Scaling Organizational Empathy With Box’s VPE, Saminda Wijegunawardena

By Saminda Wijegunawardena    |    September 30, 2019
In this Perspectives in Engineering interview series, engineering leaders talk about how to build, coach, and scale world-class technology teams.

As a company scales, it’s inevitable that individuals will grow farther removed from other people, projects, and initiatives in the organization.

Saminda Wijegunawardena, VP of Engineering at Box, calls this increasing distance “abstraction.” He writes that abstraction describes how far a person is from a relevant action or issue — vertically, when separated by org chart levels; horizontally, when separated by different business units or departments. Or diagonally, if removed in both directions.

Abstraction — the distance between individuals or teams in an organization — kills execution because they seldom have a full understanding of what all is at play, and they cannot completely evaluate their work in a broader context. It happens on any level in a company, from the C-suite leaders all the way to the most junior engineers.

And abstraction doesn’t just kill execution. “It also kills empathy,” Wijegunawardena says.

Empathy may seem distinct from execution, but he holds that it’s necessary to understand the full context of a situation before being able to reach conclusions about it. Therefore, empathy truly is within a manager’s domain.

The duties of management remain largely static as an organization scales — engineering managers can and should be responsible for technical management, execution and planning, coaching and development, team health, cultural impact, communication, and overall leadership of a scrum team. This role doesn’t change whether an engineering org is 5, 500, or 5000 strong.

The optimal approach for managers, therefore, is to maintain close connections that enable empathy even as the organization itself expands beyond their own solar systems.

Wijegunawardena has found ways to create and maintain an empathetic environment that include integrating mentorship into contributors’ regular workflow, aligning everyone around the same goals, expressing cultural acknowledgment, and hiring for character over competency.


Create intimacy for both distributed and co-located teams

Creating and maintaining personal connections are orders of magnitude more difficult when building distributed teams as compared to co-located teams. Yet why not bring that same awareness back around to creating more intimate and empathetic co-located teams, as well?

Here’s how Wijegunawardena does it:

Invite everyone into the room. “When you’re in a room, your tendency is to focus in on the people physically the room,” Wijegunawardena says. “You have to go a little bit above and beyond to recognize that not everyone is feeling first class if they are remote, and you cannot assume in the physical room that everyone recognizes that.”

So whether the room is literal (as with distributed engineers) or metaphorical (as with any engineers who may feel they have hurdles or restrictions), Wijegunawardena suggests addressing those people directly. Acknowledge them, and invite their contributions explicitly and concurrently with—even before—the other engineers in the room.

Make the practices into habits. “It’s most effective when the more senior leaders give those cues, because then other folks start to model that behavior instinctively,” he says. “Then it becomes more contagious. It becomes a wider habit.”

Make the effort, whatever tools you have. The effort matters more than the tools used to implement the effort, as well. Wijegunawardena recalls that ten or more years ago, when Box was a growing company, it could not spring for the high-end video chat systems for remote engineers, so they used Google Hangouts instead.

“We started hiring remote folks, and we wanted to reduce that abstraction,” he says. “It’s important, especially when new employees start.”

Use high-touch onboarding. “Our remote onboarding experience includes face-to-face interaction, where they're onsite at HQ for a week, and we really starting to build those relationships,” Wijegunawardena explains. “While we can’t do all these things at scale for employees over time, there's no substitute for that initial set of impressions in person. That human touch element early on forms impressions, and that sense of individual personalities goes a long way over time.”


Integrate mentorship into regular contributions

Many leaders grapple with how to balance allowing team members to contribute to projects, alongside the mentorship and training of other team members who come alongside. From Wijegunawardena’s standpoint, those two things are not orthogonal at all.

“If you have a high-risk project, it’s very convenient to go to the security blanket of putting your top engineers on it,” he says. “That misses an opportunity.”

Up-and-coming engineers need to be placed in high-leverage situations if they are ever going to be trusted in those situations. That doesn’t mean hanging them out to dry, however. What Wijegunawardena has been doing at Box is to put one of his top engineers in the backseat of a certain project, and giving a more junior engineer the front seat to lead it. That way, the senior engineers are still there to support and guide their teammates, and to ensure the project’s satisfactory delivery.

"We have fairly experienced engineers who will always want to see the other person on the team succeed instead of needing to take the leadership role on a project."

“Those are opportunities you can create to stretch engineers,” he says. “More consistent, practical procedures like pair programming are great, but sometimes the nature of the projects don’t always support that.”

After all, Wijegunawardena has discovered that engineers learn best not by one-on-one consultation with a mentor, but by doing the work with their mentors and senior peers.

“Part of the culture that I'm proud of at Box, is that we have fairly experienced engineers who will always want to see the other person on the team succeed instead of needing to take the leadership role on a project,” he says.


Align everyone around goals by constantly re-messaging them

When a team is small, it’s generally pretty simple to keep everybody working toward the same goals. But with a scaling company, abstraction comes into play—the engineers can understand the company’s goals very differently than the organizational leaders.

“I find often senior executives are like, 'Well, I've explained this, why don't the engineers get it? It's so important,’” Wijegunawardena says. “Well, they have a lot more data. They've internalized it all for a longer period, and with an eye on the future.”

