How to Ryan

Hi, welcome to the team. I’m so glad you are here at $COMPANY.

It’s going to take a solid 90 days to figure this place out. I understand the importance of first impressions, and I know you want to get a check in the win column, but this is a complex place full of equally complex humans. Take your time, meet everyone, write things down, and ask all the questions – especially about all those baffling acronyms … healthcare is full of them

One of the working relationships we need to define is ours. The following is a user guide for me and how I work. It captures what you can expect out of the average week, how I like to work, my north star principles, and some of my, uh, idiosyncrasies. My intent is to accelerate our working relationship with this document.

Our Average Week

During your first 90 days we’ll have a 1:1 every week for about 30 minutes. I try to never cancel this meeting so it might get moved around a bit. I would like to apologize for this in advance.

After 90 days I let you decide how frequently or infrequently we meet. Some people meet with me every week even after the 90 days. Some meet once a month. However, once a month is the longest I feel conformable between 1:1s.

If you are curious about the 1:1s I have with my manager I’m more than happy to tell you about their frequency and duration. I meet with my boss at least once a week for anywhere from 30 – 90 minutes. It just depends on the week.

The purpose of our meeting is to discusses topics of substance, not updates (there are other platforms for that). Sometimes they can morph into update type meetings. I’ll do my best to keep that from happening, and I ask that you do the same. I have a running list of items that I will want to discuss with you and I encourage you do have the same.

We have scrum every day unless it’s retrospective day. I act as the scrum master to help move the meeting along, but during the meeting I’m the scrum master, not the manger (I even wear a silly hat). The purpose of the scrum is to tell the team three things:

  1. What I did yesterday
  2. What I’m doing today
  3. What, if any, roadblocks I have

The scrum master will make note of the roadblocks and work to remove them as quickly as possible. Sometimes this is fast, sometimes it’s not.

Every 2 weeks we have a Sprint Retrospective and Planning session. This lasts about 90 minutes. The purpose of this meeting is to review the previous Sprint and to plan out the issues that will be worked on in the next one.

When reviewing the previous sprint we ask ourselves four questions:

  1. What did we do well?
  2. What could we have done better?
  3. What did we learn?
  4. What still puzzles us?

This is a time to be honest and constructive. If the scrum master didn’t manage the scrum well, say so. If Bob didn’t get back to you say so. If you learned an amazing new way to query the database that is more performant give a shout out.

If I am traveling or will be out of the office on PTO (yes, I take PTO and you should too once you can), I will give you notice of said travel in advance. Depending on the type of travel I may need to cancel our meeting. If it’s a weekly meeting I won’t reschedule. If it’s not weekly then I’ll reschedule for as close to the day when I’ve returned as I can.

Sometimes I work on the weekends. Sometime I work late. Unless we have a big project that you are working on and it needs to get done I don’t ask anyone else to work late or on the weekends. I want you to have a life outside of work.

North Star Principles

Humans first. I believe that happy, informed, and productive humans build fantastic products. I try to optimize for the humans. Other leaders will maximize the business, the technology, or any other number of important facets. Ideological diversity is key to an effective team. All perspectives are relevant, and we need all these leaders, but my bias is towards building productive humans.

Leadership comes from everywhere. My wife likes to remind me that I hated meetings for the first ten years of my professional career. She’s right. I’ve wasted a lot of time in poorly run meetings by bad managers. I remain skeptical of managers even as a manager. While I believe managers are an essential part of a scaling organization, I don’t believe they have a monopoly on leadership, and I work hard to build other constructs and opportunities in our teams for non-managers to lead.

It is important to me that humans are treated fairly. I believe that most humans are trying to to do the right thing, but unconscious bias leads them astray. I work hard to understand and address my biases because I understand their ability to create inequity. I am not perfect, but I try to be better today than I was yesterday. Sometimes I succeed. Sometimes I don’t.

I heavily bias towards action. Long meetings where we are endlessly debating potential directions are often valuable, but I believe starting is the best way to begin learning and make progress. This is not always the correct strategy. This strategy annoys those who like to debate.

I believe in the compounding awesomeness of continually fixing small things. I believe quality assurance is everyone’s responsibility and there are bugs to be fixed everywhere… all the time.

I start with an assumption of positive intent for all involved. This has worked out well for me over my career.

Feedback Protocol

I firmly believe that feedback is at the core of building trust and respect in a team.

