Cynthia Ng- When Work Doesn't Fit the Mold, a Chief of Staff Steps In

Cynthia Ng is an experienced Staff Support Engineer at GitLab, dedicated to keeping customers happy by fixing bugs and suggesting new features. She's a pro at sharing knowledge and connecting with the community, and she loves supporting others in various areas, especially technology, usability, and accessibility. Throughout her career, she has excelled in customer support, documentation, code contributions, project management, career development, and training. In her library work, she specialized in systems and technology, metadata and technical services, and information/knowledge management.

 

Check out this conversation video featuring Cynthia Ng our upcoming speaker for November's Leadership Summit, where she discusses her role as Chief of Staff and how she supports executives while filling operational gaps. This video offers a sneak peek into the compelling insights Cynthia will be sharing on stage in Oakland. Be sure to watch and get a taste of what's to come!

 
 

Scott Tran:

I'm curious to hear about this idea of the chief of staff when did you start thinking about it? What is the chief of staff? What did they do and do I wanna be one?

Cynthia Ng:

So when I was participating in the CEO Shadow program, I was a senior support engineer. Our shadow program, allows anyone to participate. So it was a really great opportunity for me to see more about what goes on at the executive level. Which is a two-week shadowing your CEO and our Chief of Staff to CEO is one of the people that you interact with. 

At the time, our CEO did not have an executive assistant. So, our chief of staff was actually taking care of some of that, so as a CEO shadow, I interacted with her a little bit more than maybe some of the CEO shadows normally would.

And then during my two-week rotation a CEO from another company, actually wanted to talk to Sid he was considering hiring a chief of staff.

They were actually recording the meeting and publicly streaming it during the week I was doing my rotation.

And so of course the chief of staff at my company, was there and answering questions as well. That's actually when I got a much better understanding of what a Chief of Staff is and at least how it works at GitLab. So the chief of staff can look very different depending on the organization you're in. But certainly, it was during CEO shadow where I got to sit in on this recording and discussion and got to work with our own chief of staff to CEO a bit more that I became more interested in the role in terms of what it involves. 

Scott Tran:

It's a two-week program and you got introduced to the Chief of staff, what happens next? 

Cynthia Ng:

Later on, the CTO that we had at the time, was interested in getting a chief of staff.

He wasn't sure what work that Chief of Staff role would involve. He wasn't sure whether there was enough, work for it to be a full-time role. So he wanted to evaluate in a lot of ways what that would look like. And so he was actually the one who came up with the idea of doing a quarterly rotational acting chief of staff role to the CTO.

Like anyone else, I applied to be the acting chief of staff for a quarter and our CTO and you would do like a chat with him and you would do a chat with one of the VPs in engineering and they would decide who would get the position.

And then if there were multiple candidates in a previous quarter that they were interested in, those candidates would get priority.

That actually took me a couple of quarters before I actually ended up doing it.

Scott Tran:

Why do you think, heads of support should consider, getting a chief of staff? 

Cynthia Ng:

One of the things that I had actually thought about for quite some time while I've been working in support is whether it makes sense to have something like a chief of staff.

And even if that's not, what you call it, it would be a position where someone takes on operational work that would otherwise fall through the cracks.

In support, you're so often focused on tickets and resolving tickets and obviously, there's other work around that.

But there's so much other stuff that needs to happen. Even if you have, someone who is an administrator of Zendesk and that falls under support operations. And then you have your, your support agents, or at GitLab we have engineers. And then one is focused on Zendesk. One is focused on tickets. Well, what about all this other stuff that has to happen? 

So a lot of our training, for example, was very ad hoc and was written by whoever wanted to and was interested, but there wasn't really anyone organizing the training in any way necessarily. So it's like, who does that? 

We don't have an internal within support person who organizes our internal documentation so we have our product documentation and that we have a technical writing team for, but who organizes all of our internal documentation? 

How's that organized? We don't need to adhere to a style guide or anything, but you still need to have some kind of knowledge management organization to it so that people can find it. And it has to be organized in some way. So, even today we're not quite there yet where we don't necessarily have someone organizing a lot of internal things. Who does internal tooling? Who organizes all of that and that's always a question. 

Scott Tran:

Yeah. I think there's always gonna be things that are valuable to get done, but it doesn't make sense to hire a full-time person just to do that. There are always gonna be projects of different sizes and maybe they grow into full-time roles eventually, but there's so many more that can fall through the cracks.

Cynthia Ng:

What's interesting about Chief of Staff, regardless of who they report to, whether it's the CEO, CTO, or someone head of support wanted for their own department. Is that the role that they fill typically what the company needs?

It's what the person that they're reporting to needs and so that work can shift, there isn't always a single focus. I did a lot of following up on like OKRs and stuff like that. Sometimes you just need someone around to like track things and nudge people or just again, make sure that things are getting done on a certain timeline. 

We don't have a project manager either within support or anything like that. Your head of support or executive or whoever only has so much time and their focus tends to be on the strategy and the vision or direction. And you don't want them to spend all those time doing really very operational type work. But that doesn't fit within one of your existing teams. 

Scott Tran:

So it sounds like a chief of staff can be like a multiplier for your executive.

Cynthia Ng:

Very much so

Check out the video now featuring Cynthia Ng our upcoming speaker for November's Leadership Summit

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