What is this?
Think of this as documentation for Matthew Root. Its intended purpose is to accelerate your understanding of me as a human and engineering leader and to provide insight into what our working relationship will look like. It is not intended as a substitute for getting to know me. Building a relationship, in real life, is one of the most important things we'll do together. This README should be used as a supplement and a guide rather than a replacement for that. But, as a starter, I'd like you to know that my alignment is Chaotic Good.
- Management Philosophy
- Expectations
- Communicating With Me
- Bugs & Quirks
- My Story
- Personal Interests
- Want to work together?
The following are the tenets that provide the foundation for how I prefer to manage. I strive to adhere to these all the time. If you ever find me to be in violation of one of these principles, please point it out to me. That will help me do better in the future.
- Measuring stick for success: Can someone go out and get a role that advances their career after I’ve been their manager? I believe a manager has to care about the development of people to their core.
- Put direct reports and teams first: My goal is for the focus to be on the team, as well as the people who comprise it, and not on me. I try to constantly ask what I can do to be most helpful to my direct reports and the teams I work with. The most important contribution I can make may be totally different day-to-day, week-to-week, person-to-person, or team-to-team.
- Constant improvement: I want this to be a fundamental value for both individuals and teams. Nothing should be set in stone. I value a mindset in which we don’t assume we’re ever doing something perfect. When we’ve made one improvement, let's move on to the next opportunity. Repeat forever.
- How to move mountains: I think teams can accomplish great feats when they are properly motivated and given a high degree of trust and autonomy.
- Motivation, realized: First, I try to ensure everyone understands the value of what the team is doing and how their contributions can help the team succeed. Next, I make sure that everyone knows the team's priorities and how they were determined. I also aim to be transparent and honest about goals and to have the team pick those whenever possible. Finally, I make my reports' growth a central focus and encourage them to make development a part of their everyday life.
- Autonomy, in practice: I prefer that teams decide for themselves how they best operate. When someone has an idea, I will consider it with an open mind and err on the side of trying new things. If a new idea doesn’t work, we can always revert. I aim to never micromanage anyone’s day nor their work.
- Create a safe and comfortable psychological space: I've witnessed the effectiveness that a fearless and competent group of engineers can have in a safe work environment so I strive to create one for all the teams I work with. A few ways this can be accomplished are by encouraging everyone to share their ideas, listening deeply to the opinions and feedback of others, and following through with action. Fostering a culture of blameless criticism is also highly beneficial.
- Management is important and valuable: Great managers can make a positive difference in people's lives and can materially impact the success of a team or a business. Bad or apathetic management can be equally destructive. My goal is to provide a great management experience to everyone I work with. An important distinction here is this does not mean my focus is on trying to make everyone like me all the time. Oustanding management often means telling people hard truths. Which leads into...
- Feedback is vital: It's necessary to give pointed, direct feedback on a regular basis. I believe waiting for an infrequently-scheduled review to help someone improve is failing them. I also recognize that it's equally important for me to seek out feedback from those around me, in all directions, in order to drive my own growth.
- Diverse teams make the best decisions: I want to build teams that are comprised of a variety of backgrounds and talent profiles. I view this as both a sound strategy for success and a moral imperative. To unlock the power of these different experiences, I place a high premium on effective communication.
- Let's have some fun out there: Teams spend a lot of time together; I think it's best if they can truly enjoy it. Some moments call for being dialed in but otherwise it's best not to take ourselves too seriously. When in doubt, I'll try to provide the levity.
Here is a short list of behaviors you should expect from me at all times. If I'm ever failing to meet any of the expectations outlined in this section, please let me know immediately. This is not an exhaustive list of expectations but aims to cover those that are most vital.
It's my belief that the people who report to me are the job. I'm tasked with various other responsibilities as an engineering leader but none are higher priority in my view than ensuring my direct reports are getting what they need to be successful. In practice, this means you should expect that I will make time for you when you need it, follow through on commitments I make to you, and help you deal with whatever challenges you encounter.
This is a foundational principle for how I approach everything in my life. If I'm going to do something, I try to do it as well as I can. This doesn't mean that I will always deliver outstanding results, just that I'll aim to do my best. In practice, this means you should expect me to give you a great effort on every front from our 1:1 meetings to performance evaluations to helping you navigate challenges.
