Interview with Saminda Wijegunawardena, VP, Engineering @ Box

Published on Nov 16, 2018

16 min read

image for Interview with Saminda Wijegunawardena, VP, Engineering @ Box

Location: San Francisco Bay Area
Current Role: VP of Engineering

What is your background and how did you get into management?

My background in both management and engineering management is pretty unconventional. In college, I started out as a business major. After taking electives my first year, I took an accounting course in my second year and quickly realized that it was not for me. Ultimately, I took a bunch of science and philosophy of science courses that really reinvigorated me so I decided to go pre-med. I graduated with a neurobiology degree and I was on track to go to medical school. Then I realized that to do what I really wanted to do which was brain surgery would probably require another decade of school after undergrad!

So I switched gears and ended up working an entry level position for a health services company. I was using a pretty antiquated home-grown enterprise computer system and found all these issues with it. I’d never taken a single computer science class but I ended up writing a spec to fix problems I saw. That landed me in the Information Systems department. I taught myself to code there, it was a sink or swim opportunity. I just got a book and worked on a set of bug fixes. I was in my early 20s, and I started taking on more technically complex projects shortly after and leading projects with multiple developers by my mid-20s.

Then in my late 20s, I was working at a college when my manager left and she recommended me to take over for her. I was thrust into the manager role somewhat accidentally, that was 17 years ago. I never thought of becoming a manager and early on I didn’t know what I was doing at all. There were no internet or training courses at my disposal, I just had to intuit what to do and made a lot of mistakes along the way, but I learned from all of them.

So in short, I fell into coding, I started leading projects as a tech lead and then my manager left and she recommended me and I started managing.

What are the biggest challenges you face?

My current challenges are probably shared by other leaders in the tech area and in Silicon Valley and are still the same challenges as many years prior: finding good people quickly (hiring). The talent market has become much more and more competitive. Keeping the culture bar high, the talent bar high, and just trying to find the right fit, and a mutual fit for folks to join my team and organization, it takes more energy than ever before.

I think also that managers have to be highly accountable for retaining talent. It’s a large but healthy challenge to keep their teams motivated, keep them aligned, keep them just fulfilled so that there’s a value proposition that’s constantly being realized to them in terms of why they want to be on that team at this company.

Similarly on the retention side investing to make sure your team members are growing and that they feel engaged is another ongoing challenge. I think that also takes more energy than it used to because it’s a very competitive market. Everyone has a lot of options on where they can go and you have to really make it worthwhile for people to stay.

I don’t think my current challenges are otherwise on the technical front. I think we have some good patterns and ways of solving problems. And we have a very technically talented team. But the things that I think about more often are about finding good people quickly and then finding out ways to retain those talented people by keeping them motivated through very healthy progressive means.

Also finding work-life balance and a sustainable rhythm for me is an ongoing challenge. Being a father and a husband, and prioritizing those things which are very important to me in life by balancing the energy that I spend on work because to me, it’s always family first.

I know now that hiring is one of your big challenges, and I think it’s a big challenge for a lot of people. What is your approach to hiring to try to solve that?

I think I’ve never articulated this way but your questions are kind of helping me realize the connection between those two challenges: hiring and retention.

If you’re doing the good things on the retention front, which means individual managers and teams have a sense of vision, mission; meaning they have a sense of where we’re going, their team’s purpose, and they’re part of a healthy team that’s diverse, talented, there’s no dysfunction on the team, that you really have brought in good people to the team that raise the culture and the diversity part versus erode it in some way. If you’re doing those things then you have, to put it in one metaphor, a good product to sell and offer new people to consider joining the team.

In terms of hiring, the most satisfying thing is when people come in and whether it works out or not, they have a good experience by talking to the people and they’re like, “Hey, it seems like you have a really good team and this has been challenging in a good way, the interviewing process, but I really see the culture here through the way that people interact and how they just talk to one another in the team.” I think if you’ve done your job as a leader in terms of internally building a healthy team, that’s one way that it feeds itself in terms of providing a really good candidate experience.

