles with this. We used to guide sometimes call out the little green person on your shoulder that's always whispering in your ear. You know, the imposter syndrome, which is, hey, you know, maybe you're not good enough. You matter of time before people that really figure out when you're ready for this. And, you know, what I've learned over the errors is, you know, we make up these insane rules that, then aren't even rules to begin with. And I'll give you an example. Yeah. I was working with this individual. And he said, Hmm, say you've been in the event in the chair for three months. I was like, going, Oh, it's going great. You know, I've had a couple of board meetings, and I'm really starting to get into the flow of things. And he said, Well, tell you what, on a scale of one to 10, or zero to 100%. So get 1%. Jim, like in terms of owning it? I mean, really rockin the presidency out, where are you? And I said, I'm at about a 70%. He said, Well, what do you need to get to 100?

Wow, yeah, well, you know,

I need you know, I feel like I need another six months, I feel like I need another six months more board meetings under my belt. I feel like I need to do x, y. I forget all the details at the time. But the point was, I needed a time, I needed more time, to be a CEO to feel like I was operating in 100%. capacity and BSDL doesn't have the

experiences. That's right. He said.

All right. You said you know, when? When the board when the board puts you into the role of CEO, do you think they said, hey, you know what, Jim's gonna Jim's great guy. You know, I think he's gonna be 70% effective on the rule by 70%, for the first six to nine months of his tenure, did you think that that's what the board wanted? Do you think that's what the board had in mind that you were only going to be spending? So you know, whatever percentage I said, Of course not. And again, the point of the story is, you know, I had made a complete BS rule that somehow I needed to marinate in in the role, six to 12 months, and it was only after six to 12 months that I couldn't really be a bonafide CEO. role out there. The board certainly didn't want me to do that. But I had, you know, in my own mind created an obstacle or main approach. And I see this time, time and time again at you know, hundreds of times, there are no rules, right? There are really very few limitations. I think the limitations are always brought upon ourselves. And sometimes we just need to flick the groundwork, a little brain person off of our shoulder and just going on.

That's great. I love how you refer to them as these unwritten rules that make up in our own mind's eye to see it my role as a consultant and coach and I see leaders waiting, waiting to have something right more experience under their belt, the next set of credentials, the next promotion that got all their peers on board, or the roadmap totally figured out. It's like, Ah, no, we can get in action right now. Especially when we've taken the time to reflect and we've got that picture of what success looks like. Right, that visualization, that bigger picture purpose that we're driving towards, then we ask ourselves, okay, alright, how do we get there?

Right? And and there it's step one is get it out of your head. Yeah, picture for everybody else. Because when I say, we are going to become a world class, SAS oriented software company that is nimble and responsive to our customers and delivers high octane value to our investors. I know exactly what that picture is. Because I've gone through that exercise. I know exactly what I heard all the stakeholders say in five years time. Okay, so we got 1300 employees, there's 1300 different pictures of success. And when I say world class, or high octane, or this or that, by mine, but it's not necessarily clear in terms of everybody else, that's that's got to put together their own goals and objectives and action plans gonna make that a reality. So I think, step one, after reflection and getting that fixed investment on the mind, then it becomes you must it is essential to then go in and articulate what that means. Tell people what they would be hearing tell people like you would expect, what would our meetings be like? What would the volume be? What would the passion and intensity look like, you know, even got down at one point? What color would it be? What would it taste? Because you can't be specific enough? Right? When when things don't go? Well? It's like Sarah, you know, that happens all the time, just like in every other company. When things don't go, well. Oftentimes, you can trace it back to lack of clarity on what was for sure.

Yes. Yes, clear expectations. That's one of the biggest drivers of engagement of employees, right? We were referencing earlier, Jim, Marshall, Goldsmith's book, what got you here won't get you there? What have you had to let go up? As you have worked your way up? Or through your career? How do you think about that?

Just very, very many, so many things. In no particular order, just riffing off at the top my head. Time management, my time I don't, I don't run my own schedule or calendar anymore. My Life is one big Venn Diagram of personal and professional activities. And it takes a village to manage my schedule. There's a lot of demands. Globally, there's a lot of demands in the business with all of the different functions. I have stakeholders, investors that want to talk to me, I've stakeholders in our customers, I want to talk to me employees. And then I have great family that I also want to be a great husband and a father and a son and a brother, too, as well. And Something's gotta give. And you have to just, you know, I found that leveraging my executive assistant and some of the team that I work with has been essential to try and get up, get up team of people that helped me be the most effective or efficient as I can with my time for sure. That was one thing. Yeah. I like most people, then action oriented and a problem solver. And then when I hear a problem, my without a doubt, my tendency to this day is to try and solve and to try and throw myself into that. And then that's no longer really my job as a CEO. Not that I don't do problems, or don't get involved. But I have a whole team of people, senior leaders that are very experienced and more experienced than I am and running their functions in many cases. And as well intentioned as I might be sometimes my being overzealous to try and solve problems actually thrashes the organization a little bit more.

Great awareness. I know so many leaders that would love for their senior leaders to have that awareness.

