1.2 The Professional Services Consulting Phase
1.3 The Engineering and Architecture Phase
1.4 The Management Consulting Phase
1.5 The Career Break Phase
1. My Personal Journey
1.1 I’m a Builder
I’ve been writing code since I was 11. I started with Microsoft GW Basic then QBasic, and by the time I got to University I was deep into Ada, 8085, 8086, and 80386 assembly language programming. Off my own back I built my own machine code assembler and disassembler, and experimented with fractal generation using a floating-point math library that I also built using my assembler. By the time I left university, I had written my own assembly language 3D graphics engine that could perform basic polygon rasterization, just to see if I could do it. I was a shameless posterchild for the truly socially awkward geek archetype.
Even by high school though, as much as I enjoyed writing code, I didn’t have a sense of what it might become for me, and I would not develop one for years – it was just a hobby that I thought might become important someday, somehow. I didn’t even go through high school and university with a focus on computing at all – I was on an educational track to becoming a marine biologist.1
Marine science didn’t work out to be the profession in which I would build myself, however. By the time I got half-way through my degree I had become disillusioned about the kind of person I was going to become as a scientist. As it worked out, my love of ships and the sea turned me towards the Royal Australian Navy, and after completion of my degree I would spend the next five years as a Navigation Officer, serving in several multinational naval exercises and in a wartime role in East Timor. I became a more complete person and learned to lead – at least in a military setting anyway. After leaving the Navy I emigrated to the United States and knowing nothing else but how to write software, I picked up my career there.
As it would ultimately turn out, my sense of purpose would reveal itself to not be coding at all. Of course, this was the context for everything I would do, but leading technology efforts as an executive, including the architectures and the people, was where I found my place. Even though I’m ten years removed from writing code for my job, as a technology leader I still very much consider myself a builder, but at the product and organisational level, not in code.2
1.2. The Professional Services Consulting Phase
After emigrating to the United States from Australia I started my professional career as a Professional Services Consultant for a B2B software company. With my background as a Naval Officer I was well suited to this; I was technical, relatable, used to being in the hot seat in front of a large group of people, and could assess a difficult situation for what it was.
In this capacity I found myself for a time as the client-facing services lead for a marquee project onsite in London, leading the needs analysis, installation, and configuration of the client’s installation. This was easy. I was having a problem however in that I needed to troubleshoot unexpected behaviours and bug fixes on a daily basis, and not unfairly, I was being beaten up by the client over it. I was not getting the action I needed from technology to get new builds to me. Marooned onsite, my attempts to provide assurances to the client were not working. This was a tough experience, and I felt strongly compelled to do something about it.
After a couple of months I’d had enough. From what seemed like the fitting setting of an empty upstairs room in British pub on a terribly rainy day, I told my boss over the phone I wanted to move into the engineering department, take it over as soon as I felt I could, and turn the product around – otherwise I’d quit. Even in the absence of any professional software development experience, to my core I felt this was something I could do. Such was my conviction that he said yes.
Within 6 months I led the reduction of a three-figure bug queue down to single digits, and those remaining did so only due to differing views on how the software should work. Based on results, I knew technology leadership was something I could and should do.
1.3. The Engineering and Architecture Phase
Over the years I progressed from engineer to architect, leading the architecture and delivery of several greenfield enterprise-scale platforms, and improving several brownfield platforms as well. I succeeded here, but there were always tensions in execution that I had difficulty reconciling, in that I didn’t feel I was creating the complete impact I wanted. Although I was entirely directionally in control of the architectures themselves, from one company to the next I increasingly felt a common thread of fundamental miscues related to the management constructs with which they were being run. I was not an executive, these were not in my control, and not for lack of trying, I was proving frustratingly ineffective in influencing them.
I was becoming disillusioned and started questioning my limits, wondering if I could ever matriculate to a position in which I had the authorities to do these “right”. Worse, I started questioning whether I even had a personality type befitting an executive. These doubts aside however, I knew one thing for sure: none of these projects felt good – they could have been better, and they could have been easier.
1.4. The Management Consulting Phase
I figured that if I was going to struggle with becoming an executive myself, I at least had enough technical experience and room presence to help one out. Maybe, I figured, without having delivery responsibility and helping clients with beleaguered projects I could develop the leadership voice I was seeking, turn their projects around, and get career satisfaction that way. The idea sounded great in my head, anyway.
It works out though that management consultants don’t typically have many authorities; they’re paid to analyse departments, people, processes, and chart a way forward. The authority to execute usually remains the client’s. In time I realized that many of the executives who had retained my services were the ones that had got themselves into their pickle by a combination of their own practices, resources, constraints (real or imagined) and thinking. If what felt like organic recommendations to me felt un-natural to them, or were more than their risk appetite could bear, there was only so much that could be done to notch up a meaningful win. I acknowledge that this sounds like the venting of a frustration, yet I don’t write this in that vein; this truly was often a reality of the role. Without an introspective executive who was prepared to be vulnerable and open minded, there was often not a lot I could do.
In one notable case, I worked with a manager so risk-averse they didn’t realize their biggest risk was taking no risk at all. Without solid metrics to justify a different approach, they didn’t want to risk their career making the wrong decision and were thus effectively paralysed by an artificial constraint of their own making; executives are classically encouraged to make metrics-driven decisions, after all. Yet, even in a situation in which defining and gathering meaningful metrics was clearly going to be difficult, it wasn’t enough for a decision to seem intuitively correct to execute upon it. Gathering metrics requires process data in some form, and that takes a degree of process maturity and tooling. If they don’t have that maturity, they almost certainly don’t have that data. Good luck deriving actionable metrics in that situation.
