Leading with Awareness: Empathy, Execution, and the Future of Value Creation

In this episode of Leadership Quotient, Lindsay Guzowski, CEO of The Crucible, speaks with John Sirianni, owner of Deep Tech Strategies, about leadership, organizational resilience, and the human factors that drive performance in investor-backed companies. Drawing on nearly four decades of experience across aerospace, cybersecurity, venture-backed startups, turnarounds, and M&A, John shares lessons on empathetic awareness, team design, and navigating growth through uncertainty. The conversation explores why understanding what others need for success is a leadership advantage, how strong teams are built around future objectives rather than current needs, and why operational excellence and resilience will be critical drivers of value creation in the years ahead.

Transcript

SPEAKER_01 0:00

Welcome to Leadership Quotient, a podcast by The Crucible where we explore how leadership teams in investor-backed companies are built, aligned, and scaled for impact. I'm your host, Lindsay Gazowski, and in each episode, we'll talk with the people shaping value behind the scenes, from operating partners to investors to C-suite executives, about what it really takes to drive performance through leadership. On today's episode of the Leadership Quotient Podcast, I chat with John Siriani, owner of Deep Tech Strategies, about empathetic awareness, the urgency of executing well, and why family offices might be better positioned to realize Gen Z's big goals than traditional PE. John, welcome to Leadership Quotient. To give some context around how you got from some very large companies to being a CEO to consulting and working in the PE and venture capital space, I'd love to just get sort of the elevator version of how you got to where you are today.

SPEAKER_00 1:19

So thank you for uh for the opportunity to to chat uh today, Lindsay. The um the high-level, I think, summary of my my 35 plus year career uh as an operator, uh I think is is best described in maybe three big chapters. Chapter one, uh let's call it Web 1.0. Uh that was uh first working as an engineer in the aerospace industry, uh Prattwood aircraft designing jet engines and rocket motors, and and that gave me uh a real appreciation for commercializing research and development. And that that really means bringing it out of the lab, bringing it into customers, and making a scalable business out of it. And uh what I learned as an aerospace engineer, I then took on to uh Kodak and Xerox in the early days of digital, digital imaging, digital healthcare, um, and the ability to think systematically in terms of product roadmaps, what customer segments would want uh in two, five, 10, 15 years, uh how the business models might change. Uh that seemed to resonate very well with me in the first part of my career as far as understanding not only strategy work from a from a productization and bringing solutions to market, but also on the leadership side, uh I saw demonstrated very well at those large corporations very solid leadership. Uh I also saw what happens in acquisitions when integration isn't done correctly, or integrations are done for motives that aren't really well thought through. Right. So post post-MA integration is is the bloody warfare of MA activity, really, frankly. Yeah. And after you've lived through a few of those, you're you're more wise and astute about what makes a good acquisition. It's not necessarily the technology or the market entry opportunity. Uh you've got a lot of people issues to deal with, compensation issues. And it's it's a high wire act. It's not uh it's not something you just explore, right?

SPEAKER_01 3:38

Yeah.

