Joe OS
A quick overview of how I tend to operate, mainly intended for those poor souls who have been forced by Fate or the gods or happenstance or just dumb luck to work closely with me on a regular basis. Good luck!
Motivations
- Life is short. As a result, I want to do something “big” and “important” with my life, while I can. I think the definition of those things will change as I evolve, but for now taking time to think about long-term strategy of a business excites me, and having to deal with day-to-day minutiae, conversely, does NOT. Spending time talking to my kids and raising them the best way I can excites me, spending countless hours in unproductive meetings does not.
- Working with smart, dedicated, passionate people towards a common goal really eneregizes me, hence my predilection for startups. That “us vs. the world” mentality is quite powerful.
- Conversely, if I find I’m working with people who are very short-term oriented or lack basic integrity and honesty, then it’s an immediate dealbreaker for me.
Operating Conditions
- I’m an introvert, through and through. While I enjoy working with others and have no qualms about public speaking, I tend to do my best work and feel the most energized by working in long, focused chunks in relative isolation (early mornings are best).
- Corollary to the above, interruptions (especially non-urgent ones) are the bane of my existence. I have several systems in place (strict phone/email/Slack policies) that help prevent any interactions that can wait until I’m done the task at hand. This also helps me to maintain a work-life balance in less than ideal situations. When I’m at work, I want to focus on work. When I’m home, I want to focus on my family. “Be where you’re feet are” is a common theme that I like, and I can’t find who said it first but I heard it on a golf broadcast and instantly loved it.
- Yes, I enjoy watching golf. I also used to play golf once upon a time, but the demands of fatherhood can be exacting :) Worth it!
- I tend to do my best thinking when given time to focus and experiment with ideas. I’ve recently heard this as a distinction between real-time processing compared with gradual processing. As an introvert, I favor the latter. Especially if the topic of discussion is novel or very important or strategic in nature, my best work tends to come from chewing on the topic for a while, mapping it out on a whiteboard, and really trying to flesh out the first principles involved and any first- and second-order effects.
- I’m non-confrontational by nature. I’m working on it, but likely something I’ll always struggle with on some level. Ideally, I should have some system in place (e.g. well-structured 1on1’s with superiors) to ensure I have a dedicated forum where I’m being encouraged to speak my mind and speak “truth to power”.
- I couldn’t find a YouTube link but there’s a really good clip from The West Wing where a new hire (Will Bailey) is given a document to review that has an intentional policy error. He catches the error but fails to raise his concerns to the President, failing the “speak truth to power” test. But he ends up dating a smart intelligence analyst and getting elected to Congress so things work out for Will in the end.
- I believe in extreme ownership. I freely and readily take responsibility for what my and my adjacent teams do, and own the consequences therein. In that same spirit, I’m always going to be my toughest critic. If an issue arises, my first instinct is to blame myself and nitpick what I could’ve done better. Something I’m working on, but realistically will always be there at some level.
Communications
- As my direct reports will likely tell you, I’m not terribly wordy when it comes to communication. I’ve prided myself in conciseness in writing code, and now as a manager I’m concise when it comes to how I communicate. Directed technical chats tend to be short, focused, and to the point. Most of my meetings have agendas to help maintain focus.
- Writing style is very similar to how I’d write code. Focused, essential, direct. Every sentence should have a purpose (to entertain, to disarm, to persuade, etc.)
- Especially for remote folks, I expect to have a good idea if you’re working or not (i.e. typically set by a Slack status or having your calendar up-to-date) so I know who’s online to help support urgent issues.
- As an introvert, I tend to be the listener in a group conversation, taking a higher-level view of the discussion, making sure it stays focused and productive, and jumping in when I think I need to steer it a certain way or if I think we’re missing something.
Management
- I highly value full transparency and try to over-communicate what I think is most important whenever possible. My first manager ever (Darrell) instilled this in me early, and would often confide in me and my team in confidence (“the cones of silence” as he called it) on essential information for the business. This confidence helped empower me and made me feel like a valued member of the team.
- Mutual alignment is paramount. I stole this from Reid Hoffman’s recent books. The idea being that there’s clear expectations set around what the report is expected to do in this role, what success looks like, and ensuring that the report’s career goals are aligned with that. Often times (especially at startups) this looks something like “I (the report) want to start doing X” so in response I’ll do my best to help steer work to that end (if it makes sense within the mission/constraints of the company). Clearly if there’s a disconnect here, then we need to talk through it, and I always say I’m happy to help them find work elsewhere if the current role isn’t working for them.
- However, especially for managing remote teams, I certainly try to over-communicate certain ideas or information when I think it’s really important. Remote engineers can feel isolated at times (I know, I’ve been there), so I try to give them as much news and context as possible, even the in-office minutiae that most of us take for granted. The little things add up, especially when it comes to culture.
- I schedule my day in my calendar, and am happiest when I can have that schedule have little to no interruptions. However, I know that ultimately I am a servant leader to my team and the business, so I try to make sure I have buffer time for issues that might arise. I try to have the most important items of the day in longer chunks in the morning, and save more administrative tasks for the afternoon.
- I need some well thought-out set of metrics (typically paired with a counter-balancing metric to prevent over-optimization) to measure progress. Environments where we don’t measure what matters can lead to indecisiveness and overall uncertainty about direction. Human beings like to see progress, and having good measurements can help show that and also give feedback on where growth might be stunted.
- I don’t like getting into the weeds with my direct reports. When discussing an issue, I try to help frame the issue, provide business context and vision, but don’t feel it’s productive to hold hands in how something gets implemented. If it’s urgent and the report isn’t connecting the dots then I’ll jump in, but this is usually a sign that something needs to change (either my communication or the report needs to get up-to-speed in some capacity).