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Working with Isaac

Author: @isaach
Version history:

Status: living

Stuff to know

Likely if you report to me, and possibly even if you don't, the following will be useful:

  1. I generally work ~8.30am–~5.30pm MT, and then often ~10pm–~12am MT. The time in between I aim to reserve for me and family.
    1. That’s me. You do you.
    2. Late-night email isn’t in general expected or desired.
    3. My family? A wife who's recovering from cancer; two daughters, 8 and 10.
  2. If you receive an email from me at night then the right interpretation is “because Isaac is doing work on his schedule” rather than “Isaac wants an answer right now”.
    1. Same with chats/IMs.
    2. A colleague of mine puts it well in his email footer: "Due to my own schedule and travel, you may get emails from me outside of normal working hours. Please do not feel any pressure to respond outside of your own work time". I like that.
  3. I mostly don’t care if your email processing schedule aligns with mine or not.
    1. If I need your attention on something with tremendous urgency, I’ll not be expecting you to find that out by checking your email (corollary: you’ll not be missing any massively urgent things by not checking your email at night.)
  4. I believe in “clean” downtime, as in: time off where you go firmly offline work-wise. Make sure you spend enough of your vacation days this way; it’s valuable, healthy, and important.
    1. If you plan to declare email bankruptcy on your return, make sure to let people know via your OOO message.
  5. Artifacts with URLs are good. Aim to create shared artifacts rather than ephemeral undiscoverable messaging trails.
    1. Any email chain >500 words suggests that a document should be created.
    2. Any group chat conversation >50 posts long suggests that a document should be created.
  6. I believe in the Eisenhower Matrix (urgency/significance). Be aware that not everything you’re asked to do Urgently is actually Significant; and that there is Significant non-Urgent stuff which nobody is bugging you for. Prioritize accordingly.
    1. One super-rough rule of thumb for "significant" is "stuff that in a year's time you'll (a) remember you did; and (b) be glad you did"
  7. I also believe in the Impact/Effort matrix, and that you have to be constantly vigilant as to where you’re spending your effort. Resist the lure of low-effort but low-impact work.
    1. Note that work can be moved vertically up on this matrix by making it reusable. (corollary: create reusable artifacts.)
  8. It’s important to meet in person every now and then with the people you work with. Aim to travel to sit down with colleagues in sibling sites from time to time, and probably at least once each quarter. When you’re traveling, also aim to meet in person with people to whom you’re organizationally adjacent but with whom you maybe don’t work closely.
  9. I find it useful to make a list of the stuff which needs doing, and plot it (even notionally) on the urgent/significant and the impact/effort matrix. Stack rank it, and don’t worry if stuff further down on this list doesn’t get done.
    1. There will always be stuff which doesn’t get done; the trick is make sure it’s the right stuff not to get done :).
    2. If you’re overloaded, please holler and we’ll together work out what stuff can not get done. If you need my help with anything, similarly please holler. I’m invested in your success.
  10. I highly recommend that you reserve some time on your calendar for “thinking and creating time” and defend it aggressively.
    1. “Thinking and creating time” isn’t a time for email! Use it to work on that strategy deck you’ve been meaning to get to, or that PRD that’s been languishing, ways to increase team velocity, or to think about work themes for next quarter.
    2. “Thinking and creating time” is for working on bigger thoughts which can’t be squeezed into the gaps in a series of meetings
  11. Consider keeping a tidy to-do list and maybe have your life changed.
  12. Remember that—unless you’re really explicitly given a hard requirement—most things asked of you should be treated as input into your prioritization process. This goes even for direction given by your manager: my default approach is to treat my manager as a stakeholder in my work, and my job is to weigh and balance the needs of all the various stakeholders, my boss included.
  13. I aim to have "career chats" with my directs every few weeks or so—to check in on trajectories, desires, ambitions, and so on. This can be as often as they like at their option, but if they don’t bring it up at all then I will.
  14. I've found the “I like, I wish, I wonder” feedback framework generally useful. Consider using it to give feedback and to solicit feedback.
  15. I hold myself strictly to the principle that one’s documents/spreadsheets/decks should be open for commenting across the company unless there’s a really good reason.
    1. Good reason: protecting the confidence of a partner/customer/colleague.
    2. Good reason: the document includes personnel information (perf data, upcoming org change, HC planning, anything HR-related.)
    3. Poor reason: forgot to change the sharing settings.
    4. Poor reason: can’t imagine anybody else would be interested in this doc.
    5. Poor reason: the doc’s not finished yet.
  16. Amongst other things I value decency, honesty, straightforwardness, dependability, and presence.
    1. Call me out straight away if I miss the mark on any of these.
  17. I highly value feedback, and welcome it. There are a million ways in which I can improve, and feedback is a critical part of me getting there. Thank you in advance!
  18. Ask me anything. Seriously.

// TODO in version 2

  • stuff about 1:1s.


Working with Isaac






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