Your first 30 days in a Design Leadership role: A guide

You landed a job with the words “Lead” “Head” “Product” or “Designer” in the title! Congratulations! Now that’s out of the way, the fun/hard work/fun/hard work can begin. But what do the first 30 days in a design leadership job look like? What do you need to do in the first month to set you up for success?

This guide is for anyone starting a design or product leadership role, particularly in a start-up.

I started as Lead Product Designer with Genie AI (a start-up with a mission to open source the law through the power of AI) one mad, amazing month ago and it’s been flat out ever since.

Any design leadership role, particularly at a start-up, is a beautiful, complex, many-legged beast. So how to keep yourself happy, sane and productive? I wish there were a sexier answer, but unfortunately the main tools are a) planning and b) ruthless prioritisation.

My priorities for my first month fell into 3 main themes:

• Understanding the product & our users
• Baselining the company’s design maturity, and
• Establishing the Design team

Let’s take it theme by theme.

Before you start

For my own sanity, I knew I wanted to start Day 1 with a plan. My sage former boss, Head of Design at Pion, Max Dunne advised me to go in with a plan for my first 30, 60 and 90 days.

Think about all the things you want to achieve in these 3 timeframes and list out all the key themes. These themes will help you prioritise your work — when things come up outside of these priorities, your plan can help you say “no” with less anxiety.

The below was that I brought with me on my very first day at Genie. This pan will inevitably grow and change from day one — that’s okay.

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Another Day 0 activity was to create my own GenieGPT on ChatGPT, and to feed it enough context to tailor it with all the context I could find about Genie and my role there.

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1. Understand the product & our users

Product Context Megadoc:

You to get up to speed quickly to be able to have an impact. Maggie Crowley (VP of Product at Toast) outlined an amazing toolkit to do this on her episode of Lenny’s Podcast (Skip to 48m09s for the deets). I created a Genie 101 MegaDoc to populate with stuff like company goals, key metrics, competitor landscape, personas, key product features etc.

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Review the data you have:

In Week 1, I blocked out time in my diary to review our user research database and product analytics tools. Any themes I noticed went straight in the Megadoc.

Learn by doing:

I did my first user interview on my very first day at Genie, and kicked off my first research project in the second week. Combine your project-specific questions with more high-level stuff to help you get a grip on your users’ core problems.

After about 10 user interviews, patterns will emerged and you’ll feel like you have a firmer grasp of your core user needs and opportunities. This was single most valuable thing I did for myself in my first month at Genie. It made me feel informed and capable of making decisions.

I was lucky enough to end the month watching the incredible Michael Margolis running a Bullseye Customer Sprint. If you’re in a start-up and looking for a ruthlessly efficient research sprint methodology to understand your users’ core needs, look no further.

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2. Baseline the maturity of design

In order to make an impact on the state of design, you first need to understand it.

Meet with the whole company:

I was lucky enough to get some great advice from brilliant design leader and dear friend Dan Makoski. As Genie is fewer than 30 people, he advised me to meet with every single person in the company and ask them about their take on product design. So, I met with every person at Genie from Talent, to our academic interns, to the CEO and asked them all the same 2 questions:

1. Can you describe your current levels of collaboration with Product Design?

2. If you could wave a magic wand, what could the product design team do for you?

This gave me a 360 degree view on design from the whole company, and helped me prioritise the most important things to put in place going forward. I played these back to the company and it helped set the stage for the changes I wanted to make.

Quantify it with a survey:

The only thing better than improving things is improving them and measuring it! In my first week I sent out a survey to the whole company to baseline in numbers the visibility and impact of design. I got people to rank on a scale of 1–10 against the following questions:

1. How often do you interact with the design team?

2. How much visibility do you have on what design is working on both now, and in the future?

3. To what extent does the design team impact your daily work?

I’ll run the same survey in 6 months time to quantify our impact.

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3. Establishing the design team

Genie brought me in to establish and scale the design team. With me on board we went from a team of 2 > 3 with ambitions to bring on more designers later this year. As such, there wasn’t really a sense of design as a team with a proper identity and processes.

Establish a team identity:

We went into the office and spent 1 day nailing down the core parts of our team identity:

• Our name! (We went with Product Design Tribe)
• Goals
• Values
• Ground rules
• Design Principles
• Internal design team projects
• Meetings & ceremonies
• Notion space structure

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This sounds like a lot to do in a day (and it was!) but we were aiming for a first draft of the above, with finalised versions to be polished async. If you’re ambitious and strict with time, you can do it!

Establish a Design Process:

This felt like something important to get right early. We had new projects kicking off and I wanted to make sure every piece of work got the love and design thinking it deserved.

Dan Makoski’s brilliantly versatile design methodology The Pulse from his book Uplifting Design had been invaluable to us at Pion. I made an adapted version for us at Genie.

I also made sure to outline the collaboration between Design and Engineering at every step and get buy-in for this new process from our Head of Engineering.

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Audit and restructure our Design System:

As a team, we reviewed the structure of our design system — moving away from large files for each project, to a system of design system maps and WIP files. Our brilliant designer Mayse also managed to restructure out component library in under a week! Now we have a clean slate to start from to support our new design thinking process.

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Your design system and how you use your Figma files are totally foundational for how you work as a team, so getting them right early will save your bacon in the long run.

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Look after yourself

One key skill, particularly in a start-up, is the magic of saying “no”. This can feel scary, particularly when you have just started, but if your leadership is good they will support you and trust you to prioritise.

You don’t need to do everything in your first month, and this is a time when your main focus should be on leaning as much as possible.

There is always more to do, and the most important thing is to look after yourself and keep some sense of inner peace. It will all come in time, the important thing is to be strategic about prioritising only the most important pieces of delivery, and spend the rest of the time just talking to users.