Leadership Guide

This is my Leadership Guide. This document is for you. I took the time to write it because I care about who I work with and I want them to be equipped to do their best. Use this document as an intro to the way I operate: my mental and operational framework. This document accomplishes its goal if it helps you become more effective and helps us build a better working relationship.

People First Philosophy

My guiding principle is "People First." While I love structure, documents, and organization, none of that matters without people and relationships. I don't always get it right, but this philosophy shapes and directs every decision I make. That's my first step—building a relationship. I look forward to our 1:1s where we'll continue that journey.

My Role & Responsibilities

I strongly believe that my primary mandate is to serve you, not the other way around. I am always available to assist. As a leader, I'm measured by:

• Fulfilling the role and expectations of leadership as defined by the organization
• Enabling better efficiency and growth with a "default to yes" mindset (i.e. we can do anything the business needs us to), while providing clear tradeoffs to relevant stakeholders
• Facilitating the iteration of our processes and technology within the Lean/Agile philosophy to build a scalable organization (first) and scalable product (second)
• Setting clear context so you can be successful, connecting the dots between what the company needs and what the individual needs (career growth)
• Our ability to retain and attract talent over time by deeply caring for who we have and building an Engineering Brand in our relevant market(s). We will lose people over time, but I'll measure myself by asking the question: "Do you feel that the team's EQ, IQ, hunger and speed is getting better over time?"
• Mentoring and coaching the managers I work with to increase the company's leadership capacity and aid in career growth

I subscribe to the philosophy that upper management should first strive to add value to those on their team, through air cover, perspective, sharing experiences and providing constraints that better equip you to do your job.

My Guiding Principles

I consider the study of leadership to be a craft that I constantly endeavor to master, but never will. Through this course of study, I have gathered a list of principles that inform my leadership style. I reference these often, having memorized most of them:

• People First - My guiding principle
• Keep it Simple - Everything should be made as simple as possible, but not simpler
• Clarify, Clarify, Clarify - Clarity affords focus
• Embrace Constraints - Constraints evoke creativity
• Document Plans - If you fail to plan, you plan to fail
• Prioritize & Execute - When in doubt, ask "What's most important right now" and do that
• Perception is Reality - Your behavior and results matter more than intentions
• Radiate Information - Always better to be an information radiator
• Decentralize Command - Push context and agency to the edges
• Extreme Ownership - Begin with personal responsibility. Leaders must own everything in their world. There is no one else to blame.

I take no credit for creating these principles. I have learned from many other leaders before me.

What I Expect From You

As a member of my team, I expect:

• To fulfill the duties defined by your role. If you have any questions about this role, please let me know and I can help you find the answer.
• I expect you to operate as a Directly Responsible Individual. You were hired because of your experience, skills and I am not here to tell you how to do your job. I believe you are able to operate as a professional adult and make smart decisions.
• I expect you to plan, document your plan, provide it to me for feedback and then execute your plan. This process is not for me. It is for you.
• When you need help, I expect you to ask for it as soon as possible.
• If you feel you have made a mistake, I expect you to let me know and do your best to solve it, knowing I'm available if you need help.
• You work for the company, not me or your direct manager. Optimize for the organization.

My Personal Quirks

• I have strong opinions, weakly held. I love to debate, understand and see an issue from all sides. Question everything I say, we'll all be better for it.
• I care about my words and endeavor to choose them carefully. I take this too far sometimes, overthinking my words or being overly pedantic.
• I love to brainstorm and often ask for feedback on ideas on my "drawing board". I may forget to explain this, so always assume I'm brainstorming with you. I default to clarity when giving direction, not when brainstorming. This is especially important when I get crazy ideas.
• I'm a big believer in "no broken windows" when building technology. I like clean logs, clean exceptions, clean processes. Once things go south here it's very hard to truly understand the health of the system.
• When you ask "do you have 5 minutes?" in Slack or email, please add the topic you'd like to discuss otherwise I'll think "do you have 5 minutes for me to tell you that I'm thinking of quitting." -- we're biased for bad news and I'm not different.
• According to random personality tests I've taken at random company team building events, I am classified as an INTJ personality. While I find bucketing someone into a single identifier is much like a star sign defining you as an individual, I certainly see traits that match my personality. Feel free to read up on that personality type if you want to get some insight into some broad categorization of who I may or may not be.
• I write a lot and I'll expect you to write more than you're used to. It is web scale :-)

Finding Time With Me

Calendar

A cornerstone of my personal process is planning where I spend my time, via my calendar. My calendar will contain not only appointments, but time I carve out for a specific purpose such as knocking out a project or commuting.

