Originally presented at Support Driven Leadership Summit 2023 Oakland.
Abstract
When you have a lot of work that doesn’t clearly fit into the organization chart reporting lines, a Chief of Staff may be the right person to help better execute on cross-team collaboration and your strategic vision.
In any department, team and individual responsibilities are typically defined and scoped. What happens when work doesn’t fit that scope or crosses lines in messy ways? It often falls to the head of a department, but a single person only has so much time and already has a stack of other problems. While a “Chief of Staff” is often used to describe someone reporting to an executive, whatever the title you choose for your cross-team collaboration leader, having an individual in such a role can improve efficiency, and strategic planning and execution. We’ll briefly talk about what a Chief of Staff is, how we’ve used Chief of Staff at GitLab, and how it can apply to your support organization.
Slides
Note: Links are in the slides.
Introduction
Hi Everyone, My name is Cynthia Ng, although most people know me as “Arty” and you’ll find me on the Support Driven Slack as Arty-chan.
Before I get into the presentation itself, I want to quickly thank everyone involved in organizing the Support Driven Leadership Summit, and especially Scott and Lizzie for inviting me to speak.
As a quick note, I have a number of links in the presentation. I’ll be making the slides available, so you’ll be able to get them afterwards.
Outline
Very briefly, we’ll cover:
- What a Chief of Staff is
- Where they might fit in your team
- When and Why you would want a Chief of Staff, particularly in Support
- How to get one on your team
A bit of context though to start.
About me
A little about me. I’ll not bore you with a long bio, but for the context of this presentation, there are a few things I want to mention.
While I’ve been working at GitLab for the last 5.5 years primarily as a Support Engineer, my previous experience in various positions involved “wearing many hats”, and juggling different priorities, responsibilities, and projects.
While at GitLab, I’ve still done that, but I also participated as a CEO shadow a couple years ago, worked as Acting Chief of Staff to CTO for a quarter — which is what lead me here — did two internships for learning with the Chief of Staff to CEO team, and I’m now the newest member of the team.
GitLab
As I’ll be referring to the work I’ve done at GitLab and using it as an example, I want to provide a little bit of context on the company.
GitLab, itself, is a comprehensive platform that helps people collaborate and develop software faster. Think of it as a single platform to code, test, package, and release software.
The company has over 2000 team members spread across over 65 countries and regions, and all work fully remote.
The Support team has 135 team members globally including Support Operations and Managers, and provides 24×5 support with 24×7 emergency support.
Answer these questions
To get you thinking, I’d like to ask you all a few questions.
Raise your hand if you’d say yes:
- Do you have a significant amount of work that doesn’t “fit” under existing teams?
- Do you find yourself trying to delegate that work without success?
- Do you think to yourself that you and your leadership team could be more effective and doing more “strategic” work if you simply had more time?
These are very general questions, but hopefully get you thinking.
What is a Chief of Staff?
To start, what is a Chief of Staff?
Does anyone here have one? How do you define it?
Wikipedia defines a chief of staff as someone who
“works behind the scenes to solve problems, mediate disputes, and deal with issues before they are brought to the chief executive.”
Then, as a confidant, advisor, and sounding board. And ends with a note that
“Ultimately the actual duties depend on the position and the people involved.”
And this is true. I’ve heard a large variation of what a Chief of Staff at different organizations might do. One Chief of Staff might follow the executive around everywhere, while another might end up in meetings with their executive only a couple of times a week. Sometimes a Chief of Staff role might include what others see as administrative tasks that are typically done by an Executive Assistant, though often specifically exclude them.
Range of role
Depending on what a leader needs, a Chief of Staff could be someone who can understand the company, communicate well, manage projects, and manage relationships.
Additionally, they may be expected to think strategically, analyze problems, then execute on ideas to full implementation.
At an even higher level, they might be expected to anticipate and mitigate problems, and most importantly, add value to a leader’s vision.
The level at which a Chief of Staff is doing this work also varies depending on where in the organizational structure they are. When a Chief of Staff is reporting to the CEO and essentially a member of the executive team, expectations and responsibilities will be higher than the department level that we’ll be talking about.
The key here is that you tailor the role to what you need.
Nevertheless, I’m going to define for you how I see a Chief of Staff role and where they might fit in the context of Support.
Where does a Chief of Staff fit?
At GitLab, our CEO has described the Chief of Staff as
“someone who runs the function for everything that doesn’t belong in a function.”
What do we mean by that?
At Gitlab, our organization is sorted by function. Think: Product, Engineering, Finance, Sales, Legal, and so on. Going back to one of the questions I asked earlier, what do you do when you have work that doesn’t fit in one of those divisions?
Normally, it might fall on the CEO’s plate, but one person only has so much time. This is where a Chief of Staff can naturally fit.
