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Top 5 Leadership Lessons from AMA with Valentina Thörner, of Automattic

In our leadership community in Know Your Team, The Watercooler, Val shared her expertise leading a world-class, remote support team in our first ever AMA. Here are the top 5 leadership lessons learned from it.

In our leadership community, The Watercooler, we recently kicked off a series of “Ask Me Anything” (AMA) sessions, featuring Watercooler members we respect and want to garner more in-depth leadership best practices and insights from.

Our first AMA featured Valentina Thörner, Happiness Team Lead at Automattic – a 600+ person remote web-development company most known for creating WordPress.com.

At Automattic, Val leads a seven-person support team, spreading from Scotland all the way to Thailand, and spends her days helping to find blockers and identify opportunities to make their work even more impactful. She is also currently launching concierge services for WooCommerce customers and improving their ticket quality via a review strategy.

Her AMA was overflowing with inquisitive, precise questions around leading support teams, improving employee morale, and being a remote leader.

Here are the top 5 questions and answers from the AMA…

Question #1:

“What kinds of goals do you set for happiness initiatives, and how do you measure their success?”

Val’s Answer:

We have a three year plan for our Happiness division, that ties in with a three year plan for the entire company. However, since we can’t directly influence product development or marketing activities, we focus on setting up processes that allow us to serve our customers and learn from their experiences.

Since we can’t predict the future, our long term goals are based on customer experience. We’ve coded our goal into v 1.0, v 2.0 and v 3.0 knowing that sometimes things take longer, and sometimes you can take a shortcut. By focussing on outcomes and intermediate milestones,
we give ourselves the option to experiment with different tools, processes, ideas without losing sight of the long-term goal.

For example, one goal (which will resonate with many of you who are involved with your support division) is to offer consistent 24/7/360+ customer support across all product support departments. There are several milestones to make this happen:

  • Figure out how to staff for 24 hours.
  • Organize weekend coverage
  • Find solutions for holiday coverage / vacation policies.

Depending on the support channels that you offer you can then divide this down into live chat coverage, response time for tickets, video call options, social media replies (or whatever are your channels).

By plotting these milestones for each channel on your timeline (or version line), you end up with tangible goals for the next mini versions (or quarters), for example:


  • reduce ticket reply time to 12 hours
  • offer 18/5 chat coverage on weekdays


  • reduce ticket reply time to 8 hours
  • offer 24/5 chat coverage

By the way, we usually stick to the next two quarter
With these short/term goals in mind (clearly relatable to the long-term goal), you can now start experimenting — and this is when you can actually bring your support staff on board to find solutions, or to surface resource problems. For example, when branching out into 24/7 support, we’ve realized that we need to concentrate hiring on certain timezones to be ready for growth in certain parts of the world. Being a remote company helps in this regard — no graveyard shifts for anyone.

So, for every happiness initiative, it’s important to tie those in with the bigger goal. If someone proposes a new tool: how will that affect our ability to get to our version goal? If you can make a good case for it, we’ll probably give it a try. And this is valid for both bigger projects (e.g. scheduling solution for a support division of 200+ people) as well as smaller projects (testing on demand concierge services for a subset of certain customers).

Define a hypothesis about how this will take us closer to our goal or accelerate us getting there. Test it. Analyze the result and we’ll take it from there. And that’s valid for individual Happiness Engineers as well as team leads 🙂

Question #2:

When you are trying to secure funding for your initiatives, what are the business cases you are using to convince execs that it’s the best investment of the resources?”

Val’s Answer:

I am usually involved in initiatives around Customer Support. Here the main questions to answer are:

  • How will this impact our customers? How can this make their life easier?
  • How will this improve/facilitate the work of our Happiness Engineers, and in what way?

Whatever the initiative you are trying to start, you probably have a goal in mind already. See how you can translate this into numbers. For example:

  • Can this tool save time for team members so they can answer more customer queries and thus reduce response times?
  • Will this new process improve customer will it save time for your team members so they can keep up with customer satisfaction and ultimately reduce churn?

Now, sometimes it is difficult to prove these things upfront. You might have a theory, an inkling, but you don’t have numbers yet. In this case, find allies to set up a little experiment.

For example, for a long time, we weren’t sure if live chat would work for something as complex as WooCommerce. It works beautifully on the WordPress.com site, but WooCommerce stores are usually highly customized individual solutions. So, instead of trying to roll out live chat with everyone all at once, one team decided to try it. They organized an experiment to offer live chat during a set number of hours for a month. We then analyzed the changes in incoming tickets during those hours, the customer response, etc. And suddenly we had numbers to work with and to decide if and how to move forward with this experiment.

The experiment was so small that the investment was minimal, and since it was an experiment to prove a potentially bigger opportunity, no-one vetoed.

