New lead onboarding

This is a summary of the presentation I gave at the CMS Africa Summit 2021, a virtual event.

In the wake of COVID-19, lots of businesses took their stores online. That resulted in a boom for our product, but also one for our support load. One of the ways we addressed this increased influx of requests was by more active hiring. The result of more Happiness Engineers is that you need more team leads.

Team lead growth

The above image shows our growth in just over a year. Xs represent people moving out of the lead role, pause buttons people on parental leave or sabbatical (yes, Automattic provides up to 6 months fully paid parental leave and 3 months of paid sabbatical per 5 years). Currently, of the current 13 leads (incl. those on extended leave), only 4 have been around for longer than a year.

Prepping leads: What we had

Automattic is a fairly unique company in that becoming a lead doesn’t mean you’ll get a salary bump. I’ve written more about that in this post. In Happiness, we also don’t hire from outside because a lot of the job entails coaching Happiness Engineers in doing the work, and we’ve found that a deep understanding of that work is important. We also believe that leadership is a skill that can be learned to a big degree rather than it being a character trait. So we expect leads to grow into the role rather than first expecting them to already be a stellar lead.

The only more organised programme we had in May 2020 was our lead cultivation. When we identify a potential lead, I chat to them about it. Then, if they’d like to explore this further, I reach out to HappEx; our Happiness team focused on Happiness experience, ranging from hiring over onboarding to continuous training. Our colleague at HappEx then goes through a programme with the potential lead to address several topics and considerations that will be part of being a lead. This may result in the potential lead deciding the lead role is not something for them.

For the rest, we mostly had many documents, posts, ideas that were all over the place. Because we didn’t have a lot of new leads, we figured out along the way where to get the information.


While this approach of getting information along the way is maybe okay on a small scale, it’s a waste of time for a company that’s growing fast. In chats with HappEx, other division leads and HR, we noticed that newer leads were pretty much all were struggling with the same or similar experiences and questions.

So I found the right partners and figured out what those recurring challenges were. I chatted to HappEx, HR, tenured leads, and new leads about their experiences and observations. Based on this, we wrote a long list of recommendations for the next steps.

Especially my chats with our HR wranglers turned out to be an invaluable source of insight. HR people are often portrayed as a last-resort stop; if you really can’t go any further, you chat to them. This is not the case at Automattic. Our HR colleagues are some of the nicest and most caring people I know. They are also very wise, and I loved getting their input. The list of recommendations was great, but my tightened collaboration with HR in itself would’ve already added enough value to engage in this project.

That said, we did have more than just this deepened collaboration.

Guiding principles

With each of the recommendations we had, we tried to look at a few guiding principles:

  • Automate repetition. If the same process is repeated each or several times, find ways to automate it. For example, we used the patterns function on our P2 tool to create a reusable format.
  • Sync efforts. As the company grows, many people have tasks that slightly overlap with one another. Actively look for partners and sync your efforts. For example, part of our recommendations were new approaches, but we also gave several suggestions for the lead cultivation programme that HappEx owns.
  • Clarify unclarity. This seems like an open door, but if a new lead asks a question, answer it. Don’t assume that things you take for granted are clear. An added benefit is that you will likely start questioning some of those things you’ve taken for granted.
  • Document everything. It’s only once you have a lot of new people join (and the newbies outweigh the tenured people) that you start realising how much institutional knowledge is just part of our collective memory rather than written down. We’ve written down a lot over the past months.
  • Test and tweak. When it comes to onboarding and training plans, there’s a tendency to want to create a perfect experience. You’ve identified a problem and now you want the solution to be on-point. However, that can slow you down so ship whatever you have and tweak it along the way. For example, the onboarding checklist that the leads who joined last week used is in a better shape than the one the leads before that used because we tested it on those leads.

What we have now

As a result, we now have a much more holistic and comprehensive approach to onboarding new leads. There are three major areas where we provide coaching and guidance.

Before someone becomes a lead

We have two major approaches before someone becomes a lead:

  1. Lead cultivation. I’ve introduced this above already. We continue to be strong believers of this programme as it helps future leads prep.
  2. Guilds/projects. We have a lot of tasks that are recurring or once-off that aren’t part of the job package of each Happiness Engineer. For those tasks, we set up either guilds (recurring tasks) or projects (once-off tasks). Both of these are great opportunities for Happiness Engineers to get their feet wet as leading a guild or a project allows them to experiment with a set of leadership expectations.

During the first months

When someone becomes a lead, we focus mostly on how they coach their team members in the first months rather than on the whole division. We also take the time for them to get familiar with the role of a lead and do this in three ways:

  1. Lead handbook(s). I’ve mentioned above that we try to document everything. The main place where we do that is in the lead handbooks. We have one for all Happiness leads and one for Woo Happiness leads specifically. It captures things like “imposter syndrome”, “how to lead a meeting”, “where do I request leave?” and much more. They are both very much a work in progress.
  2. Onboarding checklist. There are so many small tasks that we need to perform when someone becomes a lead. For example, we need to give them edit access to our leads Google calendar. Or we need to give them a manager role in our scheduling tool. It’s easy to forget a few tasks, unless you make a checklist out of it. We now have that.
  3. Discussion topics. I have also created a template that I share with the HR wrangler and my HappEx colleague. It’s a doc that contains a lot of discussion topics we’ve identified as something newer leads struggle with. However has a call coming up with a new lead can go to the shared Google doc, review the notes others have left there and choose a topic from the list. This ensures that I’m in sync with HR and HappEx about the needs of a new lead.

Other than these Woo Happy specific offers, our .Learn team that focuses on continuous education across the company offers new lead onboarding sessions. They also organise training provided by Reboot. This brings leads together to grow in their skills. I attended this training in 2018 and still apply some of the principles I learnt there.

Throughout their role as a lead

Finally, we have a few processes and tools that help us coach leads no matter their tenure.

  1. Leadership dens. HappEx facilitates leadership dens — smaller lead groups across all Happiness divisions. They are safe spaces where leads can express their concerns, wins, challenges, and learn from each other.
  2. Expectations. The division leads together worked on a clear document that captures what we expect of our team leads. It contains things like “you meet at least once per two weeks with each team member”, “you submit a performance review at least once per year”. Not sure for new leads, but also for tenured ones, it helps make the right decisions about priorities. It also makes it easier to understand how well they are doing as a lead.
  3. Rubric. We’ve further also developed a rubric that allows us to measure up the observable behaviour of the leads with the expectations we’ve set. It ensures that we approach their performance holistically and not zoom in too much on just one dimension of our expectations. Both the lead and I complete the rubric and the ensuing discussion about this results in our shared understanding of their performance.
  4. Culture of feedback. Finally, we try to cultivate a culture of feedback. It was only recently that I realised that subconsciously we had attracked leads who are great with feedback. They take feedback from their lead, their peers and their team members gracefully and act up on it. They also aren’t hesitant to give me feedback with candour. We are very much a learning organisation and that’s only possible when people feel safe to express areas for improvement.

Oh, we’re hiring

Does it sound appealing to you to work for an organisation like this? We’re always hiring, and I’d love to become your colleague. Go over to our Work With Us page and join our team!

Slide deck

🎵 Post written while listening to Common’s A Beautiful Revolution, Pt. 2


One response to “New lead onboarding”

  1. […] left. That’s resulted in us welcoming many new leads. Next to looking into how to do that (which I wrote about here), it’s prompted me also to regularly think about what characteristics I look for in […]

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