Interviewed by Bhargavi Shankarananda
Three TPMs share their experience in our mid-2022 edition of TPM stories — including being your authentic self, and transitioning from IC to management.
Meet Carolyn Straub! Carolyn is the head of Engineering Program Management for Google Drive and Editors, which includes Google Docs, Sheets, Sites, Keep, Presentations, Keep and more. Carolyn has been at Google for over 11 years, holding a variety of program management positions in Trust and Safety, Google Technical Services (gTech), Gmail, and has worked as a chief of staff to a distinguished engineer. She is based just outside of Boulder, Colorado and loves skiing, hiking with her two dogs, and learning.
Tell us about yourself! How has your career transformed over the years?
Hi, I’m Carolyn and I am the head of program management at Google for Drive and Editors (sheets, docs, sites, etc). I’ve been at Google for 11.5 years and had a range of roles while at the company. I originally wanted to be a professor of Ethnic Studies or a lobbyist for human rights focused non profits when I was in college, I accepted a PhD program in Ethnic studies after my BA and deferred for a year after I accepted a Fulbright Fellowship in South Korea. So I moved to South Korea for the fellowship and had every intent to start my deferred PhD program a year later. While in Asia I went on a vacation and was hiking in a remote forest when I realized that I didn’t want to go to grad school right away. So I declined my program and moved onto my dad’s fishing boat in Richmond, Ca. For the next 6 months I worked at Borders bookstore and applied to jobs — over 200 of them! I applied to everything from being a prison guard to an office manager for the NAACP. Eventually I got an interview, and it was with Google. It started as an interview for a legal research position given my rigorous research background, but after 12 interviews they still weren’t sure if they wanted to hire me so I asked the recruiter if there were any openings on other teams and she suggested an assistant role. She said that while I had no assistant background, this leader had interviewed over 50 candidates and was difficult, so why not throw me in. I went to the interview and the leader stood up the whole time, so I stood up. We walked around the little conference room while answering questions, and we talked about our similar trips to east Africa and other random topics. And I snagged the role! It’s now been 11.5 years at Google and I went from being the assistant to a VP to a program manager working on product policy, to customer operations (like customer support), to pgm-ing Gmail infrastructure programs to what I do today which is manage a global team working on strategy and ops for Drive and Editors — which I love! In my personal life, I live in Boulder, CO with my husband and our two dogs, Rue and Toblerone. We love skiing, hiking, and reading together.
What have been some of the biggest learnings in your journey?
The shift from operational program management to engineering program management was a major one. Since I don’t have a classic technical background this was more of a learning curve for me. I wouldn’t recommend ops to backend/infra focused work, maybe do something more cross stack in one’s transition. ;) But what I did learn is that sometimes making larger leaps that are scary and super uncomfortable are the best ones you can make. While I don’t want to go back to the first 6 months of learning in that transition, it was very isolating and I was a little depressed wondering if I would ever add value, that pivot has led to the best work of my career and is something I will forever be proud of.
How would you characterize career development and what this means to you?
People like to think of career development as upward mobility — promotions, scope expansion, but I think we need to wiggle out of that definition of career development because more and more is not sustainable and honestly, it can lead to a life where work is all you do. Maybe that makes you happy, maybe it doesn’t but ultimately if you have the privilege to pursue a career that brings you joy, I think that’s what you should anchor on. I like to ask people on my team and myself things like: what motivates me? What are my values? When do I feel the most excited to work — what kind of work is that? What do I want to learn next? I use these types of questions agnostic of promotion/leveling to identify what development looks like for me. So in summary, I think career development is setting an intentional path on how you want to evolve your career to optimize for what you need next.
What were the top 2 challenges in your career and what was your mantra to surmount them?
Definitely what I said above, going from an ethnic studies background to operations program management and diving into infrastructure program management. My mantra was: you can learn, and moreover, you want to learn, the challenge of being out of your depth is temporary.
Maybe the second challenge was my funniest. My first boss at Google, who I was an assistant to, asked me to help him get a team bird. Like a real life bird. Let’s just say it took quite a bit of persuasion to convince him a pet bird was a terrible idea!
What is your favorite part of being a TPM? Where do you think a TPM adds most value?
I think most people who go into this field are detail oriented and love making organization out of chaos. I’m going to be honest, that’s not me. While I like those things, I gravitate more towards program management work that is about leading negotiations with challenging partners, working to influence to move an outcome forward, intercept chafing and mend. But this is a case in point — my favorite thing about being a TPM is that you can define your role quite a bit based on the needs of your organization, program/project, and what you want to lean yourself into. Few roles have so much flexibility on how you do your day to day — there are many ways that you can bring who you are to the task of reducing risk, keeping a team on target and moving things forward.
What is the most memorable program / project that you have driven as a TPM? What made it so memorable?
When I was a program manager in trust and safety I got to work on adwords policy and led a program to update all of our ads policies. This meant both eng work and ops work impacting hundreds of people’s work — so it was very fun working across teams and functions to get it done. While I can’t go into many details it was especially fascinating because policy is actually very hard to describe consistently and clearly across diverse case studies and cultures. For example, if you have a policy to not show ads (theoretically) for anything that causes harm to living things, can you show an ad for a kids science kit that requires inserting a chip into a cockroach (where the cockroach doesn’t die)? How do you describe consistently in words the difference between artistic nudity (allowed, like the David (Michelangelo)) and pornography (not allowed)? I loved the philosophical questions this program evoked and the way it triggered me to contemplate the world in a new way.
How would you characterize your TPM or leadership style? How has this helped you in the role and/or future roles?
I would say that I’m pretty far on the spectrum of being an “authentic leader” in that I always show up as who I am, without false pretenses or a veneer. This means that it’s pretty transparent how I’m feeling, what I think about a proposal, etc and instead of hiding feelings of frustration or impatience when it happens (hey, I’m human!), I just call it out openly. For example, “hey, I’m really sorry, I might be looking frustrated and it’s because of XYZ, so I’m wondering how we can work together to solve that and move this fwd”. I think this is helpful in quickly establishing trust with working groups because there’s openness that this gives everyone permission to have. We spend such a large percentage of our time at work, that it feels impossible to me to not bring my whole self to the office and I want to make sure others feel the space to do the same.