How to remember ALL THE THINGS when conducting 1-on-1s as a (distributed) team lead

Tl;dr: I share a private Google doc with each team member, add an individualized agenda each week that includes questions specific to that team member plus information I want to share with all the team, keep notes in the shared doc, and mark action-items in red so I can scan the doc easily to find those follow-ups the next week.

In June of 2016, about a year and a half ago, I began leading a team of seven Happiness Engineers at Automattic, the maker of I am based in Virginia in the US, and my teammates are based in various cities in North and South America. In the beginning, I could mostly remember everything I needed to discuss with each team member when we chatted one-on-one each week. By keeping the 1:1s relatively informal and asking open-ended questions like, “What’s on your mind?” we were able to cover a lot of ground, have great conversations, and build relationships and trust.

Now that the team has grown to 12 members, and as our entire support division has expanded, there are a lot of moving pieces to remember: For Amy, what did I say I would follow-up on from last week? What was Rafa planning to follow up on from last week? When did this new department-wide initiative roll out relative to when I’ve spoken to each person on the team? I asked Samantha what she thought about the new weekend thing, but did I remember to ask Sam?


I recently joined a group of team leads from Automattic to train together with leadership coaches from Reboot. Our coaches, Andy and Jim, shared a 1:1 template that as soon as I looked at it, I knew I wanted to try it. It splits the time of the 1-on-1 roughly into thirds, with the first part focusing on whatever the team member wants to share, the second part focusing on follow-ups and organizational information, and the third part focusing on professional development:

First ⅓ – Team Member
Choose from these questions (pick 2-3):

  • What’s on your mind this week?
  • Tell me about your week — what’s it been like?
  • Are you  on track to meet your deadlines/goals?
  • What did you stumble over?
  • What do you think about X change?
  • Where do you think I can be most helpful?
  • What areas of your work are you confident about?
  • What worries you?
  • What’s your biggest challenge this month?
  • What’s something you’re proud of from last week?

Second ⅓ – Followup/Org/Lead

Followup from last week

  • What do my notes say I need to act on? What updates do I need to share?
  • What feedback do I need to give the team member, and for what purpose?

Information and Team lead

  • What do I need to be sure to communicate from team lead discussions?
  • What am I working on?
  • What organizational efforts/news do I need to share?
  • What appreciative feedback can I give?

Third ⅓ Professional developement
Choose 1-2 from this list

  • Is there anything to delegate?
  • What high impact work/task/project would be helpful to the team member’s development and also match with the company’s needs?
  • Are there growth or learning opportunities to discuss?
  • What are the team member’s career dreams and aspirations?
  • Where do they see themselves after this company?
  • What’s something they’re proud of from a previous job?
  • Where do they see themselves after this role?

How I use this

I keep this general template at the top of a private “1:1 Template” Google doc. Each week on Monday, I select elements from this general template to create a specific outline for that week that I’ll use for the whole team, including two or three general questions from the first section, what to share or ask about from our internal news digests for the second section, and a professional development question or direction for the third section. For example, in the first week of using this template, for the third section, I added this:

Let’s talk about what to do when the queue is low and you find yourself with time to devote to other high impact work: what should your priorities be? Options: team goals, guides/guilds work, learning, buddying, translations, documentation, [or whatever skills-based work this team member is focusing on.

Once I have the master template completed, I copy it into each team member’s shared 1:1 Google doc and then fill in the individual content, like feedback on how I perceive the team member is doing with their goals, follow-ups from the previous week, and other content specific to that person.

As we go through our 1:1, I keep notes in the team member’s shared Google doc. Anything that is an action item or will require following up on, I write in red text. When I’m prepping for the next 1:1, I can then quickly scan the notes for red content to put in the follow-up section. Here’s an example template that helps trigger me to look for that red follow-up information:

1on1 template for blog post
Sample 1:1 template before individualizing it for a team member

Sometimes we aren’t able to cover everything, so as the 1:1 progresses and I see how much time we have left in our chat, I’ll pick the highest priority items from the agenda to make sure we get to them in our allotted time. Items we don’t get to I will mark in orange and either follow-up on asynchronously through Slack, will carry over to the next week’s 1:1, or if I find it happening in multiple 1:1s, I’ll bring it up in the team call to make sure everyone gets the information.

