San Gimignano, Tuscany, Italy, December 2012

July 1st marked a nearly 3-year milestone in my professional life with my current company — the formal completion of a very significant, large-scale, highly operational SaaS project. A project I cared deeply for and put a lot of myself into, a career phase during which I learned technology and business at an unprecedented rate.

I got a crash course in large-scale SaaS architecture and infrastructure patterns, transitioned 1.5TB of data into a self-managed AWS MongoDB replica-set, laid the foundations for a messy, large scale BackboneJS SPA, led the gradual refactor into a more manageable Flux + ReactJS SPA, helped implement software best practices and CI tools into a brand new Agile process; along the way I continued working on my ME in Engineering Management, and both in school and on the job, I started learning about team management, five dysfunctions, managing up, strategic planning, the pains of prioritizing, hiring, firing, communicating, emotional intelligence, and most of all, the role of leadership in an organization.

Throughout all this, I have been extremely lucky to have been surrounded by highly motivated individuals and teams, a few critical counter-balancing and synergistic coworkers who constantly provided perspective or filled my gaps, and a boss who provided freedom-of-expression, mentorship, and opened my mind to interesting new patterns.

This intense time of focused practical and theoretical learning has helped shape what are now some “strong opinions, loosely held” about leadership, organizations, and human interactions, principles that will drastically influence and drive my future career.

Over those years, I have dealt with many frustrations and have been learning to deal with them more openly and positively. I have come to realize how many frustrations simply reflected my inability to deal with difficult situations, to empathize with other parties, or to drive change through the right means. As frustrations fluctuate, I have been learning to work on my emotional intelligence and have attempted to understand how deeper, personal feelings might affect the outcome of a change initiative. Partly by stepping back and relenting, and partly by having patience and influencing through communication and transparency, I have been able to create and nurture better relationships that have led to better outcomes.

As I have recently learned, deeply ingrained in increasing emotional intelligence skills is the need for true, deep self-awareness. As a pro-active step towards increased career engagement, now is the time to review where I am at, review what I want to achieve, and decide the next career progression I want to follow.

As an employee, and many times in the past as a job hunter, I have placed the company’s needs before mine. I have relentlessly wondered whether I have the right skills, and worked hard to gain those skills; asked whether I am delivering the right value to the company, and have actively course-corrected when the answer was no; wondered whether I am leading my teams with purpose and empathy towards maximum performance, and have worked with more experienced managers and HR to learn how to do so; asked whether the company needs this or that, whether we should pursue this technology for increased growth and how any decision I make has a systemic effect on other departments and continuously attempted to learn from my surroundings. As stubborn as I am (I am Italian after all), I have constantly doubted myself over and over again, striving for better understanding of the world and the social dynamics around me.

While I think this mindset has helped me both achieve some form of success and add value to the company, I realize that in order to grow to the next level, I need a short stint of inward focus. I have reached a point at which I need to take stock of myself. With much more self-awareness and honesty to myself than I usually do. What do I want out of a job, out of a company? What do I expect from my leaders? What is the company’s value proposition to its employees, to me in my specific situation

Hopefully, answering those questions not only provides better self-awareness and thus ability to identify and grow in the areas I need to grow in, but also provides increased empathy toward my own teams, who surely ask themselves similar questions and look to me as their leader to provide the support and guidance I am now looking for myself.

Salzburg, Austria, December 2011

0. Trust

Why “0”? Because I had all other headers outlined and even written up, before I thought about trust, then realized how important it is. How, in fact, trust is at the core of everything else.

I have placed trust high on my personal management style, continuously striving to provide teams with trust to learn, do, and fail. I now realize that I need to be trusted, as well. I look for an organization that promotes a culture of trust and transparency. An organization whose leaders are able to trust their employees and who actively promote such a culture.

I realize that trust has to be earned. I strive to earn that trust by being honest and accountable, first to myself, then to my leaders and teams. Honesty and accountability come in many forms and are assisted by empathy, clear communication channels, and lots and lots of transparency on every level.

Honesty and accountability need to be founded on integrity: if I am not honest to myself about my fundamental principles, and am not accountable to myself to uphold those principles, I cannot be honest and accountable to the rest of the organization.

1. Better the World, One Customer At A Time

For whatever twisted reason, I strive to somehow leave the world (and myself!) a slightly better place (human) than it was the day before. Do I succeed? Rarely. I swear, I get angry at bad drivers, I fall into consumerism habit, I judge, I binge-eat, I drink too much Scotch, I screw up over and over again.

Yet, most days, I persist, I envision my future, our future, and try again. And sometimes I succeed — when I do, it is usually thanks to the help from all the fantastic people around me. My girlfriend. My parents. My bosses. My teams.

I want to work for companies that have a positive effect on the world. The industries that truly interest me are fitness and wellness, healthcare, education, and most anything related to the conscious use of the great outdoors. The companies that have a crazy vision to use technology to revolutionize and disrupt those industries are those companies that truly attract me.

I want to know that my work affects people on a daily basis. I want to see change, daily, and want to hear from customers and how their lives are impacted by the work my teams and I do. I want to be able to relate to and empathize with my customers, and that likely means I need to be my own customer.

2. Knowledge — Through Continuous Learning

I am a technology nerd at heart, an engineer by education, ever since I was a kid I was drawn to it, trying to understand how it works and how to solve real-world problems with it. I desire an environment that realizes the importance of technology to solving real-world problems, and as such promotes technology education and R&D. I wish to continue growing as a software engineer, continuing to improve my best practices, but also learn fields that are new to me (ETL, warehousing, and data science are my latest infatuation).

