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Several people have recommended I write a “working with me” document to help onboard new collaborators, teammates, and contractors and I finally got around to it. Here it is.

How I communicate

I will always provide you with a quick response or answer, but will often go back and edit the message to clarify or poke at the topic with further thoughts over the course of the next hour or so. I believe word economy is important and try to be quiet if I have nothing valuable to respond with.

How to get my attention

Call my cell phone if you have my number. Otherwise, @ me on Slack. I strongly prefer that you call me though. Most of my texts are voice transcriptions and I tend to add emojis to communicate my intended tone. It’s easier to get all that right over a phone call when things are urgent. My written communication can often be read with a tone I didn’t intend. If you are messaging me on Slack, try to do it in a shared channel. DMs create communication silos and I think they are usually more harm than good. Very few things actually need to be private. If you send me a DM that I think should be in a channel I will often just forward it there myself and continue the conversation in that new location in front of a larger group.
When something is time-sensitive or you’re frustrated with my response time, call. Don’t wait on Slack.

Planning

Please never send me a planning document. Communicate your idea in 3 paragraphs or less and text it to me. I detest opening 3 pages of workslop full of theory about an unstarted task. If you really can’t get it to work in a single message, make a Slack canvas. Anything is better than a document which lives in another piece of software I have to sign into and open.
Don’t send planning docs. A long document full of theory about an unstarted task is almost always a waste of both our time. Keep it short and just start.

1:1s

I like recurring 1:1s when they are about moving towards goals. If we can set something up where one of us is working towards something and we decide on steps to get there, then a recurring meeting is useful to continuously sync on that. Progression is fun, and even more so when you keep track of it with someone who’s invested in holding you accountable.

Feedback

I try to only give unprompted feedback when it’s extremely specific and easy to understand. My mindset is that high-level feedback about a general topic or performance is only something that should be shared on request. Please send me any feedback you think would be useful. Specificity is always good. I will try to improve where I can at all times.

What I value

Please try to do something and fail before asking me for help. I find it much easier to help when you are actively experiencing a problem and want to solve it rather than just wanting my thoughts. Speaking extensively about strategy before doing something is almost always a waste of time. I prioritize failure. You are usually some number of failures away from success, and I think you should try to get those over with as fast as you can so you reach success earlier. I get frustrated seeing people play it safe, always doing what they’re good at, or ponder endlessly before closing the loop by launching and getting feedback.
Bias toward action. Try it, break it, learn from it — then ask for help if you’re still stuck. Theoretical strategy conversations before any real attempt are rarely worth the time.

My quirks

I tend to be skeptical, sarcastic, and kind of a curmudgeon. Complexity is something I avoid on principle, even when it will save me time. Newfangled toys are something I rarely find valuable.
UX is important to me, but not so much UI. I would rather something be functional and easy to use than pretty. I don’t think design is particularly valuable. Just solve the problem.

Hours and availability

I don’t sleep all that much and am easily awoken. 3am–8am are the hours I am typically hard to reach, but if you call my cell phone I will usually pick up. Just call me. Direct pings are something which I always try to respond to as fast as possible. If it’s important enough that you’re annoyed with my response time being slow, again, call my cell.

What I’m working on improving

Writing, making videos, and marketing are the core skills I want to improve in the upcoming year. I would appreciate any feedback or ideas you may have for me in those areas.