What do I want to do with my c̶a̶r̶e̶e̶r̶ life?
A design manager’s guide to jumpstart career conversations with your team.
Let’s be honest, managing can feel like you are constantly undulating between surviving and thriving. Whether you’re at the beginning stages of management or a seasoned leader of many teams, sometimes you have perfect vision for a year, and other times like you can’t see past tomorrow. Career development is one area of management that remains an elusive responsibility to many. It’s often neglected when there are other competing priorities. Yet most managers don’t realize career development is what pulled your talent through the front door, and lack of it is often the reason they retreat out the back door.
The career conversations I had with my first manager happened roughly once a quarter and involved filling out some sort of document that asked me broad questions about my career:
- What are your strengths and weaknesses?
- What are your 1 year, 2 year, 5 year goals?
- Where do you want to grow in your skill sets?
- How will you get there?
I never liked this format. It felt like I had to boil down my life and professional career into a 45 min conversation and somehow this document was going to help me reach 5-year goals. It felt difficult to be sincere and vulnerable. (It also made me wonder if I could truthfully answer these questions considering how my manager might perceive me.) I felt career conversations should be layered — there were so many aspects to peel away before figuring out what to do next, let alone the next 5 years. I needed a manager that was willing to be a nonjudgemental witness to my self-discovery in addition to opening the right doors. What I wanted was a vulnerability coach.
Vulnerability as the gateway
I first discovered vulnerability in 2010 during grad school. While attending Pratt Design Management program, a classmate of mine introduced me to The Gifts of Imperfection by Brene Brown. The book changed my life — it set me on a different path both personally and professionally. Written by renowned TedX speaker and shame researcher Brene Brown, it promotes the importance of authenticity: what it means to face your fears, be brave in your own skin, and see the power of vulnerability as a driver of tremendous growth and creativity.
Admittedly, fear was one of the main drivers that led me to Uber after almost nine years at Google Maps. When I came to Uber in 2015, I made it a mission to tackle my own vulnerability. As much as I cherished my experiences at Google Maps, I felt like I had grown complacent. I fit into my own place so well that no one pushed me to change or grow. At Uber, I was determined to tackle the fears that were blocking me from becoming a better leader. I also did a TEDx talk about my fear of public speaking in Chicago. It wasn’t easy to be this brave and share my vulnerabilities — I hoped to find inspiration from my struggles rather than hide from them.
After the talk, I committed to incorporate more vulnerability into my day-to-day life. I began asking myself, “How can I practice being vulnerable today?” on a regular basis.
Start with your values
One exercise I learned at grad school was about defining my top 3 values. This helped me access what I believed in and discover who I was at my core.
- Authenticity. Honesty in one’s self and others
- Knowledge. Information is the currency in which I learn and grow. Learning something new in people, products, and myself is what I love to do.
- Love. This has evolved for me.It used to be about relationships, but at some point I realized I was avoiding the word love. It was a hard word for me to use because I didn’t grow up with a family that talked about their emotions and love for each other. It was implied but never spoken. So for me, love is about empathy, respect, and generosity towards others.
While I use these values to decide important decisions in my life, I knew that walking up to someone and asking them what their top 3 values are can make people feel exposed or completely lost. As a manager, I wanted to try to become the career coach for my reports that I never had myself by figuring out how to build trust so that people can open up to their vulnerable selves. Here are some techniques I have used.
Vulnerability in a group setting
So, how to get others to open up? An ice breaker game, of course. The “School of Life: 100 questions — Work Edition” fit that purpose perfectly. I bought this box in Amsterdam during a work trip and was intrigued by the deep questions it asked. I thought of it as a perfect ice breaker for my team during our weekly Design Crits where we casually review each other’s work. Prior to this box of career cards, I had made make-shift versions where I wrote out 21 questions on separate post-it notes and folded them into a small box for each person to answer. They ranged from questions like, “If I were CEO, I would…” or “if I had made all the money I needed in life, I would be doing…” They were questions I would ask my team at Google in 10 min standups every Monday. We talked and dreamed about our careers instead of discussing projects. It was our favorite moment of the week.
At Uber, I was able to leverage the same vulnerability exercise with an official ice breaker game that allowed our team to be open, funny, heart-breaking, and inquisitive about each other (and oftentimes about our parents). To me, it was an important muscle in finding new connections beyond work, building empathy and trust, and being free to inhabit our true selves at that moment.
A Foundation of Trust
The school of life and top 3 values exercise led to the first Career Conversation series I would host in one-on-ones with direct reports. Combined, these activities proved my thesis that vulnerability was the foundation in which our career development conversation can grow. My monthly 1-hour career convos series usually looked like this for the first 4 months:
This toolkit has helped me more effectively tailor every individual’s day-to-day work around their core career paths and motivations. I drew inspiration for my own career path by watching my team self-reflect and apply these exercises. The most important takeaway for me during these sessions was to put on my design hat to find patterns in these disparate stories that were often never spoken aloud. When you put a spotlight on an individual’s narrative, you invariably help them prototype their life and make a plan. My goal was to make career conversations simple and something to chip away over time, together. I encourage you to try this toolkit with your team. In pursuing your team’s path for self-discovery and a thriving career, I hope that this toolkit will also help you find yours.
