This is How I Work


I’m a huge fan of the Lifehacker series “How I Work.” They interview everyone from photographers to entrepreneurs to chefs and beyond looking at their workspace, favorite apps, etc.

It’s highly unlikely that they ever come to me asking for an interview so I thought I would borrow their format and complete my own “How I Work” interview. Here it goes!

I would love to read yours. If you write your own, can you drop a comment here on this post so I can read it? Or, tweet at me (@jeremeyd).

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Practical Thoughts on Career Progression

Here's a step-by-step guide on approaching career progressions

In the past, I’ve written about how I think about my career. In short, I look at three elements—Learn, Improve, and Impact. Provided those three boxes are checked, I’m moving in the right direction.

I’ve been thinking about this more and more over the past several weeks after talking with a colleague. The prevailing view in many companies is that a career progression involves things like changing job titles and work responsibilities.

What do you do if you want to change jobs or move into another area of the company?

As someone actively interested in doing this at the moment, here’s how I think about the problem from start to finish. Keep in mind that when I use “you” throughout this post, I’m talking to myself in many ways.

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The Tragic Gap

Jessica Lawrence presenting “On leading” from PopTech. Many thanks to John Maeda for sharing on one of our internal leadership blogs.

It’s a video well worth watching. A quote I particularly enjoyed:

For those of us who are overcome with visions of what’s wrong and how it could be made right, we often find ourselves in positions of leadership because at least at first we can’t stand that gap between what is and what could be, a space that educator Parker Palmer calls “the tragic gap.”

If you want to hear Parker Palmer explain the tragic gap in more detail, read this interview.

Does that matter?

Jason Fried, founder and CEO of Basecamp, published a great piece on Signal vs. Noise that I just stumbled upon thanks to Twitter.

Being able to see what matters, to know what’s worth doing is an instinct you can hone, a skill you can build. I’d consider it a top requirement for anyone tasked with making key decisions.

I would expand that to say it’s a top requirement for anyone. Making key decisions about what to work on is something we all face.

I’ve had the same conversation a few times now with new Happiness Engineers that start at Automattic. When they first join the company, they’re obviously excited and ready to make a big impact. They dive right in to every project they find helping out here and helping out there.

For a short time, the juggling act works, and everything is sustainable. Over time, the foundation starts to crumble, and they become overwhelmed, forced to take things off their plate to maintain some sense of sanity.

I know this feeling all too well because it happened to me.

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Our Current Process for Handling Feedback


Yesterday, I read an article on NPR about performance reviews titled “Yay, It’s Time For My Performance Review! (Said No One Ever).” As you might expect from the title, the piece detailed where current annual performance reviews are falling short and how they need to adapt with the future of work.

The annual performance review has quite a few problems:

  • They’re too infrequent. Trying to summarize a year’s work in one meeting is insane.
  • They’re often lopsided with feedback flowing only one direction.
  • There are too many layers of abstraction. Managers might not work closely enough with an employee or on a project to fully appreciate the challenges.

Giving feedback in general is difficult, and no system is ever going to be perfect. We’ve been working hard on providing feedback at Automattic, and while we still face many of the same challenges above, I think the system we have in place (for my team and a few others) works decently well.

Here’s the full system laid out in detail. If you have any thoughts, suggestions, or alternatives, I would love to hear them in the comments!

Before diving into the feedback system, I want to give a hat tip to Simon. I stole much of this current system from working with him at Automattic.

Our Current Feedback Schedule

First, we needed a way to address the issue of timeliness. Providing feedback once a year is just not enough. We operate on a continuous four month cycle consisting of:

  1. Peer reviews – Having a colleague review and provide feedback on customer interactions.
  2. Leadback survey – A questionnaire providing me direct feedack on leading the team.
  3. 3-2-1-Oh – A more comprehensive deep dive into goals, performance, etc between myself and the team member.
  4. (Off)

So, January through April would be one cycle, and then we’ll start back at the top. This cycle ensures that the team member gets direct feedback on their work every other month (in the peer review and 3-2-1-Oh).

In addition to this cycle, every team member has a 1-1 with me at least every other week if not every week. I detailed more about what goes into those 1-1’s here.

Peer Reviews

If you work in customer support, you likely have a similar setup at your organization. We pair up members of the team to review one another. If you’re the reviewer, you read through 20-30 random customer interactions of the reviewee.

From those interactions, you’re looking for overall patterns or trends (both positive and negative). We’re not looking for a spelling error. We’re looking for things like tone, approaches to a problem, etc. The reviewer and reviewee meet for 45 minutes to go over the feedback. Often times, the reviewer gets as much out of the feedback session as the reviewee in terms of things they’re taking back to their own workflows.

Ideally, these peer reviews serve three purposes:

  1. Team members get valuable feedback from their peers and improve their craft.
  2. Team members get comfortable giving feedback. Like anything else, giving great feedback is a skill.
  3. We create a culture of feedback. When someone notices an error in a ticket, they don’t feel shy about bringing it up directly with the person.