However, I have also bridged the gap to the dark side (i.e., “The Business”), and strive to understand how technology influences business outcomes, and find balance between the two. Ultimately, I am striving to improve the world, in some infinitesimal way: technology becomes a means to an end, a very fun and fascinating means to an end. As such, I want to continue learning how the business as a whole operates, how strategies are defined, and how to optimize processes. While pursuing a Masters degree in business management, I look for opportunities to apply what I learn and continuously improve my understanding of the entire organization.

That desire naturally and most directly translates to wanting to understand product management. What products should we build? Which features should we prioritize? What problem are customers paying us to solve for them? I have become fascinated by answering those questions in a methodical way (through a formal product development process), and when working with other leaders within the organizations, I look to learn from and with them. I look for leaders and peers who have experience and desire to learn, and also have the empathetic skills to sit down with me and teach me, let me try, let me fail, and guide me to success.

Lastly, I want to continue evolving as a people manager, team builder, and empathetic leader. Thanks to my incessant talking and ability to be a royal pain in the ass, I have had the luck to be given growing leadership roles within my organization. This has been an incredible honor and learning experience, and since the day I became a manager I have spent the majority of my learning time on people skills, understanding team dynamics, and understanding the role of a leader within a knowledge organization. I recently attended a workshop on emotional intelligence, spending two fascinating days increasing self-awareness and learning how to affect change by listening and influencing. I now look for organizations that have those opportunities to learn and improve those very leadership skills at ever-growing scales.

3. Technology

As a separate piece from the desire to continuously learn about technology, I look for a company that identifies as a technology organization and solves some really cool, large scale problems with really cool leading-edge technologies.

It starts with the need to be surrounded by extremely smart, motivated, and experienced technologists who I can constantly interact and problem-solve with and learn from. Technology research has to be valued and allocated a constant level of resources, allowing for exploring new and powerful technologies for the sake of exploration. That also translates to dedicating resources to technology education and growth for any and all interested employees. Seminars, workshops, courses, and time for lunch ‘n learns and mentorship are critical to my own need for growth and in my opinion to the success of the organization through continuous innovation.

4. Financial Incentive

Too easily we (I!) dismiss financial incentives with thoughts such as “As long as I do what I love, I don’t care about money”. While passion, learning, and people are all incredibly important factors in a job, the financial aspect ends up playing a very big role when all is said and done.

Financial incentives come in many forms: salary, bonuses or profit sharing, benefits, PTO, perks, and lastly, equity.

Salary might be the easiest to talk about. Let’s agree on a roughly market-average base salary, taking perks and company culture into account for small fluctuations. In a base salary, I look primarily for comfort. Comfort to pay for food and shelter and transport, to be able to save for the inevitabilities of the future, and to be able to semi-regularly afford the luxuries of life on a whim. By all accounts, I have been very very lucky throughout my life and am rather spoiled. While I will fight hard against falling into an entitlement mindset, I enjoy my lifestyle with my girlfriend and am not regretful.

Bonus and profit sharing, as well as equity, are tougher nuts to crack. Overarchingly, I want two outcomes, equally important to me. One, to feel ownership of the company I work for, ownership over what I do, ownership over the value I deliver and the resulting upside. Two, to have skin in the game, to be able to stake a claim to an outsized upside when my efforts do deliver outsized returns on investment, and to feel pain when I drop the ball. The extremes of this are on one hand working for, say, IBM, on the other hand founding your own startup — the risk and reward fluctuations as an entrepreneur are of course much wider, and I can’t expect the same payoff as a salaried employee of a stable company. Is there a middle ground? Is there a way to cater to each employee’s personal aversion or attraction to risk, and reward effort and success accordingly? I don’t have answers — I will continue understanding and looking for the optimal balance and solution.

5. Time Flexibility

One of the more important factors I am looking for is time flexibility. That flexibility comes in two forms.

First, the flexibility to work when and where I feel most creative and productive. Even as a manager, a lot of my work is done in solitude. The creativity and impulse to do this work at my very best comes and goes in a typical creative cycle— I look for an organization that supports this, with flex time and trust in my ability to optimize my own creative process.

At the same time, resources are always finite. Clear business constraints, in fact, help feed the creative process and help improve efficiency and ultimately ROI. Along the way, regular critical (and positive) feedback is necessary to maintain the trust and continuous improvement necessary for this type of time flexibility.

Of course, despite doing significant work in solitude, as a manager presence and regular communication is critical to performance, and as such, I expect of myself the flexibility to be available, in person, during core hours or days of business operations.

Second, the flexibility to recharge. The creative process takes a toll on mind and body and regular recharging is necessary. For me, this takes the form of many long weekends chasing happiness in the great outdoors with my girlfriend. The occasional, last-minute, week-long trip to a romantic getaway in Napa and mountain biking in the Soquel National Forest near Santa Cruz. And a regular, month-or-two-long international trip to faraway exotic locations, to discover new cultures and people, or to climb big mountains and stake claim to first descents.

6. Status

Lastly, I will pay lip service to the usual “status doesn’t matter, all that matters is passion” buzz. However, I will openly admit that status does matter. Similar to financial incentives, it is not on the same level as culture and people, but it is another small piece of the greater puzzle. Do titles matter? A little. Does recognition within the tribe matter? A lot. That recognition sometimes comes in the form of a fancy sounding title, but a lot of times it may come in the form of greater influence, a dinner with the entire team, a day paint-balling with the whole company, or, simply, a “thank you”.

Thank you all for reading and letting me indulge in some self-centered ramblings.

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