This year I’ll be editorializing my growing list of management bookmarks. We will start this year with the following:

Manager’s club - Mega list of 1 on 1 Meeting Questions

Superficially, this list (which can also be downloaded in a structured format here) compiles questions that can be asked during periodic meetings between a manager and their reports.

What I like about this list:

  • it classifies the questions into themes.

    Busy managers tend to forget to cover various topics over time. They default to the simplistic question “what’s on your mind?” which, over time, tends to bring up the same topics over and over, following the existing momentum of the relationship. This creates blind spots.

    To avoid blind spots, I find it useful to traverse themes periodically, either over weeks or through the same conversation. It helps shape a more balanced relationship. It also prompts parties to think about topics they wouldn’t otherwise. This promotes lateral thinking and helps discover opportunities.

  • it contains more than 10 questions per theme: over the course of weeks, asking different questions every time makes it feel less boring.

What I do not like about this list:

  • it does not explore which questions are more effective and why.

    Some folk are experienced at self-reflection and would know how to answer “What are your top three motivators?” right away. Many workers in the tech industry are not, and so they would not. For those, “What do you like about working here? What’s not fun about working here?” would work better. However, conversely, a question that is too simple might appear condescending.

    Adapting the conversation to the level of depth desired by all parties is essential, and a bullet list of questions does not help with that.

  • it does not promote organizational agency.

    It’s important to make everyone acutely conscious that organizational structure is something that everyone has a say on. It is healthy and important to regularly review “what are ways our organization doesn’t work and how could we change it for the better?” and this question is not on the list.

    We will talk about this topic more in a later writeup.

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Raphael ‘kena’ Poss Avatar Raphael ‘kena’ Poss is a computer scientist and software engineer specialized in compiler construction, computer architecture, operating systems and databases.
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So what do you think? Did I miss something? Is any part unclear? Leave your comments below.


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