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January 29, 2022

Engineering Leaders Discuss the Transition from 100% Remote Work to Hybrid

Engineering Leaders Discuss the Transition from 100% Remote Work to Hybrid

Engineering leadership: lessons from 2020

Dennis Shiao
Dennis Shiao
Engineering Leaders Discuss the Transition from 100% Remote Work to Hybrid

Engineering leadership: lessons from 2020

During the pandemic, engineering teams transitioned to 100% remote work. Engineers worked from wherever they happened to be. Some remained at home, while others moved in with family. In-person meetings and standups transitioned to video conferences on Zoom, Teams, Google Meet and related platforms. 

In February 2020, Ryan began an initiative to break down silos and bring together disparate teams. When shelter-in-place orders came in March 2020, Ryan had to accelerate the initiative.

Building trust

To build trust, Ryan encouraged people to be open and honest and to demonstrate vulnerability. While some leaders are fearful of the conflict that can arise from open discussion, Ryan welcomes it. Conflict is acceptable because everyone’s issues are on the table. And once they are, there are ways to address those issues and resolve the conflict.

Ryan believes that the success of any business is built on trust. For Ryan, success is built on the following trust chain:

Trust begets debate begets commitment begets accountability.


Ryan works with a large team (i.e., 250-300 engineers). When a team this size transitions from in-person to remote work, communications challenges arise. When the team went 100% remote, hallway and watercooler conversations went away. The absence of these conversations meant that things got lost in transit. 

While rumors spread quite efficiently through emails and chat, business communications did not. Ryan quickly gathered his engineering managers to determine how to recalibrate communications. They decided to over-communicate. They switched to extremely verbose and frequent communication to ensure that everyone is informed about everything. Today, it’s still a process the team is adjusting and fine-tuning. 

Aligning engineering and product management

In the past, engineering at Care.com operated as a service provider. The product team would lob a request over the wall. Engineering would read the spec, then deliver it. During the pandemic, Ryan worked to break this model, making the engineering and product teams operate as one. Engineering, says Ryan, needs to have as much ownership of the deliverables as any other group.

If Ryan locked the head of engineering and head of product in separate rooms and asked them the same question, he expects to hear very similar answers. According to Ryan, “I always see ownership and motivation explode when engineering understands the why.”

Benefits of remote work

Ryan outlined the benefits his team discovered with remote work:

  • Better flexibility on hours
  • Productivity gains
  • Less costs (e.g., office supplies)
  • More purposeful meetings
  • Identify and eliminate inefficiencies

With remote work, Ryan found that his team could be more efficient with their time. Since Ryan places a high level of trust in his team, they’re free to schedule their days as they see fit. If they need to stop in the middle of the day to address a personal matter, they do it. As long as everyone gets their jobs done, they can schedule their work as they see fit.

Janice Little led her team at SheerID in the same way. Even as some offices reopen partially for in-person work, SheerID has a “work where you work best” policy for the rest of 2021. The company is constantly reviewing local health guidelines and adjusting policies and procedures accordingly.

Remote work: keeping a finger on the pulse of the team

How do engineering leaders keep a finger on the pulse of the team when everyone is working remotely? Ryan starts with a basic, but sometimes overlooked tactic: just ask! Speak to team members 1:1 and ask how they’re doing. Listen closely and label their concerns. 

Don’t move directly into “solve mode.” First, repeat the concern back to them to ensure you’re on the same page. Suggest ways to address the concern and work to solve it together. Surveys can be effective, especially for large teams, says Ryan. Anonymous surveys can generate more useful feedback than if team members need to provide their names. 

Ask team members what’s going well and what the organization can do better. Collect and analyze the qualitative and quantitative feedback, then figure out an action plan. Action is a priority — the team must see that leadership is actively working to address any concerns. 

When giving feedback to team members, Ryan likes to ask how they’d like to receive it:

Ryan uses the Situation-Behavior-Impact method, which identifies the “Situation,” describes observed “Behavior(s),” and explains the “Impact” of the person’s actions on you. 

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