SPEAKER_00 3:38

So uh coming out of the the late 90s, I was working for uh a company that then got acquired by by NTT. So um I was running an IT strategy and planning practice, uh working very closely with CIOs on their organization on an IT strategy, uh outsourcing all of that. And then when Y2K ended, uh laid off a lot of my staff. Uh, I was out of a job, and the market was in a bad place. And so um that was actually a benefit. I ended up going to a small electronics consulting company that itself was on the verge of closing its doors. And I mean, may not be able to make payroll in the next month or two. And that was uh a seven to eight year um exciting ride of self-development and myself, uh learning how to sell, learning how to market, um, developing channel strategy uh as I uh as a road warrior, uh working with clients all over the US and then Europe. And so that was my first taste at a turnaround, uh, very much aligned with the concept of burn the boats, right? You're not going backwards, you're only going forwards, right? So uh and what I learned about um leadership there was very much aligned with um how do you lead in the field with partners and resellers and distributors um and other technology partners when you have very little influence and very little control over the ecosystem and the partners. And so very quickly you learn to assess who you're working with, what their needs are for success, what their motives are. And as soon as you begin to lock into that, you realize that leadership is a people game. And your ability to get things done is your ability to really honor what someone else needs for success, whether it's personal, professional, uh, financial, uh, esteem. And so you learn that the gambit or the playing field is much, much, much larger than you were taught in corporate development, HR-oriented uh leadership training, which was very form formulaic and really kind of ignored the scene outside of the corporate box. Right. But that was the 90s going into the early 2000s. And so um, by the time uh 2010 came along, um, actually I was this is a very interesting leadership story that we can get into later, but uh I I learned that I had to learn more about me and who I was, right? And uh I took on a role with uh Wind River, which was a division of Intel at that time, to uh run strategy for the Solutions and Services Organization, and I needed to build my portfolio because we it was a $400 million company. Uh I moved out to Alameda, California. Um, my children went to universities in San Diego for school, so we were all Californians at that moment. Uh I had just completed uh two years on the road, traveling East Coast to West Coast every other week. And so um the move was on. We were now Californians. I was working in Silicon Valley, and I got a taste of what MA was really like. I needed I had a portfolio that I needed to improve. Uh I worked closely with the Intel corporate development and uh corporate venture capital teams, um, diligence, acquisitions, integrations. It was a fun uh three years, it really was. Still in the Bay Area, uh the next uh role was uh a corporate turnaround. I I guess I'm I'm attracted to those. Lord help me. Uh so this was a a company that uh had run into uh issues with uh cybersecurity. Uh and um that was a sell-side activity to fix the company as best we could and get it turned around and see if we can find a safe port. Uh we did. It was sold to uh AT ⁇ T. And uh after that, I I kind of felt I was growing out of the uh the Silicon Valley um scene. I moved down to San Diego to be closer to my my uh adult children, and I took on my first role as a CEO for a publicly traded company out of Australia called Techniche. They were a holding company for a number of uh asset discovery and network intelligence companies. And so I came on board uh to develop the strategy for growth and perform some acquisitions and take the company to the next level. So over the next two years, um, working for the chairman and the uh the holding company and reporting out directly to shareholders, uh completed quite a lot of activities. We fixed the company, we changed the business model, we improved the channel uh growth, we reversed uh customer loss and churn. And uh the money for acquisitions never seemed to show up. So having been lost at the altar a couple of times after two years, I said, No, I can't I can't do this too much longer living in living on uh seat 11C on uh Australian uh airlines. Uh like, you know, 14-hour flights are fun, but um after running all these consolidations, I just need to do something else. So I took an opportunity to move to Italy and uh work for uh a venture company to scout for cybersecurity technology. By by this time, I had already been in machine learning and cybersecurity technology now for uh about seven or eight years and understood it very well. So this was a full-time role to go scouting and looking for assets to acquire. Uh, right in time for the pandemic. So I got to spend some time in Italy during the pandemic. Um, at that time, um, we realized we couldn't uh set up operations. And so I set up my own shop at that point called Quantum Cybersecurity International, focused on quantum security, and uh invested in some small firms, helped start a few firms, uh, did market entry into the United States for uh quantum technology companies. I was very fascinated by the technology and the uh the really smart people developing uh the next wave of technology. Enjoyed that for about four years. And then uh the last uh uh gig which confirmed to me that I should be doing interim CEO roles was uh uh a company in Prague, Czech Republic. So I went to go do uh turnaround and help them launch uh a semiconductor that um semiconductor chip that was designed specifically for the crypto wallet industry. Uh, a very, very good lesson in cultural uh nuances and uh leading a technical team in a different environment. Uh so I led them into another round of uh investment um and set them up for a series A. Uh came back to the US and uh now I do interim projects for um PEs, uh venture family offices uh that usually have portfolio companies at some sort of risk, or they have a desire for scale up and an international scale up um as a main focus. So that's what the big story try to condense that as much as possible.

SPEAKER_01 11:56

That was great. You've had a lot of really formative experiences, and I wanted to go back to some of the earlier companies. You mentioned that there was some really great leadership and leadership development at the early firms, the Pratt and Whitney's, the Xerox, um, those places. What specifically were you able to glean from those areas and help take with you on the positive side?

