Stop when you’re feeling strong, and know where you’ll start again

It was wonderful to walk down the long flights of stairs knowing that I’d had good luck working. I always worked until I had something done and I always stopped when I knew what was going to happen next. That way I could be sure of going on the next day.

– Ernest Hemingway, A Moveable Feast

This passage has always stuck with me. Hemingway refers specifically to writing fiction, but this applies to all work. It is an approach I try to live by.

Each day, I stop work only after I’ve accomplished something good. Before logging off for the day, when my mind is in “these are all the things I still need to do” mode, I make a to-do list for the next day and prioritize the order of tasks. That way, when I open my laptop each day, I know where to begin.

An Ops tool: The Worry List

I started a new job this week as Director of Operations for Support Driven 🎉. Two of the major components of my role are to manage the various projects the company is working on and to design the work of the organization: what we will do, who will do it, and by when.

Last week, I noticed Scott, the owner, online when I logged in to check on the benefits packages we were considering. It was about 6:30am my time — which means it was 3:30am his time.

I sent him a message,”Why are you working at 3:30am?!”

The answer was simple: he had a lot to do, not enough time to do it, and he was concerned about things slipping through the cracks.

“How about this,” I said. “I can’t help yet because I need to finish out my old job. But on Monday I can dive in. To help me understand where you most need help, would you mind making me a worry list? Open a doc, dump all of your worries in it, and we’ll go through it together to figure out how to address them.”

When worries swirl around in our heads, they repeat themselves and fill an amount of brain space disproportionate to their size. They’re all jumbled together, making it difficult to know where to begin, which ones are most important, and how to organize our time to tackle them. Also, when they’re inside our brains, nobody else can see them, making it difficult for others to help.

Scott’s worry list helped me understand the work of the company right away, and how best to organize ourselves to get it done. We divided up the outstanding concerns based on who is best equipped for each of them: Scott’s on partnerships and sponsors; I’m on communications and HR; Rose and I are on events. When I’ve been here a few more weeks and gotten the lay of the land, we can revisit the list and see where else we can better design the workload.

This Worry List has become one of our central documents. In fact, we started another one for the upcoming conference we’re organizing. Naming worries forces us to pull out of them so we can see them, which changes our perspective: we end up taking a higher level view. Bounding worries by words and anchoring them on “paper” shows their true size and makes them manageable: we can prioritize them, assign them, cross them off the list.

An unexpected side effect of this exercise is that we have peace of mind now: the worries are external to us rather than inside our brains. With them documented, all of us within the organization can easily look at the list and share the load. None of us has to shoulder the responsibilities alone :-).


Saying goodbye at a distributed company: my final week at Automattic

Before starting at Support Driven, it’s time to say goodbye to old friends.

Butterfly Mind

How do you say goodbye to your coworkers of 3.5 years when you’re scattered all over the globe and none of you is in the same physical location? Last week, I sent a text to my husband, “My co-leads are going to have going away happy hour (via video) in the evening on Wednesday March 14. I imagine it could go for a while. Will that work for you?”

He replied, “Of course that’s fine. Weird… But fine 😉”

It’s times like these that being distributed is hard. We can’t get together in a pub, with the ambient sounds of end-of-workday chatter, mugs thunking on a bartop, chairs scraping across the floor, laughter at the other end of the table. We can’t sit next to each other and clink glasses as we raise a toast. We can’t hug each other when it’s all over.

But we make do. On Wednesday…

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I’m joining Support Driven full time!

I shared this on my main blog and wanted to share here :-).

Butterfly Mind

I’ve worked with Automattic, makers of, for three and a half amazing years. The company, and its faith in me, have transformed me. A leadership coach recently encouraged me to start a learning journal to jot down all the things I’ve learned the past few years. I was astonished by the list, which included successfully leading a distributed team that spans hemispheres, speaking in front of large audiences, organizing events, and, along with 14 of my co-leads, helping scale the processes and operations of a globally distributed support team of more than 120 Happiness Engineers.

An opportunity fell into my lap a few weeks ago: an opportunity to join Support Driven, a small company that exists to serve a growing community of Customer Support professionals. At first I didn’t consider it. I had everything I wanted at Automattic: smart and funny coworkers, freedom to learn and grow…

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Moving from individual contributor to team lead: how do I measure success?

Moving into a new role is a time of both excitement and terror. Omg, so much is new 😀!

Omg, so much is new 😫.

One element I found challenging when moving into a lead role is that success is measured differently from how it was measured when I was an individual contributor. As an individual contributor in customer support, my success was measured largely in terms of customer satisfaction or the number of interactions I had with customers: how many emails was I able to answer and resolve? How many live chats did I handle, and how many can I handle simultaneously? How happy were the customers I helped? At the end of each day, it was very clear how I had performed on those fronts.

When I became a lead, though, I wondered, now what are my metrics for success? Much of my work happens in invisible conversations with team members. How do I know if I’m doing a good job at the end of each day? At the end of the week? In my annual review? What do I measure, and how do I know if I’m succeeding?

If you have those questions as well, the answers to them will depend largely on how your organization is already set up. For example, if your company has clear expectations for your role, or has an official job description for the role, those will be key in defining the results expected of you. The expectations and job description will provide direction for what success looks like.

However, if your company does not provide clearly defined expectations, or if it does but they’re not granular enough to help define what a successful day or week looks like, it’s up to us (or our manager, if we have one) to outline our own expectations that we can review at the end of the quarter and say, “Did I succeed? Am I meeting expectations?”

