Be Resilient

Ron Pragides
14 min readDec 8, 2020

The term Black Swan was made famous by Nassim Nicholas Taleb in his book of the same name, which he describes as an event that has three attributes: (1) it is an outlier, outside the realm of regular expectations; (2) it carries an extreme impact; and (3) in spite of being at outlier, we devise an explanation for its occurrence after the fact.

The COVID-19 pandemic certainly qualifies as a Black Swan event, but 2020 has been a year that tested our resilience for a multitude of reasons:

2020 demonstrated the need for resilience: we’ve all had to withstand and recover from many profound events. With 2020 coming to a close, I recently shared my thoughts on Resilient Engineering Teams and Careers in my role as Executive-in-Residence at Terminal.

My Career Journey

I’ve experienced three Black Swan events during my career: the 2001 Dot-Com Bubble (boom & bust), the 2008 Great Recession (the financial housing crisis), and the 2020 COVID pandemic. You never know when a Black Swan event will occur. You may encounter several Black Swans throughout your career, so it’s important to be resilient when they happen.

Roles I’ve held during my career.

I’ve held different roles spanning Engineering Individual Contributor (IC) positions through Engineering Management roles. My career journey was not a direct, binary path to management. Between 2000 and 2004, I straddled the line between Engineering IC and first-level Engineering Manager. Without knowing the differences between those roles, I had to try them out for myself. I had to get comfortable with my own choice in terms of what I wanted to do, where I got my energy, what I wanted my career to be.

Engineers: Choose Your Own Adventure

It’s important for Engineers not to conflate Career Progression with Becoming an Engineering Manager. The best companies provide parallel tracks for Engineers to contribute to their team and to grow their careers. Engineers start their career on the ground floor and eventually face a choice: to progress as a technical lead, or take the path of leading as a manager. After seeing both sides, I eventually chose to focus on Engineering Management. Even though this was my path, it’s not the destiny of every Engineer to become a manager. It’s up to each individual to plot their own career journey.

I’ve had the opportunity to work across different teams, different companies, and different business verticals. My former colleague Amit Kulkarni (CEO, Heymarket) suggests that we can think of our careers in terms of epochs. Upon reflection, I’ve mapped my own career to four distinct epochs:

  • 1992–1998: Large Public Companies
  • 1998–2004: Startups & Dot-Com Bubble
  • 2004–2014: Scale-Ups & New Business Models
  • 2014–2020: Platforms & Network Effects

I’ve had the privilege of joining amazing companies, some of which have grown to become iconic businesses. I’m proud of all the organizations that I’ve had the chance to help build.

Each person’s career is a combination of teams and roles, woven together into a unique tapestry of industry experience. No matter what happens, be prepared for Black Swan events that might come. And remember to be resilient in how you think of opportunities for yourself.

Developing Resilient Careers

There are five principles that I believe will help anyone develop a resilient career, and I hope most of these resonate with you:

  • Be a Lifelong Learner
  • Stop & Look Around
  • Know Where You Get Energy
  • Decide for Yourself
  • Live Courageously

Be a Lifelong Learner. What does that mean? The things that interest me now are different from what I was interested in 5 years ago (or 10 years ago). Whenever a subject has been intriguing to me — from a career perspective, a business perspective, or just how the world works — I’ve tried to learn more about it. We now have multiple ways to learn about any topic: tech-talks, meetups, conferences, news & social media, MOOCs (Coursera, Udemy, etc), books, podcasts. It’s amazing to live in a time when we have Internet-connected supercomputers in our pockets. Go ahead and read some (or all) of the books that Marc Andreessen recommends. If there’s anything that you’re curious about, go learn more about it! There are few barriers to acquiring knowledge, and there’s also no penalty for stopping once you feel like you’ve had your fill.

Stop & Look Around

Stop & Look Around. One of my favorite film characters is Ferris Bueller, famous for his mantra “Life moves pretty fast, if you don’t stop and take a look around once in a while, you could miss it.” I’m going to embrace and adapt that: Industry trends move pretty fast. If you don’t stop and look around once in a while, you could miss the next one. Try to be aware of industry and technology trends as they are happening. Shifts in trends that are apparent now, in hindsight: (1) the transition from mainframes to PCs (mid-1970s to the early-1980s); (2) the emergence of the Internet for commerce & business software; (3) the ubiquity of mobile phones and their evolution into handheld Internet devices. Changing trends sneak up on you. So every once in a while, pause and reflect on what you’re seeing around you. Being observant can inform where you direct your career and how you focus your time.