SPEAKER_00 12:27

There was so much positive. Um the nice thing about being in a multi-division, multi-product, um well-run international companies such as those is that you see a multitude of leadership styles demonstrated every day and and in every way. Leadership styles from RD labs, from uh the IP management and strategy people uh from the finance teams, you just saw a level of professionalism that to this day I don't see a lot of. I mean, I certainly saw that at at Intel, and I've seen uh a lot of professionalism in small companies and startups as well. But to see it at scale in some of those large companies uh is really something that's hard to appreciate when you're there. Um, especially during those times in the in the 1980s and 1990s, the pace of change was not very fast by today's standard, right? And international competition, although it's it's there and was dealt with, was not as ruthless as it is today. So the style of management worked for the era that those companies were created, but those those management styles needed to change. Uh, and and while I was there, I could see it. I could see that the generations that were running those companies, uh, which were all publicly held companies, um they could only make certain decisions within certain boundaries. And and I and I could see the frustration in that as well. So that that also inspired in me a desire to work for an environment that was more nimble and could take advantage of changing market conditions.

SPEAKER_01 14:19

Yeah, I think that anyone who goes from some of these large companies and successfully can translate that experience into smaller companies, particularly turnarounds, um, often finds inefficiencies as a primary driver of why they're able to do that, because they see some of that bureaucracy and more stagnant business modeling as a challenge, not as a roadmap.

SPEAKER_00 14:46

Correct. Well said.

SPEAKER_01 14:50

So you noted that when you were at Vanteon, um, to become a better leader, you had to learn about yourself. What process did you undergo to figure out how to be the leader that you later became?

SPEAKER_00 15:05

Um there was a gentleman that worked there who's no longer with us. Um and he taught me the art of working with channel partners, of seeing the need of uncovering the need of of your partners, customers, and really bringing that to the forefront of what uh what needed to be worked on, what needed to be discussed, what success looked like. And so it I believe it what it did is seed in me the the notion that what I bring to the table and what success looks like as a leader may be irrelevant once the conversation starts. Right? It's very contextual because you you assume when you go into a negotiation or when you go into a planning meeting that you have some goals, but there are other people that come in who have not only goals, but emotional problems and problems at home. And they just found out that someone they love is dying of cancer and blah, blah, blah. And it goes on forever, right? And so when if you plow ahead with your metrics and what you need to get out of the meeting, you and have not uncovered some of the personal items that are uh present in the minds of others, you may find some resistance. There was a a phrase I learned a long time ago that people don't care what you know, they want to know that you care, which is which is a light bulb moment for an engineer. Oh, really? Uh so in that context, uh leading with influence, sure. Leading with cognitive abilities, absolutely, but awareness, uh empathetic awareness of of what's going on, what's really going on is is a skill. And that's something you develop over time.

SPEAKER_01 17:11

You know, to that point, um, one of the things that I think is undervalued in the private equity and venture capital space is that concept of empathy. And our clients are always surprised when they see the idealized um percentile for empathy being as high as it is on the crucible because there's an assumption that it's it's a nice to have, it's not a must-have. And we've shown the opposite that empathy is truly a key differentiator between great leaders and people who can execute but may not be able to lead.

SPEAKER_00 17:49

I absolutely love history. Um, I study history. I'm reading the fourth turning now. Um anyone who wants to understand empathy in uh in battle, uh, read up on Napoleon. Yeah, his his troops loved him. He loved his troops. It was that simple. It was very, very empathetic towards what they were going on. He'd still lead him into battle and and you know, everybody would die, but but uh he would show moments of care and empathy.

SPEAKER_01 18:23

Yeah, I'm not sure that's the popular conception of Napoleon, probably because most of us don't know much that that much about him.

SPEAKER_00 18:29

Right. And that's that's history. You have to read, you have to enjoy reading history that gets deep into some of these things, because otherwise it's just facts and figures, and and that's not really history. History are the is the people that that uh make decisions uh in the battle.

SPEAKER_01 18:48

Some people would characterize leadership similarly. Um as you've gone from leading companies into to consulting with companies, what are the biggest challenges that you see in some of these businesses you're working with from a leadership team and people perspective?

