After you’ve completed the initial interviews and projects it’s time for the trial which is aptly called chaos.  A few days before your trial begins you’ll be added to a Slack channel that’s just for your trial cohort, their buddies and the hiring team.  You’ll be able to start checking in on things in the field guide and getting to know the people going through this with you.  On Monday your Super Admin access is turned on, you’ll be assigned a buddy that’s in a time zone near you and you can get started.

The first part of the training week is self-directed learning.  You have between Monday and Wednesday to complete the training and it takes about eight to ten hours total to finish.  One of my sons had a field trip on Tuesday and I was able to go on it and fit the training in around it.

The self-guided training feels a bit like taking an online course.  Most of it is text based but there are videos too.  I took notes as I went to help me as much as I could and also to give me a spot to find items in the future.

I elected to not work a separate job during the trial.  For me that meant not scheduling any client work after September since we were on vacation at the beginning of October.  You can do the trial fitting it in around your work schedule.  Many people have no choice in that.  You will need to plan some days off though for the trial.  Thursday and Friday of the first week need to be full days.  The first weekend will also take a lot of your time.  Just be aware and plan for that.

You’ll work with your buddy on Thursday.  This is a full-time Happiness Engineer (HE) who is going to help you throughout the process.  They’ll show you the ropes and get you into your first tickets to help our customers.  Also they will show you how chat works.  Most of our support is done via chat so getting a handle on that is important.

From there you’ll go back into tickets and continue there through the weekend at least.  You’ll want to get accustomed to helping users, working with our tools and finding answers before jumping into live chat.  There are lots of Automatticians (a12s) around who can help you if you get stuck in Slack.

A few of the people in my trial group dropped out pretty early on.  It’s good to recognize if this isn’t for you.  That’s part of the purpose of having a trial vs a traditional interview process. The candidates get the opportunity to evaluate what the job actually is while the company gets to see how the candidates handle what they’ll be doing every day.

You’ll write a post to your personal P2 (that’s an internal blog) every day that you work.  Your buddy will give you feedback on your customer interactions regularly and your hiring lead will also give you feedback more around your overall performance.

Each week you’ll write a self-assessment for the week.  Here’s a pro tip.  Keep a log of interesting interactions you’ve had as you have them.  Link to the chat or ticket, tell what was interesting and how you handled it.  That way when it’s time to write your assessments you have a good library to work with.  You’re going to have lots of customer interactions so you don’t want to be digging through all of them.

My background for the past decade is solidly WordPress.  I started and ran a successful theme company for eight years and have made numerous themes, plugins and helped thousands of customers.  I went into this thinking I already knew quite a bit.

There was way more that I didn’t know.  My experience with WordPress was almost exclusively with self-hosted sites.  While it’s the same software they look differently now.  WordPress.com uses Calypso as their dashboard and it’s great, but I wasn’t as familiar with where things were there.  That was minor though.

There were lots of domain based questions that I had to look up answers for.  Running a theme shop I rarely fielded a question about domains.  Also there are quite a few billing questions.  We have great tools to support our Happiness Engineers, but you still have to learn how to use them and what tool is appropriate where.

Even the business sites where users can run plugins and their own themes are a bit different than your typical self-hosted WordPress.org site.  There was (and is) lots to learn.

Don’t be afraid to ask for help.  No one knows everything.  A full time HE told me that things constantly change so even if it was possible to know it all, it would still change and you wouldn’t know it all anymore.  Some people are members of guilds which specialize in knowledge about a particular topic.  They are a tremendous resource for everyone, trial and full time HEs needing help in their area of expertise.

You will make mistakes.  You’ll give someone the wrong answer, or the wrong instructions.  It’s going to happen many times.  Acknowledge your mistake and learn from it.

Look for ways to contribute.  If you spot a bug, post about it in the right P2 or on GitHub.  All software has bugs so when you see one, verify it and report it.

If you see something that can be improved, let that be known too.  As new users we have a unique perspective that people who have been working for a long time have lost. We have fresh eyes and the things that don’t make sense to us are likely to be some of the things that don’t make sense to our users too.

I found the experience to be a bit of a rollercoaster of emotions.  I was on top of the world when things went well and I felt horrible when a mistake I made caused extra work for others.  Keep on pushing.  Don’t give up.

As a distributed company, Automattic depends on people being able to self-motivate.  You won’t always have someone telling you what to do next.  Pay attention to your buddy and understand what you need to do so you can go and do it.  It’s on you to actually make it happen.

You can drop out at any time if you realize this isn’t for you.  If you decide you want to come back and try again later you can always apply again.

Most Happiness Engineers spend their time helping out users in chat.  Really focus your energy and time into improving your skills there.  That will help out immensely.

Week five is a shorter week in reality.  Your assessment will be due on Wednesday and it will cover the entire time of your trial (remember to keep those notes up).  After that you’ll have a chat with your hiring lead and then if all goes well they will recommend you to HR for hiring.

Originally this was where everyone had the “Matt Chat” with Matt Mullenweg, but now HR handles that.  Most everyone ends up working on WP.com support as that is where the largest number of users and requests are, but some will end up with Jetpack or WooCommerce. My hiring lead ended up sending me to work with WooCommerce as part of team Cosmos. We provide support for people in North American time zones.

Don’t fight the chaos.  Just roll with it, never stop learning and don’t forget to apply so you can get started!