On the other hand, if things are on fire and crappy in your team or company, it shows when people are talking to you so I think that building out the teams and all those mission, vision, values, all those things are existential things to tackle and if you do all those things, then good things tend to happen.

The other part is making sure that everyone really understands down to individual engineers where we are as a business. I run a very transparent management team. I don’t have meetings with just my directs, executives and the senior management folks. We meet with everyone from TLM (which is our Tech Lead / Manager role; engineers who are growing into the manager role but are still in an IC role) and then the first level managers. Every week I have a flat management team meeting, about 15 of us, and I cascade everything very transparently around what’s going on with the business because I feel like people make better decisions the more data that they have. Channeling the state of the business and where we are in the opportunity and the strategy in those conversations when we’re talking to candidates really helps in pitching to a candidate. Candidates have said “Wow, everyone on your teams seems to understand how their team impacts the business and what their role in realizing the vision is.”

I think the other part is just having good interviewing and candidate experience practices,. We really engage with the candidates early on. We engage with them through the process at the end of the process, and realizing the strength of relationships and always being open to maintaining those relationships because I think good things happen karmically in ecosystems that way.

Creating a good experience for candidates and having a rigorous interviewing process but a fair and healthy process that the candidate feels is challenging but not like they’re getting interrogated also comes to mind in terms of how I approach hiring. There is also, of course, building your tech brand, blog posts, marketing the team, all those other kinds of things.

What is your advice for managers who are just starting out?

There’s are two misassumptions that I overcome with mentoring new managers.

One is that people like me just always knew this stuff and I’m like, “No.” A lot of things I preach is because I made a lot of mistakes early on. When I first became a manager and was drafted into it. I really didn’t know what I was doing and I didn’t have any management training. It was so long ago, there were no blogs or posts or any of these kinds of like the stuff that you’re doing that really enable people from a community standpoint. It was a pretty isolated experience. I learned by wanting to improve and through more and more experience.

The other part is when I look at new managers, especially the folks that have really never done it and are just kind of transitioning early in their careers, they have a desire to fast forward and learn everything at once. Learning frameworks and reading articles and books are prerequisites but they are not substitutes for application and iteration.

You can read about how to manage out a person but it’s not even close to the pain and the challenge of going through it including the emotional aspects and the internal conflict if the person is a really good person but they’re just not meeting the bar in some way. Those kinds of things you can’t read about and just imprint. It’s not like the Matrix where you just plug in and you know Kung Fu. It’s a learning process and it’s the hardest thing for me to really impart upon young new managers that you’re just going to have read and we’re going coach and we’re going talk about these things.

Then a year later, I ask them to tell me how they look at the world differently around management and these situations that we talked about. After getting them to introspect, and retrospect they realize, “Yeah, this is much harder than I thought.” Hiring is always much harder. Managing underperformance is much harder. Learning to time manage is a huge jump for someone going from an IC to a management role because you’re just in more meetings and you’re there to protect the team. You have to learn by experience and there’s really no fast forward. It really translates into patience.

Time management is a huge challenge for managers in general, so what is your workday like and how do you manage your time, emails, meetings etc.?

This is very fresh for me because last week in our last management team meeting I gave a talk called “Scaling GSD”. Scaling GSD means as you take on more responsibilities, and you become a manager, and a manager of managers, how do you continue to scale GSD without being bogged down. No matter how much scope I’ve taken on I’ve been able to maintain a certain bar.

A few things that come to mind. First, everyone has a fixed economy of time. No one has more or less time so how you use that time for yourself and also importantly use that time for others is really instrumental in affecting time management.

Most people think about managing their own time but especially as a manager and leader you have to be really conscious of how you manage other people’s time. I’m not just talking about resource management in terms of how you allocate sprint capacity or things like that but I mean really with your peers or stakeholders, anybody you’re interacting with. It comes down to simple things like when I go through my emails, I quickly scan and see, can I turn something around fast, unblock someone else, because really it’s not just unblocking someone else, it’s possibly unblocking a whole team or department.

