As a Manager, Using ‘Radical Candor’ With My Team Has Been Transformative — Here’s Why

It’s an adage you’ve probably heard before: keep your personal life separate from your professional one. But while maintaining an awareness of professional boundaries is, of course, important, the idea that these two spheres can remain totally separate from each other isn’t just unrealistic — it could also hold you back from reaching your true potential.

That’s why Kimberly Lin, Group Product Manager for Squarespace’s Commerce team, believes in taking an integrated approach. By subscribing to a practice of “radical candor” with her direct reports, Lin says she’s able to gain an understanding of how the personal intersects with the professional, and how best to support them in each. It’s a value system that Squarespace as a whole backs.

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“I care deeply for the people I work with, and this is definitely true for the people I manage; I am curious about what motivates them, and I’ve found that the best way to truly understand and empathize is to ask questions and listen,” Lin said. “My manager takes this approach (with me) as well, and it makes me feel respected and gives me the ability to focus on my work rather than feeling like I haven’t been heard.”

Recently, Lin shared with Fairygodboss the tactics she uses to manage in a holistic, empathy-driven way, as well as what excites her most about being a manager at Squarespace.

Tell us a bit about your job. What’s your current role, how long have you been in this role, and what were you doing previously?

I’m the Group Product Manager for the Commerce team at Squarespace, and I’ve been in this role since July 2018. I specifically manage the development of new ecommerce tools, which help empower our customers to succeed on our all-in-one platform. I joined Squarespace in October 2015 as the Product Manager for the Commerce team, at a time when both our Commerce and product teams were a lot smaller. I feel grateful to have been a part of Squarespace as our company and teams have grown.

Before Squarespace, I started my career as a consultant, helping our clients integrate their systems with enterprise software. I realized that the work domain and travel lifestyle were not for me, but that I liked understanding our users’ needs, designing solutions to problems, and working closely with teams to launch new features. I then worked at Travel Tripper, a small hotel tech company that built booking engines for small properties, and subsequently at Shapeways, a 3D printing marketplace where I worked on ecommerce and built tools to help designers sell their products.

Through these jobs, my role has been to drive product development from conception to launch by understanding customers, defining problems we need to solve, prioritizing the most impactful products, and partnering with engineering and design to create solutions that impact the lives of our users.

What were your initial thoughts when you learned you were becoming a manager?

I first learned that I would have the opportunity to hire for and lead the Commerce PM team in January 2018. Since I joined Squarespace, I have always been transparent with my manager that I wanted the opportunity to lead a team of PMs one day. We had a lot of conversations about when would be the right time and the competencies I could develop in the meantime, so the conversation and transition happened organically. I was incredibly excited and optimistic, both by the larger scale of impact I could have on Squarespace and also by the new experiences that would challenge me and help me grow.

How has your day-to-day work changed since you became a manager? What about your overall approach to work?

At the surface, the mechanics of my day haven’t changed much — I am still in a lot of meetings and spend a lot of my time talking to people and thinking about products, similar to my time as a full-time product manager.

However, what has changed meaningfully is what success means in my role and what I find rewarding at the end of the day. I find it rewarding when I can help a PM on my team discover a new path, or when they successfully advocate for and change someone’s mind about an approach. I find it rewarding when they show meaningful improvement in a development area, and when they nail a presentation. I am successful when my team is successful — both in terms of their contribution to the company and also how they progress against their personal and professional goals. As an individual contributor, I saw the impact of my work instantaneously because I was the one directly doing it. As a manager, I see the impact of my work gradually over time, but it is tremendously more rewarding. 

What’s the No. 1 thing you hope your direct reports are getting out of working with you?

I hope I empower my direct reports to be fearless in participating to their fullest. It sounds really cheesy! I have seen countless examples of people at work (myself included) who hold back on sharing their opinions because they are insecure, fear there will be consequences for disagreeing, or believe people with “authority” know better. Ultimately we hire people because we want to hear their perspectives, and diversity in thought is what helps us arrive at the best solutions. Insecurity, fear, and doubts can creep up on any of us, so I hope to create a safe and non-judgemental environment where we can be direct and talk through ideas, hopefully guiding them to a point where they are confident in where they stand and empowering them to engage fully. It’s not about being right but rather sharing’s one thought process, and of course listening to others, and being willing to compromise when appropriate.

What’s one strategy you’ve used when managing an individual (or team) that you think has been particularly effective?

I enjoy Radical Candor and its approach to career conversations. In essence, each person’s ambitions are influenced by their past experiences, their current outlook, and where they see themselves in the future. Radical Candor recommends a three-part conversation, which I hold with all my direct reports when they join: a.) life story, b.) dreams, and c.) career action plan. By walking through these conversations, I get a well-balanced view of what motivates them and why.

The Life Story conversation in particular is my favorite — it’s an opportunity to hear how this person came to be who they are and it oftentimes is very revealing about the person’s character. I remember every one of these conversations vividly and have walked away inspired and with a deeper understanding of the person I’ll be supporting, both personally and professionally.

How do you think about making sure your direct report(s) feel well-supported in their lives both in and out of the office?

I care deeply for the people I work with, and this is definitely true for the people I manage. I am curious about what motivates them, and I’ve found that the best way to truly understand and empathize is to ask questions and listen. While I may not always agree, I always work to understand their perspectives. My manager takes this approach as well, and it makes me feel respected and gives me the ability to focus on my work rather than feeling like I haven’t been heard.

I don’t believe there is a clear separation between what happens inside vs. outside the office. Many times, what happens outside of work influences the energy we bring to the office, and vice versa — and that’s ok. Each person has a different comfort level with how much personal information they share at work, so I never expect people to divulge information they don’t want to, but I always try to give space to people when I know or notice someone is having an off day and let them know they can always take a moment to themselves.

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