If you’re looking for someone to help make you the best leader you can be and accelerate that important work immediately, then it may be time to consider hiring a Chief of Staff.
For founders and senior operators, a Chief of Staff (CoS) is their right-hand person. A partner. A co-pilot. A conduit between them and the rest of the world.
If you ask anyone who has had a CoS previously, it’s unlikely they’ll ever go back to flying solo.
What the role entails is entirely up to the exec and company’s needs. A CoS will move between operating tactically, strategically and operationally, often connecting the dots across teams and filling the gaps where a project doesn’t fall neatly within one function’s area of responsibility.
So, how do you figure out if you need a CoS and what they should do? On the flip side, if you’re considering stepping into a CoS role, what do you need to know before you make the leap?
Gill Findlay, Chief Operations Officer
What are some of the signs that you need a CoS?
If you look at your diary, and it's filled with back-to-back meetings and only a smattering of time to do other ‘real work’ and thinking, that’s a sign.
I saw the benefit of having a Chief of Staff at SafetyCulture when we were over 100 people, and I had quite a few (read – way too many) direct reports. We were levelling up our leadership team, scaling quickly and the organisation was evolving weekly.
When I took the role at Immutable, the business was already scaling fast and we were over 100 people. Before I started my role, I knew a CoS would make me better from day one.
When I’m not in meetings or 1:1s with direct reports, I’m interviewing candidates, which means I have very little time during the week to ensure actions discussed during meetings are implemented. Having a CoS means I know somebody will take ownership of the next steps, cascade information down to the people in the org who need it, and hold me to account! Also when I can’t be there - I make sure they are.
How do you scope the role of CoS?
A CoS can be anything from an experienced EA, right through to the 2IC to the CEO, and everything in between. I firmly believe that wherever they are on that spectrum, the CoS shouldn't have a team of direct reports or have P&L responsibilities. That’s how I see the difference between the CoS, Chief Operating Officer, Director of Operations etc. The role of the CoS is to support the executive team and make them more effective.
You can break down the scope of the role into specific strategic projects and business as usual. BAU can involve being an integral part of executive meeting cadence, strategic planning processes and internal communications.
A big part of scoping the role is being self-aware and understanding what you’re not so good at or don’t enjoy. You want to pick a partner who complements you — a yin to your yang.
You also want to be able to leverage their skills and experience. Identifying aligned strategic projects where they can add value is essential.
When Emily joined, one of her first projects was a compensation review (salaries and ESOP). We committed early in my tenure to pay above market, combined with limited capacity in our people team (they were some of the people we needed to hire quickly!) – it was a no brainer for her to tackle this. Emily did a fantastic job pulling that together; getting the data, benchmarks, analysis and execution. There’s no way I could have done that better than her. You want to hire a CoS who can execute on some things better than you!
What do you look for in a CoS?
I mentioned previously there should be a yin and yang dynamic, but there should also be similarities in how you like to work. Emily and I are both action-oriented and decisive. We know scaling is hard, so as a COO you need to keep pushing things forward daily. I need a CoS that is all about GSD (Get S**T Done!).
A CoS should have excellent verbal and written communication skills. They have to be able to synthesise a lot of information, communicate it with clarity and conviction to many different stakeholders.
It is unlikely a Chief of Staff who isn’t well-organised or execution-focused could be successful. I couldn’t see how that could work. They need to manage multiple, conflicting projects and their own time well.
How do you distinguish between what you should do, and what you should delegate?
The exec is high-level, and the Chief of Staff needs to be in the detail.
Where there is a cross-functional project, it’s my job to get strategic alignment and buy-in at the highest level. It’s then the job of the CoS to follow up with the execution, facilitate the project and keep things moving forward. The CoS is often reporting status, blockers and success metrics to the exec.
How do you measure the effectiveness of your CoS?
At Immutable, we don’t set OKRs for the Chief of Staff as we don’t want to be too prescriptive about goals (Amy Glancey, the rock star Chief of Staff at Atlassian, and I bonded over this POV). If there are too many constraints around what the CoS does, they can’t be flexible and fluid, which is what you want them to be, as what needs to get done typically changes a lot.
For the BAU element of the role, how well a CoS is performing is directly linked to the productivity of the executive team as a whole, which you can gather feedback on from different forums. For example, we have a prescriptive goal for our weekly executive meeting and we measure the effectiveness of that time by scoring it out of 10. We want to see that score trending upwards or averaging an 8 out of 10 or more every quarter.
