Dan Na, Senior Engineering Manager at Squarespace

How to push through friction as your team grows

In this episode of Lead Time Chats, Jean Hsu, VP of Engineering at Range, chats with Dan Na, Senior Engineering Manager at Squarespace, about pushing through friction.

Dan and Jean discuss:

  • The inevitable friction that arises in fast-growing teams and companies
  • Mindsets for thinking about pushing through friction as part of the job
  • The normalization of deviance and how it shows up on engineering teams
  • Focusing on what you can control vs. being a victim of your circumstances
  • When and how burnout shows up, and frameworks for alleviating or avoiding it.

Additional Resources:

Takeaways from Dan

There are productive and unproductive ways to look at friction

“Early on in my career, I often developed a sentiment of like, man, is everyone an idiot? Don't they know that I'm doing this work because it's better for all of us? If everyone could just see that this was important, then everything would be so much easier. And the problem with that is that it's this very negative, spiraling, unproductive mindset that almost guarantees burnout. And as I've gotten more experience, I learned that people are busy, people have competing priorities, dramatic company growth introduces a lot of problems. It's not because everyone's an idiot and that is the most reductionist and easiest and most destructive conclusion.”

Focus on what's in your control when pushing through friction

“With enough resolve and the right attitude, you can be the person who finally changes those things for the better. I can't control company growth. I can't control a lack of responsiveness in Slack. I can't control gaps in ownership due to reorg, but I can't control how I respond to them.  If I look for alternatives to push for the outcomes that I want without compromising my mental health and my attitude, I can ultimately have an impact in the face of all this friction. I'm not a victim of my circumstances anymore.”

Prepare for and factor in friction on your journey

“Knowing about friction from the start makes it much easier to avoid this burnout.  It's kind of like if I'm going to go on a road trip, and I know it's going to take awhile, and right before I leave, I check my phone and I'm like, oh, there's a bunch of traffic... I probably prepare a little bit differently. Like, let's say there's only one way. I can't redirect around the traffic. I have to go through the traffic no matter what, but I know that the traffic exists. Sudden traffic is infuriating for everybody. But traffic that you know exists is like, okay, maybe you prepare it a little differently. Maybe you fill up your playlist with podcasts, you take some snacks, you fill up your gas tank. You just set yourself up for a smoother ride, despite the fact that you're driving the traffic either way.”

Valuable advice Dan received from a mentor

“When you're facing a conflict or a difficult decision, or you're generally unhappy about something, you really only have three choices.

You have three buckets it's accept it, or change it, or move on.

And so when you accept it, it doesn't mean that you're just like resigning yourself or giving into something. It literally means that you decide you can live with the status quo and you choose not to give it any more energy.

If you change it, you decided that you can't accept the status quo, and you're going to do anything in your power to change the situation, and that involves pushing through friction. You should probably set a time box on this because pushing through friction endlessly will burn you out. At the end of your time box, you can kind of assess, is this something that I was able to push through? Is it worth continuing to push through? Should I move into one of the other buckets, whatever.

And then the third option is to move on. So if you've tried to change it, you've realized you can't, you're unable to accept it, then maybe it's time to move on. And this could be like from a problem, from a company, anything.”

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About Lead Time Chats

Listen in on unscripted conversations between Jean Hsu, VP of Engineering at Range and engineering leadership coach, and engineering leaders and other influential folks in tech.

Lead Time Chats is brought to you by Range. Range helps hybrid teams check-in asynchronously about what matters most. Know what's happening through status updates that pull from tools like Github and JIRA without scheduling yet another meeting.

Checking-in with Range creates more focus time for heads-down work, all while feeling a deeper sense of connection and belonging with your team. To learn more about Range, you can check it out here.

Season 3 Episodes

» Episode 1: Jen Kim on how startups can hire better

» Episode 2: Kate Heddleston on managing burnout on your team

» Episode 3: Jessie Duan on the Chief of Staff to CTO role

Season 2 Episodes

» Episode 1: Camille Fournier on making boring plans

» Episode 2: Tess Rinearson on early career engineering managers

» Episode 3: Kim Scott on building for systemic justice

» Episode 4: Sumeet Arora on moving on from a big company

» Episode 5: Rachael Stedman on IC manager work

» Episode 6: Chris Bee on Behaviors of Effective Eng Leaders

» Episode 7: Lynne Tye on the Engineering Hiring Landscape

» Episode 8: Beau Lebens on Distributed Team Meetups

» Episode 9: Indrajit Khare on Getting Acquired by Google

» Episode 10: Jack Danger on Technical Debt

» Episode 11: Sarah Milstein on Successful Remote and Hybrid Teams

Season 1 Episodes

» Episode 1: Will Larson on the path of the senior engineer

» Episode 2: Duretti Hirpa on mentoring junior and mid-level engineers

» Episode 3: Cate Huston on working with an external coach

» Episode 4: Juan Pablo Buriticá on common eng manager mistakes

» Episode 5: Gergely Orosz on the decision to go into management

» Episode 6: Lara Hogan on leading effectively in a pandemic

» Episode 7: Kaya Thomas on common early career engineer challenges

» Episode 8: Uma Chingunde on starting a VPE role in a pandemic

» Episode 9: Katie Wilde on supporting your team's mental health

» Episode 10: Akhil Gupta on navigating uncertainty in new roles

» Episode 11: Harper Reed on giving everyone a voice in team meetings

» Episode 12: Marc Hedlund on sponsorship

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Lead Time Chats: Dan Na on pushing through friction
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