148: JJ Reeder - Thriving in Distributed Work: Self-Managed and Digital-First

"JJ" Jessica Reeder, a workplace innovation and culture transformation leader, shares insights from her deep experience designing communications systems, scaling multicultural teams and aligning culture with strategy. Bringing pivotal learnings from early fully-remote companies such as Toptal and GitLab, JJ explains how self-management, thorough documentation, and systematized collaboration underpin successful remote work. She describes the cultural shifts required for hybrid and distributed workforces and advocates for systems thinking and clear communication to empower modern work managers.

TAKEAWAYS

[01:24] JJ didn't know what studying linguistics would entail when she chose it but she loved it.

[02:47] Linguistics gives JJ a framework to understand the history of humanity and migration.

[03:10] Living in another culture opens up her global perspective and gives her a different lens.

[04:24] JJ's appreciation for engineers stems from their clarity and direct information transfer style.

[05:49] JJ transitions early to working remotely focused on content and communication projects.

[06:35] Noticing the growth of formal distributed work, JJ joins one of the first all remote companies.

[07:14] JJ starts building a distributed community across cultures for a global virtual developer network.

[08:15] Nurturing connections among talented remote professionals requires deliberate strategies.

[08:56] Remote talent feels more connected when engaged with a peer community.

[09:54] JJ moves to GitLab to explore systematized connectivity and is launched into remote work consulting by the pandemic.

[13:01] GitLab was designed for remote work with full documentation, tools, and systems.

[14:11] Realizations they need to understand other companies' different perspectives.

[16:44] Conviction in remote work but recognition that unprepared managers are challenged.

[18:30] JJ highlights self-management as a cornerstone of GitLab's decentralized operating model.

[19:07] Clear documentation and SOPs reduce managerial load while teaching remote processes.

[20:35] Others' embrace of remote work affirms JJ's long-held belief in the global distributed workforce.

[22:34] JJ studies industrial organizational psychology and joins Upwork for an applied learning experience.

[23:24] JJ helps Upwork transition from an office-based to remote-first workforce.

[24:12] Engagement is often relationship based, differing between employee and freelance contributors.

[25:00] Emotional connection isn't always needed; the mission can generate engagement.

[26:43] JJ finds that many workers thrive as project contributors without deep social integration.

[28:08] More varied distributed operational models are needed, especially for larger companies.

[30:36] Distributed work effectiveness requires more than dedicated time for human connection.

[31:25] Clearly documenting and consistently applying standard operating procedures and behaviors is crucial.

[32:05] Standardizing—behaviors, tools, expectations—was a major Upwork project JJ worked on.

[32:47] Accessible knowledge and intentional transparency are essential and must be intentional.

[34:58] The Forest Ranger book gives JJ great insights about distributed operations.

[36:19] The 'manual' shows how philosophy, behavioral standards, transparency and documentation empower independent workers.

[37:24] To train distributed workers, companies must clarify expectations—behaviors, work, standards.

[39:15] Hybrid work requires embracing a digital-first mindset even when working partially in-office.

[40:54] IMMEDIATE ACTION TIP: To become digital first, one, understand time—such as core hours, two, communicate digitally—with documented processes, and three, systematize collaboration—designating how and where work is done.

[41:57] Communication processes must be modeled by leadership and enforced by managers.

[42:26] Systematized collaboration tools create visibility, drive cohesion, and replace physical context.

RESOURCES

"JJ" Jessica Reeder on Linkedin

JJ's website

The Forest Ranger book

QUOTES

"This decentralization of management. Instead of someone managing your work, there's somebody who is directing your output or directing your outcome. So understanding how to empower people to self-manage their work."

"Collaboration is really just about trading work back and forth and doing it in a very effective way."

"To be effective at our work, we need to have a source of motivation. We need to have proof that our work is doing something that we believe in. We do need to have some sort of a mission that we're contributing to, but we don't need to necessarily be deeply emotionally engaged."

"Having standard operating procedures and behavioral standards is clearly documented and consistently applied throughout the organization is crucial in remote work. It is absolutely a deal breaker if you don't have people understanding how they are supposed to work."

"One of those things where you have to decide - how transparent of an organization do we want to be. If we don't buy in on transparency, then we're going to have challenges with distributed work."

"Becoming a digital first organization doesn't block your ability to have a functioning hybrid organization. In fact, it enhances it. It really will make your hybrid organization more powerful. It will help people to get the most out of work, whether they're in the office or not."

"All of the things that you need to have a highly functioning team can be empowered by really embracing the digital first mentality."

"Collaboration needs to be systematized. It needs to happen on as few disparate tools as possible."