Each week at RemoteRated.com, we speak with leading remote CEOs to share practical insights on running and growing remote teams and companies. This week, we speak with Chris Bourdon, co-founder & CEO of With, an innovative solution for remote teams to connect and collaborate, seamlessly bringing shared experiences and personal interactions into the virtual realm.

Chris built a career with over 15 years at Apple, a company known for its operational excellence and forward-thinking approaches — bringing this same commitment to excellence to their own product, Chris and the With team are finding opportunities to make collaboration and synchronous interaction more productive and more natural in a remote world.

The full video of the interview is below, we’ve condensed the conversation to make the takeaways easy and practical!

Chris’ Essential Remote Advice:

  • Recognize that written communication may not always be the best approach, particularly for disagreements or for conflict resolution. Sometimes a synchronous conversation is the best approach to ensuring things don’t get too heated or that nobody gets misunderstood. As a leader, always be mindful of when to move things from chat or email into a real conversation.
  • As a leader, proactively seek to keep in touch and have one-on-one conversations wherever and whenever possible. Don’t lose sight of the relationships that drive the business, and the connections between individuals that enable that. While one-on-ones might not be infinitely scalable, they are worth prioritizing.
  • Early on, find people that embrace challenges and don’t need micromanaging. It’s critical that you find people who are comfortable and excited to take on a challenge, and go get it done without the need for constant check-ins and questions.
  • Create structure for task-level check ins, as well as personal development check-ins. In remote operations, these things can easily get mixed together, often to the detriment of both. Create conversations and interactions that allow team members to check in and work on their projects and personal development separately.
  • Take writing seriously! Great remote operations are often asynchronous, which is in turn driven by great documentation, great documentation is driven by great writing. As a leader and manager, seek workflows, tools, and habits that allow you to write effectively and consistently.

Join us next week, where we will be speaking with a remote CEO working to make remote workplaces diverse, fun, and adventurous!