“It was really close, but we’ve decided not to extend an offer at this time.” I thanked the Lyft recruiter for her time and asked a few follow up questions on areas where I might be able to improve. After we hung up, I stepped outside and paced along the Cumberland River in downtown Nashville to reflect on the experience. But mostly, I wandered around and allowed that moment to suck.
To be honest, I was crushed. It felt like I missed my only shot with a “true” tech company—whatever that meant. I grew up in the Midwest and spent most of my twenties in Nashville. It’s one of my favorite cities in the world, but the talent is shallow outside of music and healthcare. I didn’t have direct exposure to the best product leaders in technology. I was more or less figuring it out on my own for the first six years of my career. Product at Lyft felt like a missed chance to level up my career in every way—position, company, equity, network, mentors, trajectory.
Over the next few days, I journaled to work through the disappointment of a missed opportunity. But the last thing I wrote at the end of that sequence of entries was, “I’m grateful for the opportunity. I’m proud of the way I prepared. I’m proud of my ability to take chances and risk failure. This will be a learning opportunity that I will use to grow and better myself.”
Get rejected, then get better.
You can’t control whether or not an opportunity is a good fit or the way someone evaluates you. But you can control the risks you take, the way you prepare, how you respond to feedback, and the energy you dedicate to improving.
Interviewing as a catalyst for growth
As it relates to your career, interviewing above your weight class is a way to throw yourself into the deep end and orient yourself towards a growth mindset. It’s really your only viable option. Otherwise, you’ll crumble.
Interviewing can be uncomfortable. You have something at stake. Both failure and rejection are real outcomes. But it’s an arena to practise taking risks to better understand your gaps, learn from top-performing teams, and become more receptive to tough feedback. It will also challenge you to get your thinking clean by distilling your frameworks for solving problems into their simplest form.
You can let fear of rejection and failure define you. Or you can face those moments with courage, learn from them, and use them as momentum to improve. With a growth mindset, risks are a tool to accelerate the rate at which you learn.
The irony is that in the days after I received the disappointing news from Lyft, not getting what I wanted created a deeper well of motivation and momentum than success might have in that same moment. Without that constructive feedback and the pain of coming up just short, I wouldn’t have put in the same time or energy to level up my skills.
What’s your fight?
As you pursue growth through calculated risks—like interviewing above your weight class—you must also determine what matters to you. Why is this important to you? What are you aiming towards? What’s your overall strategy? Otherwise, you will forever find yourself being pulled into races you’re not willing to run. You need something deeper than chasing external recognition and approval or you will be torn in a thousand directions without making meaningful progress in any one of them. You can’t be everything to everyone.
One of my guiding principles in life is self-sufficiency. I aspire to be someone who is always in the arena doing the work. As part of that, I want to reach the top of my craft in product. My ultimate goal is to use that to ship meaningful work that improves people’s lives and one day mentor others or write from a place where I’ve actually done the things I’m talking about. Failure in my eyes is forever operating in theories and refusing to take risks in my own work.
What tactics will you explore?
Once you know what you’re after, you need to determine what tactics you’re going to use to help you achieve your goals and level up your skills. This starts by reflecting on the interview and asking yourself the right questions based on the information gathered.
In the days and weeks after my interview, I reflected and got to work. The first step was reviewing the format and feedback from the interview itself. The final interview was four segments focused on analytics, partnership with cross-functional stakeholders, leadership (vision and strategy), and product execution. I knew that things got off to a shaky start because of how nervous I was going into the final round. I also received feedback that I was strongest in product execution. Based on my self-assessment, I knew I was mediocre in the analytics and strategy sessions. My answers lacked depth and were mostly theoretical.
My current team had the right structure in terms of being cross-functional, but lacked the frameworks that a product-driven organization had. Mainly in how we spoke about product, the emphasis we placed on metrics, and a lack of product strategy. Strategic principles in product were foreign to me. I also felt completely unequipped to handle challenging questions on analytics or get creative in the metrics I was exploring.
After reflecting on the interview experience and where my gaps were, I asked myself the following questions and used these to jumpstart the year of accelerated growth that followed.
- Where can I go to learn from the best leaders in product management?
- Can I develop greater comfort in navigating product metrics?
- How can I develop a deeper understanding of strategy?
- Is it possible to hone my confidence and develop better public speaking skills so I’m more comfortable in this arena?
- What can I do to differentiate myself and bring my own unique approach to product?
