README

Inspired by Manager Readme, I recently decided to write up my own version. It's important to explicitly call out that this exercise was not to replace any formal onboarding that a new team member goes through, but instead to supplement it. There are quite a few detractors to Manager Readmes out there, but I'm working really hard to make it as introspective as possible. Anyway, enjoy!

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Hi! Welcome to the team! I’m Tony. My official title is Director of Cloud Enablement, but to you, I’m just your manager (or peer, or manager’s manager, or whatever our working relationship is).

This document is intended to enhance, not replace, our working relationship. Indeed, the intention of this document is to understand how I think, act, react, and work. This document is intended as a user guide for me and how I work. It captures what you can expect out of the average weekly working with me.

While I may have some opinions and nuance about how I work, this document should not, in any way, influence the way you work.

My Leadership Style

I’ve been working professional on technology since 2006. My career has taken me from software engineer, team/tech lead, software architect, software manager, enterprise architect, and now Director of Cloud Enablement. Throughout that journey, I’ve refined my leadership approach, but it’s still built on the same foundational elements.

You are an adult. This is, by far, the most important value you need to hear. I trust adults implicitly. Adults are self-sufficient. Adults know when to escalate bad situations. Adults know how to praise one another. Adults tell one another when they are overloaded and/or stressed out. I will always treat you as an adult first, until you are no longer being an adult. At that point, I will treat you like a child. Children need to earn trust. Children need their hands held crossing the street. Children throw tantrums. Children are unable to prepare for the future. Don’t be a child.

Do less. Delivery of value will always take precedent over being busy. The easiest way to deliver value is to have less balls in the air. In fact, I will regularly challenge you to take items off your plate, either by delegation or by backlogging the work for later. If you aren’t sure of the priority of items in the backlog, just ask!

Bias towards action. This is an Amazon leadership principle, and I am shamelessly stealing it. I do not want to be in hours of contemplative, theoretical meetings, and I do not want you to be either. Actions are very rarely irreversible. Try something small, detail your experiment, and learn from it. Keep experimenting.

Be honest. We don’t lie to each other. This includes both positive and constructive feedback. This is part of the social contract between you and me. I expect this to be difficult for you sometimes, and that’s okay! We will get better at it together.

My Schedule

I’m technically an in-office employee. This means that I’ll be in Westlake around 3 days per week. On those days, expect me to be in the office from 9:30am US Eastern until about 5:00pm US Eastern. For the days that I’m remote, the hours typically shift an hour earlier.

I’m very particular about my calendar in Outlook--it’s always up-to-date, especially if I am unavailable. Additionally, except in very specific cases, my entire calendar is available to everyone in the organization.

Interruptions

My job is to be interrupted, especially by you. I am, first and foremost, a servant leader to you. Do not hesitate to ask for time with me! I’ll be very honest about my availability, and I will typically make the time for you.

Focus Time

Upon inspection of my calendar, you may notice that I aggressively block many hours of the week as Focus Time (thanks Microsoft Viva!). This Focus Time is to block meeting scheduling from people outside of my organization. It does not apply to you! Book right over the top of it.

About The Spring

In the Spring (from February to the first weekend in June), I coach Track and Field at our local High School. Practice runs from about 3:00pm US Eastern until 5:30pm US Eastern. During those times, I have my cell phone on me, but I’m mostly unavailable. To accommodate this schedule interruption, I am typically picking up extra time in the evening, outside of most people’s normal working hours. If something is urgent, I’m available.

You may notice that I have explicit Commute Time on my calendar during these months. I can be considered Available, But Working Remotely during those specific times.

If you feel like you can’t reach me during these times, do not hesitate to reach out! I can’t fix a problem if I don’t know about it.

Communications

Nowadays, there are about three hundred different ways to communicate with me. In an effort to set some expectations, here are the different ways that I regularly receive communications.

Face-to-Face (Physical or Virtual). This is for both scheduled meetings and impromptu conversations. Need to discuss something that doesn’t fit a textual model? Message me on Slack to confirm availability, then set it up. If it’s not urgent, schedule a meeting.

Phone Call. This is a very urgent mode of communication. If you get a unprompted phone call from me, expect that the contents of the phone call need immediate attention. I will not call just to talk about my day.

Text Message. I rarely will text you. If you get a text from me, it’s typically because I’m unable to call at the moment. You can safely assume it is significantly less urgent than a phone call.

Instant Message (Slack / Teams). This is our normal mode of conversation. I consider IMs to be asynchronous communication. You should have no expectation of immediate responses from me. I try to respond quickly, and I will be upfront if I’m unable to respond with substance.

Email. The purest form of asynchronous communication. There’s almost no expectation of me responding to an email in less than 24 hours.