I believe organizations operate at their highest level when information is not restricted. In the interest of this, I commit to being transparent and to proactively share as much as I can. The flip side of this is that you should feel empowered to ask me for information. Two important exceptions to this policy of transparency are sensitive personal information and conversations around performance; I will always keep these confidential.
Simply put, I'll trust you until you give me a reason not to. I want my direct reports to have a lot of autonomy and that's only possible when paired with trust. You shouldn't find me micromanaging your work, schedule, or decision-making. I'll likely ask you a lot of probing questions but this is generally due to curiosity or a desire to gain more context.
Giving feedback, both positive and constructive, is one of the most important functions I perform in my role as a manager. Since feedback has such high value, not giving it to you as soon as I have it would be doing you a disservice. You'll often find me giving you feedback right away, in the moment, when I perceive something. When it's not possible to provide that realtime feedback or when I come to have feedback outside of direct interactions with you, I will provide this to you in our next 1:1. It's my goal for you to always know how you're doing. If there are surprises for you in a performance feedback loop, it's an indication that I'm not being effective at this.
When you need it, I'll help get you oriented in the right direction. In the event that I don't know what that is, I'll either identify someone who will or commit to coming back to you with an answer.
If you're going to do something, do it as well as you can. I don't expect that outcomes will be perfect all the time, just that you'll give your best effort. When you find yourself not striving to do your best on something, I encourage you to take a step back and examine why that is. Perhaps it's not an activity you should be spending your time on.
It's important for you to prioritize your growth. When you become more capable and can rise to new challenges it benefits you (better career opportunities), me (my success is based on your increasing success), and our employer (solving bigger problems, higher productivity, etc). You may not succeed in improving every day but, if that's your goal, it's likely to happen more days than not. Making this type of incremental daily progress leads to noticeable improvement in weeks, a significant change in months, and a radical difference over the course of a year. Get a little bit better every day and don't ever quit. That's the path to greatness.
Treat our software, team, engineering organization, and company like you own it. If you've got equity, the latter will be literally true, but this means more than that. It's about acting like an owner and caring about what goes on in a way that you would if it was entirely yours. When you see a problem, call it out. If you've got a solution, suggest it. Help us push forward on more fronts than just building software.
Nothing that we've created to this point, from software to processes to structures, is perfect and cannot be improved upon. Don't assume that present state is the correct future state. The opposite is generally true for software startups as they grow. Most of what we've done in the past will need to evolve or be replaced with something better along the way. Try to examine what you find with a beginner's mind and regularly consider how we could be doing better, everywhere.
Feedback is equally important for me to receive. Positive feedback helps me to validate my methods and, because I'm a human, it also feels good. Constructive feedback gives me insight into how I can improve. Regardless of the type of feedback you may have for me, know that I view it as a gift and am eager to have it. I typically try to solicit your feedback directly on a wide range of topics in our 1:1s but I may not always hit upon an area where you have feedback for me. Because of this, it's important that you take the initiative as necessary. Getting your feedback in a timely manner is also quite important. If something isn't going well, I prefer to make a change quickly rather than to have the problem fester.
I believe that it's important to find a healthy balance between work and the rest of life. I want this balance for both of us.
There's so much more to living a fulfilling life than success at work. Let's work hard while we're here and focus on life when we're not. To make you more comfortable about pursuing this balance, I'll endeavor to always model appropriate behavior. That means that you should not encounter me doing the following things*:
- Staying late in the office; I usually head home by 6pm
- Working on weekends
- Using email or Slack off-hours
- Scheduling meetings very early or very late in the day
Given that I try to not do these myself, it would be unfair of me to expect you to. If you find me not leading by example --by exhibiting the above (or other) behaviors or encouraging behavior from you that leads to poor balance of work with life-- please voice your objection. The most likely explanation is that I did not consciously realize I was doing this and speaking up will help me to correct course.
I prefer people to make better use of their time rather than just working longer hours. If you find that you're needing to work well beyond 40 hours to be successful in your role, we should have a conversation about what adjustments can be made to make this not the case.
*An exception here is emergency situations, such as a production outage, which may require atypical behavior.
My primary guideline for communication is to consider what channel is most appropriate for our interaction. If you're looking for more than five minutes of back-and-forth, let's talk in person. If you have a quick question, Slack is great. Just trying to disseminate some non-urgent information to a broad group? Email seems like a solid choice. Here are a few other details about how I operate, broken down by channel:
I'm happy to make time to discuss something in-person whenever you need to, whether that's scheduled via a meeting or ad-hoc. For the latter, a heads up on Slack is cool or just stop by and give me a good old-fashioned tap on the shoulder. If I've got my headphones on it typically means I'm focused on something but that should never stop you from interrupting me. Again, you're my first priority.
