• Successful Organizations Don't Suffer Fools

    Managers are essential to scaling a successful organization but have a large blast radius if things go wrong.

    The best organizations don’t suffer fools. The center of gravity (culture and decision making) is with individual contributors. This works because ICs are better evaluators of a manager than other managers or leaders, making it more obvious when it’s not working out.


  • Thinking Better Thoughts

    I remember when I first started working at Stripe I felt like the dumbest person in the room. I was amazed at how smart everyone seemed and the writing…gosh, the writing! If I wanted to be like that too, something needed to change.

    At first I thought I needed to improve my critical thinking. Looking for a solution, I poured over mental models and frameworks.

    It didn’t really help though. I can hang my thoughts off of a neat model but can still get away with sloppy thinking—just packaged in a smarter looking format.

    Turns out, what I’m really trying to do is ‘think better thoughts’.

    (As an aside, it’s wild that humans can even have this kind of metacognition!)

    I don’t want to be smarter, I want to be more creative, reason about problems clearly, and draw upon useful knowledge. Better thinking is a skill I can take steps to develop, being smart is merely a judgment (and a lousy one at that).

    How do you think better thoughts?

    One of my favorite Paul Graham-isms has to do with finding startup ideas. The best way to find amazing startup ideas is to become the kind of person who has amazing ideas.

    As annoying as it sounds, the only surefire way to have better thoughts is to be the kind of person who has better thoughts. Afterall, identity is a powerful motivator and improving thinking is a collection of habits and behaviors.

    To me, that’s reading better books and writing things down.

    Read better books

    (I’m going to focus on non-fiction books here due to their practicality in thinking better thoughts, but of course there fiction books which apply.)

    It’s not like I read one book and suddenly think better, but reading increases the cardinality of thoughts I can have. Reading helps me think “wider” and combine more ideas—an important element of creativity and discovery. Thinking wider leads to compounding benefits as more ideas become available like an ever expanding pallet.

    Reading books about thinking was surprisingly helpful. The Clock of the Long Now helped me think about long term thinking and deep time. The Beginning of Infinity helped me explore epistemology and how to not fool myself. The Minto Pyramid Principle helped me think about writing and how to explain things to others effectively.

    Reading books opens up new pathways follow your curiosity. Those new pathways lead to other books to read and more ideas to think about. For example, The Beginning of Infinity led to thinking about consciousness which led to reading I Am a Strange Loop and physics.

    Not just any book will do. I feel that “better books” are ones that are relevant to your interests but slightly off the beaten path. A simple heuristic is to look for canonical books in the field if inquiry that gets mentioned often by people working in the field but are seldom actually read.

    Write things down

    There are many benefits to writing and it gets even better when I write about what I’m reading. I take notes to clarify my understanding of the ideas I find interesting. I think about what I’ve read more if I’ve written anything about it. It sharpens the ability to express ideas to others.

    This last point proves to be another important part of thinking better thoughts—writing grows knowledge and enables others to add to it. Human knowledge is meme replication so ideas need to be effectively replicated. This is critical for making progress as a group whether you are working on a team or building a company.


    Now that I’ve written this down, the through-line here is that cultivating curiosity is a useful strategy for thinking better thoughts. Reading books and writing naturally leads to more curiosity.

    The difference between “go read these books about philosophy, it’s good for you” and “why does Godel’s incompleteness theorem keep coming up in these other books, what did he find” are huge. One feels like homework, the other feels like discovery.


  • The Jump to Remote Work Universality

    Remote work has not yet made the jump to universality. We’re still in the phase of “specialized work objects” which are a combination technology to perform the work, jobs that can be performed remotely, and businesses that can operate anywhere.

    What needs to be true to achieve remote work universality?

    Technology to perform the work We already have this with networked computers and the internet. Access is widely available (though not ubiquitous) and software allows millions of people to do their job.

    Jobs that can be performed remotely Some jobs are not possible to be done remotely, though I would argue this is more of an extension of the technology problem. Over time more jobs will be possible to be done remotely through automation, robotics, or applied AI.

    Businesses that operate anywhere There are myriad rules and regulations that are different in every location. Compliance has no universal object that enables them to operate anywhere (though that’s what we are working on at Mosey).


  • Run an AWS ECS Task From the Command Line

    To run a one-off ECS task from the aws CLI in Fargate you need to specify the subnet, set assignPublicIp to enabled (otherwise it will fail to pull the container image), and optionally include overrides to run the command you want.

    Example:

    aws ecs run-task\
    --cluster foo\
    --task-definition bar\
    --count 1\
    --launch-type FARGATE\
    --network-configuration '{"awsvpcConfiguration": {"subnets": ["subnet-123456"], "assignPublicIp": "ENABLED"}}'\
    --overrides '{"containerOverrides": [{"name" : "MyTask", "command" : ["python", "example.py", "arg1_here"]}]}'
    

  • Designing for Non-Experts

    Building tools to help users that are not experts in the thing they are using the tool to do presents unique design challenges. You can’t assume prior knowledge. You must provide a sense of progress towards mastery even though the subject matter might be unfamiliar. You need to simplify without being overly reductive. You need to identify the unknown-unknowns without being overwhelming.

    A tool that enables non-experts to become experts is incredibly valuable especially when the expertise is difficult or expensive to acquire on one’s own.