The answers to these came in a messy, often serendipitous way. I didn’t instinctively know the answers to each. But I felt like they were the right questions to get started.
How will you answer your questions?
The first place I looked was to product conferences. I wanted to understand how the best product leaders were thinking and talking about product. What models and frameworks are they using to build great experiences? What lessons resonated strongest with them? I personally benefited from Front and Mind the Product. The trick is you have to take that back and figure out a way to apply it to your current role if you want to cement that knowledge.
Naturally, these connections that I made at conferences with other product managers led to suggestions for certificates, workshops, and career development programs. I slogged my way through a Foundations in Data Science certificate at Stanford to learn that wasn’t quite what I was looking for. But that experience allowed me to get specific and pursue a more relevant Metrics for Product Managers workshop through Mind the Product. I took the information gathered during that session to craft better KPIs and carve out more time to be curious and explore opportunity areas using our analytics tools.
During the product metrics workshop, I sat next to a product manager who had travelled from Australia to San Francisco for the conference. At one point in our conversation, she mentioned that the best career development program she had ever taken was the Growth Series at Reforge. I made note of it and researched it as soon as I got home.
Reforge turned out to be one of the most impactful six weeks of my life. It forever changed the way I think about strategy and the product frameworks I use—especially as it relates to acquisition, retention, engagement, and monetization. I cannot recommend it enough. Again, you have to take these ideas, skills, and frameworks back to your current role. But Reforge challenges you to do exactly that with community-driven conversations, breakouts, and tactics for applying what you’ve learned to your current position. It’s up to you to gain a higher vantage point so you can apply the relevant frameworks to the product you’re focused on.
All of this provided a solid start on honing product-specific skills. When I shifted my focus to building my confidence in public speaking and high-pressure environments, I also explored a few directions. Toastmasters felt too formulaic—I didn’t need help crafting logical arguments, I needed to push my comfort zone in front of an audience. I shadowed an acting class but that was too niche and focused on improving skills in front of the camera. So I ended up signing up for an eight-week improv class.
Improv was slightly traumatizing but worth it. Improv greatly expands your comfort zone because at a certain point you just can’t care anymore about planning the perfect thing to say—you’re forced to be more flexible and let go. When you get here, you can find your way to a relaxed state of concentration in high-pressure situations (e.g. interviews). Speeches, presentations, and interviews become an opportunity to riff on key ideas, principles, or lessons learned, rather than perfecting a single right answer.
At the same time, I continued to read books across various disciplines. I’ve always believed this is the single most underrated thing you can do to level up your career. Product demands a multidisciplinary approach. The more flexible and wide-ranging your mental models, the stronger your decision making and the less rigid your thinking. In product, this allows you to evaluate things from multiple perspectives and gain the right vantage point to find the best path forward.
Putting it all together
As you’re reading this, the importance here is not in the specifics of what I did. Your path will certainly look different and the best thing you can do is embrace the uniqueness of your circumstances. What matters are the risks you take, the mindset you adopt, and the questions you ask yourself in challenging moments. That’s how you build momentum.
Over the following year, I wasn’t perfect. After the experience with Lyft, I was turned down in a handful of other interviews. But each one taught me something new and fueled my push to improve. It also allowed me to continue to refine my models and frameworks. With each interview, I built confidence in myself and my product skills.
By using this as momentum, I moved into a position where I had multiple offers and could be selective in choosing the best team, product, and problem I wanted to spend my time solving. This led me to my current role at Snapdocs which is the most fulfilling position I’ve had in my career—thanks to the depth of our team, the complexity of the problems we’re solving together, and the impact we aspire to have.
Push forward, don’t retreat
Interviewing above your weight class is one of the best ways to test your confidence, frameworks, and identify where your gaps are. It’s a method to shift into a growth mindset and use it as motivation to learn and level up your skills.
If you have the courage to take calculated risks, the self-awareness to reflect, and the humility to accept where you are today, you begin to gain real visibility into your gaps. And once you know your gaps, how are you going to challenge yourself to learn and grow? What questions will you ask? How will you leverage that knowledge and create your own momentum?
True growth isn’t found in the moments when things are perfect but rather when things get painful and on their surface feel disheartening. A willingness to risk rejection can be a greater catalyst for your career than any single achievement or accolade. But you must also use that knowledge to think deeply about where you’re going and what tactics you can leverage to get there.
Your deepest fire is closer than you think. It’s kindled by leaning into the challenging moments when you find yourself at the edge of your current limits and you decide to push forward rather than retreat.
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