At $COMPANY, there is a formal feedback cycle which occurs once a year per employee.

During that formal feedback cycle (also called the Annual Review) we will discuss the previous year. There’s a form ($COMPANY loves forms). I’ll fill it out and we’ll discuss it.

This means that at anyone time I could be finishing up 5 reviews or 1.

Notice I say finishing up. I try to make the reviews I write as living documents so I can capture everything from the year, and not just everything from the last month.

If during the Annual Review you are surprised (positively or negatively) by anything, I have not done my job. Please let me know. Feedback is the only way we know we are doing something well, or not well.

I won’t assume you know what I’m thinking, and I ask that you don’t assume I know what you’re thinking.

Disagreement is feedback and the sooner we learn how to efficiently disagree with each other, the sooner we’ll trust and respect each other more. Ideas don’t get better with agreement.

Meeting Protocol

I go to a lot of meetings. In the morning scrum many times I will indicate that today I have several meetings. I don’t enumerate all of them because I don’t think everyone wants to know specifically which meetings I’m going to. If I think it’s important for the team to know, I will say, I have meeting X today. If I don’t indicate what meeting I have and you want to know, ask. If it’s not private / confidential I will tell you.

My definition of a meeting includes an agenda and/or intended purpose, the appropriate amount of productive attendees, and a responsible party running the meeting to a schedule. If I am attending a meeting, I’d prefer starting on time. If I am running a meeting, I will start that meeting on time.

If a meeting completes its intended purpose before it’s scheduled to end, let’s give the time back to everyone. If it’s clear the intended goal won’t be achieved in the allotted time, let’s stop the meeting before time is up and determine how to finish the meeting later.

Nuance and Errata

I am an introvert and that means that prolonged exposure to humans is exhausting for me. Weird, huh? I tend to be most active when I’m not running the meeting and there are fewer people. If I’m not running the meeting and there are many people I am strangely quiet. Do not confuse my quiet with lack of engagement.

When I ask you to do something that feels poorly defined you should ask me for both clarification and a call on importance. I might still be brainstorming. These questions can save everyone a lot of time.

I tend to be very reserved but this is not a sign that I am uninterested, it is just who I am. Every once in a while that reserved facade is cracked and I display emotions. That’s when you can tell I’m really excited about a thing (either good or bad).

During meetings in my office I will put my phone on DND and log out of my computer if we won’t be using it. If we will be using my computer I close Outlook and only have the applications open that need to be open. During meetings I will take notes on my phone. I have a series of actions programmed on my iPhone to help keep me on top of things that I need to do. Rest assured, I’m not texting anyone, or checking the next available movie time. When I am done typing a note, I will put the phone down.

Humans stating opinions as facts are a trigger for me.

Humans who gossip are a trigger for me.

I am not writing about you. I’ve been writing a blog (off an on) for a long time and continue to write. While the topics might spring from recent events, the humans involved in the writing are always made up. I am not writing about you. I try to write all the time.

This document is a living breathing thing and likely incomplete. I will update it frequently and would appreciate your feedback.


Basketball Conference Finals OR How the actions of one person can fire up the other team and lead them to win

Last weekend I watched both games 7 of the NBA conference finals. I have no particular affinity for the NBA (I prefer the Madness in March associated with the NCAA) but I figured with 2 game 7s it might be interesting to watch. I was not wrong.

On Sunday night Cleveland was hosted by Boston in a rematch of a game 7 from 2010. One of only 2 game 7s that LeBron James had lost.

This game had all the makings of what you would want a game 7 to be. A young upstart rookie (Tatum) with something to prove. A veteran (James), also with something to prove.

What really stuck our for me, for this game, was what happened at the 6:45 mark in the fourth quarter. Tatum dunked on LeBron (posterized is the term ESPN used) to put the score at 71-69 Cleveland. What happened next though, I think, is why the Cavs won the game.

Tatum proceeded to bump his chest up against the back of LeBron’s shoulder, like a small child might run up to a big kid when he did something amazing to be like, “Look at me … I’m a big kid too!”

LeBron just stood there and looked at Tatum with incredulity. The announcers seemed to enjoy the specticle more than they should have. But LeBron just stood there, the Boston crowd cheering wildly at what their young rookie had just done. To dunk over LeBron, arguably one of the greatest, in a game 7? This is the thing that legends are made of.

