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What should I ask when I don't know what to ask? 2026-01-11 link

It can be hard to get started on tasks that you do not know how to accomplish. Often it's hard to start formulating a plan because you do now know what questions to ask. In those situations these templates can help.

What are things I could <ACTION> to <RESULT>.

Action is often one of:

  • read up on
  • verify
  • ask
  • check
  • consider
  • adjust
  • attempt
  • [should] avoid
  • communicate
  • confirm
  • determine
  • do
  • explore
  • ensure

Result is the intended outcome. Avoid implying in the result that you are not going to execute the result. Those generally result in bad questions:

What are things I could ask to make you take over the task of rebooting the Zulip server tomorrow.

Some examples of good questions are:

  • What are things I could verify to make sure it is safe to reboot the Zulip server tomorrow?
  • What are things I could communicate before shutting down the Zulip server tomorrow?
  • What are things I could consider before sending out a downtime notification to clients?

Questions about decisions

It can often be unclear how the current situation came about. It can help a lot to ask about the context of the situation:

  • What was the risk we were trying to address by adding a Zabbix alert for high cpu usage?
  • Why do we reboot servers one by one instead of restarting them all at the same time?

Brainstorming questions

Brainstorming questions can help get people unstuck by providing more ideas:

  • Can you think of ways of upgrading Zulip without rebooting it?
  • Can you think of downsides to the idea of running multiple Zulip instances so we can upgrade one without downtime?
  • Can you think of ways to split up this problem into parts we can investigate?

Recommendations

Other people often have experience handling similar situations. It can help to ask their opinion. Make sure not to accidentally delegate responsibility to them!

  • If you had to choose between half an hour of downtime for Zulip or setting up multiple Zulip instances, which would you choose, and why?
  • We are trying to decide between upgrading Zulip and migrating to a different chat platform. Which solution do you think will require less work?

Expertise questions

  • In your experience, how much downtime can we expect when doing a Zulip upgrade?
  • If you had to execute this upgrade, how much time do you expect this to take you?
  • Were there complications last time around you did a Zulip upgrade?
  • I wasn't able to find anything on google, do you know where I can find documentation about doing a Zulip upgrade?

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