I Survived the First 90 Days
A case study on how to set yourself up for success even with the most challenging transition
Getting out of your comfort zone is essential for continuous learning and growth. As the poet Robert Frost famously said, "The only way out is through." This mindset, shared in the article I co-wrote over a year ago titled "Feeling Comfortable With Being Uncomfortable," has become a guiding principle in my life.
However, making the decision is just the first step; succeeding in the next stage is an entirely different story. This is exactly how I felt when I recently transitioned from a software development agency to an in-house design practice. While I could talk endlessly about making bold decisions and stepping out of your comfort zone to progress in your career, I'd be lying if I didn't acknowledge the uncertainty that comes with every transition into uncharted territories.
Fortunately, a book that I added to my reading list some time ago, and have even recommended in the past, has guided countless leaders worldwide through successful transitions, I'm talking about "The First 90 Days." In line with my learning style, I appreciate frameworks that I can leverage to optimize my process and use as a recipe for success, so I decided to give it a go.
It's important to note that this is not intended as a book review, nor is it a one-size-fits-all solution. Each context is unique, and how you apply the principles of the book to your transition will depend on the specific challenges you're facing.
Let's dive in!
1. Getting Started
At its core, Michael Watkins proposes a guide for individual leaders to diagnose situations, define core challenges, and design plans to generate momentum. The ultimate goal is to achieve early wins that instill confidence and create virtuous cycles to move forward. Instead of discussing my learnings chapter by chapter, I want to share how the overarching framework influenced my decisions and approach.
When I decided to embark on this transition, I intentionally took a break, only to find out later that it was the very first recommendation in the book, and for good reason. Allowing myself time for a mental and physical break enabled me to process the change. Simultaneously, it provided an opportunity for introspection and to celebrate this step in my journey.
Comparing this experience with past transitions, this deliberate pause made a clear difference in my state of mind during those crucial initial days. If you have the opportunity to take a break, please don't hesitate.
2. Learning and Diagnosing
Taking time off had an additional benefit for my state of mind: It made me more receptive to learning. A common pitfall during transitions is assuming that there's nothing new to learn before diving into action, which is far from the truth.
Following the book's framework, the first step was to plan what I needed to learn upon joining Reelgood. In initial conversations with my manager, I expressed my interest in understanding the business, the market, and the culture. He facilitated this by sharing his experience and connecting me right away with cross-functional team members for diverse perspectives.
At the same time, I analyzed the transitions I was going through and the situations I was about to encounter. The book enumerates several types of transitions, and in my case, I was (and still am) experiencing:
Moving to a new industry: Entertainment
Changing roles: Transitioning from agency-type to in-house
Joining a new company: Reelgood
As for the situations I would have to navigate, we're starting a Design System from the ground up, the B2C product is going through a pivotal phase, and our small but mighty design team is just getting started with the basics of DesignOps. Realizing that each of these situations will require a distinct strategy, pace, and key decisions to succeed, made the next steps easier and is a recurring theme throughout the book.
3. Negotiating Success
With the situations mapped out, the next step was diving deeper into the challenges for each and how to negotiate success. Rather than interpreting this as a green light to pursue my own agenda, I looked for early wins that aligned with the needs of others.
The book emphasizes the importance of negotiating and aligning expectations early on, ensuring mutual clarity from the beginning. With this in mind, and armed with newfound knowledge, it was time to align on the challenges I would tackle. This led to one of my favorite questions: What does success look like?
This is how my initial set of goals took shape in collaboration with my manager. They weren't rigid metrics, but rather an actionable plan to secure early wins and establish the foundations for long-term goals like these:
Lead growth design of the onboarding and NUX (New User Experience)
Plan and execute the foundations of the Design System, socializing its impact and facilitating the learning process
Drive a more systematic and lean UXR practice to increase user empathy
Each of my goals is directly tied to the situations I mentioned earlier. More importantly, this exercise enabled me to be strategic about my onboarding process beyond the first 90 days.
In the past, I've made the mistake of rushing to act on things, implementing disruptive changes too soon, or seeking a quick fix. Not this time. Instead, I paid close attention week by week to understand what was truly needed from me. I approached each task with a growth mindset, using previous learnings to integrate with the team's culture and processes.
4. Making Things Happen
This all sounds great, but it wouldn't matter at all if I didn't follow through. What helped me the most in making it all happen? Managing myself, which is, of course, easier said than done. With experience comes habits, both good and bad, so unless we approach these transitions with a beginner's mindset we can fall into the trap of our weaknesses.
The most significant lesson for me wasn't about creating a structure for learning and success, but about better understanding myself and using this structure for continuous growth. Through introspection, I identified areas for improvement:
Improve relevant business acumen by understanding the streaming industry
Increase user empathy by studying their behavior, needs, and pain points
Develop a true data-driven design through quantitative and qualitative research
Turning these into action items, here's how it played out:
In addition to catching up on Slack messages each morning, I now immerse myself in streaming industry news, treating it like my morning newspaper with an OJ.
I've collaborated with the CEO on a B2B project, giving me a deeper understanding of the business.
With abundant data available, I've committed at least an hour each week to reading and watching user feedback, which is always enlightening.
Coincidentally, a two-month Data Analysis course recently became available, allowing me to dive deeper into interpreting numbers.
I've become well-acquainted with Mixpanel for UXR, creating dashboards to leverage our data and uncover insights from it.
Given my affinity for structure, I've integrated these new habits into my calendar as dedicated time slots. Taking a page from
's playbook, my weekdays now include structured reflection and a healthy dose of Poolsuite.fm to capture my weekly learnings and plan for the next week.
Parting Thoughts
While transitions are inevitably full of uncertainty, they also present an incredible opportunity for growth. Now, 90 days later, while there's still much more to learn, I can confidently say that using this book as a guide turned the process far less daunting. As for how am I doing, I'm sure Eli (my manager) can tell you all about throwing me into the water and surviving to tell the tale.
The book may take some time to finish if you fill out most of the activities included. To make your process easier, I'm happy to share a blank copy of the Notion document I created while reading the book.
Learning shortcuts
The Learning Leader Show - Episode 180
Interview with Michael Watkins about the bookHow to on-board yourself when you join a new team by Wes Kao
7 principles to set yourself up for success during onboardingA User Guide To Working With You by Julie Zhuo
If electronic devices and IKEA furniture come with a manual to make your learning process easier, why not have your own user manual for others?The case study exercise by David Hoang
David's tracking approach for continuous progress documentation
It's always more fun to learn with others than doing it alone, so don't hesitate to reach out on Threads @laurieesc if you want to continue the conversation. If this article has been helpful, share it with a friend!
Over and out,
Laura ✌️
With Poolsuite.fm, anything is possible! Thanks for sharing your first 90 days Laura!