How do you manage the workflow between you and your CoS?
We do a 1:1 on Mondays - directly after the executive team stand-up - which we never miss or reschedule, at least a half-hour catch up every second day, and we’re regularly on the phone or Slack as the day progresses.
The time you dedicate to catch-ups needs to be high value. In our half-hour catch-ups, we’re either making a decision, talking through something we need action and then working out the time to get it done.
Emily Close, Chief of Staff
What traits do you need as a CoS?
As a CoS, you have to be comfortable thinking strategically and executing tactically. The expectation is that you’re actively contributing to the strategic direction of the company, but also responsible for ensuring strategies are implemented.
You also have to be a person that enjoys enabling other people’s success. A big part of my role is making the exec team’s life easier and ensuring that the projects that fall between the seams of the leadership team are owned and accounted for.
It probably comes as no surprise, but you need to have an innate drive to execute. A mountain of work can pile up in a company that’s scaling so quickly, so as a CoS you need to be hyper-organised and structured in your approach to ploughing through it.
What are the main challenges of a CoS role?
Given that you’re juggling many tasks, it’s often easier to tackle the low hanging fruit. However, it’s important to take stock of, and prioritise the projects that can change the company's trajectory. These projects typically cover meaty cross-functional issues and allow you to build relationships across the company. You can help unblock some of the challenges other teams haven’t had a chance to get to as they’re so busy focused on their day job.
What’s great about being a CoS?
It gives you an intimate opportunity to learn from the most senior leaders in the company to see how they make decisions, triage what’s important and what’s not, put out fires, cultivate relationships, and manage their teams. I aspire to be a COO one day, so I’m in a privileged position sitting side-by-side with Gill and seeing how she navigates the day to day operations and challenges that come with scaling a A$3.5b company.
I enjoy working with so many different people and departments across the company. I’ve naturally supported more in areas where I can bring my experience to the table (finance, ventures, investor relations), but I've really enjoyed the visibility into (and the opportunity to learn more about) how we set a product strategy, design the levelling architecture of the company, execute on our GTM flywheel and expand our Studio to a metaverse of games (amongst a heap of other things!).
I’m also lucky because the company is at a great stage for the CoS role. We’re still setting up so many new functions, embedding processes, doubling in headcount and expanding into new geos, which means there’s lots to get involved in as CoS.
What are the career paths for CoS?
At Immutable, the CoS role is seen as a 12-24 month incubator role, where you're given exposure to all areas of the business. You can then use the opportunity to move into another senior role to hone in on your craft.
Given we’re scaling so quickly, there are many roles that would suit someone from a CoS background across finance, comms, ops, corporate development, partnerships and strategy. I could imagine a CoS transitioning into a senior role in almost every function of the company, especially if a large part of their time to date has been working closely with that particular team in enabling them to meet their strategic objectives.
A good stint for a CoS is ~2 years, given some of the projects that you own run on an annual cadence. This ensures you can add more value next time around, and both you and the company reap the benefits from the initial investment.
You're going on maternity leave soon, what advice do you have for the incoming CoS at Immutable?
Sit in as many functional leadership meetings and squad delivery updates as you can in the first few months. This means you’ll start to learn the language, accelerate your understanding of what matters, and build relationships to be a helpful conduit between the rest of the company and the exec team.
It’s a good idea to constantly review where you see yourself as a senior leader long-term. At the start, you’ll over-index on projects that fit your strengths. But make sure you’re also exposing yourself to other areas of the business that you’d like to learn more about to ensure you come out the other side of the 12-24 months experience as a more well-rounded operator.
📚 CoS must-reads and helpful resources
- Gill: Chief of Staff Network Australia, The Case for a Chief of Staff
- Emily: The Ultimate Guide to Running Executive Meetings — 25 Tips from Top Startup Leaders
🚩 Red flags when hiring a CoS
- Gill: Seeing the role it as a means to an end, rather than an opportunity to learn.
- Emily: High ego, low energy.
🤩 The best thing about working at Immutable is...
- Gill: I can’t pick just one. The team, the high ownership and high performance culture – and it’s SO MUCH FUN!
- Emily: Unconstrained opportunity.