When I was Acting Chief of Staff to CTO, it was work that didn’t fall under an existing Engineering department. A quick note that this is similar but not reflective of our Engineering division.
Here’s a hypothetical example of how a Support department might look. By “regional” here, I’m referring to the fact that you’ll likely have a leader for each region (Americas; Asia Pacific; and Europe, Africa, and Middle East) if you have global support.
Again, back to that question: what work does your Support department have that doesn’t fit into one of your existing subdepartments?
Anyone want to give an example?
Some examples:
- training
- internal documentation: organizing, auditing
- preparing for non-product changes, especially internal ones
- process/workflow reviews and improvements
- projects: evaluating vendors, migrations, other research
As each organization is different, what falls outside of existing subdepartments will differ and over time, that will change.
For example, you may not currently have someone to liaise closely with the product release team and need that until you find one or more people permanently. A Chief of Staff could help you figure out the structure and how that would work for your Support team; whether it’s a full time Product Analyst, or a liaison responsibility for existing Support team members; then hire or find the right people and help them into the role.
Why a Chief of Staff
Hopefully, the reasons why you might want a Chief of Staff are becoming obvious, but let’s cover some of the benefits.
Benefits
A Chief of Staff can help
- Save time. They can help delegate work, and do some of the work.
- Better internal communication. Since they’ll have an overview of what’s happening in Support, and what the leadership team is working on, they can help provide more communication and transparency.
- Better decision making. Not only can they help guide strategic work, such as developing OKRs, they can be that confidante, advisor, and sounding board we talked about earlier.
- Increase the leadership team’s impact and especially you, the leader, by helping to focus and prioritize on the most critical work.
- Increase effectiveness and productivity through that improved communication and information flow, and processes and workflows.
Even if you’re convinced of the benefits, the question then is ‘when?’.
When to have a Chief of Staff
Naturally, as any organization grows, you start adding more and different positions.
I asked at the beginning about delegating work and wanting to be more effective and strategic in the work that you do. If you said yes to those questions, and especially if you’ve been thinking about it already, you’re likely close to or at the point when you might need a Chief of Staff.
In particular, when you’re concerned about:
- Poor communication flow
- Inefficient or slow decision making
- Needing to increase productivity
- Inefficient workflows and processes
- Spending a large amount of time “putting out fires”
Basically, the opposite of the benefits, then it might be time.
Most likely, you won’t be thinking about this sort of role if you’re in a small startup, but rather when the organization grows to a certain size.
While we don’t currently have one in our Support department, I honestly started thinking about proposing this sort of role over 2 years ago, when our Support team was around 100 people. Since the beginning of last year, we’ve had a Director of Global Readiness who takes care of a large portion of the work that I had thought a Chief of Staff in Support could be covering, so I never formally proposed it.
As I said, every organization is different, so while talking to others about when and why it worked for them, ultimately, you need to evaluate that and make the case for your team.
How to get a Chief of Staff
Finally, we arrive at getting a Chief of Staff. There’s a lot that goes into recruiting and hiring, so I’m only touching on a few things that I believe are important to point out for this type of role.
Communicate the role
Really the most important thing is to communicate well what the role is. This is doubly important when you’re trying to get buy-in for creating the role and then externally, for people applying to the role.
Obviously, be clear about what responsibilities this role will cover. Especially with the wide range of what a Chief of Staff can be, candidates need to know what level of skills they need and the level of results they’re expected to achieve. For example, are they going to be managing a team? In a Chief of Staff type role in Customer Support, often the role includes managing the Support Operations team.
Similarly, what level of leadership and project management experience do they need?
Because a Chief of Staff is often tasked with a large range of work, you also want to delineate it from other roles. For example, at the executive level, the description for a Chief of Staff often includes how it’s different from the Executive Assistant role.
And in this case, if you’re hiring someone specifically for Support, how important is it to you that they have Customer Support, and Support Operations experience?
Alternative job title examples
One last thing you might consider is whether you want to use the Chief of Staff title. I know that’s what we’ve been talking about this whole time. However, in some organizations, having “Chief” in the job title is reserved for executive group members, or someone who reports directly to an executive. So you might instead have VP, Director, or some indication of the level of the role, and then:
- [VP/Director/etc.] Strategy and Operations
- [VP/Director/etc.] Special Projects
- [VP/Director/etc.] Global Readiness
Certainly these are many other titles used for similar roles. And none of them might fit depending on what you want the role to cover.
Take away
Alright, that was a whirlwind of information and yet there is so much more I could say, so please definitely find me or reach out later if you’d like to chat more, or check out the links in the slides, which again, I’ll post a link to.
To wrap up, I’ll leave you with this quote:
“A [Chief of Staff] should handle several principal duties, all focused on making time, information, and decision processes more effective.”
So in essence, hire someone to step in for you.
Thank you.
