# Emil Sit's Manager Readme

**Director of Engineering at Toast**

# **Hello! I’m Emil!**

This guide is intended to help you interact with me, in a professional context. This is a living document, which will be updated as necessary. Updates may be from you: suggestions and feedback (such as "feature requests" or "bug reports") are welcome from everyone.

This document first explains general information that may facilitate your interactions with me. Later sections will be most useful for those in my reporting chain.

**Disclaimer** : This README applies to me only, and in no way should be considered to apply to any other manager or human in Engineering at Toast.

# My Role

I am a Director of Engineering. My key responsibilities are:

- Developing my teams to help align their growth and success with the growth and success of Toast.
- Managing my areas of ownership to success.
- Evolving people processes (notably the engineering ladder, leadership training) to meet the needs of our growing Engineering organization, in collaboration with our HRBP, VPE and other directors. I also work some on recruiting and onboarding.
- Managing Toast Engineering's externally visible culture through social media and other external media.
- Acting as "prime" for various special projects that vary over time.

Prior to Toast, I worked for 2+ years at HubSpot, leading part of the engineering group that built the HubSpot Sales product. Before that I worked on enterprise software, at VMware, Cisco Systems and a small startup called Hadapt. I also completed a PhD from MIT in Computer Science, focusing on distributed systems. I grew up in NYC. I enjoy classical music and photography. Happy to talk about any of these things with you in more detail!

# Communication

There are many ways to get in touch with me. I prioritize them roughly as follows:

- In person
- My personal cell (voice/text) — please use this only in emergencies (OpsGenie has this number). If you have a high priority operational issue requiring immediate attention, see our Emergency Response Procedure.
- Email. I check email pretty regularly. I also use email to manage accountability (ensure closed loop communication) and to develop situational awareness (see below). Many things are routed through email including:  

  - GitHub mentions
  - JIRA mentions
  - New Red Flags
  - Wiki updates

- Slack DM (this might get faster reply than email, but I would say that email is more reliable)
- Slack channel traffic

The reality is more nuanced; this is a general guide to the likelihood and timeliness of my response.

## Meetings

My goal is to help make Toast, and you, successful. To that end, I am happy to share information or meet with you.

It is not your responsibility to manage my time. My time is my responsibility to manage. (I believe the converse as well: it is your responsibility to manage your time!)

If you need something, please ask and if necessary schedule a meeting. My calendar often looks completely full but many things on it can be moved, rescheduled or ignored. I can almost always make time available in a given day or within 2-3 days. If appropriate, send me something to review before the meeting.

## Scheduling Guidelines

I prioritize the following types of meetings and ask that you not book over them:

- 1:1s
- Interviews
- Staff meetings

I will decline, reschedule or request further information if I cannot meet at your proposed time. If you think I can help with something, ask!

## Personality and Communication Style

If you have an understanding of your preferred communication style, let me know and I will endeavor to keep that in mind in our interactions. You can let me know this at any time. The below is how I tend to interact.

I tend to be direct and transparent. When I ask questions, which I often do, I am looking to understand; it is usually a sign that I am interested. I sometimes forget to explain why I am asking questions, and do not mind being reminded to explain.

As an engineer, I prefer things to be precise and consistent. I am detail oriented. I try to remember to focus on the big picture when it is more appropriate to do so.

I can come across as being judgmental or condescending. This can happen particularly when I am stressed. This doesn't excuse the impact my words have on you, and I am working to not communicate in this way. Please call me out on if you observe or experience this.

My DiSC profile rates me as a CD, which mixes the [Conscientious](https://discinsights.com/personality-style-c) and [Dominant](https://discinsights.com/personality-style-d) styles. I also have done the [Workplace Big 5 survey](http://paradigmpersonality.com/wp-content/uploads/2017/08/Introduction-to-the-WorkPlace-Big-Five-Profile.pdf) (N=52, E-44, O=47, A-43, C-44), which notably points out that I lean introverted (E-44). Personality tests are not the whole story of course, but it can be a good starting point for a conversation.