Those things where I can get quick answers, quick turnarounds or quick inputs, I prioritize those first. The things that I’m not blocking someone, I then look at how urgent or important it is and those aren’t necessarily the same things. Something can be urgent but not important and it’s noisy and distracting and then some things can be important but not urgent and so the important things might be things like I keep in my inbox and I decide to look at it later when I have some focus time and not between meetings where I’m in more tactical mode, running around during the day on meetings.

People look at their calendar when they become a manager often as an enemy and that they’re now a slave to their calendar. I think that’s the wrong view. The calendar’s a tool and it’s about how to leverage it. Like driving you can either be a victim of the road or you can defensively drive and be proactive. Defensive calendaring is engineering your calendar. For example, I’ve got two 30 minute blocks in the morning and afternoon that I don’t violate, unless there’s a very extreme situation, like an all-day meeting or something like that. That gives me a break to come back to my desk, check emails, chat with folks, see what’s going on, see if there are any Slack messages and just keep things going for the department. Or I use that time to take a walk, renew myself in some way. And then most of my time is spent in meetings facilitating discussions, driving decisions and so running effective meetings is ultimately super, super important.

There’s a lot of tips we can learn from computers in time management. For example, if you’re just doing memory swaps, which are very expensive, you’re just copying state over and over again. That’s not a great use of time to repetitively status report, and you have to find opportunities and ways to minimize that and ensure you write once/read many. Also looks for activities that might be redundant for you but could be a development opportunity for someone else on your team.

Delegating something where there’s actual work opportunity, so they’re now extending a reach and they’re actually growing in the process and finding ways that make the best use of their time while not impacting negatively your time. Those are those things that I think are really important. I call this making sure there are notes to your future self like either calendar reminders, work blocks, etc three months later to remind yourself that you need to do something, like even catch up with a set of people in your network at work, things that would otherwise fall through the cracks.

There’s a bunch of those different things that I captured in this talk around how to scale GSD, not brute force scaling the amount of time you spend linearly around those things. And it’s delegation, defensive calendaring, all those different things that I think around time management including not trying to solve everything yourself, and that also goes back to delegation.

What is a personal habit that you feel contributes to your success?

What is probably most unique for me is practicing mindfulness. Fifteen years ago I was doing hours of meditation a day. After becoming a husband, father, and taking on more responsibility, it’s fairly challenging to find that kind of time anymore. I try to do a little bit of mindfulness every day during the train ride and that kind of centers me. It builds self-awareness and a sense of how I’m actually feeling because it’s very easy for my personality to just getting in a state of constant doing versus a state of watching, and that is very impactful for me.

I think it’s impactful for a lot of folks but it brings a clarity of focus for me. Prioritizing that time it’s just like exercise. Mindfulness is an exercise for my mind and my soul in that way, and finding a sense of peace and awareness to see where I’m at and just notice things and be detached from what otherwise might be frenetic or fast-paced that’s happening.

Could you share an internet resource or tool that you can’t leave without and that helps you in your job?

That’s easy: Ben Thompson’s Stratechery. I think that I would trade ten other things for that in a moment, e.g. Medium, Stack Overflow, any of those other great sources like Martin Fowler’s blog, etc. Stratechery has been one of the most powerful reads for me the last few years, it has really expanded my business acumen.

I think Ben Thompson is a very thoughtful and insightful writer. There’s very little fat in his writing. There’s very little ego or bloat in his analysis. He just always cuts to the point. It always resonates with me tremendously, it’s been really formative. I think it’s added a whole different pillar of strength and capability to my skill set because it’s led to other insights, discussions, explorations and other things because of how compelling his business strategy acumen is. It’s very tech focused but not always in my immediate domain so it also stays fresh.

If you could recommend one book to managers, what would it be and why?