Leadback Survey

It’s imperative for leaders to get feedback from their team members. I end each 1-1 with some variation the following:

What can I be accountable to you for the next time we talk?

It adds a layer of accountability, and frequently, members of the team will give me things to do whether that’s clarifying the direction for the team or taking care of a specific roadblock.

Still, think of the last time that your supervisor asked you for feedback on their leadership style? It’s super intimidating! There’s a strong desire to only provide positive remarks.

The leadback survey (again, which I stole from Simon) comes as a Google Form generally consisting of three “sections” each comprised of a multiple choice question and explanation section. Here’s an example from the last leadback survey I sent out:

Question: I know exactly what I need to do when I come to work each day for Sparta to be successful as a team.

Follow-up: If you selected anything other than “Yes,” walk me through a recent scenario where you weren’t sure what to work on to push Sparta further as a team.

The responses are completely anonymous. At the end of the month, I read through all of the responses and write up a p2 post summarizing the answers and detailing how I’m going to try to address each point.

I’ve done two of these so far. I generally try to pick 1-2 themes that I want to focus on and repeat a similar line of questioning in back to back leadback surveys to gauge improvement. Each survey then contains 1-2 returning focus areas I’m looking at for improvement and 1-2 new focus areas.


This is a popular feedback framework across Automattic that breaks down like this:

  • 3 things you do/have done well.
  • 2 areas or skills you’d like to develop further, the more specific the better.
  • 1 way your team lead and Automattic can support you.
  • And — oh! — a sentence or two on what most excites you and how you want your career to develop here.

(If you’re interested in more about the format, Andrew wrote about it here.)

I setup a 1-1.5 hour timeblock with every member of the team. Then, I ask the team member to do their own 3-2-1-Oh self-evaluation and send it over to me a week in advance. This allows me to read through their responses, make notes, and send them my thoughts in return. When we get together, we’ve already read over each other’s responses and have a better framework for the discussion.

The most difficult part of 3-2-1-Oh’s is condensing four months worth of work down into six bullet points. The goal is for these sessions to be iterative. They should build upon one another. Andrew elaborated a bit on this in his article linked above:

It’s better to keep someone on course through a series of small adjustments than through a U-turn. My goal is to have these conversations on a quarterly basis. Trying to improve a host of things about your work in that limited amount of time isn’t realistic. It’s better to narrow your focus and then regularly revisit and adjust goals.

Here’s what typically goes into a prep session as the team lead (when I’m reviewing someone else’s 3-2-1-Oh):

  • Randomly checking tickets/chats. I read through 20 support interactions to get a sense of how the individual is handling support. Yes, they get this through the peer review as well. This is more of an accessory to the peer review process.
  • p2 posts/Trac tickets/GitHub reports. I’m looking for everything from how much and how often they’re communicating to how detailed and well-organized your bug reports are.
  • Collecting feedback from peers. I reach out to everyone else on the team and those the individual interacts closely with asking for feedback (all anonymous).
  • Notes from previous 1-1’s. What kinds of larger tasks/projects did they attempt over the past few months? Did they deliver on the items we discussed in 1-1’s?

Coming out of a 3-2-1-Oh, we should have a shared sense of where we’re trying to head over the next four months and the incremental steps we need to take to get there. The feedback is then summarized and sent over to HR (the team member gives it a stamp of approval).


That’s a snapshot of how we’re approaching feedback currently on Sparta. The normal caveats apply. The process is likely to evolve; your mileage may vary; and other teams at Automattic handle feedback differently.

I would love to hear about your feedback cycle if you have one though! We’re always looking for ways to improve.

Building Your Own Inner Scorecard


I recently read Ego is the Enemy by Ryan Holiday. Since finishing the book, I continue to come back to one specific topic—living your life by an inner scorecard not an external one.

A person who judges himself based on his own standards doesn’t crave the spotlight the same way as someone who lets applause dictate success.

I began thinking about all of the external scorecards we try to live up to on a daily basis. Most of them are meaningless. The car you drive, the money you have in your bank account, the clothes you wear—they’re all vanity metrics.

Here’s the thing: We all know this. There are countless quotes and books that reiterate this over and over. So, why do we continue to focus on these vanity metrics?

We continue to act on these metrics because we haven’t taken the time to develop our own. We haven’t built out our own internal scorecard so we fallback on those designed by others.

Take a few minutes today and write down what’s really important to you. What really leaves you feeling fulfilled? If you had all the time in the world, what would you spend it on? What characteristics do you want to embody?

Set out the standards, actions, habits, and routines that really matter and then give yourself a grade. Then, pick one to focus on and bring it up to an A+. Ignore everything else.

Need some inspiration? Here are the standards/actions I try to hold myself to.

Standard: Putting my family first and spending time with them.
Grade: B
Next steps: I feel like I’ve made progress in this arena with habits like shutting down at 5pm. I still let work crowd into times that I should be spending with family. I’m continuing to work at this through things like planning an awesome vacation for us next year and more regular dinner dates.