How it’s going

This format is helping me make sure I go over important things with everyone on the team, and that I’m hitting on three major components: the team member’s current strengths and concerns, organizational level information, and professional and skills development. Since we are spread all over the western hemisphere and I meet with different team members at different times during the week, I like the consistency of starting with a team-wide template then individualizing it. I’m also hopeful that I’m asking better questions to help uncover accomplishments and concerns that we weren’t digging deep enough to get to previously. I think I need to add this as a followup in 1:1s in the near future:

What do you think of our 1:1s in recent weeks? Have they seemed any different to you?


Customer Support Skills Tree

A perennial topic in the customer support industry is “What does a career in support look like?” As support professionals, we want to see a path before us and want to know how to develop along that path, especially if our interest does not lie in managing people and climbing a leadership ladder.

There are many ways of looking at a support career, from traditional ladders, to support as a theme park, to a choose-your-own-adventure model as described in the recent Career in Support episode of the Support Ops podcast. These are high-level views of support as a career, and they lead to more granular questions about support careers: what are the rungs, theme park lands, and adventures available to us,?

Something that comes up fairly regularly at Automattic, the company where I work, is this: if a Happiness Engineer (our title for support experts) isn’t interested in leadership, what are other options for career development? What are those other adventures or theme park lands we can explore as we master customer support, and how do we get to them?

To help address these question, my team got together to develop a Happiness Engineer skills tree: a starting point for any team member to assess our skills within our support division (Happiness) and to identify opportunities for development to master customer support at Automattic. We used our colleague Davide Casali’s Skill Trees: a getting started guide, and from there we developed this diagram of customer support skills:

Customer Support Skills tree for
Customer Support Skills Tree

Progressing from rookie to master in these skills will help me as a support agent develop in my career, and if I know where I want to go next, this visual will help me see what skills I need to master to get there. One way to think of each skill is as a fruit or acorn: when it’s ripe — when the Happiness Engineer has reached mastery — that skill can be used to start a new tree, using that specific skill as the seed. For example, someone who has mastered a particular product can use that mastery to teach others, research or develop support tools, act as a liaison between support (ie, customers) and product developers, and be an expert resource for others.

I’m not 100% sold on the tree metaphor, but I haven’t yet come up with a better model that makes sense to me given how I see the skills flowing throughout a career. For example, mastery of a single skill is not all that’s necessary to develop fully in a career, while a single acorn can grow a new tree. With the diagram outlined above, my team and I determined that the highest level skill listed there — adaptability — is an overarching skill that will serve us anywhere. For support specifically, the skills really should build from left to right, as the skills on the left are foundational to all else in a career in support. At any rate, “tree” is the best we’ve got for now, and maybe this diagram will help someone else come up with a metaphor that is more apt :-).

How we created this tree

We initiated the tree by passing out post-it notes and asking two questions:

  1. Think about the last time you had an amazing support day — you rocked live chat, or email responses, or concierge sessions. What did you do that day that made it a success?
  2. Think about your role model(s) in support. What things do you see them doing that you admire?

We each wrote one quality, behavior, or action per post-it note, shared our thoughts, stuck all the post-its to the wall, and then grouped them to create a draft of a skills tree.

We were surprised to find that the most common contributors to success were not technical skills, knowledge, or confidence. Instead, they were behaviors: self-care (good sleep, breaks, proper meals, mood-setting, me-time), time & task management (planning the day ahead of time, checklists, keeping organized), goal-setting & accountability (establishing measurable goals, tracking progress, post-success or post-failure analysis), and focus & follow through (mono-tasking, following up to bring things to fruition). For this reason — that these were ubiquitous in the descriptions of amazing days in support — we determined that those behaviors were foundational to success.

As I mentioned before, we stumbled with the tree metaphor, but as speakers of left-to-right languages, we decided to put those behaviors at the far left of the diagram to indicate they should be mastered first. From there, we added the next group of behaviors we found to be useful no matter what path a Happiness Engineer chooses to follow, and continued to progress towards the right.

When we built the tree, we began and ended with adaptability. Adaptability is essential at nearly every point in a person’s development:

  • Doing something that scares you
  • Acting/doing without waiting for permission
  • Being OK with mistakes and learning from them
  • Being able to change focus quickly
  • Anticipating issues of product changes/launches
  • Working where help is needed

We placed adaptability at the top of the diagram to illustrate its overarching importance.