He finds that leaders are simply never finished communicating a company’s strategy, mission, and vision. They have to re-communicate it, re-message it, re-deliver it, over and over again. And not because engineers and lower-level managers are dense, by any means, but because they naturally have a different perspective.

"Communicating and re-communicating goals organically starts creating alignment and makes the company start to feel like a smaller team. We’re all going in the same direction. And it kills that abstraction."

“The view of reality at the C-level is shaped by the future,” he explains. “They have access to more information, they know where the company is going, they direct and influence where the company is going. When you get to the ICs, their reality is shaped almost always by the past. They don't have access to the information or the promise of a better tomorrow, so they live in what they experience—why we didn’t split the monolith earlier, et cetera. And middle management is literally in the middle, where they have some view of the past but they don't have access to all information.”

So if there is a way to communicate the organization’s vision and direction, Wijegunawardena recommends it. Personally, he mails out OKRs and is transparent with all communications, from email to Slack and PowerPoints. He hold regular AMAs with the team, invites guest speakers into the team, welcomes management people from the market and finance divisions to create awareness of the challenges they’re going through and why they operate the way they do.

“That organically starts creating alignment and makes the company start to feel like a smaller team,” he says. “We’re all going in the same direction. And it kills that abstraction.”


Develop a means of cultural acknowledgment

One way to make sure any employees feel recognized and valued is to acknowledge their contributions. Of course, accomplishments like delivering a huge project are prime times to do that. But an organization’s culture likely will establish its own milestones—often some form of years of service—that can engage team members more than a plaque on the wall, and regardless of whether they’ve moved to management or remained technical contributors.

“Box has engineers who have been here six, seven, eight, nine years from early, early days through astronomic growth, both technically and in terms of where we are on the market,” Wijegunawardena says, “and I think acknowledging them on a cultural level is super important. The fact that they’ve been here that long often says that they are cultural exemplars.”

"Now you have a one-two punch of cultural exemplars and strong technical figures. And you can find ways to put them in the right roles."

He recalls that Pixar celebrated half-life days, when people had worked at Pixar for exactly half their life so far. Of course, not every organization has been around enough decades to have half-life days—so he sees other ways to recognize commitment and tenure. At Box, for instance, engineers have formed cohorts around the year they started at the company. They aim to preserve the things that made Box a unique company from the start.

“They become our technical luminaries as well as our cultural exemplars,” Wijegunawardena says.

Whether an organization implements means of acknowledging team members for their duration and accomplishments, or the teams develop those means themselves, he stresses the importance of cultural acknowledgment for both preserving and developing an organization’s culture and allowing contributors to feel valued.

“They build a lot of relationships and influence and capital that way,” Wijegunawardena says. “Now you have a one-two punch of cultural exemplars and strong technical figures. And you can find ways to put them in the right roles.”


Hire for character over competency

Many of Wijegunawardena’s strategies for creating and maintaining an empathetic environment focus on the team members already in an organization. Yet developing that empathy going forward is founded on the people a scaling organization hires.

Great engineering talent exists in just about every hiring pool. So Wijegunawardena considers another aspect first.

“Hire for character first, competency second,” he says. “You can develop competency; it's very hard to change character. So make sure to consider character as you interview, and make sure that you're keeping that bar high in terms of the behavioral traits that you're looking for in a top performer.”

He acknowledges that in the speed of hiring in an incredibly competitive market, it’s easy to unconsciously lower that bar. Every engineering leader works with the pressure of building products and delivering things to market, so they often skimp on hiring the ideal candidates in favor of hiring competent ones.

"Hire for character first, competency second. You can develop competency; it's very hard to change character."

“We all know what the cost of lowering your bar is on your team, your culture, your net output, your finances,” Wijegunawardena says. “All that stuff is impacted by making a bad hire.”

Furthermore, he recommends reducing abstraction by hiring for diversity—in every dimension. By bringing in various perspectives, an organization actually trains itself to consider voices from outside its standard box.

“Keep your options open, look for people of different backgrounds,” Wijegunawardena says. “Create a pipeline that you can bring in people of different tenures. We want the high potential entry-level folks, we want the senior experienced people. Even as you scale, you want a rich pipeline of folks. Make sure you expand your pipeline at the top of the funnel. You're enriching the culture by looking at people from different backgrounds and company profiles.”



A scaling organization naturally grapples with growing amounts of abstraction — the distance between individuals and teams that makes it challenging for them to understand, and therefore to care about, how and why others within the company operate the way they do.

Box’s Saminda Wijegunawardena holds that abstraction kills both execution and empathy. He offers these five strategies for building empathy and alignment across an engineering organization:

  • Create intimacy for both distributed and co-located teams by including often-excluded engineers (such as, for example, remote contributors) and making those behaviors habits.
  • Integrate mentorship as part of engineers’ regular contributions by putting junior engineers in positions to push themselves, and senior engineers in positions to coach them.
  • Align everyone around goals by constantly re-messaging them, knowing that every single person in an organization has their own perspectives on the organization’s goals, visions, and directions.
  • Develop a means of cultural acknowledgment that recognizes your cultural and technological exemplars for their ongoing contributions.
  • Hire for character over competency. You can train for competency, so focus your hiring practices on the behavioral and personality traits that will contribute positively to your culture—especially by considering diversity in all its dimensions.

About the author

Saminda Wijegunawardena VP, Engineering at Box