If we aren't co-located and you want to talk, send me a message on Slack and we can jump on a videochat.
Generally, the easiest way to get in touch with me. I try to stay on top of Slack and respond in less than an hour during the workday. The one complication is meetings because it's my goal to be focused and not doing other things. I typically play catch up on Slack between meetings. In the event that I'll need more time to respond, I will try to let you know that.
I'm quite averse to it and try to spend as little time as possible dealing with it. Typically, I'll lump my email processing into a morning session and an afternoon session. However, if the day is full, this can slip. When something is urgent, please do not use email or we're both going to have a sad time.
If it's off-hours and urgent, please page me.
I generally try to avoid disseminating my mobile number at work. If you think you'll need it, let's talk.
Nope.
Like most humans, I come equipped with a handful of flaws and personality traits that you may find challenging. There are ways in which I try to control or compensate for each of these tendencies but I'm not always successful. My hope is that by being open about these aspects of my personality you will feel comfortable calling them out if they become a problem for you.
My Insights personality profile is quite red. When we interact, I probably won't beat around the bush and may be more direct than you prefer. I also tend to become more intense as I bring more of my focus to bear on a problem. My brow may furrow and I might even look mad. Be aware this is typically not a reflection of my emotional state, it's just how I look when my brain is getting down to business on a good challenge. If my directness or intensity becomes too much, there's no harm in letting me know so I can dial it back a bit.
This manifests most acutely when I'm excited about a topic. If I'm ever talking so fast that you can't understand me, kindly ask me to slow down and//or repeat anything you may have missed. When I get on a ramble, I'll typically call it out on my own and take stock with you about whether what I'm saying is useful. If that doesn't happen, please don't feel bad about interrupting me and steering back to the point.
My least favorite bug. When I've got a strong opinion, my tendency is to dig in and defend it. This is most problematic if I transition away from being open-minded in a discussion. However, I love a good debate and am always pleased to have my mind changed as it usually means I'm seeing the world with more truth. If you find me pushing back against you, lean into it and help me to hear you. If you ever find me being overly stubborn, point it out; it won't be a surprise although you may catch me getting red in the face from embarrassment.
I prefer to move fast and I feed off progress. When this isn't happening, my brain will push me towards something new. This can occur on a variety of fronts: projects, books, and even conversations. A consequence of this tendency is that I am generally better at starting than finishing. When projects drag and lose momentum my interest tends to go with it. If you manage me, helping to keep new challenges in front of me is the best way to keep me happy. If you report to me or are a peer, you'll find I'm at my best when I can step back and let you do your thing after I've put in enough energy to foster escape velocity.
If you're interested in learning more about what's transpired in my life and the path I've traversed to this point, please check out STORY.md. I've placed that in a separate file so you won't get the impression that I believe reading it is mandatory or that my story is meaningful. It will help you to understand me a bit more and there are a few jokes so it might be worth your time. Please, choose your own adventure.
Besides having a genuine love of technology, and software in particular, I am passionate about a number of other activities. Here's a sampling of those:
- Learning: a huge part of why I love being a manager is to help others to learn and grow. I'm also extremely passionate about my own pursuit of knowledge in the interest of trying to better understand the universe. Genetics, neuroscience, psychology, and space are a few recurring topics for me.
- Games: videogames make up the majority of my gaming time but I also really enjoy tabletop games. I'm particularly invigorated these days by cooperative games. I've spent way too much time playing Dota 2.
- Reading: I read both fiction and nonfiction. I'm always looking for new book recommendations so this is one of my favorite topics to connect with people on. The majority of my fiction reading is spent on sci-fi and fantasy but I dabble all over.
- Physical fitness: while I don't spend much time playing organized sports as I get older, I still take my physical fitness quite seriously. This means both eating healthy and putting in solid work at the gym. If you're looking to improve your fitness, I'd be happy to help in any way I can.
- Music: my dad is an audiophile so this was inevitable. I like just about everything except country and opera. I spend most of my time listening to a mix of classic rock, 90s, electronic music, and hip hop. Abbey Road is my favorite Beatles album.
If any of the above resonated with you and we're not already working together (and you'd be interested in changing that), please connect with me on LinkedIn. We're always looking for great engineers to add to the Square team.