Not that I'm thrashed free, but it's hard. I think now, listen, at the end of the day, everybody works for a CEO but prior to becoming a CEO, what are the single biggest skill sets by far that that we see at flex area I've seen for decades now that prevents people from making it to the next level or actually helps them break through is the ability to get people that do not work for you directly to do something. It's called work in the matrix or any organization. people erroneously think that the day you step into a leadership role. When you have whatever title you've got that somehow you're given an imaginary crown, and you're a king or a queen and you issue IIDX and everybody just follows That doesn't happen never happens like that. And, you know, you may be responsible for something, but you don't always control everything. And you have to, you have to figure out how to form alliances and build professional friendships. And really understand the subtle art and skill set of mobilizing a variety of people that you can't just fire if you don't like them. For you, but you've got to, you've got to figure out how to tap in to what they've got going on and to go and solve big problems and the people that have continued to grab more responsibility at Flexera. Ladies, are the ones that have mastered that skill. It's by far one of the hardest, if not the hardest skill set that we see people struggle with as they try to get in a leadership position for sure.

Yeah, yeah. I can call it out form alliances and work the matrix. I was talking to a leader not too long ago, and he actually did. He stepped into a people leadership role. And Jim was immediately finding ways to engage and empower the team members. And I was this innate to you. He had had the experience of running projects, where he needed to influence people across the organization. And he had learned how to form the alliances, when you you know, quote, unquote, don't have the formal authority, but like you say, it's not like you put this crown on and you've got this formal authority, anyways. Yeah. But he had learned how to authentically in a meaningful way get people involved and engaged with the work and with him and with the vision.

Absolutely. And some of the very best people are doing this are project managers or people that have a like a PMO, for project management. And, you know, there's there's six sigma black belts and people that are schooled in this, and they understand that and they understand the, the way in which you use metrics and goals and accountability and deadlines and reports and dashboards to change human behavior and get people to act in unison to go and tackle a common problem. But it's a subtle skill set. A lot of people struggle with it. Yeah. And I think, you know, at least at flex era, in my experience, I think it's one of the biggest impediments that prevent people from getting to where they want ultimately want to get to from a leadership perspective.

Yeah, yeah. Yeah. How do you get others involved in doing the work? Right and not being now that that person who is trying to solve all the problems yourself, or making the IIDX and expecting others to, to jump in? Yeah. How do you how do you influence? One of the things you said, Jim, when I interviewed you for the courage of a leader book, I said, What advice would you give to emerging leaders? And you said I would give to all I'll give this advice to all leaders. Ask for advice. And counsel, can you say more about why that would be? The first piece of advice you'd give?

Nobody can do it alone. Nobody, there's not a one person on planet earth that can accomplish anything that's even remotely Great. By themselves, nobody is expected and nobody can know everything. And there are so many people out in our professional in our personal lives that have experience and have perspective and are in a position to give you guidance and input and advice and counsel for a variety of things, whether it's a one off problem or multi year journey, on becoming a CEO. And yet, for whatever reason, people view it as a sign of weakness. people or people who view produce Geez, that person's got such a big job and a big title he or she must be too busy for somebody like me, again, little gremlin on your shoulder what you know why in the world, somebody want to take time to help me. But I really believe that the advice I was given back in I think it was 9590 9899. Generally, I think most most people like to help others and simply asking for your advice and counsel demonstrates that that you really are looking for genuine help, you know, looking to have an angle that exploit them or sell them at the end of the day. And I've just found that regardless of how busy one is, regardless of one's stature, or job or scale was the job. To this day, I still use that. I go out, can I have your advice and counsel and the way I typically arrive at that is, like, like I saw, there's always a variety of different problems on my desk. And some of those problems I've never seen before. Some of them just seem really complicated. I don't even know where to start. One of the places to start is you know who in my network, or even if they're not in my network, who has probably seen this one or many times, and yeah, if I could just get 15 minutes with them? Could they help me? Off away LinkedIn requests or an email? Could I like your advice and counsel on the following subject, and at least nine times out of 10, if not something higher, you'll get people that will be more than happy to help you. It's free consulting. And it's one one really powerful weapon that I've used effectively over the years. Yeah,

yeah. I got to imagine it also helps form alliances. That's right. It Yeah, your leader inside of a matrix organization, if you genuinely, authentically are asking for some advice, or some counsel like writing, what's your perspective from another area of the organization? Looking at at this? Yep. Yeah. Yeah, tapping into people's expertise, right.

Most of the problems any of us are facing, they have been faced before, there have been people that have confronted them, there are some people that have solved them and been wildly successful in doing that, why don't try to find those individuals and just just figure it out. And even if it's not a specific well defined problem, the technique and the tool works the same if you're just looking for career advice. So as an entry level, first year out of college, finding your way in a new role, or you're a 25 plus year veteran that is out and about and wanting to get some breakthrough results. Look for people that you admire, look for people that are doing the job that you aspire to do, and ask for their advice and counsel. Most people will be more than happy to spend time

with you. Yeah, yes. I have found that to be true as well. given us a lot of great stuff that you've shared with us today. I love the Hey, you're you're taking on that next layer of responsibility. Reflect, visualize, what is that picture of success look like? Maybe you're asking for advice and counsel in that moment. Yeah, exactly. Right. And being cognizant of, hey, you know, we're, we're moving to that next picture of success. What do we need to let go of? To get there? Yeah. And yeah, and who do we need to empower and get on board? And we have to articulate where we're headed. That's right. Really great stuff. Jim, thank you so much for your time today, and congratulations on all the success with Flexera

Thanks, Amy, I appreciate you having me.

My pleasure.