Maybe it’s somewhat controversial but I think most management books are not really good 🙂 I think there’s kind of a formula of most management books which are if someone has built a brand as a leader and they convey some fairly obvious platitudes like treat people well, build trust and things like that which could be condensed into a one-page document. The rest of the book is filled with anecdotes to fill a page count!

That is my experience with a lot of management books, but there’s a handful that really stands out and one of the best is Leaders Eat Last by Simon Sinek. It contains a blend of industrial psychology, neuroscience, with great empirical analysis from everything from the military to the Congress and the tagline of the book is Why Some Teams Pull Together and Others Don’t. Its thoughtful analysis was really formative for me three or four years ago when I read it.

I also find Harvard business management (HBR) articles to be really impactful because they’re very data-driven and analytical versus an ex-CEO talking about how they did a great job on X or whatever. While some of those ex-CEO pieces are useful, I found them to be filled with more fluff than cutting to the point. HBR articles are great as a periodical but as for a book, no question it’s Leaders Eat Last by Simon Sinek.

What is your approach to mentoring and coaching members of your team?

I mentor and coach obviously the folks that are reporting into me and then I do skip levels with all the other managers in my team, there are about 11 other managers and I ask them to pick a development area specifically they want to focus on with me, meaning something I can mentor and coach them on. And sometimes it’s business strategy, sometimes it’s time management, it could be anything.

So, the approach varies a little bit but for my directs, I tie it back to having a very thoughtful development conversation where we go outside for 90 minutes, two hours, I learn about themselves as individuals, what motivates them, where they feel is there a peak in their career or some experience that really shaped them and then kind of reverse engineer what’s giving them energy, what takes their energy away. Where are their strengths, where are the areas they want to develop what their stories should be after they leave here and just gather a lot of really important data and then reflect that back to them and see what things they see and that’s kind of the base.

And then it’s really tying them to what goals. But I guess the approach is really getting them to own their development. Being a coach, I’m not doing it for them but facilitating the introspection and getting them to own their development and I think they feel more empowered in that way ultimately and helping them self-identify development goals and generally at least some portion of those to get to the next level of their career, e.g. managers to senior managers, senior managers to directors, directors to senior directors and so forth. And engineers as well, engineer to senior and so forth.

Some of those things are very specific to promotion at the next level in some timeframe but some of them are just innate about to how they want to grow as an individual. Being more self-aware, being a better public speaker, contributing to the community. In short, it would just be around learning out them, gathering a lot of data, and finding out about who they are as individuals and what their role is and what they want to do for their next level promotion. And then second is driving introspection so they can own their own set of goals and providing coaching mentoring directly in that area if I can provide it, or finding them mentors who can.

I always make sure anyone reporting to me has an ecosystem of mentors, people in their peer community, people outside of our department, people in completely different parts of the business, depending on what they’re trying to go after in terms of their goals. Building that kind of mentoring ecosystem I think is really important to coaching and development. Those are the kind of things that come to mind in terms of my approach.

That’s awesome. Okay, the last thing is where can people go to learn more about you?

https://www.linkedin.com/in/wijegunawardena/ is probably the best place. I’ve published a few posts and you can learn about me by seeing what people have written in terms of recommendations and endorsements about who I am and how I lead.

I think those are accurate In terms of describing who I am as a leader but then also my philosophy and mindset. I’ve taken emotional intelligence (EQ) and wrote a post called Organizational Intelligence (OQ) about how you try to scale those elements of emotional intelligence. I have a post on abstraction & latency vs execution and how the more abstracted you are, and the more latency there is how execution suffers in a project or organization and be closer to the data and closer to seeing what’s happening, it’s like CAP theorem for execution. Linkedin is where you can learn about who I am in my career as well as how I approach the world of management and leadership.


This series asks engineering managers to share their experiences with the intent of helping other engineering managers learn and improve. Have someone you want to see featured or questions you think we should ask? Contact me.

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