    See also:

    • No-code tools built for a citizen developer
    • Mosey helps anyone manage multi-state employment and tax compliance without needing to be a lawyer or accountant

  • Remote Work Requires Trust

    Some of the biggest criticism of the remote work movement is that people aren’t actually doing work. There are several flavors of this: working in your pajamas, not doing real work, or, the most sinister, that the company culture will suffer. This fails closer inspection immediately.

    All of these are a euphamisms for “I can’t see you working so work isn’t happening”. Unfortunately, this is a common fallacy, particularly for managers that need a sense of control. This position reveals a major failure of management—lack of trust.

    Tell me you micro manage your employees without telling me you micro manage your employees.

    All working arrangements require trust regardless of whether it is in-person or not. Remote work exacerbates this problem and forces managers to confront their parochial errors about how work actually happens and how to measure progress. Remote teams need to be more deliberate about everything, not the least of which because managers can’t rely on surveillance.


  • Broken Escalators Are Still Stairs

    Like the Mitch Hedburg joke, “when escalators break they become stairs—sorry for the convenience” reminds us about the importance of designing systems that fail gracefully. Escalators can still be used even when their function no longer works unlike elevators where you get stuck until it’s fixed.

    What are some other examples of systems that still work?

    See also:


  • Outsourced Thinking

    Having to think about everything all the time would be impractical so people rely on other people to think certain thoughts for them. This happens all the time without us noticing or caring most of the time. For example, reading what an expert has to say about something is more efficient than deriving your own opinion from source materials.

    The problem with that is people can be wrong, misinformation can mislead you, disinformation is purposely trying to mislead you, and experts are just people too. You have to be mindful when you are outsourcing your thinking otherwise you won’t be thinking clearly when it matters most.

    See also:


  • How to Write for Remote Teams

    Writing is the much-discussed secret to building great remote teams. How do you write for a remote team?

    There are three things to do to make writing the core of a remote team. Write project briefs. Take meeting notes. Broadcast widely.

    Write project briefs

    Project briefs are the foundation of great remote teams. They drastically improve the clarity of ideas and work. They make it easy for the team to share feedback. They are an artifact for future coordination.

    Project briefs need to have an opinion. It’s not a scientific paper, it should be convincing.

    Project briefs should be about solving a problem. Problems are a conflict between ideas—if there is no conflict there is no problem.

    How do you write a good brief?

    SCQA is by far the best format I’ve seen for structuring a project brief (The Minto Pyramid Principle is also great for business writing generally). Situation, complication, questions, and answer.

    Don’t start by asking what the problem is, ask what the situation is. So much error happens between the facts of what’s going on and the interpretation of them—SCQA avoids this pitfall by putting space between them.

    Writing briefs has a natural advantage over other forms of communication. When you write, your misunderstandings become obvious. It’s a natural forcing function for improving clarity.

    Reviewing briefs structured in this way becomes much easier. Is the situation indisputable? Was the interpretation of the complication reasonable? Is the key question answered fully?

    I’ve read a lot of bad documents. It usually comes down to not answering the key question fully or the answer being disguised as the problem.

    Once you have project briefs, there is an anchor point for coordination. You can link supplementary docs to it. You can share it with new teammates. You can reference it over and over to keep the team focused (“what are we trying to do again?").

    Take meeting notes

    Any meeting with three or more participants and any meeting that others could be interested in should have notes. Those notes should be shared broadly.

    Everyone can’t attend every meeting and remote teams that make it easy to absorb context asynchronously is a big advantage.

    As an artifact, meeting notes are surprisingly useful. Referencing it just once to remember that one thing a user said that one time is worth the price of entry.

    In meetings, it’s easy for everyone to think they agreed and were on the same page. Writing meeting notes reveals when that’s not actually the case. Putting it down in writing has an air of finality that’s useful to take advantage of. It’s too easy to let things pass in conversation otherwise.

    Broadcast widely

    As we’ve seen, the value of writing for remote teams is clarity and coordination, but there’s another important way writing helps—building trust.

    Writing should be shared internally as broadly as possible. Transparency improves trust (there are no secret conversations where the decisions are being made). Ambient awareness leads to serendipity.

    That doesn’t mean everyone should read everything, but they should be able to. Filtering content is a much easier problem to solve than building a culture of writing. People can choose what they tune into and how to best use it in their work.

    A remote team that is in the practice of constantly sharing briefs, meeting notes, and other artifacts will find that trust is built into the system. There’s clarity, transparency, and accountability.


  • FMLA and Remote Work

    The rules for when a company must provide federally mandated medical leave to employees may change due to remote work. So far though, proximity to an office is still an important criteria. In Texas, a court ruled that an employer was not liable for FMLA because the employee was working remotely, reporting to an Ohio office, and was not within 75 miles of the office because they worked from home in Texas.

    So far the states are interpreting rules that weren’t written with remote work in mind.

    How Does the FMLA Apply to a Remote Workforce?

    See also:

    • Compliance is dynamic, as people move around the eligibility of FMLA makes it more difficult for employers to administer

  • Everybody Is Great When They're Rested

    It’s an easy excuse to tell yourself you can’t do something because you’re tired. If only you were well rested, you could do something great.

    The reality is, doing anything demanding where you need to peak performance means you will be tired often. But so is everyone else. What you do even when you are tired can give you a meaningful advantage over those that pack it in.

    I overheard this listening to Hard Knocks and I always feel a bit more energized seeing how professional football get ready for the highest level of competition.