But while the crowd and the announcers saw James look like he was a mere mortal … what I saw was the game turning around. The look on James’ face wasn’t one of ‘damn … that kid just dunked on me. It was, “Damn … now I’m going to get mine and I have a punk to show how this game is really played.”

From that point on the Cavs outscored the Celtics 16-10 … not a huge margin, but a margin enough to win. What the score doesn’t show is the look of determination on LeBron’s face as he carried his team to the NBA Finals. Not because he scored all 16 points (he only scored 7) but because he checked his ego at the door and worked to make his team better than the other team. In short, he was the better team mate than Tatum in those last minutes and that’s why the Cavs are in the Finals and the Celtics aren’t.

Tatum’s reaction to dunking on LeBron is understandable. Hell, if I had done something like that when I was his age, I would have pumped my chest up too.

But it the patience and reservedness (that perhaps come with age) that make you a great player or team member. You don’t really want to rile up a great player because that’s the only reason they need to whoop your butt.

Perhaps Tatum will learn this lesson. Perhaps he won’t.

Because you see, acting like a a little kid isn’t just the right of a rookie.

James Harden pulled some immature shenanigans too in his team’s loss to the Warriors. At one point, with the Rockets up 59-53 with 6:13 in the 3rd, Harden when for a layup and was knocked down … accidentally in my opinion.

When a player from the Warriors tried to help him up he just sat there and then flailed his arms until one of his teammates can to help him up. Big man there Harden.

By the end of the 3rd quarter the Rockets were down 76-69. By the end of the game they’ve lost 101-92.

You see, when it comes down to it a great teammate will do what’s best for the team, and not do what’s best for their ego. It doesn’t seem to matter, old or young, rookie or veteran, not having the ability to control your emotions at key points in a game (or in life) can be more costly than you realize.

Sometimes it’s game 7 of the NBA Conference finals, sometimes it’s just a pick up game with some friends at the park, but in either case, being a good teammate requires checking your ego at the door and working to be the best team mate you can be, not being the best player on the court.

To put it another way, being the smartest person in the room doesn’t make you the most influential person in the room, and when it comes down to moving ahead, being influential trumps being smart.


Using Drafts 5 at Work

I have many meetings that I go to in any given day. One of the things that I’d been struggling with was being able to keep track of what I needed to do after a meeting and/or documenting certain types of meetings more effectively.

I have been using a Workflow I created a couple of years ago to get the pertinent details of a meeting into Drafts. I spoke about updating that workflow to incorporate drafts 5 here.

Once I was able to get the information into Drafts 5 a new opportunity arose. I was able to run a Workflow in Drafts!

I decided that getting the information into Drafts was great, but I needed a good way to get it out.

There were two sections in the Draft that I decided I could leverage to help:

  1. Actions
  2. Notes

Broadly speaking there are 3 types of meetings I go to:

  1. Daily Standup aka Scrum
  2. One-on-One with direct reports or my manager
  3. General Meetings

Categorizing the meetings helped me to create Draft Actions that run Workflows for each meeting type.


This workflow runs through the Actions of the Draft and adds each one to OmniFocus in a Project called Scrum with a Tag of Work. The due date set for these tasks is noon of the same day. My goal is to have the items that come from Scrum totally processed by noon of that day and for 80% of them I can. Some actions are more involved, but having them in OmniFocus helps me to make sure that they get taken care of.

It also creates a calendar meeting for the next business day with my Scrum template and lets me know which team member will start that next day.


This workflow runs similarly to the Scrum workflow. It adds the Action items to OmniFocus with a due date of noon the same day, tagged with Work and in the One-on-One Project.

Instead of creating a calendar meeting for the next business day at 8:30 it appends items from the Notes section to a Dropbox file. The Dropbox path is predefined, but the name of the file matches the name of the person I met with (luckily I don’t have 2 Tom’s reporting to me).

General Meetings

This is the simplest workflow. It adds all of the items under actions to OmniFocus with a due date of noon, project of Meeting Follow Up and Tag of Work.

After the Actions are run from Drafts the notes are archived in Drafts.

I’m toying with the idea of archiving the notes from these meetings into Dropbox, but I’m not sure that it gets me anything … so I haven’t really looked at it too deeply.

Workflow links

The links for each of the workflows can be found here:

Parse Scrum Notes

Parse One-on-One Notes

Parse Meeting Notes