I am motivated by goals and checklists, so I knew I would need to incorporate both to help me measure my own success. From there, I followed this progression:

  1. Ask: what impact do I want to make? What results do I want to see from my team?
  2. What are milestones on the path to those results? What action can I take to achieve them?
  3. Create goals for the milestones and set timeframes to achieve them.
  4. Log my time each day and where I spend it. Each week, compare my time expenditures to my goals progress: am I prioritizing the right work to achieve the results I want to achieve?
  5. At the end of the time period, evaluate my performance. Did I meet my goals — did I succeed? If not, why not? Were the goals unreasonable, or were they reasonable but there are areas I can improve in order to achieve them?
  6. Iterate in the next quarter.

My journey

The impact I want to make

The first step in becoming a lead and figuring out how to measure my own performance was to define what I thought success looked like. What results did I want to see?

After reading a lot about leadership, and after studying our new lead expectations within our support division, I decided that I would feel successful in my role if the team was performing its expected function while also feeling productive, engaged, empowered, psychologically safe, and supported. Those are the results I wanted to see for my teammates.

Milestones on that path

Engagement, empowerment, feeling productive and supported — these are not small results, and the first step in defining success was to accept that I wouldn’t achieve them all immediately. Psychological safety, for example, requires trust, and trust requires time and demonstration of trustworthiness.

Each quarter, I think about what’s next in our journey to these results, then break everything down into smaller pieces can allocate to specific time frames. After breaking the journey into milestones, I ask, “What’s my first step to get to this milestone? What action do I need to take?”

Defining goals to achieve the results I want to see

Once I have the milestones and first steps, I’m ready to define goals. I loosely use the OKR (Objectives and Key Results) format, meaning I set an objective, then define some key results that, when achieved, will contribute to the objective being achieved. So for example, when I was a new lead, one of my objectives for the quarter was, “Level up the team,”  with the following key results:

  • Complete in-depth ticket and chat reviews for each team member (reviews will help team members learn and improve, and therefore level up)
  • Know the career aspirations for each team member (this helps me look for strengths and opportunities, provide feedback in the context of the team members’ aspirations, and look for opportunities where that team member can grow and shine)
  • Empower the team to become self-leading in 6 areas (I believe that a team will feel productive, engaged, psychologically safe, and supported when the team is empowered to lead itself)

Tracking time and progress

Knowing where your time goes is a key element to measuring success in any role, as is looking at outcomes. Time spent in meetings and 1:1s isn’t productive if there are no results from those meetings and 1:1s. So measuring success, especially in a role that doesn’t have obvious metrics, will likely include some level of tracking both time and outcome.

I use a time tracker to help me understand where I spend my time, but many of my colleagues simply use pen and paper to log their work each day: “Unexpected ping from Danielle about staffing an event,” “Chatted with John about weekend expectations.”

I use Trello to track my goals. I love being able to incorporate checklists and to move cards to the in-progress and done columns for a quick visual of how I’m doing.

goal tracking trello
Personal goal tracking to help me evaluate my performance as a lead

How do I put time tracking and goal tracking together? On a weekly basis, I usually have tasks for each result I want to see. So maybe this week one task is to review 3 team members’ interactions. At the end of the week, if I’ve only reviewed one team member, I need to ask myself why. Where did my time go? What did I prioritize over this task and was it the right thing to prioritize?

Longer range, of I’m mid quarter and I’ve got most of my key results in the In Progress column, with maybe something in the Done column and something in the TODO column, I’m probably on track. If we’re mid-quarter and everything is still in the TODO column, it’s time to check my time tracking and see where I’m spending my time, because I’m clearly not prioritizing correctly.

Self-Evaluating at the end of the goal period

At the end of my time period, which is a quarter, I check my Trello board to see how I did on my goals. It’s not always clear-cut that everything in the “Done” column equals success or several things still “In Progress” equals failure. If I completed everything, maybe my goals weren’t ambitious enough. If I completed nothing, was it because I failed, or were the goals unrealistic?

The more important question is: how is the team now compared to the beginning of the quarter? This question, along with reflection on both goals and results, helps me evaluate my own performance and whether I am providing what my team needs to succeed.


I am often naive and overly ambitious. In the quarter goals outline above, I didn’t realize how much I was trying to take on in one quarter. But that’s okay! Part of this process includes understanding how to set goals to begin with.

When I’m setting goals, I often know going in that some are going to be harder than others, and some higher priority than others, but I didn’t always explicitly state that when setting the goals. Over time, recognizing these distinctions helped me define goals better. Now, if I know a goal is high priority, I define it as such. If I know a goal is a stretch, I acknowledge that as well. Then at the end of the quarter I can assess: I completed the high priority goal but missed the stretch goal, I’m okay with that. I’ve also started being more realistic about what I can accomplish in a quarter, as well.

And finally, inspired by our Automattic Creed, I give myself permission that whatever I didn’t finish this quarter, if it’s still important, I can carry it over to the next:

I am in a marathon, not a sprint, and no matter how far away the goal is, the only way to get there is by putting one foot in front of another every day. Given time, there is no problem that’s insurmountable.






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: Continue reading “How to remember ALL THE THINGS when conducting 1-on-1s as a (distributed) team lead”

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,? Continue reading “Customer Support Skills Tree”