Know Where You Get Energy. Be true to yourself. Start by figuring out: What You Love. If you had your choice of anything, what would you love to do? Start there but also figure out What You Are Good At. The overlap between those two things, if you can find it, defines where your passions lie. In the context of your career, obviously you want to know What You Can Be Paid For. The overlap of these different circles shows what can be a profession and also a passion of yours. But to make the circle complete you should strive to focus your energy on What The World Needs. There is a really special place at the intersection of: What The World Needs + What You Can Be Paid For + What You Are Good At + What You Love. The overlap of these four different circles is described by the Japanese term Ikigai, which means “a reason for being”. (I was reminded of this concept by my former colleague John Greene, who recently joined an early startup in search of his Ikigai.) If you can actually align what you LOVE, what you’re GOOD AT, what you CAN BE PAID FOR, and what THE WORLD NEEDS — no matter what it is — it’s pretty rare. If you can find your Ikigai: you’ll be fulfilled, you’ll be fully engaged, you’ll be directing efforts to a worthwhile endeavor — and it’s not going to feel like a job, because you love it! This is a powerful way to think about how a vocation, a mission, a profession, and a passion can all line up.

Decide For Yourself

Decide For Yourself. When I was growing up in the suburbs of Chicago, my parents had certain ideas for me. For most of us, our parents do a lot to shape us and our views of the world. My mom was a registered nurse. My dad was in real estate and also had a background in accounting. Each of them, in turn, would have wanted me to follow in their footsteps. Of course, my mom really wanted me to be a doctor, for the prestige that holds and what that means in the community. (My parents immigrated from the Philippines, and for their generation it was really important for people to want to be doctors.) I just couldn’t do it. I was not interested in the medical profession, regardless of whether being a doctor was an important job or whether it would impact other people’s lives. I understood those things, but I wanted something different. I wanted to do something in the Engineering realm—I knew that would bring me joy and satisfaction. I had to make that choice for myself. Just like anyone that embarks upon their career: you have to live with your decisions. This applies not just to your field of study. It doesn’t apply just to the career path you choose. It happens every day: the decisions you make on the job, the projects you choose to accept (or decline from, or volunteer for), the roles you choose to step into, the companies you choose to join (or start, or leave). Of course, there are people in your life that influence you: your parents, your spouse, your kids, and your friends. But it’s important for you to take all those as inputs, and maybe find a quiet place and really reflect—not just in one session but over time. Over a few nights. Sleep on it. Because whatever you choose—whether you take the red pill or the green pill—you have to live with the consequences. Don’t blame your parents if you choose to be a doctor because they want you to, if it’s not really where your passion is.

Yes, that’s me.

Live Courageously. You need to live with your own decisions and you need to make your own choices. Don’t make choices to please others—make one that’s informed for you. After that, take the leap. Trust your instinct. Trust in yourself. Trust in the ways you’ve thought about your decisions. Remember that you’re the one who is in control, and you’re the one who can put things into motion. Don’t wait for life to happen to you. Actualize and make true your decisions and your choices.

(That is actually me in the photo—a much younger me).

Building Resilient Teams

Creating resilient teams is important no matter what company you’re at, or where you are on the planet. This history of humankind demonstrates that we accomplish great things together, as teams. Here are my recommendations on building resilient teams:

  • Hire for Potential, Ability, and Culture
  • Set Clear Goals
  • Divide-and-Conquer
  • Build Trust with Transparency
  • Provide Meaning and Purpose
Hire for Potential, Ability, and Culture

Hiring. You need to hire for potential. Think of a young Tiger Woods. Early in his amateur career, people knew this kid had potential on the golf course. Be open to where talent can come from. Keep on the lookout for folks you can hire that (in 2/3/5 years) could be amazing and will be additive to your team. With the right nurturing and coaching, you can groom individuals to become amazing teammates and strong contributors. High-potential individuals should make up a portion of your team. People continually evolve and grow in their careers—don’t lose sight of that fact.

Great teams also need people with amazing ability & skills who are already top performers. You need to hire some superstars; the equivalent of Michael Jordan in his prime. (I grew up in Chicago, so I’m partial to the Bulls of the Jordan era.) Michael Jordan was a consummate perfectionist; he was at the top of his game, and he was always pushing himself. He was always pushing and challenging his teammates, too. And if you’ve watched the ESPN documentary on Michael Jordan, you know that—every once in a while—he might not have been the nicest person to hang out with. But his teammates appreciated how Michael got the most out of every single one of them. As you’re thinking about team formation, strive for a combination of current superstars that can lead by example and high-potential individuals that can become the next generation of leaders.

You also need to hire for culture. When you’re building a team you are implicitly creating a Team Culture. You want camaraderie. The team will need to be resilient through failures to eventually experience successes. Hopefully you will celebrate success like the USA Women’s Soccer Team after a victory; you can see the pure joy that they have. But there’s also going to be the hard times. You need to be able to work with people through the ups and the downs, because that will inevitably happen. Make sure that when you hire for your teams that you have: the right characters, the right personalities, the right people on the playing field. You’ll know you can lean on them and trust them.