How we use this tree

At performance review time, I ask team members to provide a self-evaluation using this tree. They rate themselves as rookie, pro, or master of each of the skills on the tree. I invite members to add other skills to the tree if we’ve missed anything they see as valuable, and especially if they have a particular direction in their career that is not represented anywhere on the current tree.

We use their self-evaluation to identify where to focus next. Where a Happiness Engineer is a rookie, we decide among the skills that need development and determine which one(s) would be most impactful to focus on. Where they are masters, we talk about how they can use that mastery to help others through teaching, sharing workflows, and other forms of spreading knowledge.

Developing new skills trees

As we progress along the paths we want to pursue in our careers, it’s worth creating a skills tree for where we see ourselves in the future. If a support agent wants to develop toward marketing, what would that eventual marketing skills tree look like? What seed do they need to plant — what skills do they need to master in their current role — to plant that new tree, and what other skills from the marketing skills tree can be developed in their current work in a way that benefits both the company and the agent?

The hardest part of this step, though, is also the most basic: knowing where you want to go.

On the Freshdesk blog: How handles over 2000 support requests each day

After reading recent posts about my daily and weekly routines as lead of a distributed support team at Automattic, Arun Sathiya reached out to ask me more about support for the Freshdesk blog’s “Secret Sauce to Customer Support” series. I was happy to spend a Saturday afternoon chatting with him via Slack. On top of reminding me that operating as a 100% distributed workforce is still somewhat novel, the interview process and the questions Arun asked made me really proud of our Happiness team. I work with some amazing people.

My favorite question Arun asked was, “What do you think is the secret sauce to customer support?” You can read the full interview, including my answer to that question, on Freshdesk’s blog: This is how handles over 2000 support tickets every day. Thank you, Arun!

Weekly routines of a Distributed Support Team Lead

Earlier this week, I wrote about my daily routines as the lead of a distributed customer support team. While I do have rituals and routines in my daily work, as a lead I’ve found it is the weekly routines that empower me to be productive and make sure I follow through on expectations and commitments.

With weeks that have more than a dozen one-on-ones (1:1s), multiple video calls, team and division tracking, and anywhere from two to ten P2 (internal blog) drafts to review, edit, and write, the week rather than the day is the time frame I most identify with for planning and containing my work.

When I first began as a lead, I struggled mightily with how to organize my time to make sure I could stay on top of everything. After a little over a year, Continue reading “Weekly routines of a Distributed Support Team Lead”

Daily Routines of a Distributed Support Team Lead

My name is Andrea Badgley, and I lead a distributed team of 12 Happiness Engineers (customer support professionals) at Automattic, the maker of, Jetpack, and WooCommerce. I am based in Virginia in the eastern US, and my 11 teammates are based in Canada, the US, Venezuela, Peru, Brazil, and wherever they happen to be travelling in any week or month of the year (one US-based teammate is currently working and nomading in South America). All of us are within 3-4 time zones of each other, depending on who’s on Daylight Savings Time and when, and it only took me about a year to stop being jarred when our Brazilian teammates are wearing wool hats and winter coats while those of us in North America are wearing shorts and flip flops.

I’ve been with Automattic for three years, first as a live chat Happiness Engineer, and for the past 16 months as a team lead, and I’m so accustomed to Continue reading “Daily Routines of a Distributed Support Team Lead”

Take Control! Techniques for Efficient Live Chatting

I gave a talk this past weekend at SDX Portland on tips for controlling and ending chats. Here are the slides and script 🙂

Live chat is fast. That’s why it’s great for customers, and that’s why it’s a challenge for support professionals. Unlike email support, the customer is waiting for answers in real time, and unlike phone support, a live chat agent is often handling multiple conversations simultaneously.

If you watch the Support Driven Slack, you’ll see questions pop up about live chat at least once per week. Along with staffing, two of the biggest concerns with live chat that repeatedly appear are: Continue reading “Take Control! Techniques for Efficient Live Chatting”

A day in the life of a live chat Happiness Engineer

I lead a live chat team at Automattic, and as we expand our live chat offering into the weekends, I work a couple of weekend days each month. Today is one of those weekend workdays for me.

On weekends I do more customer-facing-support and less team-lead stuff than I do during the week, and I’m excited to share my experiences in direct support to help folks who are looking to become Happiness Engineers see what the day-to-day job is like. Continue reading “A day in the life of a live chat Happiness Engineer”