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Career Development Doc

I'm Jenny, a Design Lead for Square's ECOM team. I developed this 1-on-1 doc to help my designers prioritize their career development and design beyond their day-to-day.
At a certain point in my career, I shifted my focus from designing the user experience to the experience of designing. Now instead of designing the websites, emails, ads, etc, I'm designing the workflows for others to create and manage assets. Just as important, I'm building the infrastructure that will help my team members get better each dayーthe systems and rituals designed to multiply the individual talents of my direct reports. 10% projects, peer reviews, etc.

A prime example is this Career Development Doc, a 1-on-1 doc I've devised to get my team out of the weeds and help them design beyond their day-to-day. This technique has made me a better manager, and afforded my designers space to grow and make work they're proud of. I've seen this Coda doc deployed by other managers in Square, and even outside of it.

Now I'm publishing it here, so you can try it too. But first, let me tell you a bit about how this doc is constructed and a few of its guiding principles.

Make space for conversation.

Have you ever gone into a 1-on-1 wanting to have a conversation about career goals or peer feedback, and then not really knowing where to point to?

When you create a career development hub, you can see all the puzzle pieces come together. Before, notes and proof points were everywhere: Individual development plans lived in Google Sheets, performance feedback in Apple Notes, goal-tracking in Google Slides, and hype (more on this later) in Google Keep. Bringing them all in one place means you both see a more accurate picture of where they are, which gives you better context for what they want. By having a Development section in our doc, I give space and structure to those conversations that we all know are important to be having but slip by the wayside as things get busy.

Write Operating Principles.

Before you can start collaborating on an employee's career development, you need to arrive at a mutual understanding. Tell them your approach to management, and ask them to write a set of Operating Principles, or areas that you both agree are critical for communication.

One-on-ones, all-in-one.

This is the section we look at every week. There's a table for agenda items, which we both use to capture notes, action items, reminders, and whatever else. Keeping these agenda items up to date is critical to maximizing our 1-on-1 time. (I like using a table instead of the freeform text editor because we can archive and filter out old entries if it starts feeling cluttered.)

Write a Development Plan.

Each person on my team has a career development plan, which we actively look at together every quarter. Most managers know that career conversations are necessary for talent retention. The common pitfall is that it's only a conversation. And inevitably, the practical demands and responsibilities of the job eclipse your good intentions to follow through. By putting career goals in writing and revisiting it every quarter, you show your investment in their longterm growth.

At the beginning of the year, I ask my reports to write down their personal goals (the goals should be unique and personal to them, or else they won't feel as invested). Every quarter, they update progress towards those goals, at which point we talk about where the person's at and align on what they need to do in order to grow in their career.

I find once a quarter is a good cadence to revisit. Of course we can always revisit more frequently as needed if their focus changes or performance reviews surface important areas for improvement.

Be your own hype person.

At Square we have a saying that you’re the owner of your career, you should be your own hype person (
). I wanted that ethos to live prominently in the doc. This Hype Section is the
je ne sais quoi
of the Career Development Hub, a place that’s just for the employee to collect bits and bobs of feedback, self reflection, and accomplishment to highlight for their manager— Slack screenshots of praise, etc. It’s a repository, of sorts, and should be added to at random, when things come up. I encourage everyone on my team to add to their hype docs regularly.

Remember you have resources.

Finally, there’s a section for the employee to access resources that build their skillsets, including modules from Skillshare,, and MasterClass. There’s a calendar view here so the employee can see when certain classes are coming up, and be reminded to register for them.

Career development doc.

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