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:

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:
- 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?
- 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.
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