Set Clear Goals for your teams. Most teams and companies know WHAT they’re doing (i.e, what product they want to build). Most companies furthermore, have an opinion and very clear statements of HOW they’re going to do it (i.e., how they’re going to layer on different pieces of functionality, or parts of code, or different services). But surprisingly, teams and companies usually aren’t well-informed on WHY they’re doing it.

  • WHAT: We’re building widgets.
  • HOW: Here’s how we’re going to build the widgets.
  • WHY: Remind me, why are we building these widgets?

I’m inspired by Simon Sinek and his book “Start With Why” as well as his TED talk on “How Great Leaders Inspire Action”. Sinek urges leaders “Start With Why” which is the opposite of what teams & companies usually do. In his TED talk, Sinek describes “The Golden Circle” (shown above). I like to describe it as a tasty piece of candy: start with the creamy center, which is the WHY. That is the very reason—the True North—of why you’re doing something. For a project to really inspire the team, everyone has to understand the WHY. This is something that a lot of companies and teams might skip over when they’re thinking about processes, organizing teams, and distributing work. If you’re on a team and you don’t know WHY your team is doing something—you should ask! If you’re leading a team, you’re usually preoccupied with the procedures and processes. As a leader, periodically ask yourself: “Is everyone on the team aware of WHY we’re doing this?” You can never reinforce the WHY too much. It’s a really good way to continue to inspire and align people, and remind them of the overall mission.

Divide-and-Conquer. There are Computer Science algorithms based on Divide-and-Conquer. It’s also a way that I generally try to solve problems, and how teams should organize as they grow to face larger problems. Let’s start with the smallest atomic unit of a team: squads. A squad is a small, tight, autonomous team. Everyone trusts each other because you’ve hired well. Everyone knows the mission as to WHY you’re doing things. This is a unit, a very tight corp working towards a singular mission.

As a company grows, to divide-and-conquer you need to aggregate squads into tribes. An example of different tribes that I’ve experienced: a tribe for “applications” and a tribe for “platform”. The “applications” tribe focuses on end-user functionality. The “platform” tribe builds infrastructure components. Each tribe subdivides their problem further to define areas of ownership for their constituent squads. This method of organization gives each squad autonomy, an area of focus, and subject matter expertise that they can obsess over.

Over time, companies grow to tackle larger problems. Strive to organize teams in a way that creates: (1) autonomous squads at the most granular level; (2) tribes for higher-level goals solved across squads; and (3) a collection of tribes that, in aggregate, work towards the company mission. Constructing teams in this way gives power to each individual: each person will have the focus to deliver and will understand their contribution to their squad.

Tribes and squads are focused on their own subset of the product. If you stop there, you could lose the ability to think holistically about the overall organization. As you continue to grow, you’ll want to introduce guilds into the organization. Guilds are cross-cutting and can be considered an overlay across tribes and squads. You might want to create a guild for “front-end” topics. Similarly, you might have an “infrastructure” guild to decide on backend architecture. Each of the guilds that you form should have sufficient representation from the tribes and squads to contribute to their decisions. It’s a different way of Dividing-and-Conquering: a combination of guilds (for strategic choices) across tribes and squads (for project delivery) provides full coverage. Tribes and squads see the trees, while guilds see the overall forest.

The concepts of squads, tribes, and guilds comes from “Scaling Agile @ Spotify” written by Henrik Kniberg & Anders Invarsson. This is how Spotify organized their teams. It’s also how I’ve seen teams in the past — we just didn’t have the terminology until Spotify formalized it.

Build Trust with Transparency. Transparency with team members helps keep them motivated & inspired, because they know exactly how the company is doing and how their work fits into the larger picture. With transparency, individuals across teams will have enough information to understand that, in aggregate, all teams are contributing towards a higher-level set of goals.

If managers aren’t transparent with what they’re expecting, they can’t expect their employees to trust them. Ideally, the organization will have transparency across-, up-, and down- the org chart. After all, you’re building a team—and competition is not within teams. When employees win, managers win (and vice-versa). When individual teams win, the company wins. Competition, if it exists, should be outside the company walls.

When does a team operate well, no matter what kind of team it is? It’s when you trust each other, and you allow information to flow to all the different team members. Then everyone can act on the information in an appropriate way for their role on the team.

Meaning and Purpose. I assume you don’t want to provide “just another job” to your team members. Of course you should hire people for what they’re good at—their potential and their ability. As part of the offer process: explain WHY the team exists, WHY the company exists, and WHY it’s going to make a difference in the world. If you can unlock that, and you can get people to see the importance of your mission—then you will keep them aligned and motivated.

You can’t necessarily control what people love. But if you’re building teams—as a manager or a team member—you can always remind folks WHY their work is important for the team, for the company, and hopefully the planet.

Farewell to 2020: a year that tested our resilience.

(An excerpt of this post appears on the Terminal Blog)



Ron Pragides

Led pre-IPO teams at @BigCommerce @Twitter @Salesforce. Follow me on twitter: @mrp