SPEAKER_00 19:10

I've had the the uh the fortune experience to be involved in founding technical startups and and my whole almost 40-year career has been in deep tech, very advanced, leaning forward, coming out of the lab, and something brand new to market. And so, you know, don't ask me to run a restaurant chain or a hospital. I have no idea. Um and so the teams that are founders and are are very, very, very technical and very engineering oriented. And if you did a Myers Briggs on them, they'd all go into one corner. Um the the finance guys and and the investors are come at it with a completely different psychological makeup, completely different, right? And so uh the beautiful thing about bringing experienced board members in and setting up an advisory board, um, and that's where I actually kind of enjoy that, because I I I very quickly assess where the hole is in the enterprise and try to try to fill it. So I'll I'll give an example. Uh I was um just before I went out west, I was interviewing for a position uh back in New York, cold winter day, as as we have in New York, and uh I met the chief operating officer for coffee. Let's call him Bill, and we sat down, and and Bill was maybe 10 years my senior, and he started the the position was for VP of uh corporate development and channel development. It was a small, small regional software company, analytics company. And he said, Um Hey John, how would you handle the situation? What would you feel about this situation? And I said, Well, Bill, I would I think, well, you know, this and these are the background, and I think this. And he said, Oh, well, how would you feel about uh this kind of situation? Uh and I thought about it and I said, Well, Bill, I think this and I think this, and he he looked at me and he said, John, I didn't ask you what you thought, I asked you how you felt. And I sat back with a stunned look on my face. Oh, there's a difference. He said, Let me tell you about the Enneagrams. And he went into uh, you know, the nine personality types and the views of the world and and uh the strengths and the weaknesses, and and I was just absolutely stunned. And he said, I'm I'm I'm a two, I'm a helper. I show up and this is what and this is how I lead. We have other people on the team, and there's some are healthy, some are not, but I need to balance the team. And so, you know, he said, I he said, I think I know, you know, your your views on things. I just need to make sure you're a healthy version of what you are so that you can help balance the team. And from that point forward, this was 2009, from that point forward, Lindsay, uh, I became very devoted to many different methodologies of assessing who I was, trying to understand how I approached situations and the people I worked with. Um, the very next uh company I went to go work for, uh, the conversation I had with the uh the head of the division, um, he told me about the NA grams in the interview, and I said, Yes, I'm familiar with them. I'm a seven, you're an eight. And he looked at me and said, Anybody who knows themselves that well, you're hired. So knowing yourself is uh is is a big part of it. And then being able to without labeling others, without bringing in some form of of mystical science, be able to help uh investors and and leaders and founders understand where the blind spots are likely going to be for the mission that's that's coming up. I was um in the turnaround at Vantion, we had some consultants come in, and this is where I learned the difference between leadership styles and the two that stuck with me the steward versus the um shepherd. Right. So some leaders are shepherds, they shop shepherd the flock, they take care of the people, and then the mission takes care of itself. Others, very mission-oriented. They've got the spreadsheets out, they've got the numbers, uh, they know what they want, they're managing the mission, and they hope other people will manage the people in order to get them to do the mission. And so mission-oriented uh versus people-oriented, there's a lot of styles out there. I don't I I don't know what I am or what blend I am, but I know that different environments require a different approach. And so I don't ever really approach this with a formula. I guess I just rely on uh experience to and my gut to tell me where the hole is likely to be, where the where the risk is likely to be. And that honestly, that's one thing I learned about uh project management. My earlier years in IT consulting, I taught project management, PMI and uh project management institute. And uh these were in the early days of Six Sigma before it became a fad. Um, I actually learned it in Japan. And uh what became clear is that projects fail because of people, pure and simple, right? And so if you're not managing that part of it or at least understanding risks that come to the program or to the venture due to the people, you've missed it. You've absolutely missed it.

SPEAKER_01 25:00

Right.

SPEAKER_00 25:02

Sorry to go on, but that's comes to mind.

SPEAKER_01 25:06

Oh no, that's that's fascinating. And I I appreciate that self-development journey. Um I always caution people that some of those tests are more statistically valid than others. Um, but they all give good insights and they all give a perspective and lens through which to create self-development if you choose to engage them that way.

SPEAKER_00 25:31

Exactly.

SPEAKER_01 25:32

When you're thinking about teams, and you mentioned, you know, integration and mergers and acquisition earlier, and um how difficult that can be if people aren't considered in that process. How do you think about helping the groups with which you work design for the future team they need, not just the present team they need?