# Leadership and Management Philosophy

My job as a leader and manager is to drive results for the company. I do that by aligning results for Toast with you and your team.

If I have the responsibility to lead and manage you, I intend to:

- ensure you have the clarity to know how to prioritize your day to day
- ensure you and your team have or develop the technical and soft skills needed to execute your day to day
- help you develop yourself and your career, aligning with Toast’s goals as much as possible

You are in the best position to do your work. You are responsible for you and your team delivering results on a regular cadence and communicating the impact of those results.

I need to make sure you know what that work is, why that work is important and that you have the skills to do it successfully. As you get more clarity on the vision and develop more skills, I will work with you and your team to increase your autonomy and scope. My preference is not to micromanage.

Sometimes I will know (roughly) what needs to be done and I should share that information with you promptly. Other times you will know what needs to be done, and I hope that you will share that with me promptly. If we find we are not sharing information, we should hold one another accountable.

I have been influenced by leadership ideas such as [leader-leader](http://robertgreiner.com/2013/12/leader-leader/) (as opposed to leader-follower), servant leadership, [radical candor](http://firstround.com/review/radical-candor-the-surprising-secret-to-being-a-good-boss/), and [extreme ownership](https://www.youtube.com/watch?v=ljqra3BcqWM).

I like learning things and developing as a leader and manager. In that process, I make mistakes. Sometimes I can figure those out on my own, but other times, you may be the best person to teach me about those mistakes. You will be doing us both a huge favor if you hold me accountable, and tell me if something I am doing negatively affects you. I am open to feedback at any time.

# Information Flow

Frequent, high-quality communication is essential to our work. Err on the side of over-communication (dial it up to 11!) and I will help you adapt downward from there. Optimize for quality over quantity, frequency over perfection, and effectiveness over politeness; this should be a minimal impact to your time.

## Situational Awareness

I like having good situational awareness of what is happening with you and your team. I find that this helps me protect the team from outside inquiries by either proactively informing other leaders or being able to answer questions when asked. It also allows me to have richer conversations with you, whether in formal 1:1s or hallway conversations. I believe that developing your own (and your team’s) situational awareness will help you be more effective as well.

I much prefer using group distribution mechanisms (e.g., email lists, public Slack channels, JIRA ticket comments, GitHub PRs) as much as possible over direct conversations (e.g., long cc lists, slack direct messages). This is not to say that you shouldn’t turn to your neighbor and have an in-person conversation; definitely do that! But record context in forums that are visible not just to you and your neighbor.

Feel free to invite me to meetings such as standup, planning/grooming/retros, design reviews, etc. I may not attend all of them as I am sensitive to my personality leading me to dominate discussions. I will attend them occasionally to maintain awareness of how you and your team are interacting. I am happy to attend (or NOT attend) any specific meeting if you feel it would be helpful.

I like you to make me aware of notable incidents (e.g., potential production outages, problems impacting developer productivity, release blockers that we own). I tend not to monitor Slack channels actively, so an at-mention or direct message in Slack may be sufficient to draw my attention to an evolving issue. (If you don’t directly report to me, you can do it this through your lead/manager, but that’s not always the most efficient; I favor solving for the customer over respecting reporting hierarchy. At-mentions are cheap. Favor over-communication.)

## Status Updates

For general project status (e.g. is your team on track to meet the quarter's objectives and key results, a key deliverable is late), I prefer to receive these in email. Unless I am directly involved in any work tracking process (e.g. JIRA/Trello), I prefer to hear about progress relative to milestones and in context, not just work accomplished. This is because I will probably not remember exactly where a particular work item fits into the overall picture of the project. I also like to recognize and share the team's progress by forwarding emails to other leaders within the company. By providing context in a status update, you are making it easier for people across Toast to recognize your accomplishments.