The best way to get time with me is to put an appointment on my calendar, which you are always welcome to do. We will have a regularly scheduled 1-on-1, but if you need any additional time, please just schedule it.

Slack

If you need a quick answer to something, start with Slack. That's the best way to get a quick answer from me. I'm pretty good with a lot of context switches. This is my job. Please don't assume I'm too busy.

My Availability & Response Tree

My core working hours are 8am until 6pm, Monday through Friday. I have a long commute, so a significant portion of this is on the train, but I am typically working. Check my calendar for more info.

I am generally available on Slack from 7am until 10pm. I do not work that entire time, but I am available. Before you contact me outside of core working hours, please consider the urgency of your message and consider the best medium against the response tree below:

If I do not respond, check my calendar.

Weekly Plan

Motivation

I strongly believe in making plans, documenting them and iterating on plans as we execute together. Asking for a weekly plan is how we can engage together in this process. It encourages you to lift up your head from the day-to-day craziness and look a week forward to what you should do next.

You own your time, not me. If you need help, please let me know and we'll work together on time management practices to get this done.

It is also important for me to know you are working on the right things and these weekly plans are a simple way for me to read a high-level view of your plan and make sure there are no big conflicts with other priorities. If there are, these plans help us uncover those sooner than later.

This plan may duplicate some information that comes through the existing portfolio planning process. That is acknowledged and intentional.

Preparing for it

Set time on your calendar: The goal is for this to take a maximum of 30 minutes. It will help to set up the time.

Pick the best time for you during the week where you feel best equipped to put together this information based on your schedule. It doesn't matter if it is Monday, Wednesday or Friday, just that it is consistent.

Writing this information down will require you to:

• Go over your calendar, reviewing what you did and what you plan to do.
• Review your tasks in your project management system (your team and your own tasks) and make sure everything is well organized for you.
• Think about other things that bother you on the day-to-day and determine how a fix can be prioritized.

Sample Template

Each section shouldn't contain more than 6-8 bullets. This template is a guide, feel free to use as much/little as needed.

Our 1:1

I'm big on 1-on-1's. I consider them some of the most important time on the calendar where we have an opportunity to get to know one another better and I can help you. I do my best to protect our time together, but that is not always feasible. If I have to reschedule, I apologize. If you need time sooner, please feel free to book additional time on my calendar without guilt. I strive to be available. See my calendar and availability sections above.

I believe that these meetings are for you to set the agenda. What would you like to talk about? What is going well? What's bugging you? These don't need to be about work unless you really want to talk about work. Please come prepared. I leave the agenda up to you and am never worried about filling the time.

If there are things that I want to ask you, I'll do it here, but this is your time. If I have feedback, I will also provide it during this time. I enjoy walking to coffee or even just walking on a nice day as a great way to conduct a 1:1. If you do too, let me know!

Beyond that, I will go one step further and ask you three questions at the end of every 1-on-1 we have:

• "Anything else on your mind?" - Just in case you forgot something!
• "What do you need from me?" - Am I blocking you on anything? Do you have any additional requests?
• "What can I do better?" - This is me opening the conversation to receive feedback from you - please provide it if you have it!

I know that this gets repetitive - but it's very important to me to ask those questions every session.

"Where do I stand?"

Part of my job is to track where your performance stands at all times - and obviously provide you with feedback on how to improve. I categorize people based on one of three particular levels of performance rating (based on standard HR rating scales):

• Exceeds - Performance exceeds expectations
• Meets - Performance consistently meets expectations
• Does Not Meet - Performance was consistently below expectations

It is really important to note that a Meets is not a bad level to be at - I have high expectations of everyone that reports to me, and meeting those expectations is a great thing! If you ever disagree with my rating of your performance, please bring it up - I am happy to discuss why I see you at a certain level. You will generally know when you are in the Improvement Needed level. You will definitely know when you are approaching or are at the Does Not Meet level.

Feedback

I am a strong believer of Radical Candor; I want to ensure that you are receiving honest and actionable feedback on a consistent basis. There should never be a scenario where a performance review, or in the worst case scenario, a Performance Improvement Plan, is the first time that you hear negative comments or feedback. I will provide you with feedback and guidance to the best of my ability, and will do my best to ensure that you understand the feedback that I provide to you. I will always ensure that feedback is given in a private setting.

Feedback should go both ways. I am relying on you to let me know when I am doing something detrimental to my position, our relationship, or the company. If at any point you feel you have feedback to provide to me, I will listen and internalize the feedback you give me.

Recommended Resources

Acknowledgments

Thanks to Software Leadership Weekly for the idea.