SPEAKER_00 25:58

Oh, great question. Um my early strategy work uh inspired uh a hunger to learn how to do it really well. And so living in Silicon Valley for a while, um, and interacting with Intel and Cisco, and there's a lot of simple formulas for doing a vision strategy execution plan, the five-year, the three-year, the 18-month. Uh and so the highest risk is not getting a vision, and I mean a real vision, not a not a we feel good vision, but a really good with with governing principles and uh strategic milestones and operational plans and something that you could actually fund and launch. When you get to that point, you've essentially designed the culture that you need for the next three to five years. And if that isn't done, you're basically shooting from the hip, right? You're just guessing. So most of the time, the the qualifying questions I have for the investors or the the current founders or whoever's and is what does done look like? What does success look like at the three-year milestone at the five-year milestone? And frequently you're gonna get it's like a traffic accident. You get 16 views of of what uh what actually happened and what could happen. And you gotta bring that together because you can't design an operation and you can't select the people unless you know whether you're driving to Seattle or Chicago. And so uh that's that's usually the problem is that the vision is not clearly set. And quite frankly, I I've been quite surprised. My earliest days uh working with venture and corporate capital, there's a lot of zombie companies that were acquired, and then they're just floating around with no sponsor because the cycle time of finding a technology company, acquiring the technology company, integrating the technology company, the original sponsors uh on the business unit that that wanted that are already on to another company themselves. And so there's a uh a lead lag problem in corporate venture capital that it seems like that's changing um as the market begins to speed up. Um but I don't I don't believe that um the tailwinds that have been in the PE industry of um reduced uh capital costs and um and uh multiple expansion, that those days are a little behind us. And so the PE firms are gonna have to get a little bit more uh focused on good management, purposely focused on operational excellence. And that comes sometimes, you just don't have enough time to train the crew, right? I'll use a sailing analogy. The wind is changing and and things are happening, and you don't have time to like teach people on you know how to tie knots. And so uh if you know you're gonna be in a crisis situation um or or need to change the direction of the company, you need to bring in talent that's kind of been there and done that before and can make the decision with confidence and or uh make a decision and then tack halfway through it because there's a better course of action. And so um, I don't know if that answers your question, but sure.

SPEAKER_01 29:36

Yeah, and a team that can work together to do it. It's not enough usually just to find talented people that can individually execute, it's making sure that that team can execute with and for each other.

SPEAKER_00 29:51

Yes. Uh there's a, as you know, there's a problem if you put too many leaders in the room um and or too many followers in a room. So this is where I get back to uh whether whether you use one personality type or one assessment model or another, it kind of uh doesn't necessarily matter, but to to design the team that's going to perform, uh, there has to be the right balance of uh of a lot of things. And that's I don't you're in that science, so uh you have a better appreciation than I do. Um, I don't know that I have a great track record, but I I've got enough scars to know that it's you call in the experts when you need to, and usually you need to very quickly.

SPEAKER_01 30:36

So as we wrap this up, you've been in the deep tech space for, again, as you noted, basically your entire career. This world is shifting, and the needs of leadership and management may be shifting as well. What do you see as the leadership needs for that next wave of value creation?

SPEAKER_00 31:02

Wow. Um so the next wave of value creation for an existing enterprise underneath as a portco underneath a PE firm or a just generic in technology companies?

SPEAKER_01 31:19

You can answer it either way. Um I was really getting at the idea that to your point, you know, multiple expansion is less of a lever as we go forward. There's an increasing speed of technological advancement that also allows less technical people to be able to contribute in ways that previously they couldn't. What kind of skills and and traits do you think the leaders are going to need in the investor backspace to make sure that they can achieve the returns in the next five, eight years?

