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Working with Sean

A quick guide to working with me, and my expectations for our team.

Working with Sean

Last Updated: July 7, 2021

Hi! I'm really excited that we're going to be working together. This document provides a little bit of context about me, my motivations, and some ways we can effectively collaborate. If you like it, I encourage you to write one yourself and share it with the team - but that's totally up to you.

My Story

I started my career in the federal government working at NASA. I'm a big space geek (I dressed up as John Glenn more than once for Halloween growing up). I don't have a formal engineering background - I taught myself PHP, Python, HTML, CSS, Javascript, and more traditional sysadmin-y things over the years mostly as a hobby.

I maintain a homelab and love to tinker with technology, but I also need to disconnect. My wife and I own Hawk Hill Farm, a 100-acre regenerative sustainable farm near Eugene, Oregon. She runs the farm full-time, and I spend most of my time outside of work on it. My favorite hobbies are travel and camping - I've been to 30 countries and recently spent five days backpacking in Joshua Tree.

How I Work

  • I start my days fairly early and like to disconnect at 5. I don't expect you to keep the same hours - we can work out a schedule that best fits your life.
  • I don't expect you to respond immediately when I send you something. I tend to over-communicate - if something is critical, I'll let you know.
  • I am quick to try and find a general path to resolution, and then hone in over time on the specific way to solve the problem. I know some people like to be more methodical, and just because I bring up a potential way to solve something doesn't mean that's the way it needs to be done. I have a tendency to immediately go in to problem solving mode, even when people might just want a listening ear. I'm working on that.
  • I enjoy lively (positive) debate and like to be proven wrong. I push back on blanket statements that aren't backed up by facts.
  • I am a very organized person. I strive to always have an agenda and expected outcome for meetings (and communicate that out in advance). It is helpful for me if, when planning meetings, you include an agenda and expected outcome so that everyone can come prepared.
  • I also tend to take detailed notes. I typically will write these on paper and then later type/scan them in and send them out to you/the team as appropriate. It may take me a few days to do this. Feel free to correct the record if I missed something.
  • Feedback is really important to me. I need to know when I am doing things right and when I'm messing up. I try my hardest to foster an environment where you will feel comfortable giving me feedback and vice-versa. Feedback is a bit like working out - no one really likes it, but it helps us become better humans.

What's Important to Me

  • Your Happiness - unhappy teams don't function. While there will always be aspects of a job we don't enjoy, I will strive to ensure that you are happy to show up to work every day. I know sometimes things outside of work can affect this. If I ask about your happiness and you don't want to discuss it, that is 100% okay.
  • Engagement - you should be empowered to share ideas, provide feedback, and generally feel part of a team. I want you to come to work excited to be creative and make something new. Engagement is a team effort, and it's important to me that we all remain open to the ideas of our teammates.
  • Clear Success Criteria - it's important that we all know what we need to do in order to be successful. I value OKRs and will work with you to make clear, measurable goals. If we don't feel as though our work is tying back to our success criteria, it means we need to re-prioritize, which is okay. Things change.

If I am failing to put you in the best possible position in the above three areas, I'm not doing my job. We are partners in this together, so please talk to me if you feel as though there is more I can be doing to align things to make you feel happy & successful!

Our Roadmap

We will work together on two levels - directly together, as well as team-wide as we collaborate to build a highly effective engineering group. There are a few things I think are really important to help ensure success here:

You and Me

  • Soon after we start working together, I will schedule a ~60 minute session with you to go over any projects you are currently working on, your background, and your career goals. This can help both of us understand what new projects may be most appropriate to you, any important existing relationships in the organization, as well as ensure that I can understand how I can best help with your professional development.
  • We will have a weekly 1:1 meeting. I view 1:1's as being the most important meetings of the week for me to attend - they are a great way for us to maintain open communication and continue to build our relationship. The format of the 30 minutes will always be the same. The first 10 minutes are for your agenda - anything you want to tell me, about anything. Your work, your family, your hobbies, your challenges, your career, our working relationship, etc. The primary focus of this meeting is going to be you. The middle ten minutes are for me, to share whatever I need with you. We'll probably talk about projects we are working on together, updates from the broader team, and new initiatives coming down the pipeline. The last 10 minutes are for us to talk about our collective futures - professional development, opportunities, etc. We may not always have 10 minutes equally dedicated to each topic, which is why I put the topics you want to cover first - that is most important.¹
  • Every half, we will do an individual OKR creation and retrospective meeting. I will ask that you come to this meeting prepared with your evaluation of how you did with your current OKRs, as well as a draft for your next half OKRs. I'll share a detailed template with you before we meet.

Team Relationship

  • Every team works differently, and ours is no exception. I don't think there is a formula of working together that can be easily replicated between teams, but I do think there are some common qualities that we can work towards that tend to be successful. If there are already things the team is doing that work, we'll want to keep those, and I'll spend some time talking with everyone to ensure I don't mess that up.
  • In general, I find that Slack-based updates works well for distributed teams. For instance, something like a quick update at the beginning of the week of what you will be working on, any help you need from other people, and if you will be out later on in the week. Typically, I will post a quick update on Monday afternoon around my goals for the week and on anything notable that is happening.
  • It is also useful to try and have a broader team-wide meeting on a regular schedule (either weekly or bi-weekly). I try and avoid having these meetings just be going around the table and saying what you are doing - that should happen elsewhere. Rather, I view these as opportunities to talk through issues we may collectively be facing, doing technical deep dives on a project you are shipping, etc.
  • I will try and find components of project management strategies that work and incorporate them in to the team. We'll work this out together with our partners in program management.

Creating an Inclusive Environment

Having a diverse and inclusive team is critical to our success. I have no tolerance for harassment, bullying, or discrimination. I expect everyone on our team to be respectful of each other and our coworkers, and I expect them to be respectful of us. I will address this immediately if I either witness it or it is brought to my attention. I also recognize that each of us have unconscious biases, and I would immensely appreciate you calling out mine if you observe them so I can improve as a person.

As our team grows, it is important to me that we source candidates who are from underrepresented groups in technology. I will work with our recruiting team to help ensure this, and appreciate any advice, suggestions, or help you are able to provide.  

A Final Word

I am incredibly excited to be here with you and work together to create an environment where we can all do our best work. I'll be updating this document occasionally as I grow. I maintain a high standard for myself - and I am always seeking to improve. Please let me know if there is anything I can do to better serve you as we start working together!


¹ Adopted from the Manager Tools 1:1 Email