The People Angle: A Lens on Career Advice & Job Seeking in Tech

How to think about “the people you’ll work with” when growing your career

My most important career lesson comes from my dentist (who is also my father).   He has practiced for 50 years and could have retired years ago.   It wasn’t money or the craft of dentistry that keeps him practicing.  It’s not a desire to stay busy – he has a fulfilling hobby outside work as an artist. 

He just can’t envision giving up the relationships he has with his patients and staff.  After 50 years, he’s accumulated a deep sense of connection across generations of families that comprise his patient base.   My early years were filled with dinner table conversations about the latest updates from his patients’ lives and pauses during those trips to the movies as he runs into patients. Human storytelling and connections were always on display.

Choosing a new team or job for its “people” is a common decision criterion in tech careers.  Every job has a human dimension to it and in tech a force multiplier to a person’s impact is working on problems that require hundreds of people to effectively solve.  I talk about this in my career retrospective in a section entitled “Software is about people, not bits” and I will expand upon it here.

What does choosing a job based upon “the people you’ll work with” mean?  What skills should you develop to maximize potential relationships?   How does the art of working with others mature as you grow in your career?

I wanted to share my own journey across this dimension, written as a note to my younger self.  The result is a maturity model for the People Angle in career decision making. 

🙋‍♀️ Stage 0: Focusing on the excitement of problem solving

When you first start out your career, it is natural to choose a job based upon the type of work you’ll do and not who you work with.   Examples abound: You are biased to look for hard technical challenges.  You have a friend who likes to work only on gadgets.   It’s intriguing to be on the forefront of technology.

Some people stay in this stage of development for their entire careers – jumping from job to job, motivated by the degree of intellectual interest in the problem they are solving.  For you, though, your goals balance out with a more holistic view of inclusion and leveraging systems larger than yourself.

Questions to ask to push yourself in this stage include: “What motivates me?” “What do I think about even outside the office?”  “Am I satisfied with only thinking about my own technical problems?”

🏈 Stage 1: Work as a social circle

In this stage, your work group becomes a place to hang out.  In the one or two years after you graduate college, the newness of the work problems wears off and you are looking for social connections. 

Flag football clubs, microwave Peep jousting tournaments, office pranks – these are fond memories of bonds forged during a period when you and others are finding an identify for a new chapter in life. 

For you, though, work as the center of your social life doesn’t last.  You develop relationships with people with similar interests outside of work. Marriage and family creates a center of gravity bigger than any social pull that work can provide.  You’ll build lifelong friendships with early in career buddies and you enjoy being around work colleagues, but the stable state is two poles: one around professional relationships and another social circle around family.

Questions to ask to push yourself in this stage include: “What is fun at work mean to me?”  “Do I have an outlet at work to relax?” “Do I want my social circle to be overlapping with my work?”

🧠 Stage 2: Prioritizing intellectual horsepower

Here you begin to wake up to the fact that the people you work with are important to getting your goals accomplished.   You naturally gravitate towards working with “smart people.”

The crux of this stage is that you prefer situations where conversations feel high bandwidth and problems can be synthesized quickly.  It feels more like the TV show The West Wing than The Office.

Questions to ask to push yourself in this stage include: “Whose opinions do I respect the most?” “How does my team come up with diverse and new thoughts?” “How frequently am I frustrated by the pace of conversation?”

🤝 Stage 3: Learning to trust

As you progress in your career, you develop shared wins with smart people.   Your concept of people graduates from inputs like intellectual horsepower to outputs like a shared track record of delivery and success.  The concept of trust enters your vocabulary.    

One specific example from my career starts five years ago as we were rebooting the user experience for our product.  We doubled the size of our design and user research team.   At the time, we were too much an engineering and product centered organization, so it was my job to create a platform of influence for these new design leaders.   I learned to trust that they were better product designers than I ever could be and established systems and norms to empower their work.

Questions to ask to push yourself in this stage include: “Who am I depending on and how do I hold them accountable?”  “What does trust in the workplace mean to me?”  “Who needs my support and how do I provide it?”