SPEAKER_00 32:00

All right, so uh I'll I'll try to back into this. Because I don't have a clear hard answer, but I let's start with the context. Um the next three to five years geopolitically are gonna be a challenge. Uh supply chains are are being reformatted. Um we have AI growing, we have Web3, blockchain, DeFi, proof of human, um regulation is changing very quickly. So the faster that the the markets change, the faster organizations are going to need to either react or plan accordingly for and so the urgency of executing well um operational efficiency, financial stability, and resilience, um, the ability to keep the company resilient, I think is the the number one mantra for the next three to five years. Now I thought that that was actually upon us in in 2020 and 2021, and to some extent it was, but money was free-flowing at that point in time, right? Uh things are are changing. There's a bit of a liquidity crunch going on in private credit, um, there's all sorts of drama going on. So on one hand, you need a leadership team that does not get phased or confused about the context and the drama and can very quickly look at all of that noise and pick out the signals that that actually matter. And then having had the pleasure of working with a lot of young people in Prague and uh some startup companies in India, I am really, really, really impressed with the attitude of the younger generation, and I don't say younger generation is as in their 20s and early 30s. Their mantra is do the right thing for humanity and society, which was not necessarily what we thought coming out of college in the in the late 1980s and early 90s. And so there's a desire to make an organization that does well for humanity. And I'm not sure that the PE firms necessarily put that on the top one or two items of the quarterly review. So there's a mismatch in funding models, uh, but they're at the same time, the growth of family offices uh worldwide is very, very impressive. And they have a different mantra. So I guess what I've been able to see since 2014, 2015 in Silicon Valley, I saw the rise of family offices over the smaller boutique VCs. And we're playing a different global game now when it comes to funding and exits and acquisition. So I don't have an answer other than it's it's the decisioning process has to be faster, more well-informed, data driven, and the the leadership team can't be confused about the exit strategy. So one of the things that frustrated me most over the last 10 to 15 years, I know hold times are going up, and I don't remember what the latest statistics are, but PE firms are needing to hold on to their portfolio uh companies longer. And and that's a big problem because the tech is changing faster, right? So we're seeing a narrowing of valuation. I'll use a sailing analogy. Uh, it's time to get the safe port, right? You know, just because you've got new crew and and new supplies doesn't mean you need to go back out into the hurricane again, right? And so uh I I I don't know how to provide any kind of wisdom other than let's be real about the potential upside versus the uh likely waves and weather that you're going to hit, because there's very little differentiation worldwide. Yes, of course, in the area of AI with with uh big investments and large data centers, uh the platform leaders will continue to pull out. Um, but that's not the that's not the entire world, right? That's that's one piece of it. So I don't know that I have any other recommendations.

SPEAKER_01 36:44

I think that was insightful enough. So thank you.

SPEAKER_00 36:49

Uh Lindy, this has been a pleasure. What uh in everything we've covered, is there anything you want to highlight as uh to underscore um to people like myself who are uh running or advising Portcos or um to your audience regarding which what the takeaway is here?

SPEAKER_01 37:11

Yeah, I think there are several things that were really interesting in what you noted. I mean, the one of the through lines was that understanding what others need for success, whether it's your channel partners' customers, whether it's the people on your team, whether it's the desires of these up-and-coming business owners, even if that's not the capital funding model that private equity has traditionally used. I think that's a critical insight that most people overlook because it looks two rungs out, not just to the immediate person or issue in front of you. And I think that that's a construct that is important for leadership, it's important for funding, it's important for running companies, it's important for advising companies. So one takeaway look look a rung past where you think you should be looking right now, and you'll generate additional success.

SPEAKER_00 38:07

That reminds me, um, where did I really learn that? Uh, doing business in in Tokyo.

SPEAKER_01 38:15

Do you have a quick story on that front?

SPEAKER_00 38:17

Yeah, so I've I've had the pleasure of working probably in 25 countries. And so our lessons that we take from the American culture are one point of view. Uh the way teams make decisions in Japan uh is is uh a little bit, it takes longer. Uh, but when you finally do build that partnership, it may last a generation or two. Right. And so I would I would encourage those that are discovering who they are and and how they're competing to take a look at this is a large planet. And the way business is done uh in the Middle East, uh in South America, in Asia, uh it's done differently because the cultures are different and because individuals need different things to be successful in their own corporations. So, lesson learned.

SPEAKER_01 39:16

And that wraps up another inspiring episode of Leadership Quotient. I'm grateful to John for a substantive and candid discussion. To our listeners, if you found this conversation valuable, be sure to subscribe to Leadership Quotient wherever you get your podcasts. You can also learn more about The Crucible and how we're helping investor backed companies align leadership teams for scale at the Crucible.com. We'll see you next time for more real conversations on leadership, talent, and value creation.