1:1 Meetings

1:1 meetings are for you. When you start, I will send you a survey about 1:1’s to determine your ideal cadence, day, time, and topics that you would like to discuss. From there, I will schedule our regular 50-minute 1:1 at your defined cadence, day, and time.

The Agenda

You own the agenda for our 1:1. When I schedule our 1:1, I will be explicitly clear on when you should expect to receive the collaborative agenda, and I try to make it at least one full business day prior to the 1:1. This agenda will live in my personal space in Confluence in an area that only you and I can see and contribute.

I will very likely have items in every agenda, but this is, first and foremost, your opportunity to tell me how you’re doing, what you need, what you wish could be different, how you feel about our team and your teammates, what your career goals are, etc. These are for the conversations you might not necessarily have with me when we’re sitting at our desks amongst coworkers. If you’d like to give me a brief status update on things you’re working on or that you’re stuck on, that is fine with me, but those are generally better-suited to a quick chat while I’m at my desk, a Slack message, or a separate meeting.

The Slack Channel

I create a private Slack channel for our 1:1s. These are explicitly to be used as a sort of scratchpad for items that you or I want to discuss in an upcoming 1:1 whose agenda is not yet available. These are removed from Direct Messages (DMs) on purpose, as I reserve DMs for normal work chatter, and 1:1 topics will typically get lost in the shuffle.

Skip-Level 1:1 Meetings

I am trying very hard to have 1:1’s with everyone in the department. I am bad at this, and it is something I am working to improve. If you and I haven’t met, anticipate that I will be correcting that.

Feedback

I’m going to be asking you for your feedback on how the team and department are running. I’m going to do this a lot. I’m going to do this in a multitude of ways. Sometimes, I will put you on the spot in a 1:1, hoping for a top-of-the-mind answer. Other times, I will send out an anonymous survey, hoping to get more detailed, challenging feedback.

These are not the only times to provide feedback! Feedback should be provided and received as soon as possible. Instead of waiting for our next 1:1, or the next State of the Team survey, or the next watercooler conversation, grab me and let’s talk it out.

Quarterly Check-Ins

At the conclusion of every quarter, you will be expected to complete a Quarterly Check-In. This process is for you to provide self-reflection feedback to me. From there, you and I will have a discussion about that feedback. During this, I will be supplying my own feedback. This is currently the only HR-mandated feedback cycle at Hyland, so I will be very keen for you to complete it on time.

Leadership Reviews

Once a year, I will be sending out Leadership Reviews, in which you will provide me with feedback on my leadership competencies. I ask that everyone in the department fill this out for me. Following the review cycle, I will be sharing the results of the feedback with the department.

The Tony Experience

I’ve been using this term to describe what it’s like to work with me the first time. The alternative title was “My Nuances,” but I figured this would land more elegantly. Below is a list of interesting personality and professional quirks that I’m aware of.

I am an extrovert. Working with people, especially groups of people, is empowering for my mind and soul. I am most effective when I am working collaboratively with people. This isn’t a quirk, but it’s something to understand about me.

I’m very open , and I will talk about anything. I want to know about every non-protected detail in your life, be it unique or mundane. This isn’t some management consulting exercise to remember you--I genuinely care about you and your life. However, I recognize there are lines that are not crossed, and I will endeavor to never cross them. You should feel no obligation to share anything with me, either. I understand there’s a weird power imbalance with these last two statements, and I am working on defining these boundaries more explicitly.

Strong opinions, held weakly. When a decision has to be made, but there is no one making it, I will make a decision, even if it’s mostly wrong. In fact, I will typically come to the table with a decision in my head, and I’ll explain it to everyone with the caveat that I am likely wrong, but it’s a good start. You should challenge me on my assertions and assumptions regularly.

I work in visible bursts. My job is mainly around strategic initiatives and large shifts in organizational and operational structures. This type of work can be difficult for me to crowdsource, so I tend to wander off into the desert for a few weeks at a time before coming back with a completed work product. Yes, this runs directly counter to my previous statement about collaborating with people, I know. This isn’t the best way to work, and I’m actively working on improving this.

When I ask you to do something nebulous , it’s likely because I haven’t thought about it all the way through. You should ask me to clarify and prioritize the work if you are uncertain. Sometimes, this will make the nebulous thing go away completely.

I’m great at starting new things , and poor at finishing them when I know the end result. This is especially true when the end result is weeks or months away. If I tend to give you work that feels started-but-unfinished, it’s because I know you are an exceptional operator of work that can take it across the finish line. As my career has moved further away from individual contribution, this quirk has diminished.

I’m regularly hyperbolic. Things are rarely as good or as bad as my inner salesman believes. Most of this can be chalked up to me being excited about the topic, in one way or another. Call me out on something in which you don’t believe the hype--I won’t be offended.