In the years to come though, I would develop an empathy for those executives, love them or loath them. They felt boxed in by their circumstances, were under massive stress, were looking for ideas their risk appetite could tolerate, and operated from a constantly triggered state of mind. Their bosses were no better off either, and their being one level further abstracted from the coalface, they felt even more powerless to turn the ship around (whether they’d admit it openly or not). Besides, no executive enjoys having their soft underbelly exposed by openly debating the merits of their past ideas, so it’s a fine line that needs to be walked in the management consulting role. The one thought offered in the spirit of honesty and enablement can be taken as insensitive and end a relationship.
For all this experience, still I sought real decision-making authority and self-determination as a technology leader. From architecture to team to culture, I still wanted to build something, I wanted to build it right, and I wanted the experience to feel right.
1.5. The Career Break Phase
Meanwhile, my wife was going from strength to strength in her own career, and she got the opportunity to pursue her own executive path.3 We relocated between states, and I took a break for three years in support of her career development by playing stay-at-home dad for two pre-kindergarten girls. Although I continued with some remote management consulting from time to time, I did little to maintain or develop my professional network and I lost touch with a lot of quality people. I didn’t understand the real value of a quality network.
Looking back further than those three years though, I recognize now that I really short-changed myself in this aspect of my professional development for much longer than that. Not only did I fail to avail myself of the different perspectives on my challenges from peers at my level or above, I did not develop a strong pool of talented engineers and leaders up or down my Rolodex. I was lazy in my approach to attending events and generally schmoozing. I had focused on those with whom I had worked in the past and that was about it.
Not helping matters was that historically, after all my attempts to find professional relevance and acceptance at the level I desired, I had always felt imposter syndrome at any networking event I did make it to. I would skip out after some perfunctory conversations and give myself a pat on the back for trying, but ultimately know I’d created a non-developmental experience. Now this wasn’t my being shy – more my sense of an underdeveloped persona as a corporate-savvy technologist. I was also jaded and cynical about technology leaders in general, and my attitude and frustrations were a little too close to the skin for me to present as grounded. I wasn’t attracting the right kind of people and I was certainly missing out on the benefit of listening to their different perspectives.
All my frustrations aside though, objectively I truly believed there was a dearth of really good technology leader role models in the industries and geographies in which I’d worked – at least over that timeframe, anyway. I had seen a lot of projects struggle or outright fail and saw few individuals accessible to me as people I wanted to emulate as leaders. Whether I was right or not, the net result was that I was not developing a respected leadership voice, and I was not becoming savvy; I had just become opinionated. I considered whether I would even return to this career full time. Yet – for all these perceptions and misgivings, part of me still needed to prove to myself I could become more.
1.6. The Golden Opportunity Phase
One day everything changed. By way of a windfall through one of the few healthy connections I had managed to foster during my time away, I was introduced to the founders of a company that needed a technology leader for a young product they needed to take to the next level. Solely through confidence, presentation, and experience, they gave me an opportunity to prove myself as Interim CTO, and almost instantly got promoted formally into the CTO role. They supported my ideas, gave me a product challenge beautifully suited to my background, and a large team to play with. I created a plan and made it so.
I took this role right at the beginning of lockdowns due to the COVID pandemic and I barely got to meet anyone on my team. Granted, 20 or so of them were near-shore teams I would have had to manage remotely anyway, but adopting a new department, contemplating their challenges, coming to understand the architecture, and creating a new vision and roadmap was particularly challenging in a remote setup. The scenario forced me to be creative and thoughtful, and because I had broad authority, I was able to rise to the occasion and institute changes across the whole department and platform, with great success. By the time I hit my stride my department had grown to 45 people both onshore and offshore, and included Product, Development, QA, Infrastructure, Site Reliability Engineering, and DevOps.
Through it all, I found my voice, got to practice my leadership skills in a variety of scenarios and forums, and became the person I wanted to become - comfortable in my technology leadership skin, and not defined as an architect for me to provide the value I was aspiring to provide.4 My time as a CTO changed my outlook on myself, on technology leadership, and my prospects for my future. Although certainly my entire career previous to this position gave me critical know-how, experience, and a strong sense of how to do things right, all of that merely set the stage for the truly transformational changes that occurred in me during this time.
Through it all, I always have and still feel like one of the crew and enjoy connecting with my team as equals. I’ll confess that it sometimes feels conceited to refer to myself an executive - maybe for all the twists and turns along my journey, it’s the part of me that still needs to pinch myself from time to time. Either way, it’s what I do, and it’s what I was meant to do.
With fair measure given to every facet of my career, this series will describe the learnings that mean the most to me. Hereinafter, I will make little reference to the stage of my career at which I developed the knowledge and skills, and I will not reference a particular client or company; after all, the experience I attained is the sum-total of all of it.
Next Up
With my introduction over, in my next post I'm going to discuss my views on effective leadership, with some special focus on the challenges posed by leading remotely. I think it's appropriate to continue here as the personal journey I've taken has informed many of my views on how to lead effectively, and what it feels like to be lead effectively. It will also set the tone for the remainder of this series and the role leadership effective leadership of people plays in managing a technology organisation.
You can view my next post titled "Leadership and Leading Remotely" here.
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