For information that pertains to you individually, I recommend using a tool called 15Five on a weekly basis. 15five allows asynchronous capture of your personal wins and challenges, and for me to provide feedback or dig in further. A status update tends not to include feelings or details about people, whereas 15Five is a great tool for adding such color. You will then be able to look back at your history of 15Five reports and project status updates to see a record of your own accomplishments and growth over time.

For example, a status update might read:

> We are on track to complete our new feature Foo next week. The team deployed and elevated the quxx service in production; although there was a small snag with the database, Alice and Bob quickly fixed it. Currently 30% of customer traffic is using the quxx feature and Candace will provide a separate update on metrics shortly. Next week we will complete elevation to 100% of customers!

A 15five update from the same team leader might read:

> Wins:
> 
> Bob was a little bit nervous when the database alerted after deploying quxx. He asked for help right away and Alice jumped in to debug. I'm happy to see Bob internalizing my feedback to ask for help sooner.
> 
> Challenges:
> 
> The team is excited about finishing Foo, but we're not sure what we will be working on next. I need to follow up with Candace.

My thinking in this area has evolved over the past 2 years; I used to like 15Five for both status and general feelings. I am finding that separation of these concerns helps make it easier for people to provide both.

# 1:1s

You should expect to have a 1:1 with me every week to two weeks if you report directly to me. I currently aim to have skip levels on the order of every 2-4 weeks. The frequency of these meetings will depend somewhat on our relationship and your needs. If you want to change the frequency of these, don’t hesitate to ask.

Your 1:1 should be primarily your time. I prefer to receive status updates asynchronously, in email or a tool like 15Five, not at 1:1s (see above). You can come with things you might like advice/opinions on. I am open to being sent an agenda ahead of time. If you do not have topics to discuss, I will use that time to learn more about your background and your experience at Toast.

An important part of our 1:1 discussions should be to help us align on how you are feeling about things and how I am feeling about things.

Periodically we will use 1:1 to review your career growth plan (if you directly report to me) or check in on how you are feeling about it (if you report to a team lead or manager). Your career is ultimately your responsibility, but I will help you align your goals with the opportunities that Toast affords.

These opportunities may lie in on your current team, or it may lie elsewhere. I hope that these opportunities will help you learn new skills and knowledge and create the impact you need to succeed.

I find it personally challenging to manage scheduling 1:1s for everyone in my organization and that I interact with; it's a bit overwhelming for me to find a slot that will be convenient for you and avoids conflicts with my other meetings. Therefore, it's easiest for me if you schedule this meeting with me. I appreciate your help here.

# Work Values

My default tendency is to find and do “the right thing”. For most of my life, that has been “the technically right thing”. Mixing a natural tendency for perfectionism with a number of jobs at enterprise software companies (where software is shipped to a customer and they stay on that version for months if not years) has led me to focus on getting things as close to perfect as possible. However, Toast works in software-as-a-service model where we can ship changes to customers relatively quickly. I have learned in working at SaaS companies to favor speed and shipping things that are “not bad” as opposed to “perfect”.

Get code into production as quickly and safely as possible. Favor incremental changes, with controls (e.g., feature flags) and observability (e.g., metrics, alerts) that allow you to manage risk and know when things are (not) working. If something (tooling, process) prevents you from doing so as fast as you like, work with me and your fellow Toasters to make us able to go faster.

Effective collaboration is important to me. That’s why I wound up in leadership and management. I am not a fan of inefficient process.

I strongly value learning and self-development. I am constantly searching for new perspectives, technologies, and ideas. I practice new things and (try to) admit to mistakes. I encourage you to do the same. From a management perspective, I subscribe to newsletters like [Software Lead Weekly](http://softwareleadweekly.com/). I read books and listen to podcasts about leadership. There are many avenues for you to learn more about how to do your job better out there on the Internet and at Toast: go find them and take advantage of them.

I do work hard and you will often find me online on weekends and late into the night. I don’t generally expect you to be online at those times (though operational needs may require that you work occasionally in off hours). They just happen to be times where it is convenient for me to catch up on things.

If you made it this far, thanks for reading! Let me know what the best way to work with you will be.