Standard: Continuously learning something new.
Grade: C+
Next steps: A year ago, I would’ve given myself an A+ here. While I’ve continued to read, I’ve fallen off the habit of taking online courses, tinkering on small side projects, etc that led me to learning JavaScript. I’m planning on picking this back up in the winter and learning PHP.

Standard: Using my skills as a force multiplier to help others succeed.
Grade: B-
Next steps: This relates to my day-to-day work at Automattic. My goal as team lead is to help the members of my team be successful. I’ll write more about this in the future, but I’m still learning a ton and falling down as many times as I succeed here.

Standard: Spending part of my time and energy for social good.
Grade: A
Next steps: I feel really great about the work I’m doing with Drink for Pink this year. I think we’re on the right track to push breast cancer research forward and help develop a better way of thinking about nonprofits in general.

This isn’t all-encompassing. It’s just an effort in figuring out what’s important, determining your own standards so you don’t fallback on those set by others.

Also, writing these down once isn’t good enough. Revisit them every month and find out if you’re making progress.

Monthly Review: September 2016


I publish a monthly review of habits, work, etc. You’ll be able to find them all here.

September was a pretty amazing month! I had a chance to get together with all of my amazing coworkers in Whistler, BC for the Automattic Grand Meetup; I took a few days off to hang out with my wife and watch her crush her first CrossFit competition; and I stayed consistent with my workouts even on the road.

For habits and goals, it was a mixed bag as you’ll see below. I am really happy with the progress I made on the habit of shutting down by 5pm.

Speaking of monthly reviews, Belle B. Cooper, who inspired me to do these in the first place, is putting together a collection of monthly reviews from across the web. It’s going to be a really cool project. I would encourage you to check it out and contribute if you write a monthly review (you should).

See below for everything I worked on in September!

Full recap of habits, books, etc below!

How do you push people without killing morale?

I recently read a piece by Christian Bonilla over on Smart Like How about pushing people without killing morale. I particularly enjoyed this bit about energy and enthusiasm as a bank:

Think of the energy and enthusiasm of your team as a bank with high interest rates. When you borrow from the energy bank, it takes time to pay off that loan. You have to let reserves build back up. Borrow too much or for dumb reasons, and the bank will cut you off.

The whole article is worth a read. Christian emphasizes another piece that I think might even be understated.

The goal is to make the person understand the need so that they take ownership of the assignment and get it done. If you have to force someone, that means they’ve refused to take ownership and you’ve got a potentially toxic situation on your hands.

The best leaders do three things really well:

  1. Set a standard of excellence on the team that drives everyone forward.
  2. Describe what the future should/could look like.
  3. Provide frameworks and tools so that team members can self-evaluate their progress.

If you have all three things in place, you’ll rarely have to force anyone to do anything. If you have to “pull rank” (to quote the article), look back through the list above. I would bet at least one of the three items wasn’t detailed enough.

Kicking Off Another Year of Drink for Pink


Unless we’re Facebook friends, you might not be aware that I helped to start Drink for Pink, a 501(c)3 nonprofit based out of Denver, Colorado, in 2015. We partner with local breweries to raise money for local breast cancer research all within Colorado. Last year, we raised close to $5,000, and we’re hoping to double that amount this year.

Last night, we had our kickoff event at Rails End Beer Company. I’m always blown away by the amazing people that show up to support Drink for Pink at our events, but last night, I was fortunate to meet two amazing individuals that really exemplified why we’re even in existence.

First, I met a woman currently going through chemotherapy to treat breast cancer. I met her family currently going through the battle alongside her.

Second, I met a man that attended several of our events last year. In fact, during our October events in 2015, his sister was undergoing a double mastectomy to treat an early stage of breast cancer. Thankfully, she’s fine. He’s back to support us for a second year.

It was an honor to speak to those two individuals and know that we’re making an impact, a difference even in the tiniest possible sense.

We started Drink for Pink because we really believe that Average Janes and Joes can have a huge impact on the world if they combine their efforts. We believe that nonprofits can be run differently, in a fully transparent way where donors know exactly where their money is going.

I’m beyond excited to get this October started and see what kind of a difference we can make. If you’re in the Denver area, check out our events page and come see us. If you’re outside of Colorado, read more about our mission, like our Facebook page, and consider donating.

Monthly Review: August 2016

A photo by Luke Porter.

I publish a monthly review of habits, work, etc. You’ll be able to find them all here.

August was a pretty amazing month. I was able to fly down to Florida and visit family and friends for a long weekend. When I got back to Colorado, I teamed up with some friends from the gym for a 200-mile Ragnar Relay from Copper Mountain to Snowmass. It was a ton of fun, and I can’t wait to do the next one.

As for goals and habits, I made progress from July. My reading was a big success in particular. Here’s a full breakdown and list of what I’m going to focus on in September.

Full recap of habits, books, etc below!