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Jessie Duan on the Chief of Staff to CTO Role

Lead Time Chats: Season 3, Episode 3 Takeaways

October 27, 2021

In this episode of Lead Time Chats, Jean Hsu, VP of Engineering at Range, chats with Jessie Duan, Chief of Staff to the CTO at Roblox, about the Chief of Staff role.

Jessie and Jean discuss:

  • What the Chief of Staff role looks like and the different kinds of work it entails
  • How the role is similar and different to past roles like engineering manager and tech lead
  • The importance of influencing without authority and learning how to effectively navigate relationships throughout different functions
  • Learning to let go of optimal solutions in favor of getting something done

Takeaways from Jessie

Chief of Staff role is both similar and dissimilar from past roles

“When I think about the work that I do, I think it falls into maybe into a few major buckets. I think the first is strategic work. This past year, we've re-done a lot of our team building processes, so we revamped hiring, onboarding, perf management. This strategic bucket is going to be helping figure out what is the direction, and of course shepherding the revamp of these new things.

A second bucket is just operational work. So right running staff meetings, prepping a big presentation. I stepped into basically TPM our company-wide engineering efficiency effort for awhile, because the CTO was responsible for it and needed someone to do that.

Both of those first buckets are similar to what I've done before, the strategic one is maybe on a bigger scale, but the operational work is not that different from just being an EM.

Third is basically representing the CTO and his views. I feel like I have to be pretty careful. This is what the CTO thinks versus this is what I personally think and kind of clarifying on that. But you know, I'll sit in on meetings for him sometimes, or basically kind of represent when he's not immediately there.

The last kind of bucket of work is a sort of being a Jack of all trades, like kind of immediate problem solving. And I don't know, he might toss a question or problem at me like, Hey, are on-call shifts a burden at the company.

I would then figure out, okay, well, should we survey all thousand plus engineers. Do I try to ping some key people? How do I weigh the input of the most vocal people versus not? Are there metrics we can look at? There are a lot of these things that kind of pop up where I can take burden off of him by taking this smaller problem, running with it, and bringing the results back.”

Driving initial steps of a problem and then handing it off is a core part of the role

“If something is solely my responsibility with no potential end in sight or future organization or teams to transfer it to, I think that is potentially actually bad because it means I don't have bandwidth to take on other kinds of urgent or maybe more immediate things that come up over time. So I don't think I'm a good permanent home for things. I think I'm a good, Hey, we need someone to figure this out. Like here's this problem that's going on, we need something to figure out what to do next, maybe drive initial steps of it, but then eventually like get it to a good place such that others can take it on.”

Learning how to influence without authority is critical

“I was surprised at how much people navigation I ended up doing. I was more used to being an EM or tech lead and kind of having a pretty clear domain where it was my responsibility, and I was clearly the decision maker for things within this scope.

Onboarding. I don't own that. I shouldn't own that. It's our HR department that actually owns that. Learning and figuring out how to navigate that, how to really work closely with them, but also be taking input from a couple hundred engineering managers, a thousand engineers, and figure out how to get their input, consolidate that and do something, and then also partner with these other functions.”

Getting something done is more important than the optimal solution

“I still second guess myself a lot, but that's one of the things I struggle with too. I'm a perfectionist. I'm Type A, I like figuring out the optimal solution and then making it happen. I've had to learn or figure out, it's better to do something than try to pursue the perfect solution.”

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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

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

S3 E3: Jessie Duan on the Chief of Staff to CTO Role
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