I’ve now worked with 3 Thinking Assistants, and there are a couple more I haven’t gotten to try out yet. So far I’ve been doing it with remote ones, who I share my screen with. If you would like to try them out I can DM you information and my sense of their various strengths.
The baseline benefit is just them asking “hey, are you working on what you mean to work on?” every 5 minutes. I think I a thing I should do but haven’t yet is have them be a bit more proactive in asking if I’ve switched tasks (because sometimes it’s hard to tell looking at my screen), and nagging me a bit harder about “is this the right thing?” if I’m either switching a lot, or doing one that seems at-odds with my stated goals for the day.
Sometimes I have them do various tasks that are easy to outsource, depending on their skills and what I need that day.
I have a google doc I have them read in advance that lays out my overall approach, and which includes a journal for myself I’m often taking notes in, and a journal for each assistant I work with for them to take notes. I think something-like-this is a good practice.
For reference, here’s my intro:
Intro
There’s a lot of stuff I want done. I’m experimenting with hiring a lot of assistants to help me do it.
My plans are very in-flux, so I prefer not to make major commitments, just hire people piecemeal to either do particular tasks for me, or sit with me and help me think when I’m having trouble focusing.
My working style is “We just dive right into it, usually with a couple hours where I’m testing to see if we work well together.” I explain things as we go. This can be a bit disorienting, but I’ve tried to write important things in this doc which you can read first. Over time I may give you more openended, autonomous tasks, if that ends up making sense.
Default norms
Say “checking in?” and if it’s a good time to check in I’ll say “ok” or “no.” If I don’t respond at all, wait 30-60 seconds and then ask again more forcefully (but still respect a “no”)
Paste in metastrategies from the metastrategy tab into whatever area I’m currently working in when it seems appropriate.
By default, just watch me work (coding/planning/writing/operations), and occasionally give signs you’re still attentive, without interrupting.
Make a tab in the Assistant Notes section. Write moment to moment observations which feel useful to you, as well as general thoughts. This helps you feel more proactively involved and makes you focused on noticing patterns and ways in which you could be more useful as an assistant.
The Journal tab is for his plans and thoughts about what to generally do. Read it as an overview.
This Context tab is for generally useful information about what you should do and about relevant strategies and knowledge Ray has in mind. Reading this helps you get a more comprehensive view on what his ideal workflow looks like, and what your ideal contributions look like.
Updating quickly
There’s a learning process for figuring out “when it is good to check if Ray’s stuck?” vs “when is it bad to interrupt his thought process?”. It’s okay if you don’t get it perfectly right at first, by try… “updating a lot, in both directions?” like, if it seemed like something was an unhelpful interruption, try speaking up half-as-often, or half-as-loudly, but then later if I seem stuck, try checking in on me twice-as-often or twice-as loudly, until we settle into a good rhythm.
I’ve now worked with 3 Thinking Assistants, and there are a couple more I haven’t gotten to try out yet. So far I’ve been doing it with remote ones, who I share my screen with. If you would like to try them out I can DM you information and my sense of their various strengths.
The baseline benefit is just them asking “hey, are you working on what you mean to work on?” every 5 minutes. I think I a thing I should do but haven’t yet is have them be a bit more proactive in asking if I’ve switched tasks (because sometimes it’s hard to tell looking at my screen), and nagging me a bit harder about “is this the right thing?” if I’m either switching a lot, or doing one that seems at-odds with my stated goals for the day.
Sometimes I have them do various tasks that are easy to outsource, depending on their skills and what I need that day.
I have a google doc I have them read in advance that lays out my overall approach, and which includes a journal for myself I’m often taking notes in, and a journal for each assistant I work with for them to take notes. I think something-like-this is a good practice.
For reference, here’s my intro: