A Day in the Life: Trish Craine (Technical Program Manager, Squarespace)

Trish Craine

What has been your journey in tech so far?

I feel like I’ve always been a project manager, even when I was a kid. At a young age, I was always trying to find the most efficient way to do something and had a keen awareness of dependencies. My liberal arts education (read: English Literature major) led me to the book publishing industry, where I eventually became a managing editor at a publishing house — effectively, a project manager of making books. When a redesign of one of the company’s websites was going sideways, I was given the opportunity to project manage my first software project, and I haven’t looked back since.

Briefly describe the role of Technical Program Managers at your company

Simply put, TPMs aim to make shipping software easier and more predictable at Squarespace. From asking tough questions in meetings (“How do we know we’ll be done with this feature?”) to updating our stakeholders on project status to driving technical roadmaps to meet company goals, we help drive the project planning and delivery process by systematically identifying and solving problems.

What has been the biggest challenge you’ve faced moving into your current role? How are you working to overcome the challenge?

Having built a career as an individual contributor, it was a tough shift in mindset when I was no longer managing my own program, but instead taking responsibility for the output of others. At times I found myself handling obstacles my team was facing as their peer, but I was the person who could actually unblock them by making a priority decision and increasing their bandwidth. Once I fully realized that I can help improve the output of others — whether by coaching or unblocking them — I was able to support my team more effectively.

What does your typical day look like?

My days are usually split between weekly one-on-ones with my team (direct reports, manager, and fellow TPM leads) and pockets of time where I can focus on what I need to get done for the week, like strategic thinking around TPM staffing and giving input on our company’s planning process. The dedicated time to speak one on one with my team every week is the best place for me to hear about their wins, understand and coach them through their challenges, learn about risks a business-critical project is facing, and pass on any information I have that can help them move their work forward. The time I spend with my manager is similar, but with me on the other side, and when I meet with my colleagues who are helping lead the TPM team, we learn from our shared experiences and take action on things that will help our team overall.

What’s the best and worst part of your job?

Instead of getting my energy from shipping software, these days the best part of my job is matching my team with the right opportunities and seeing them succeed and add value to the company. I’m grateful that so many of those opportunities have been in that sweet spot of filling an important business need and getting that team member closer to their career goals.

What is the best piece of advice you’ve received?

I’ve always gravitated toward being transparent. When I was running a program with projects, I made sure that my teams knew every piece of information I knew. Having shifted into a management role, my instinct for transparency remains strong, but it’s not always required and can sometimes create confusion or frustration. I’ve been advised to ask myself: “Is this piece of information truly going to help this other person?” That has helped me clarify the intention of my instinct to overshare.

What is your most useful resource (book, blog, newsletter)?

Lara Hogan, who is a management coach for the tech industry, gave a talk at Squarespace a couple of years ago on sponsorship and mentorship that really resonated with me. (The irony is not lost on me that having this opportunity to share my version of “A day in the life” is the result of being sponsored by someone.) Since then, I listen to everything she has to say and find that her advice is an appealing blend of concrete actions managers can take to improve and timely topics (e.g., inclusivity and leading through crises).

What’s one thing you’d like to learn, develop or work on in 2020?

I want to master the art of being brief and to the point when communicating.

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