The One Strategy for Working Remotely

March 12, 2020

Join my mailing list…

I worked remotely for Stitch Fix for six and a half years, originally as an engineer, then as a manager, director, technical project manager and architect. With all the tips and tricks going around, I want to talk about the one strategy to be successful working remotely. This strategy should be the basis for everything you do, and any productivity hacks that don’t roll up to this strategy should be set aside. The strategy is to build and cultivate trust.

What is Trust Anyway?

Trust is built on three concepts:

  • Competence - can you do a thing?
  • Consistency - can you do a thing every time?
  • Motivations - are you doing the thing for the right reasons?

This framework is very useful for understanding interpersonal working relationships. Think about a person at work that you don’t totally trust. I bet the reason comes down to one of the above criteria. Know that could help you figure out how to improve your relationship with them.

It works in reverse, too. What are instances where your manager micro-manages you? These are an indication of a lack of trust, and your manager’s behavior toward you can give you a clue as to what might be the reason. This also works with co-workers, of course.

So why is this important for remote work?

Trust Bridges Gaps in Communication

When you are not physically co-located with your manager and co-workers, the ability of everyone to manage each other and communicate is hampered. It becomes physically impossible to force communication to happen. Thus, management and collaboration happen differently than if you are all in an office together.

Practically this means that more time passes between interactions. It also means interactions are coerced into a coarser medium than conversation. Emails and Slack messages leave quite a bit open to interpretation.

Think about someone you don’t totally trust. If they send you a curt message in Slack, you might interpret that more maliciously than it was intended, and part of the reason is the lack of trust. A similar interaction with someone you totally trust would be interpreted differently.

In a co-located team, ambiguous communication can be easily corrected and clarified by conversation. It even can happen in the moment. You might say something to a co-worker and notice their brow furrow. Reading that clue, you can clarify, or ask if you missed something. Not so with email or Slack.

The trick to being effective then, is to constantly be aware of the trust others have in you, your trust in them, and seek to take actions that maintain or build that trust.

Empathy Builds Trust

Many of the tips and tricks going around right now can be useful at building trust (or maintain the trust that exists). But they might not be right for you or others you are interacting with. To figure this out requires empathy. Empathy isn’t as magic as it might feel like. Empathy is:

the ability to understand and share the feelings of another.

You don’t have to feel what others feel. You just need to understand and this is not as hard as it sounds.

In our run up to IPO at Stitch Fix, I ended up working on an ERP implementation with our finance team. They were all in San Francisco and most of them had not worked closely with engineers before, and certainly not engineers that were three timezones away. Their framework for these projects was consultants who came onsite Tuesday-Thursday and conference calls on Monday and Friday.

Instead, they were told that their engineering partner on the most important project at the company was some guy they never heard of who not only wasn’t in the office, but wasn’t even in their timezone.

It’s not hard to imagine how that might feel.

So, instead of swooping in with Slack logins, emoji guides, and Google Doc conventions, I met them in person. I spent a week with them for the sole purpose of establishing a level of trust on which we could build and helping them start to empathize with me, so we could figure out how to work together effectively.

Without taking a moment to think about what this experience would be like for them, I would’ve made bad decisions and the team would’ve been way less effective.

But, once trust is established, it must be maintained.

Empathy and Openness Maintain Trust

Trust has a half-life. If you don’t top it up, it gradually goes away. But each interaction you have with someone is an opportunity to build it or keep it going. Since empathy is important to building trust, you need to know about people to better empathize. But they need to know about you, too.

A simple technique that works from small Slack chats to big video chats and even huge presentations is to make sure that the interaction touches on three things:

  • The subject of the interaction, i.e. whatever it is you need to interact with people about.
  • What’s going on with you.
  • What’s going on with others.

Imagine video chats where all you talk about is the agenda in the meeting. Imagine that over time. Everyone becomes cogs in the machine, talking heads. This will not build trust and will not produce an effective team.

And when that team rarely (or never) sees each other in person, they don’t interact with each other as humans. Thus, each interaction is potentially the only chance to connect with people and build trust.

Sharing what’s going on with you is easy, especially because even the most banal details can help. Talking about the weather is a tiny baby step to learning about who other people are. Eventually, others will share similar information and you can begin to form a more well-rounded relationship.

Humanizing each other is more of a life hack around trust. The best way to build trust in the workplace is to get your shit done.

Getting Things Done Builds a Lot of Trust

The best way to build trust as I have described it is to demonstrate your competence by consistently delivering your work without incident. The most effective communication is often your work product.

When your boss and co-workers see you producing results, it unambiguously establishes competence and, over time, consistency (your motivations will likely not be questioned).

Getting things done is not so simple, especially in a remote environment. You must strive to produce results several times per week if you can. The ability to demonstrate progress is critical. Nothing erodes trust more than radio silence about your work for days or weeks on end.

There are a lot of tips and tricks about how to do this, but I’ll spare you. The point is that you need to find a way to demonstrate progress on a regular basis. This requires:

  • knowing what problem you are solving.
  • being productive.
  • empathizing with your boss and co-workers.

Many developers miss the empathy part. You can deliver working code all day long, but if it’s not done in a way that others can understand, it’s useless. And it’s often not obvious just how everyone perceives progress. It may sound reductive, but if your boss doesn’t understand the work you are producing, you may as well not be producing anything in their eyes.

For example, I used to send text-based updates about work in progress that I had done but wasn’t in production yet. Crickets. I then changed to screencasts and got tons of engagement. Not saying screencasts are right for you, but you have to empathize with your audience and change tactics if things aren’t working.

Beware Tips & Tricks

Tips and Tricks should be taken with a grain of salt. View them as inspiration for how you approach your specific problems. Anything that doesn’t help you build trust should be questioned, and what works for one company or person won’t work for another.

Ask yourself every day how you have managed the trust you have with your co-workers. What did you do to maintain that trust? What might you have done that could’ve eroded it? Ask this every day and you’ll become more effective at your job and your team will get better at being remote.