⚔ Stage 4: Seeking out healthy conflict resolution

This is the stage where you realize the best successes at work are forged in crisis and healthy conflict.   It is an amazing experience to work in an environment where multiple ideas are debated, tension leads to non-linear breakthroughs, and conflict resolution is productive. 

There is a famous F. Scott Fitzgerald Quote that goes: “The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.”  This quote can apply to organizations as well as people.

A recent example from my career is the launch of a new product at Microsoft called Microsoft Search. This was born from a coalition of diverse parts of the company – our consumer Bing group, our acquisition of a company called FAST, our AI research group, our core compute and database group underpinning our services, and the SharePoint group that has historically owned the scenario.   You can imagine the competing priorities and tensions that different lens and business goals brought to the table for this coalition: bringing existing customers along, incubating new tech, competing business models, different philosophies on how to build great product.   It was messy at times, my reputation was far from perfect as I pushed what I knew to be right, yet we developed an environment of shared trust that allowed effective decision making. Critically, we kept the focus on ideas and customer needs and not hierarchy and politics.

The details of how we accomplished this are outside of this post, but a basic overview is this graphic that I created to share the approach with other senior product leaders at the company:

The key to this stage is to care enough to not just “go with the flow” and accept mediocrity.  It takes clarity on what roles you and your team play, empathy and shared understanding of competing viewpoints, and a framework for encouraging and resolving dissent among people who care deeply.   I’d recommend the book Radical Candor by Kim Scott for tips here.

Questions to ask to push yourself in this stage include: “How does my organization resolve conflict?”  “Who pushes me to do my very best work?”   “What value does my team provide to the larger organization?”   “Can I be honest and effective at the same time?”

🤗 Stage 5: Finding your first team

You’ve gone from loving hard problems to social hang outs to betting on people to using conflict productively.  Honestly, it is pretty exhausting!   This stage thinks about how the people around you can be a source of emotional support and fill you with energy.

I talk about the concept of a “first team” in my career retrospective.   This is where you can be yourself, vent in a safe place, and feel your most psychologically safe at work.  This may or may not be the people you work with most closely.

As an example, a few years ago I decided to lean in to developing a sense of first team with my direct peers.  This wasn’t the group of people I worked with closely (those were leaders in other teams), but it was a forum to safely share my fears and vent, work problems without fear of being judged, and put energy back into my fuel tank.  It was never urgent or imperative that I built these relationships yet in hindsight it was the #1 thing I have done in the past 10 years to make me love my job more.

Question to ask to push yourself in this stage include:  “Who is my first team?” If you ask yourself that question and it brings a smile to your face as you think about that group of people, you’ve found a good home.

🥕 Stage 6: Returning to sources of motivation

The final stage returns to the themes of stage zero: It’s about what motivates you to do your best work.   You realize it’s not primarily about gadgets and hard problems.   Your motivated by a deeply intuitive sense of how your work enables people to live better lives.

The product I’ve worked on for a long time recently celebrated its 20th birthday.   One of the things that overwhelmed me was the outpouring of stories from partners and consultants who built on top of our platform.   Here’s a few select social stories that paints how the product had an impact on their careers, supported their families, and built community:

I am prouder of these stories than any other metric we define for success on our team.   For me, success is more than the graph that’s up and to the right or the cool tech problems solved or an obsession with disruption.  It’s about the people I’ve known and a well-developed intuition about how I’m helping them.   Just like my dentist.

Coda on Privilege

We end most Mind The Beet posts with a note on where we chose to spend our volunteer time and money.  There is no doubt that when I talk about networking and feeling safe to use radical candor with peers that I am coming from a place of enormous and multi-dimensional privilege.  Seeing Helen navigate work life in the tech sector as a woman continues to give me perspective of one aspect where it is 10x easier for me to navigate and feel safe than her given our genders and historical norms in tech.   There are many causes that advance a more equitable and representative tech workforce.  A team member of mine is involved in SWE, which you can donate to here: Society of Women Engineers (swe.org).  Helen and I also donate to the Center for Excellence in Diversity and Engineering fund from our alma mater, UCLA: Funding Initiatives | UCLA Samueli School Of Engineering