The Art Of: Getting Remote Engineers to Report Blockers

James Lim
2 min readFeb 3, 2024

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I manage multiple platform-ish teams, and I make it a point to show up in the office every day. I want to make sure that I am available to support my teams when they need me, and being in-person helps me share and gather information in ad-hoc conversations. This also helps me feel vibe and morale and gives me the opportunity to build relationships with other departments.

Remote engineers, unfortunately, do not have this opportunity to provide or receive impromptu support, either from me or from the rest of the team. This challenge is unique to their experience. We also noticed that there was more reluctance to report blockers during async standup reports on Slack. This lack of communication led to delayed projects and missed deadlines. While addressing this issue, we discovered that prompting them with the right questions can make a significant difference.

Changing the Questions

It took a bit of prodding, but eventually some engineers shared with me that traditional questions such as “What are you blocked on?” made them feel incompetent. One said, “I should be able to do this on my own! ‘Blocked’ just sounds bad.”. Sharing blockers in a very public Slack channel was difficult for them.

It struck me like a lightning bolt — of course telling everyone you are blocked in a public Slack channel is different from walking over to a colleague’s desk. However, sharing updates in a public channel has several benefits, and we were not ready to give that up.

After some trial and error, we found that by reframing the questions, we could create a more positive and engaging environment. Here are three alternative questions that yielded promising results:

  1. What frustrated you yesterday?
  2. What are you spending a lot of time on?
  3. What surprised you yesterday?

The Results

We implemented these new questions in our daily stand-ups, not only within our own teams but also with other engineering teams. The results were encouraging. We observed increased engagement, as all engineers felt more comfortable sharing their experiences and challenges. Furthermore, we noticed that these revised questions fostered collaboration, as people responded more actively to their peers’ reports.

I noted that:

  • A simple “Omg I had that same problem two weeks ago — here’s a silly workaround” is powerful for camaraderie.
  • When engineers shared surprises, peers often responded with similar surprises and shared related documents (e.g. design docs, investigation notes, incident retrospectives) that helped everyone in the channel acquire context.

I encourage you to try it — let me know how it worked for you.

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James Lim
James Lim

Written by James Lim

Engineering@Modern Treasury (ex-Affirm, ex-Samsara) - jimjh.com

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