So if you don’t have the numbers yet, design an experiment small enough to go under the radar of resistance and create those numbers.
Sometimes you’ll be wrong. Or you are too early. And that’s fine. At the very least you’ll have learned something, and you’ll reuse those numbers (that did not prove your current case) in other circumstances.

Question #3:

(Okay, this is more than one question hehe…)

“What do you think are the main challenges of being in a large fully-distributed team?

Are the teams organized around timezone overlap?

What do you think Automattic does differently that makes it capable to pull off remote culture at scale, while so many others fail?

How do you do social bond events? Do you have events like company/team off-sites?”

Val’s Answer:

What do you think are the main challenges of being in a large fully-distributed team?

Time zones. For example, I am in UTC+1 and start my day pretty early (thanks, kids). One of my colleagues is in UTC-8, so we have to actively plan to catch up. If a high % of the teams is in a similar time zone (e.g., we are still quite US-centered), then it’s easy to miss discussions if you are in another time zone. We have to actively work on posting these topics and their results, waiting a couple of hours so that other time zones have an option to participate.
To account for this reality, I have shifted my schedule a bit. Once a week I work two hours after dinner, when my kids are in bed, to get my finger on the pulse of what is going on in the US side of the world (and pick the brains of my colleagues in that timezone).
Cultural differences can also be a challenge, e.g., how the US sees vacation as a privilege and Europeans see it as their right. Summer vacation planning can be stressful if one party thinks taking off more than a week is irresponsible and the other party thinks that anything less then 2 weeks is disrespectful to one’s family.

What do you think Automattic does differently that makes it capable to pull off remote culture at scale, while so many others fail?

Some things that probably influence here:

  • Communication. This includes documentation. Document everything, communicate everything, post, slack, discuss, summarize — and make sure you have a search engine powerful enough to wade through all of your internal creations (knowledge base, blogs, slack conversations, internal tools) so that past discussions can be referenced.
  • Trust. We mostly work on goals. Yes, your full-time position will most likely take you 35–40 hours a week, but no one will time track you (though, as a lead, and for productivity purposes, I’d encourage you to track yourself). We kind of trust that everyone is doing their best. And curiously, this has the effect that most people actually do do their best. And I like to think that those who don’t, don’t last too long.
  • Company — employee fit. We have a very intensive trial process during the application process. This is not only for us to find out if the person is the right fit, but also for the potential employee to evaluate whether they like this kind of work. Remote work requires a lot of self-organization and self motivation, and those coming from a “normal” corporate job sometimes realize that this environment is too lonely and too entrepreneurial (in the sense of organizing yourself). And that’s fine. We give both parties the time to figure out if this can work for both parties.

How do you do social bond events? Do you have events like company/team off-sites?

Yes we do. Once a year the entire company meets (well, let’s say 95%) for roughly a week. Each team will also have one team meeting a year, usually for about a week. Some projects and some task forces will also meet in person occasionally. These meetings are usually a mix of project work and socialization (and yes, some tourism). Outside of these meetups it very much depends on the team to organize their activities. My team does quarterly pizza parties, where we all have lunch/dinner (depending on the time zone) together and talk about stuff (anything but work). Other teams have joint challenges where they cheer on each other — it very much varies per team though.

And then, of course, there’s about 500 slack channels where you can bond with people around joint interests: dogs, cats, running, WOW, cooking, knitting, book club, toddler parents, linux users, home owners, etc etc

Question #4:

“What are the top three skills or characteristics you look for in hiring a support team member?”

Val’s Answer:

  • Ability to learn quickly.
  • Empathy.
  • Attention to detail.

Everything else can be learned.

Question #5:

“Can you share a little bit about your approach to developing and rolling our a new service offering (re: concierge services for WooCommerce)? We are trying to do something similar internally and I’m finding that designing a new service is a bit more abstract and challenging than focus on a product.”

Val’s Answer:

  1. Define your goal. For example, in our case, we want to increase renewals and reduce refunds. Boom, there are your numbers to track against.
  2. Define a test cohort. In our case that were people that have just bought product X.
  3. Depending on how many data you need, define how many people you want to include in your experiment and decide a timeline. In our case, we did a 1-week experiment past April (to find out if anyone would be interested) and are now doing a more structured 6-week test.
  4. Get volunteers to do those calls.
  5. Set up the documentation so your volunteers know what to do.
  6. Set up a booking system (youcanbook.me, calend.ly would work).
  7. Make sure you get an invitation to people that should participate (worst case: send them out manually — that’s what I do currently).
  8. Create a template so your volunteers can post comprehensive notes of their calls.

And then analyze your data after the experiment.

You might find out that people tend to have the same questions over and over again. You might find out that you have 60% no-show. You might find out that everybody asks how to pay for a second session — and then you can take it from there.

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Written by Claire Lew

CEO of Canopy. My mission in life is to help people become happier at work. Say hi to me on Twitter at @clairejlew.