Square’s 1-on-1 Toolkit: The secret to managing your team’s careers

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Square’s 1-on-1 Toolkit: The secret to managing your team’s careers

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.
Copy this doc, then read on to learn how to use it to up-level your team’s career development.
Copy this doc

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 doc, a 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?
The is my mission control for managing my teams; it’s where we define actionable goals that are tied to specific sections of the career ladder, track progress towards each goal, set 1:1 agendas so that time is well-spent and focused on clear objectives, and capture kudos—all in one place.
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. Integrating all these pieces provides a more accurate picture of where an individual is, where they want to go, and how best to support them in getting there. By having a dedicated development section in this doc, I have created space and structure to prioritize career growth—conversations that we all know are important but can easily slip by the wayside as things get busy.

Write a partnership agreement.

Before you can start collaborating on an employee's career development, it’s helpful to arrive at a mutual understanding. The is an opportunity to share your unique management style, and ask them to write a set of shared expectations, or areas that you both agree are critical for communication.
Since publishing this template, I’ve seen a ton of creative additions to this section. Everything from an embedded map of an employee’s work location to pictures of family, pets, and recent vacations. Personalizing your partnership agreement with each employee makes it feel more fun and less formal, which opens up the doors for communication.

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

We look at the section 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 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 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
person (
). I wanted that ethos to live prominently in the doc. This Hype section is the je ne sais quoi of the 1-on-1 Toolkit, 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 pages regularly.

Remember you have resources.

Finally, there’s a page for the employee to access that build their skillsets, including modules from Skillshare, Lynda.com, 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.
Want to dive deeper into 1-on-1 best practices? Check out Raechel Timme’s of expert advice.

Square’s 1-on-1 Toolkit.

The rest of the doc is fairly straightforward. Here’s an outline of the different parts of the doc:

Here's the fun partーthis doc is meant to be copied and used! If you would like to try this technique and need help implementing it, the Coda team has graciously offered to help. Click below to get assistance:
Copy this doc

I spoke about Square’s 1-on-1 ritual during the Coda Block Party 2021 keynote, which you can watch below 👇

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