Working With Me

tl;dr

⚖️ Work-Life Balance

I absolutely love all of the jobs I’ve ever had in my career; though, it wasn’t until getting to Stripe though that I found my dream job. I absolutely love all aspects of the work at Stripe, but the most rewarding component of my job is getting to work with and help others. This type of work can take it’s toll on us though; in this kind of work, we give up our most valuable resource, our time, to someone else (often times complete strangers).

I learned years ago that my good mental health allows me to be more effective and more productive at my job, so I take a firm stance on maintaining a healthy work-and-life balance.

📆 Organizing my Time

I’m a somewhat particular about organizing my time. In many ways, I do my best to emulate a mom of 6-children that somehow manages to know the names, birthdates, social security numbers, medications, doctor, and dentist appointments of all of her children. I do this in a few ways, but primarily, my time is organized into two buckets: Tasks and Meetings.

TasksI manage all of my tasks in my Hobonichi Tencho Weeks Mega planner 1 (old-school pen-and-paper) using an adapted Bullet Journal method 2. I put all of my tasks that I need to do for the week in my ledger and carry over any that I can’t get to by Sunday. (I’ll do this for a maximum of 3-weeks before I discard the task as “not important”.)

MeetingsI track all of my meetings in Google Calendar and operate entirely digitally, so people can coordinate when I’m available to meet and when I’m not. If a meeting slot is open during my work hours, you’re welcome to use that time to schedule with me.

There isn’t enough time in the world or bujo blogs to follow.

💬 Real Time Messages (Slack)

I tend to be multi-threaded and often incorrectly assume others are too. I will work on something, reach out to you in Slack, but expect a message in real time even though I don’t hold myself to that same commitment. This is something I recognize about myself though, so try not to let instances where there is a delay on Slack or something gets “left on read” bother me too much. Instead, I’ll usually ping you again or switch the channel to email.

Anyone is welcome to ping me on Slack; in fact, I often prefer that as a means of getting my attention urgently. However, I won’t always respond in real-time. I will often jot down a task for myself in my physical planner, then follow-up on it later. Please try not to take offense to this behavior.

I commit to trying to get back to every message I’m sent within a few days.

📧 Emails

I use the inbox zero approach to handling emails. That said, my job can sometimes mean I have hundreds or even thousands of emails sent to me per week. Therefore, I try to prioritize the emails I commit to reading by declaring “inbox bankruptcy” in a scripted way.

Specifically, I have a handful of filters (eg. emails sent directly to me, emails sent directly to my management chain, emails sent to me from my reports, etc.) that get filtered into a priority bucket that doesn’t let them get automatically deleted. Whereas, anything outside of this filter will be “culled” on a regular cadence in line with the importance of the mailing list for which the message is associated.

While I basically live in email, I appreciate a friendly ping here-and-there to remind me if there is something time-sensitive waiting on me in my inbox. Marking something as [Urgent] or with [Action Required] in the subject line will also push it to the top of my Inbox.

💼 Meetings

In the past few years at my current role, I’ve learned that the value I get out of meetings is rarely from the meeting, but more from the commitment to do something outside of the meeting afterward. As a remote employee, I find that meetings are more often a good way to “stay connected”, but when put under the guise of actually getting something done rarely map to our expectations of them.

In other words, if you want to have a coffee chat with me – definitely let’s do that! I appreciate a bit of a break to get to know someone and catch-up on life outside of work.

If you have a project we’re coordinating on, try and collaborate with me asynchronously (either through real time messaging or emails), as I’m much more likely to deliver something quickly.

☕ Coffee Chats (25-min)

I love a good coffee chat, but I like to keep them timeboxed. Too long, and I feel guilty about letting tasks slide into the next day (or week); too short, and I don’t feel like I’ve made a genuine connection.

I think 25-minutes is the sweet spot for me.

🤝 1:1’s

I look at 1:1’s (one-on-one’s) as a necessity of a healthy relationship with a report, manager, mentor, or stakeholder. It allows both of you to air challenges, blockers, frustrations, victories, or anything else in a safe way.

General Preferences

As a Manager or Mentor When running a one-on-one as a manager or mentor, I look at the one-on-one as something for my report and not something for me. There are lots of ways to trickle up progress on tasks, I don’t need to waste anyone’s time by having that person regurgitate their progress to me in a meeting.

The only time I might go out of my way to take control of the conversation is to guide it towards a pressing issue, a performance conversation, or a career development conversation.

No one should ever be surprised by a lackluster performance review, so I try my best to ensure we discuss any problems as soon as we see them.

As a Report or With a Stakeholder When participating in a one-on-one with my manager or a stakeholder, my preferred agenda is something similar to the following:

As a report, I look at it as my personal responsibility to take notes in these meetings and assign each of us action items.

📈 Metrics and Data

As an Engineer, I appreciate informed decision making. As a manager of an entirely remote team, that becomes even more important. Recognizing how we individually contribute through data keeps us away from an “brick and mortar” work environment and building the right metrics that demonstrate our impact on the people we work with is one of my highest priorities.

You can expect me to lean heavily on any available data.

  1. Hobonichi Tencho Weeks Mega ↩︎

  2. Bullet Journal Method ↩︎